阅读说明：本技术 罗汉果苷化合物及其用途 (Mogroside compound and application thereof ) 是由 甘贤文 印丹婷 R·布劳奇利 于 2020-03-24 设计创作，主要内容包括：本文呈现的各个形态涉及从含有罗汉果苷的植物(例如罗汉果)提取物中制备食物成分、调味料和甜味剂的方法。本文还提供了由所述方法制得的组合物的制剂和用途。(Various aspects presented herein relate to methods of preparing food ingredients, flavors, and sweeteners from mogroside-containing plant (e.g., luo han guo) extracts. Also provided herein are formulations and uses of the compositions made by the methods.)

1. A compound selected from compounds of the formula:

and any salts thereof.

2. The compound according to claim 1, wherein the compound is of the formula:

or any salt thereof.

3. The compound according to claim 1, wherein the compound is of the formula:

or any salt thereof.

4. The compound according to claim 1, wherein the compound is of the formula:

or any salt thereof.

5. The compound according to claim 1, wherein the compound is of the formula:

or any salt thereof.

6. Use of a compound according to any one of claims 1 to 5 for imparting sweetness or enhancing sweetness to a flavored article.

7. Use according to claim 6, wherein the flavoured product comprises one or more sweeteners selected from: sucrose, fructose, glucose, sucralose, one or more rebaudiosides, acesulfame potassium, a rare sugar, erythritol, aspartame, cyclamate, one or more other mogrosides, or any combination thereof.

8. Use according to claim 6 or 7, wherein the flavoured product comprises one or more sweet taste enhancing compounds, one or more umami taste enhancing compounds, one or more cooling enhancing compounds, one or more bitter taste blocking compounds, one or more acidity regulating compounds, one or more mouthfeel improving compounds, one or more flavour masking compounds, or any combination thereof.

9. Use according to any one of claims 6 to 8, wherein the flavoured article is a food product or a beverage product.

10. An edible composition comprising one or more compounds of any one of claims 1 to 5.

11. The edible composition of claim 11, further comprising one or more sweeteners selected from the group consisting of: sucrose, fructose, glucose, sucralose, one or more rebaudiosides, acesulfame potassium, a rare sugar, erythritol, aspartame, cyclamate, one or more other mogrosides, or any combination thereof.

12. The edible composition of claim 10 or 11, further comprising one or more sweet taste enhancing compounds, one or more umami taste enhancing compounds, one or more cooling enhancing compounds, one or more bitter taste blocking compounds, one or more sour taste modulating compounds, one or more mouthfeel improving compounds, one or more flavor masking compounds, or any combination thereof.

13. The edible composition according to any one of claims 10 to 12, further comprising a bulking agent, a food product, or any combination thereof.

14. An edible composition according to any one of claims 10 to 12, further comprising water.

15. The food composition of claim 14, further comprising carbon dioxide, citric acid, malic acid, or any combination thereof.

Technical Field

The present disclosure generally provides certain mogroside compounds, and their use to impart or modify the taste of edible compositions. In some forms, the present disclosure provides edible compositions, such as flavored food or beverage products, comprising one or more mogroside compounds disclosed herein.

Background

The natural source of sweet compounds is still sought after because the negative health effects of sugar intake by a large population have plagued health officials and whole humans. Sweet plant extracts that contribute almost zero to the caloric (calorie) contribution of the human diet are being sought to find sweet and flavor compounds that can replace sugars, thereby reducing the occurrence of obesity, diabetes and cardiovascular disease.

Various products for solving these problems have been proposed so far. For example, artificial high intensity sweeteners have been developed that provide sweetness at very low doses. Among the high intensity sweeteners already available on the market, sucralose, aspartame, acesulfame potassium, cyclamate (cyclamate) and saccharin are well known alternatives to caloric sweeteners. However, natural or naturally derived products are more strongly desired by more and more consumers than their artificial counterparts. However, many natural low-calorie sweeteners impart a long-lasting off-taste to the food to which they are added.

Lo Han Guo (Siraitia grosvenori), also known as monk fruit, is a member of the Cucurbitaceae family. The plant is native to certain regions of south and east asia, especially the south china. The sweetness of the luo han guo fruit is mainly derived from triterpene glycosides, which are present in high amounts in the fruit. These triterpene glycosides are commonly referred to as mogrol glycosides or mogrosides. Many mogrosides have been identified in luo han guo. An obvious example is mogroside V (shown in fig. 1), which is the highest concentration in the fruit compared to other mogroside compounds present. Mogrosides all have the same core structure, e.g., mogrol or oxo-mogrol core, and often differ from each other in the number and type of glycosidic residues bound to the mogrol or oxo-mogrol core. Examples of a series of mogroside compounds are described in U.S. patent application publication No. 2012/0059071. Some mogroside compounds have a relatively sweet taste, typically 100 times sweeter than sucrose. Examples of such sweet mogrosides include mogroside V, and its isomer isomogroside V. Isomogroside V is disclosed in U.S. patent application publication No. 2011/0027413. Even so, such readily available mogrosides tend to impart a bitter aftertaste, which limits their widespread use relative to rebaudiosides and other steviol glycosides.

U.S. patent application publication No. 2010/310751 discloses sweetening compositions useful in place of sugar that comprise one or more extracts from the fruit of plants of the cucurbitaceae family, such as mogroside V and monoammonium glycyrrhizin. PCT publication nos. WO 2015/082012 and WO 2018/089469 disclose triterpene glycoside compounds and sweetening compositions comprising various triterpene glycoside compounds. PCT publication No. WO 2017/075257 discloses compounds useful as sweeteners or sweetness enhancers.

Despite these previous efforts, there is a need to develop new sweeteners or sweet taste improving compounds. The present invention now meets these needs and provides significant improvements in this area.

Disclosure of Invention

In a first form, the present disclosure provides a compound of formula (I):

or a salt thereof, in the form of any one of its stereoisomers or a mixture thereof; wherein R is₁And R₂independently-OH or a sugar moiety, wherein the sugar moiety is a monosaccharide or oligosaccharide; wherein the monosaccharide or monosaccharide unit of the oligosaccharide is selected from: glucose, rhamnose, galactose, xylose, fructose, mannose, tagatose, sorbose, ribose, arabinose, xylulose, ribulose, 6-deoxyglucose, 6-deoxygalactose, 6-deoxymannose, 2-deoxyribose, hamamelose (hamamelose) and glucuronic acid; wherein the oligosaccharide consists of 2 to 5 monosaccharide units; wherein R is₃Is an-OH group, or R₃Combined with the hydrogen atom attached at position 11 to form an oxo (═ O) group; wherein R is₄、R₅And R₈Independently a hydrogen atom, -an OH group, or combine with a hydrogen atom attached to the same carbon atom to form an oxo (═ O) group; wherein R is₆Is a hydrogen atom or an-OH group; wherein R is₇Is a hydrogen atom, -an OH group or a sugar moiety, wherein the sugar moiety is selected from a monosaccharide or oligosaccharide, wherein the monosaccharide or oligosaccharide has a monosaccharide unit selected from: glucose, rhamnose, galactose, xylose, fructose, mannose, tagatose, sorbose, ribose, arabinose, xylulose, ribulose, 6-deoxyglucose, 6-deoxygalactose, 6-deoxymannose, 2-deoxyribose, hamamelose and glucuronic acid; wherein the oligosaccharide consists of 2 to 5 monosaccharide units.

In some embodiments of the foregoing forms, R₄、R₅、R₆、R₇And R₈Four of the groups are hydrogen atoms and the other group is not a hydrogen atom. In some further embodiments, the compound of formula (I) is not 22-hydroxybryodesmosogenin, 7-oxomogroside IIe, 7-oxomogroside IIIe, 7-oxomogroside III, 7-oxomogroside IV, 7-oxomogroside V, compound 25 described in PCT publication No. WO 2017075257, or 20-hydroxy-11-oxomogroside Ia 1.

In a second form, the present disclosure provides a compound of formula (II):

or a salt thereof, in the form of any one of its stereoisomers or a mixture thereof; wherein R is₁And R₂independently-OH or a sugar moiety, wherein the sugar moiety is a monosaccharide or oligosaccharide; wherein the monosaccharide or monosaccharide unit of the oligosaccharide is selected from: glucose, rhamnose, galactose, xylose, fructose, mannose, tagatose, sorbose, ribose, arabinose, xylulose, ribulose, 6-deoxyglucose, 6-deoxygalactose, 6-deoxymannose, 2-deoxyribose, hamamelose and glucuronic acid; wherein the oligosaccharide consists of 2 to 5 monosaccharide units; wherein R is₃And R₄independently-OH, or combine with a hydrogen atom attached to the same carbon atom to form an oxo (═ O) group. In some embodiments thereof, the compound of formula (II) is not 22-hydroxybryodin.

In a third form, the present disclosure provides a compound of formula (III):

or a salt thereof, in the form of any one of its stereoisomers or a mixture thereof; wherein R is₁And R₂Independently an-OH group or a sugar moiety, wherein the sugar moiety is a monosaccharide or oligosaccharide; wherein the monosaccharide or monosaccharide unit of the oligosaccharide is selected from: glucose, rhamnose, galactose, xylose, fructose, mannose, tagatose, sorbose, ribose, arabinose, xylulose, ribulose, 6-deoxyglucose, 6-deoxygalactose, 6-deoxymannose, 2-deoxyribose, hamamelose and glucuronic acid; wherein the oligosaccharide consists of 2 to 5 monosaccharide units; wherein R is₃And R₈Independently an-OH group, or combine with a hydrogen atom attached to the same carbon atom to form an oxo (═ O) group. In some embodiments thereof, the compound of formula (III) is not 7-oxomogroside IIe, 7-oxomogroside IIIe, 7-oxomogroside III, 7-oxomogroside IV, 7-oxomogroside V, or compound 25 described in PCT publication No. WO 2017/075257.

In a fourth form, the present disclosure provides a compound of formula (IV):

or a salt thereof, in the form of any one of its stereoisomers or a mixture thereof; wherein R is₁And R₂Independently an-OH group or a sugar moiety, wherein the sugar moiety is a monosaccharide or oligosaccharide; wherein the monosaccharide or monosaccharide unit of the oligosaccharide is selected from: glucose, rhamnose, galactose, xylose, fructose, mannose, tagatose, sorbose, ribose, arabinose, xylulose, ribulose, 6-deoxyglucose, 6-deoxygalactose, 6-deoxymannose, 2-deoxyribose, hamamelose and glucuronic acid; wherein the oligosaccharide consists of 2 to 5 monosaccharide units; wherein R is₃And R₅Independently an-OH group, or combine with a hydrogen atom attached to the same carbon to form an oxo (═ O) group.

In a fifth form, the present disclosure provides a compound of formula (V):

or a salt thereof, in the form of any one of its stereoisomers or a mixture thereof; wherein R is₁And R₂Independently an-OH group or a sugar moiety, wherein the sugar moiety is a monosaccharide or oligosaccharide; wherein the monosaccharide or monosaccharide unit of the oligosaccharide is selected from: glucose, rhamnose, galactose, xylose, fructose, mannose, tagatose, sorbose, ribose, arabinose, xylulose, ribulose, 6-deoxyglucose, 6-deoxygalactose, 6-deoxymannose, 2-deoxyribose, hamamelose and glucuronic acid; wherein the oligosaccharide consists of 2 to 5 monosaccharide units; wherein R is₃Is an-OH group or is combined with a hydrogen atom attached to the same carbon atom to form an oxo (═ O) group. In some embodiments thereof, the compound of formula (V) is not 20-hydroxy-11-oxomogroside Ia 1.

In a sixth form, the present disclosure provides a compound of formula (VI):

or a salt thereof, in the form of any one of its stereoisomers or a mixture thereof; wherein R is₇And R₂Independently an-OH group or a sugar moiety, wherein the sugar moiety is a monosaccharide or oligosaccharide; wherein the monosaccharide or monosaccharide unit of the oligosaccharide is selected from: glucose, rhamnose, galactose, xylose, fructose, mannose, tagatose, sorbose, ribose, arabinose, xylulose, ribulose, 6-deoxyglucose, 6-deoxygalactose, 6-deoxymannose, 2-deoxyribose, hamamelose and glucuronic acid; wherein the oligosaccharide consists of 2 to 5 monosaccharide units; wherein R is₃Is an-OH group or is combined with a hydrogen atom attached to the same carbon atom to form an oxo (═ O) group.

In some further embodiments of any of the foregoing modalities, the monosaccharide unit of the monosaccharide or oligosaccharide is selected from: glucose, rhamnose and galactose. In some other such embodiments, the monosaccharide or monosaccharide unit of the oligosaccharide is selected from: glucose and rhamnose.

In some other embodiments of the foregoing, the oligosaccharide is selected from: glucosyl- (1 → 2) -glucose, glucosyl- (1 → 3) -glucose, glucosyl- (1 → 4) -glucose, glucosyl- (1 → 6) -glucose, glucosyl- (1 → 3) - [ glucosyl- (1 → 2) ] -glucose, glucosyl- (1 → 4) - [ glucosyl- (1 → 2) ] -glucose, glucosyl- (1 → 6) - [ glucosyl- (1 → 2) ] -glucose, glucosyl- (1 → 2) -glucose, glucosyl- (1 → 3) -glucosyl- (1 → 2) -glucose, glucosyl- (1 → 4) -glucosyl- (1 → 2) -glucose, glucosyl- (1 → 6) -glucosyl- (1 → 2) -glucose, glucosyl- (1 → 2) -glucosyl- (1 → 4) -glucose, glucosyl- (1 → 3) -glucosyl- (1 → 4) -glucose, glucosyl- (1 → 4) -glucose, glucosyl- (1 → 6) -glucosyl- (1 → 4) -glucose, glucosyl- (1 → 2) -glucosyl- (1 → 6) -glucose, glucosyl- (1 → 3) -glucosyl- (1 → 6) -glucose, glucosyl- (1 → 4) -glucosyl- (1 → 6) -glucose, glucosyl- (1 → 6) -glucose, glucosyl- (1 → 2) -glucosyl- (1 → 6) - [ glucosyl- (1 → 2) ] -glucose, glucosyl- (1 → 3) -glucosyl- (1 → 6) - [ glucosyl- (1 → 2) ] -glucose, glucosyl- (1 → 4) -glucosyl- (1 → 6) - [ glucosyl- (1 → 2) ] -glucose, glucosyl- (1 → 6) - [ glucosyl- (1 → 2) -glucosyl- (1 → 2) ] -glucose, glucosyl- (1 → 6) - [ glucosyl- (1 → 3) -glucosyl- (1 → 2) ] -glucose, glucosyl- (1 → 6) - [ glucosyl- (1 → 4) -glucosyl- (1 → 2) ] -glucose, and glucosyl- (1 → 6) - [ glucosyl- (1 → 6) -glucosyl- (1 → 2) ] -glucose. In some other such embodiments, the oligosaccharide is selected from: glucosyl- (1 → 2) -glucose, glucosyl- (1 → 4) -glucose, glucosyl- (1 → 6) -glucose, and glucosyl- (1 → 6) - [ glucosyl- (1 → 2) ] -glucose.

In some other embodiments of the first form, the compound of formula (I) is selected from: 1- [ (6-O-hexopyranosyl) oxy ] -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest (secocholest) -5-en-24-yl 6-O-hexopyranosyl-hexopyranoside (Compound 1), 1- (hexopyranosyl-oxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O-hexopyranosyl-hexopyranoside (Compound 2), 24- [ (6-O-hexopyranosyl) -oxy ] -11,22, 25-Trihydroxyl-9, 10, 14-trimethyl-4, 9-Ring-9, 10-Ring-opened cholest-5-en-1-yl 4-O-hexopyranosyl-hexylpyranoside (Compound 3), 1- [ (6-O-hexopyranosyl-hexylpyranosyl) -oxy ] -7,11, 25-Trihydroxyl-9, 10, 14-trimethyl-4, 9-Ring-9, 10-Ring-opened cholest-5-en-24-yl-hexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranoside (Compound 4), 1- [ (6-O-hexopyranosyl-hexylpyranosyl) -oxy ] -25-hydroxy-9- (hydroxymethyl) -10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-24-ylhexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranosyl (compound 5), 9-formyl-1- [ (6-O-hexopyranosyl) oxy ] -25-hydroxy-10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-24-ylhexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranoside (compound 6), 1- [ (6-O-hexopyranosyl) oxy ] -11,20, 25-Trihydroxyl-9, 10, 14-trimethyl-4, 9-Ring-9, 10-Ring-opened cholest-5-en-24-ylhexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranoside (Compound 7), 1- (hexopyranosyloxy) -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-Ring-9, 10-Ring-opened cholest-5-en-24-yl 6-O-hexopyranosylhexopyranosyl-hexopyranoside (Compound 8), 24- [ (6-O-hexopyranosylhexopyranosyl-pyranosyl) oxy ] -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-1-ylhexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranoside (Compound 9), and (24- { [ hexopyranosyl- (1 → 6) hexopyranosyl ] oxy } -1, 25-dihydroxy-9, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-10-yl) methylhhexopyranosyl- (1 → 6) - [ hexopyranosyl- (1 → 4) hexopyranosyl- (1 → 2) ] hexopyranoside (compound 10).

In some other embodiments of the first form, the compound of formula (I) is selected from: (1S,4R, 9. beta., 11. alpha., 24R) -1- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl ] oxy } -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside (22-hydroxy-mogroside IVa, Compound 1a), (1S,4R, 9. beta., 11. alpha., 24R) -1- (. beta. -D-glucopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-Cyclo-9, 10-Ring-opened cholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-mogroside III, Compound 2a), (1S,4R,9 β,11 β,24R) -1- (β -D-glucopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-Ring-9, 10-Ring-opened cholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-11-epi-mogroside III, compound 2b), (1S,4R,9 β,11 α,24R) -24- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-1-yl 4-O- β -D-glucopyranosyl glucoside (22-hydroxy-isomogroside IVa, compound 3a), (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -7,11, 25-Trihydroxyl-9, 10, 14-trimethyl-4, 9-Ring-9, 10-Ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- ((1 → 6) ] - β -D-glucopyranoside (7-hydroxy-mogroside V, Compound 4a), (1S,4R,9 β,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-9- (hydroxymethyl) -10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (19-hydroxy-11-oxomogroside V, Compound 5a), (1S,4R,9 β,24R) -9-formyl-1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → f 2) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (19-formyl-11-oxomogroside V, Compound 6a), (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,20, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (20-hydroxy-mogroside V, compound 7a), (1S,4R,9 β,24R) -1- (β -D-glucopyranosyloxy) -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-ring-9, 10-ring opening cholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (20-hydroxy-11-oxo mogroside III, compound 8a), (1S,4R,9 β,24R) -24- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-cyclo-9, 10-ring-opened cholest-5-en-1-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (compound 9a), and [ (1S,4R,9 β,10R,24R) -24- { [ β -D-glucopyranosyl- (1 → 6) - β -D-glucopyranosyl ] oxy } -1, 25-dihydroxy-9, 14-dimethyl-11-oxo-4, 9-Cyclo-9, 10-Ring-opened cholest-5-en-10-yl ] methyl β -D-glucopyranosyl- (1 → 6) - [ β -D-glucopyranosyl- (1 → 4) - β -D-glucopyranosyl- (1 → 2) ] - β -D-glucopyranoside (Compound 10 a).

In a seventh form, the present disclosure provides a compound, wherein the compound is selected from the group consisting of: 1- [ (6-O-hexopyranosyl) oxy ] -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-ylhexopyranosyl- (1 → 6) - [ hexopyranosyl- (1 → 4) hexopyranosyl- (1 → 2) ] hexopyranoside (Compound 12), 1- [ (6-O-hexopyranosyl) oxy ] -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-ylhexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] Hexapyranoside (compound 13), 1- { [ hexapyranosyl- (1 → 2) - [ hexapyranosyl- (1 → 6) ] hexapyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-seco-chol-5-en-24-ylhexapyranosyl- (1 → 2) - [ hexapyranosyl- (1 → 6) ] hexapyranosyl (compound 14), 1- [ (6-O-hexapyranosyl) oxy ] -25-hydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-seco-5-en-24-yl 2-O-hexapyranosyl-hexapyranoside (compound 15), and any salts thereof, in the form of any of its stereoisomers or mixtures thereof.

In an eighth form, the present disclosure provides a compound, wherein the compound is selected from the group consisting of: (1S,4R, 9. beta., 11. alpha., 24R) -1- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-ring-opening cholest-5-en-24-yl beta-D-glucopyranosyl- (1 → 6) - [ beta-D-glucopyranosyl- (1 → 4) -beta-D-glucopyranosyl- (1 → 2) ] -beta-D-glucopyranoside (Compound 12a), (1S,4R, 9. beta., 11. alpha., 24R) -1- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl Glucosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-ring-opening cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (compound 13a), (1S,4R,9 β,11 β,24R) -1- { [ β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (11-epi-mogroside VI, Compound 14a), (1S,4S,9 β,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-cholest-5-en-24-yl 2-O- β -D-glucopyranosyl Glucosyl- β -D-glucopyranoside (11-deoxymogroside IV, compound 15a), and any salts thereof.

In a ninth form, the present disclosure provides a method of enhancing sweetness of a flavored article, the method comprising: providing a flavored article and introducing the compound of the first to eighth forms into the flavored article, such as a flavored food or beverage product. In some such embodiments, the compound is incorporated in an amount effective to enhance the sweetness of the flavored article.

In a tenth form, the present disclosure provides the use of a compound of any one of the first to eighth forms for enhancing the sweetness of a flavored article, such as a flavored food or beverage product.

In an eleventh form, the present disclosure provides an edible composition comprising a compound of any one of the first to eighth forms. In some embodiments thereof, the edible composition comprises a carrier, such as a bulking agent (e.g., erythritol, a rare sugar (allolose), a cellulosic material, or any combination thereof) or water.

In a twelfth form, the present disclosure provides a flavored article comprising the edible composition of the eleventh form. In some embodiments thereof, the flavored article is a flavored food or beverage product.

Drawings

Fig. 1 shows the chemical structure of mogroside V.

FIG. 2 shows a typical LC-HR-MS spectrum of (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy mogroside IVa, Compound 1 a).

FIG. 3 shows (1S,4R, 9. beta., 11. alpha., 24R) -1- { [6-O- (. beta. -D-glucopyranosyl) -. beta. -D-glucopyranosyl]Typical of oxy } -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside (22-hydroxy-mogroside IVa, Compound 1a)¹H NMR spectrum.

FIG. 4 shows (1S,4R, 9. beta., 11. alpha., 24R) -1- { [6-O- (. beta. -D-glucopyranosyl) -. beta. -D-glucopyranosyl]Oxy radicalTypical of { 11,22, 25-Trihydroxyl-9, 10, 14-trimethyl-4, 9-Ring-9, 10-Ring-opened Chol-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-mogroside IVa, Compound 1a) } -11,22, 25-Trihydroxyl-9, 10, 14-trimethyl-4, 9-Ring-opened Chol-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside¹³C NMR spectrum.

FIG. 5 shows a typical LC-HR-MS spectrum of (1S,4R,9 β,11 α,24R) -1- (. beta. -D-glucopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O-. beta. -D-glucopyranosyl-. beta. -D-glucopyranoside (22-hydroxy-mogroside III, Compound 2 a).

FIG. 6 shows a typical representation of (1S,4R,9 β,11 α,24R) -1- (. beta. -D-glucopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O-. beta. -D-glucopyranosyl-. beta. -D-glucopyranoside (22-hydroxy-mogroside III, Compound 2a)¹H NMR spectrum.

FIG. 7 shows a typical representation of (1S,4R,9 β,11 α,24R) -1- (. beta. -D-glucopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O-. beta. -D-glucopyranosyl-. beta. -D-glucopyranoside (22-hydroxy-mogroside III, Compound 2a)¹³C NMR spectrum.

FIG. 8 shows a typical LC-HR-MS spectrum of (1S,4R,9 β,11 β,24R) -1- (. beta. -D-glucopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-11-epi-mogroside III, Compound 2 b).

FIG. 9 shows a representation of (1S,4R,9 β,11 β,24R) -1- (. beta. -D-glucopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-11-epi-mogroside III, Compound 2b)¹H NMR spectrum.

FIG. 10 shows a representation of (1S,4R,9 β,11 β,24R) -1- (. beta. -D-glucopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-11-epi-mogroside III, Compound 2b)¹³C NMR spectrum.

FIG. 11 shows a typical LC-HR-MS spectrum of (1S,4R,9 β,11 α,24R) -24- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-1-yl 4-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-isomogroside IVa, Compound 3 a).

FIG. 12 shows (1S,4R, 9. beta., 11. alpha., 24R) -24- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl]Typical of oxy } -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-1-yl 4-O-beta-D-glucopyranosyl-beta-D-glucopyranoside (22-hydroxy-isomogroside IVa, Compound 3a)¹H NMR spectrum.

FIG. 13 shows (1S,4R, 9. beta., 11. alpha., 24R) -24- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl]Typical of oxy } -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-1-yl 4-O-beta-D-glucopyranosyl-beta-D-glucopyranoside (22-hydroxy-isomogroside IVa, Compound 3a)¹³C NMR spectrum.

FIG. 14 shows a typical LC-HR-MS spectrum of (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -7,11, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (7-hydroxy-mogroside V, Compound 4 a).

FIG. 15 shows (1S,4R, 9. beta., 11. alpha., 24R) -1- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl]Oxy } -7,11, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6)]Exemplary of-beta-D-glucopyranoside (7-hydroxy-mogroside V, Compound 4a)¹H NMR spectrum.

FIG. 16 shows (1S,4R, 9. beta., 11. alpha., 24R) -1- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl]Oxy } -7,11, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6)]Exemplary of-beta-D-glucopyranoside (7-hydroxy-mogroside V, Compound 4a)¹³C NMR spectrum.

FIG. 17 shows a typical LC-HR-MS spectrum of (1S,4R,9 β,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-9- (hydroxymethyl) -10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-ring opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (19-hydroxy-11-oxomogroside V, Compound 5 a).

FIG. 18 shows (1S,4R, 9. beta., 24R) -1- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl]Oxy } -25-hydroxy-9- (hydroxymethyl) -10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-24-yl beta-D-glucopyranosyl- (1 → 2) - [ beta-D-glucopyranosyl- (1 → 6)]Exemplary of-beta-D-glucopyranoside (19-hydroxy-11-oxomogroside V, Compound 5a)¹HNMR spectroscopy.

FIG. 19 shows (1S,4R, 9. beta., 24R) -1- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl]Oxy } -25-hydroxy-9- (hydroxymethyl) -10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-24-yl beta-D-glucopyranosyl- (1 → 2) - [ beta-D-glucopyranosyl- (1 → 6)]Exemplary of-beta-D-glucopyranoside (19-hydroxy-11-oxomogroside V, Compound 5a)¹³C NMR spectrum.

FIG. 20 shows a typical LC-HR-MS spectrum of (1S,4R,9 β,24R) -9-formyl-1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-ring opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- ((1 → 6) ] - β -D-glucopyranoside (19-formyl-11-oxomogroside V, Compound 6 a).

FIG. 21 shows (1S,4R, 9. beta., 24R) -9-formyl-1- { [6-O- (. beta. -D-glucopyranosyl) -. beta. -D-glucopyranosyl]Oxy } -25-hydroxy-10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6)]Exemplary of-beta-D-glucopyranoside (19-formyl-11-oxomogroside V, Compound 6a)¹H NMR spectrum.

FIG. 22 shows (1S,4R, 9. beta., 24R) -9-formyl-1- { [6-O- (. beta. -D-glucopyranosyl) -. beta. -D-glucopyranosyl]Oxy } -25-hydroxy-10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-24-yl beta-D-glucopyranosyl- (1 → 2)) - [ beta-D-glucopyranosyl- (1 → 6)]Exemplary of-beta-D-glucopyranoside (19-formyl-11-oxomogroside V, Compound 6a)¹³C NMR spectrum.

FIG. 23 shows a typical LC-HR-MS spectrum of (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,20, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (20-hydroxy-mogroside V, Compound 7 a).

FIG. 24 shows (1S,4R, 9. beta., 11. alpha., 24R) -1- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl]Oxy } -11,20, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6)]Exemplary of-beta-D-glucopyranoside (20-hydroxy-mogroside V, Compound 7a)¹H NMR spectrum.

FIG. 25 shows (1S,4R, 9. beta., 11. alpha., 24R) -1- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl]Oxy } -11,20, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6)]Exemplary of-beta-D-glucopyranoside (20-hydroxy-mogroside V, Compound 7a)¹³C NMR spectrum.

FIG. 26 shows a typical LC-HR-MS spectrum of (1S,4R,9 β,24R) -1- (. beta. -D-glucopyranosyloxy) -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-cyclo-9, 10-ring-opened cholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (20-hydroxy-11-oxomogroside III, Compound 8 a).

FIG. 27 shows a representation of (1S,4R,9 β,24R) -1- (. beta. -D-glucopyranosyloxy) -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (20-hydroxy-11-oxomogroside III, Compound 8a)¹H NMR spectrum.

FIG. 28 shows (1S,4R,9 β,24R) -1- (. beta. -D-glucopyranosyloxy) -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-cyclo-9, 10-ring-opened cholest-5-en-24-yl 6-O-. beta. -D-glucopyranosyl- β -D-glucopyranosylExemplary of glycosides (20-hydroxy-11-oxomogroside III, Compound 8a)¹³C NMR spectrum.

FIG. 29 shows a typical LC-HR-MS spectrum of (1S,4R,9 β,24R) -24- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-ring-9, 10-ring-opened cholest-5-en-1-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (Compound 9 a).

FIG. 30 shows (1S,4R, 9. beta., 24R) -24- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl]Oxy } -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-1-yl beta-D-glucopyranosyl- (1 → 2) - [ beta-D-glucopyranosyl- (1 → 6)]Typical of-beta-D-glucopyranoside (Compound 9a)¹H NMR spectrum.

FIG. 31 shows (1S,4R, 9. beta., 24R) -24- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl]Oxy } -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-1-yl beta-D-glucopyranosyl- (1 → 2) - [ beta-D-glucopyranosyl- (1 → 6)]Typical of-beta-D-glucopyranoside (Compound 9a)¹³C NMR spectrum.

FIG. 32 shows a typical LC-HR-MS spectrum of [ (1S,4R,9 β,10R,24R) -24- { [ β -D-glucopyranosyl- (1 → 6) - β -D-glucopyranosyl ] -oxy } -1, 25-dihydroxy-9, 14-dimethyl-11-oxo-4, 9-ring-9, 10-ring-opened cholest-5-en-10-yl ] methyl β -D-glucopyranosyl- (1 → 6) - [ β -D-glucopyranosyl- (1 → 4) - β -D-glucopyranosyl- (1 → 2) ] - β -D-glucopyranoside (compound 10 a).

FIG. 33 shows [ (1S,4R,9 β,10R,24R) -24- { [ β -D-glucopyranosyl- (1 → 6) - β -D-glucopyranosyl]Oxy } -1, 25-dihydroxy-9, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-10-yl]Methyl beta-D-glucopyranosyl- (1 → 6) - [ beta-D-glucopyranosyl- (1 → 4) -beta-D-glucopyranosyl- (1 → 2)]Typical of-beta-D-glucopyranoside (Compound 10a)¹H NMR spectrum.

FIG. 34 shows [ (1S,4R,9 β,10R,24R) -24- { [ β -D-glucopyranosyl- (1 → 6) - β -D-glucopyranosyl]Oxy } -1, 25-dihydroxy-9, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-10-yl]Methyl beta-D-glucopyranosyl- (1 → 6) - [ beta-D-glucopyranosyl- (1 → 4) -beta-D-glucopyranosyl- (1 → 2)]Typical of-beta-D-glucopyranoside (Compound 10a)¹³C NMR spectrum.

FIG. 35 shows a typical LC-HR-MS spectrum of (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 6) - [ β -D-glucopyranosyl- (1 → 4) - β -D-glucopyranosyl- (1 → 2) ] - β -D-glucopyranoside (compound 12 a).

FIG. 36 shows (1S,4R, 9. beta., 11. alpha., 24R) -1- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl]Oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 6) - [ β -D-glucopyranosyl- (1 → 4) - β -D-glucopyranosyl- (1 → 2)]Typical of-beta-D-glucopyranoside (Compound 12a)¹H NMR spectrum.

FIG. 37 shows (1S,4R, 9. beta., 11. alpha., 24R) -1- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl]Oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 6) - [ β -D-glucopyranosyl- (1 → 4) - β -D-glucopyranosyl- (1 → 2)]Typical of-beta-D-glucopyranoside (Compound 12a)¹³C NMR spectrum.

FIG. 38 shows a typical LC-HR-MS spectrum of (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (Compound 13 a).

FIG. 39 shows (1S,4R, 9. beta., 11. alpha., 24R) -1- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl]Oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) - β -D-glucopyranosyl- (1 → 6)]Typical of-beta-D-glucopyranoside (Compound 13a)¹H NMR spectrum.

FIG. 40 shows (1S,4R, 9. beta., 11. alpha., 24R) -1- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl]Oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) - β -D-glucopyranosyl- (1 → 6)]Typical of-beta-D-glucopyranoside (Compound 13a)¹³C NMR spectrum.

FIG. 41 shows a typical LC-HR-MS spectrum of (1S,4R,9 β,11 β,24R) -1- { [ β -D-glucopyranosyl- (1 → 2) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranosyl ] -oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (11-epi-mogroside VI, compound 14 a).

FIG. 42 shows (1S,4R,9 β,11 β,24R) -1- { [ β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6)]-beta-D-glucopyranosyl group]Oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6)]Exemplary of-beta-D-glucopyranoside (11-epi-mogroside VI, Compound 14a)¹H NMR spectrum.

FIG. 43 shows (1S,4R,9 β,11 β,24R) -1- { [ β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6)]-beta-D-glucopyranosyl group]-oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6)]Exemplary of-beta-D-glucopyranoside (11-epi-mogroside VI, Compound 14a)¹³C NMR spectrum.

FIG. 44 shows a typical LC-HR-MS spectrum of (1S,4S,9 β,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-ring opened cholest-5-en-24-yl 2-O- β -D-glucopyranosyl- β -D-glucopyranoside (11-deoxymogroside IV, Compound 15 a).

FIG. 45 shows (1S,4S, 9. beta., 24R) -1- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl]Oxy } -25-hydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 2-O-beta-D-glucopyranosylExemplary glycoside (11-deoxymogroside IV, Compound 15a)¹H NMR spectrum.

FIG. 46 shows (1S,4S, 9. beta., 24R) -1- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl]Typical of oxy } -25-hydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-ring-opened cholest-5-en-24-yl 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoside (11-deoxymogroside IV, Compound 15a)¹³C NMR spectrum.

Detailed Description

In the following description, reference is made to specific embodiments which may be practiced, and which are shown by way of illustration. These embodiments are described in detail to enable those skilled in the art to practice the invention described herein, and it is to be understood that other embodiments may be utilized and that logical changes may be made without departing from the scope of the aspects set forth herein. The following description of example embodiments is, therefore, not to be taken in a limiting sense, and the scope of various aspects set forth herein is defined by the appended claims.

The present disclosure provides high intensity sweeteners, sweetness modifiers, and sweetness enhancers comprising mogroside compounds disclosed herein. In some embodiments, the mogroside compounds disclosed herein are obtained from an extract of the fruit of luo han guo (Siraitia grosvenori). In other embodiments, the mogroside compounds disclosed herein are synthesized by enzymatic methods. In some embodiments, these mogroside compounds are used as ingredients to create, enhance, improve and modify the sweetness of flavored products and edible products or as taste modifiers.

The present disclosure also provides a sweetening composition and a flavored article comprising the sweetening composition, wherein the composition comprises a mogroside compound disclosed herein. In some embodiments, the mogroside compound is present in an amount to produce, enhance or improve a sweet taste effect. In some embodiments, the flavored article comprises a food substrate, a food substance, or an edible product.

Mogroside compound

In a first form, the present disclosure provides a compound, wherein the compound is a compound of formula (I):

or a salt thereof, in the form of any one of its stereoisomers or a mixture thereof; wherein R is₁And R₂Independently an-OH group or a sugar moiety, wherein the sugar moiety is a monosaccharide or oligosaccharide; wherein the monosaccharide or monosaccharide unit of the oligosaccharide is selected from: glucose, rhamnose, galactose, xylose, fructose, mannose, tagatose, sorbose, ribose, arabinose, xylulose, ribulose, 6-deoxyglucose, 6-deoxygalactose, 6-deoxymannose, 2-deoxyribose, hamamelose, glucuronic acid, and any combination thereof; wherein the oligosaccharide consists of 2 to 5 monosaccharide units; wherein R is₃Is an-OH group or is combined with a hydrogen atom attached to the same carbon atom to form an oxo group (═ O); wherein R is₄、R₅And R₈Independently a hydrogen atom, -OH group, or combine with a hydrogen atom attached to the same carbon atom to form an oxo group; wherein R is₆Is a hydrogen atom or an-OH group; wherein R is₇Is a hydrogen atom, -an OH group or a sugar moiety, wherein the sugar moiety is a monosaccharide or oligosaccharide; wherein the monosaccharide or monosaccharide unit of the oligosaccharide is selected from: glucose, rhamnose, galactose, xylose, fructose, mannose, tagatose, sorbose, ribose, arabinose, xylulose, ribulose, 6-deoxyglucose, 6-deoxygalactose, 6-deoxymannose, 2-deoxyribose, hamamelose, glucuronic acid, and any combination thereof; wherein the oligosaccharide consists of 2 to 5 monosaccharide units.

In some embodiments thereof, R₄、R₅、R₆、R₇And R₈Is a hydrogen atom and the other is not a hydrogen atom. In some other embodiments thereof, the compound of formula (I) is not 22-hydroxybryodin, 7-oxomogroside IIe, 7-oxomogroside IIIe, 7-oxomogroside III, 7-oxomogroside IV, 7-oxomogroside V, as described in PCT publication No. WO 2017/075257The compound 25, 20-hydroxy-11-oxomogroside Ia 1.

Note that various nomenclature may be used to describe the mogroside compound. For example, "7-oxo-mogroside IIe" refers to a compound that is linked to "7-oxo-mogroside II E" or "7-oxo-mogroside II_E"and the like. Therefore, lower case letters may be used in the following cases: more typically, the space is followed by capital letters or capital letters in the form of subscripts.

In a second form, the present disclosure provides a compound, wherein the compound is of formula (II):

or a salt thereof, in the form of any one of its stereoisomers or a mixture thereof; wherein R is₁And R₂independently-OH or a sugar moiety, wherein the sugar moiety is a monosaccharide or oligosaccharide; wherein the monosaccharide or monosaccharide unit of the oligosaccharide is selected from: glucose, rhamnose, galactose, xylose, fructose, mannose, tagatose, sorbose, ribose, arabinose, xylulose, ribulose, 6-deoxyglucose, 6-deoxygalactose, 6-deoxymannose, 2-deoxyribose, hamamelose and glucuronic acid; wherein the oligosaccharide consists of 2 to 5 monosaccharide units; wherein R is₃And R₄independently-OH, or combine with a hydrogen atom attached to the same carbon atom to form an oxo (═ O) group. In some embodiments thereof, the compound of formula (II) is not 22-hydroxybryodin.

In a third form, the present disclosure provides a compound, wherein the compound is of formula (III):

or a salt thereof, in the form of any one of its stereoisomers or a mixture thereof; wherein R is₁And R₂Independently an-OH group or a sugar moiety, wherein the sugar moiety is a monosaccharide or oligosaccharide; whereinThe monosaccharide or monosaccharide unit of the oligosaccharide is selected from: glucose, rhamnose, galactose, xylose, fructose, mannose, tagatose, sorbose, ribose, arabinose, xylulose, ribulose, 6-deoxyglucose, 6-deoxygalactose, 6-deoxymannose, 2-deoxyribose, hamamelose and glucuronic acid; wherein the oligosaccharide consists of 2 to 5 monosaccharide units; wherein R is₃And R₈Independently an-OH group, or combine with a hydrogen atom attached to the same carbon atom to form an oxo (═ O) group. In some embodiments thereof, the compound of formula (III) is not 7-oxomogroside IIe, 7-oxomogroside IIIe, 7-oxomogroside III, 7-oxomogroside IV, 7-oxomogroside V, or compound 25 described in PCT publication No. WO 2017/075257.

In a fourth form, the present disclosure provides a compound, wherein the compound is a compound of formula (IV):

or a salt thereof, in the form of any one of its stereoisomers or a mixture thereof; wherein R is₁And R₂Independently an-OH group or a sugar moiety, wherein the sugar moiety is a monosaccharide or oligosaccharide; wherein the monosaccharide or monosaccharide unit of the oligosaccharide is selected from: glucose, rhamnose, galactose, xylose, fructose, mannose, tagatose, sorbose, ribose, arabinose, xylulose, ribulose, 6-deoxyglucose, 6-deoxygalactose, 6-deoxymannose, 2-deoxyribose, hamamelose and glucuronic acid; wherein the oligosaccharide consists of 2 to 5 monosaccharide units; wherein R is₃And R₅Independently an-OH group, or combine with a hydrogen atom attached to the same carbon to form an oxo (═ O) group.

In a fifth form, the present disclosure provides a compound, wherein the compound is a compound of formula (V):

or a salt thereof, in the form of any one of its stereoisomers or a mixture thereof; wherein R is₁And R₂Independently an-OH group or a sugar moiety, wherein the sugar moiety is a monosaccharide or oligosaccharide; wherein the monosaccharide or monosaccharide unit of the oligosaccharide is selected from: glucose, rhamnose, galactose, xylose, fructose, mannose, tagatose, sorbose, ribose, arabinose, xylulose, ribulose, 6-deoxyglucose, 6-deoxygalactose, 6-deoxymannose, 2-deoxyribose, hamamelose and glucuronic acid; wherein the oligosaccharide consists of 2 to 5 monosaccharide units; wherein R is₃Is an-OH group or is combined with a hydrogen atom attached to the same carbon atom to form an oxo (═ O) group. In some embodiments thereof, the compound of formula (V) is not 20-hydroxy-11-oxomogroside Ia 1.

In a sixth form, the present disclosure provides a compound, wherein the compound is of formula (VI):

or a salt thereof, in the form of any one of its stereoisomers or a mixture thereof; wherein R is₇And R₂Independently an-OH group or a sugar moiety, wherein the sugar moiety is a monosaccharide or oligosaccharide; wherein the monosaccharide or monosaccharide unit of the oligosaccharide is selected from: glucose, rhamnose, galactose, xylose, fructose, mannose, tagatose, sorbose, ribose, arabinose, xylulose, ribulose, 6-deoxyglucose, 6-deoxygalactose, 6-deoxymannose, 2-deoxyribose, hamamelose and glucuronic acid; wherein the oligosaccharide consists of 2 to 5 monosaccharide units; wherein R is₃Is an-OH group or is combined with a hydrogen atom attached to the same carbon atom to form an oxo (═ O) group.

Any of the foregoing six forms of compounds, including any embodiment thereof, may also be referred to herein as a "mogroside compound".

In some embodiments of any of the foregoing modalities, the monosaccharide unit of the monosaccharide or oligosaccharide is selected from: glucose, rhamnose, galactose and any combination thereof. In some other embodiments, the monosaccharide or monosaccharide unit of the oligosaccharide is selected from: glucose, rhamnose and any combination thereof.

In some embodiments of any of the foregoing modalities, the oligosaccharide is selected from: glucosyl- (1 → 2) -glucose, glucosyl- (1 → 3) -glucose, glucosyl- (1 → 4) -glucose, glucosyl- (1 → 6) -glucose, glucosyl- (1 → 3) - [ glucosyl- (1 → 2) ] -glucose, glucosyl- (1 → 4) - [ glucosyl- (1 → 2) ] -glucose, glucosyl- (1 → 6) - [ glucosyl- (1 → 2) ] -glucose, glucosyl- (1 → 2) -glucose, glucosyl- (1 → 3) -glucosyl- (1 → 2) -glucose, glucosyl- (1 → 4) -glucosyl- (1 → 2) -glucose, glucosyl- (1 → 6) -glucosyl- (1 → 2) -glucose, glucosyl- (1 → 2) -glucosyl- (1 → 4) -glucose, glucosyl- (1 → 3) -glucosyl- (1 → 4) -glucose, glucosyl- (1 → 4) -glucose, glucosyl- (1 → 6) -glucosyl- (1 → 4) -glucose, glucosyl- (1 → 2) -glucosyl- (1 → 6) -glucose, glucosyl- (1 → 3) -glucosyl- (1 → 6) -glucose, glucosyl- (1 → 4) -glucosyl- (1 → 6) -glucose, glucosyl- (1 → 6) -glucose, glucosyl- (1 → 2) -glucosyl- (1 → 6) - [ glucosyl- (1 → 2) ] -glucose, glucosyl- (1 → 3) -glucosyl- (1 → 6) - [ glucosyl- (1 → 2) ] -glucose, glucosyl- (1 → 4) -glucosyl- (1 → 6) - [ glucosyl- (1 → 2) ] -glucose, glucosyl- (1 → 6) - [ glucosyl- (1 → 2) -glucosyl- (1 → 2) ] -glucose, glucosyl- (1 → 6) - [ glucosyl- (1 → 3) -glucosyl- (1 → 2) ] -glucose, glucosyl- (1 → 6) - [ glucosyl- (1 → 4) -glucosyl- (1 → 2) ] -glucose, and glucosyl- (1 → 6) - [ glucosyl- (1 → 6) -glucosyl- (1 → 2) ] -glucose.

In some embodiments of any of the foregoing modalities, the oligosaccharide is selected from: glucosyl- (1 → 2) -glucose, glucosyl- (1 → 4) -glucose, glucosyl- (1 → 6) -glucose, and glucosyl- (1 → 6) - [ glucosyl- (1 → 2) ] -glucose.

In some embodiments of the first form, the compound of formula (I) is selected from: 1- [ (6-O-hexopyranosyl) oxy ] -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O-hexopyranosyl-hexopyranoside (Compound 1), 1- (hexopyranosyl-oxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O-hexopyranosyl-hexopyranoside (Compound 2), 24- [ (6-O-hexopyranosyl) oxy ] -11,22, 25-Trihydroxyl-9, 10, 14-trimethyl-4, 9-Ring-9, 10-Ring-opened cholest-5-en-1-yl 4-O-hexopyranosyl-hexylpyranoside (Compound 3), 1- [ (6-O-hexopyranosyl-hexylpyranosyl) oxy ] -7,11, 25-Trihydroxyl-9, 10, 14-trimethyl-4, 9-Ring-9, 10-Ring-opened cholest-5-en-24-yl-hexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranoside (Compound 4), 1- [ (6-O-hexopyranosyl-hexylpyranosyl) oxy ] -25-hydroxy-9- (hydroxymethyl) -10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-24-ylhexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranosyl (Compound 5), 9-formyl-1- [ (6-O-hexopyranosyl) oxy ] -25-hydroxy-10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-24-ylhexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexylpyranoside (Compound 6), 1- [ (6-O-hexopyranosyl) oxy ] -11,20, 25-Trihydroxyl-9, 10, 14-trimethyl-4, 9-Ring-9, 10-Ring-opened cholest-5-en-24-ylhexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexylpyranoside (Compound 7), 1- (hexopyranosyloxy) -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-Ring-9, 10-Ring-opened cholest-5-en-24-yl 6-O-hexopyranosylhexopyranosyl-pyranoside (Compound 8), 24- [ (6-O-hexopyranosylhexopyranosyl-pyranosyl) oxy ] -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-1-ylhexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranoside (Compound 9), and (24- { [ hexopyranosyl- (1 → 6) hexopyranosyl ] oxy } -1, 25-dihydroxy-9, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-10-yl) methylhexapyranosyl- (1 → 6) - [ hexopyranosyl- (1 → 4) hexopyranosyl- (1 → 2) ] hexopyranoside (Compound 10), in the form of any one of its stereoisomers or a mixture thereof.

In some embodiments of the first form, the compound of formula (I) is selected from: (1S,4R, 9. beta., 11. alpha., 24R) -1- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl ] oxy } -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside (22-hydroxy-mogroside IVa, Compound 1a), (1S,4R, 9. beta., 11. alpha., 24R) -1- (. beta. -D-glucopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy mogroside III, Compound 2a), (1S,4R,9 β,11 β,24R) -1- (β -D-glucopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-11-epi-mogroside III, compound 2b), (1S,4R,9 β,11 α,24R) -24- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-1-yl 4-O- β -D-glucopyranosyl glucoside (22-hydroxy-isomogroside IVa, compound 3a), (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -7,11, 25-Trihydroxyl-9, 10, 14-trimethyl-4, 9-Ring-9, 10-Ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- ((1 → 6) ] - β -D-glucopyranoside (7-hydroxy-mogroside V, Compound 4a), (1S,4R,9 β,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-9- (hydroxymethyl) -10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (19-hydroxy-11-oxomogroside V, Compound 5a), (1S,4R,9 β,24R) -9-formyl-1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → f 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (19-formyl-11-oxo-mogroside V, Compound 6a), (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,20, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (20-hydroxy-mogroside V, Compound 6a) V, Compound 7a), (1S,4R,9 β,24R) -1- (. beta. -D-glucopyranosyloxy) -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-ring-9, 10-ring-opening cholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (20-hydroxy-11-oxomogroside III, Compound 8a), (1S,4R,9 β,24R) -24- { [6-O- (. beta. -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-cyclo-9, 10-ring-opened cholest-5-en-1-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (compound 9a), and [ (1S,4R,9 β,10R,24R) -24- { [ β -D-glucopyranosyl- (1 → 6) - β -D-glucopyranosyl ] oxy } -1, 25-dihydroxy-9, 14-dimethyl-11-oxo-4, 9-Cyclo-9, 10-Ring-opened cholest-5-en-10-yl ] methyl β -D-glucopyranosyl- (1 → 6) - [ β -D-glucopyranosyl- (1 → 4) - β -D-glucopyranosyl- (1 → 2) ] - β -D-glucopyranoside (Compound 10 a).

In some embodiments of any of the foregoing forms, the mogroside compound is selected from: 1- [ (6-O-hexopyranosyl) oxy ] -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-ylhexopyranosyl- (1 → 6) - [ hexopyranosyl- (1 → 4) hexopyranosyl- (1 → 2) ] hexopyranoside (Compound 12), 1- [ (6-O-hexopyranosyl) oxy ] -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-ylhexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranosyl-24-ylhexopyranosyl Glycoside (Compound 13), 1- { [ hexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-ylhexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranosyl (Compound 14), and 1- [ (6-O-hexopyranosyl) oxy ] -25-hydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 2-O-hexopyranosyl-hexopyranoside (Compound 15), in the form of any of its stereoisomers or a mixture thereof.

In some embodiments of any of the foregoing forms, the mogroside compound is selected from: (1S,4R, 9. beta., 11. alpha., 24R) -1- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-ring-opening cholest-5-en-24-yl beta-D-glucopyranosyl- (1 → 6) - [ beta-D-glucopyranosyl- (1 → 4) -beta-D-glucopyranosyl- (1 → 2) ] -beta-D-glucopyranoside (Compound 12a), (1S,4R, 9. beta., 11. alpha., 24R) -1- { [6-O- (beta-D-glucopyranosyl) -beta-D-glucopyranosyl Glucosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-ring-opening cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (compound 13a), (1S,4R,9 β,11 β,24R) -1- { [ β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (11-epi-mogroside VI, Compound 14a), and (1S,4S,9 β,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 2-O- β -D- Glucopyranosyl- β -D-glucopyranoside (11-deoxymogroside IV, Compound 15 a).

In a second form of the embodiment, the mogroside compound is a compound of the formula:

also referred to herein as 1- [ (6-O-hexopyranosyl) oxy ] -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O-hexopyranosyl-hexopyranoside (Compound 1).

In another embodiment, the mogroside compound is a compound of the formula:

also referred to herein as (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-mogroside IVa, compound 1 a).

In another embodiment, the mogroside compound is a compound of the formula:

also referred to herein as 1- (hexopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O-hexopyranosylhexopyranoside (Compound 2).

In another embodiment, the mogroside compound is a compound of the formula:

also referred to herein as (1S,4R,9 β,11 α,24R) -1- (β -D-glucopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-mogroside III, compound 2 a).

In another embodiment, the mogroside compound is a compound of the formula:

also referred to herein as (1S,4R,9 β,11 β,24R) -1- (β -D-glucopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-11-epi-mogroside III, compound 2 b).

In some embodiments, the mogroside compound is a compound of the formula:

also referred to herein as 24- [ (6-O-hexopyranosyl) oxy ] -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-1-yl 4-O-hexopyranosyl-hexopyranoside (Compound 3).

In another embodiment, the mogroside compound is a compound of the formula:

referred to herein as (1S,4R,9 β,11 α,24R) -24- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-1-yl 4-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-isomogroside IVa, compound 3 a).

In some embodiments, the mogroside compound is a compound of the formula:

also referred to herein as 1- [ (6-O-hexopyranosyl) oxy ] -7,11, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl-hexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranoside (Compound 4).

In another embodiment, the mogroside compound is a compound of the formula:

also referred to herein as (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -7,11, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (7-hydroxy-mogroside V, Compound 4 a).

In some embodiments, the mogroside compound is a compound of the formula:

also referred to herein as 1- [ (6-O-hexopyranosyl) oxy ] -25-hydroxy-9- (hydroxymethyl) -10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-24-yl-hexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranoside (Compound 5).

In another embodiment, the mogroside compound is a compound of the formula:

also referred to herein as (1S,4R,9 β,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-9- (hydroxymethyl) -10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (19-hydroxy-11-oxomogroside V, Compound 5 a).

In some embodiments, the mogroside compound is a compound of the formula:

also referred to herein as 9-formyl-1- [ (6-O-hexopyranosyl) oxy ] -25-hydroxy-10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-24-yl-hexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranoside (Compound 6).

In another embodiment, the mogroside compound is a compound of the formula:

also referred to herein as (1S,4R,9 β,24R) -9-formyl-1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (19-formyl-11-oxomogroside V, Compound 6 a).

In some embodiments, the mogroside compound is a compound of the formula:

also referred to herein as 1- [ (6-O-hexopyranosyl) oxy ] -11,20, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl-hexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranoside (Compound 7).

In another embodiment, the mogroside compound is a compound of the formula:

also referred to herein as (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,20, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (20-hydroxy-mogroside V, Compound 7 a).

In some embodiments, the mogroside compound is a compound of the formula:

also referred to herein as 1- (hexopyranosyloxy) -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O-hexopyranosylhexopyranoside (Compound 8).

In another embodiment, the mogroside compound is a compound of the formula:

also referred to herein as (1S,4R,9 β,24R) -1- (β -D-glucopyranosyloxy) -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-ring-9, 10-ring-opening cholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (20-hydroxy-11-oxo mogroside III, compound 8 a).

In some embodiments. The mogroside compound is a compound of the formula:

also referred to herein as 24- [ (6-O-hexopyranosyl) oxy ] -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-1-ylhexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranoside (Compound 9).

In another embodiment, the mogroside compound is a compound of the formula:

also referred to herein as (1S,4R,9 β,24R) -24- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-ring-9, 10-ring-opened cholest-5-en-1-yl β -D-glucopyranosyl- (1 → 2) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (Compound 9 a).

In some embodiments, the mogroside compound is a compound of the formula:

also referred to herein as (24- { [ hexopyranosyl- (1 → 6) hexopyranosyl ] -oxy) -1, 25-dihydroxy-9, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-10-yl) methylhhexopyranosyl- (1 → 6) - [ hexopyranosyl- (1 → 4) hexopyranosyl- (1 → 2) ] hexopyranoside (compound 10).

In another embodiment, the mogroside compound is a compound of the formula:

also referred to herein as [ (1S,4R,9 β,10R,24R) -24- { [ β -D-glucopyranosyl- (1 → 6) - β -D-glucopyranosyl ] oxy } -1, 25-dihydroxy-9, 14-dimethyl-11-oxo-4, 9-ring-9, 10-ring-opened cholest-5-en-10-yl ] methyl β -D-glucopyranosyl- (1 → 6) - [ β -D-glucopyranosyl- (1 → 4) - β -D-glucopyranosyl- (1 → 2) ] - β -D-glucopyranoside (compound 10 a).

In one embodiment, the mogroside compound is: 1- [ (6-O-hexopyranosyl) oxy ] -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-ylhexopyranosyl- (1 → 6) - [ hexopyranosyl- (1 → 4) hexopyranosyl- (1 → 2) ] hexopyranoside (Compound 12), 1- [ (6-O-hexopyranosyl) oxy ] -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-ylhexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] Hexapyranoside (compound 13), 1- { [ hexapyranosyl- (1 → 2) - [ hexapyranosyl- (1 → 6) ] hexapyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-seco-chol-5-en-24-ylhexapyranosyl- (1 → 2) - [ hexapyranosyl- (1 → 6) ] hexapyranosyl (compound 14), and 1- [ (6-O-hexapyranosyl) oxy ] -25-hydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-seco-5-en-24-yl 2-O-hexapyranosyl-hexapyranoside (compound 15), in the form of any of its stereoisomers or a mixture thereof. In some other such embodiments, the mogroside compound is not compound 30 of PCT publication No. WO 2017/075257, mogroside VI, a compound of CAS No. 2096516-62-8, or a compound of CAS No. 2096516-27-5.

In some embodiments, the mogroside compound is a compound of the formula:

also referred to herein as 1- [ (6-O-hexopyranosyl) oxy ] -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl-hexopyranosyl- (1 → 6) - [ hexopyranosyl- (1 → 4) hexopyranosyl- (1 → 2) ] hexopyranoside (Compound 12).

In another embodiment, the mogroside compound is a compound of the formula:

also referred to herein as (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 6) - [ β -D-glucopyranosyl- (1 → 4) - β -D-glucopyranosyl- (1 → 2) ] - β -D-glucopyranoside (Compound 12 a).

In some embodiments, the mogroside compound is a compound of the formula:

also referred to herein as 1- [ (6-O-hexopyranosyl) oxy ] -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl-hexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranoside (Compound 13).

In another embodiment, the mogroside compound is a compound of the formula:

also referred to herein as (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (Compound 13 a).

In some embodiments, the mogroside compound is a compound of the formula:

also referred to herein as 1- { [ hexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranosyl ] -oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-ylhexopyranosyl- (1 → 2) - [ hexopyranosyl- (1 → 6) ] hexopyranoside (compound 14).

In another embodiment, the mogroside compound is a compound of the formula:

also referred to herein as (1S,4R,9 β,11 β,24R) -1- { [ β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (11-epi-mogroside VI, compound 14 a).

In some embodiments, the mogroside compound is a compound of the formula:

also referred to herein as 1- [ (6-O-hexopyranosyl) oxy ] -25-hydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 2-O-hexopyranosyl-hexopyranoside (Compound 15).

In another embodiment, the mogroside compound is a compound of the formula:

also referred to herein as (1S,4S,9 β,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-ring-opened cholest-5-en-24-yl 2-O- β -D-glucopyranosyl- β -D-glucopyranoside (11-deoxymogroside IV, Compound 15 a).

Extracting at least one compound from Monk fruit (silatia grosvenori) according to some forms provided herein

Referring to examples 1 to 15, at least one compound according to the morphology proposed herein may be obtained from momordica grosvenori (Siraitia grosvenor) extract. In some embodiments, the luo han guo extract may be first dissolved in a solvent, such as water, and the resulting solution applied to an adsorbent resin.

In some embodiments, the solvent is water. In one embodiment, 60kg of Lo Han Guo extract is dissolved in 150L of deionized water. Although any extract of Lo Han Guo is suitable for use in the extraction methods disclosed herein, in one embodiment, the extract of Lo Han Guo is obtained from Gui Lin Layn Natural Ingredients Corp. In some forms, the Lo Han Guo extract comprises 3.5% w/w mogroside V.

In some embodiments, the adsorbent resin is an XDA macroporous resin.

In some embodiments, after the solution is applied to the adsorbent resin, the resin is first washed with water, then with a 5% ethanol solution, and then with a 95% ethanol solution. In some embodiments, the final eluate using a 95% ethanol solution is collected and comprises at least one compound according to the morphology set forth herein.

In some embodiments, the collected eluate is applied to an HPLC column. In some embodiments, the HPLC column is a C18 flash chromatography column. In some embodiments, the C18 flash chromatography column is a Daiso ODS, 40-70 μm, 100X 490mm column. In some embodiments, after applying the collected eluate, the C18 flash chromatography column is eluted with water followed by 10%, 20%, 25%, 30%, 40%, 50% aqueous ACN and 100% ACN at a flow rate of 70 mL/min.

In some embodiments, 16 fractions (fractions 35-50) can be collected using a Daiso ODS, 40-70 μm, 100X 490mm column.

In one embodiment, the fraction comprising at least one compound according to the morphology set forth herein is further purified by first applying the fraction to a C18 flash chromatography column, and then eluting the column with ACN. In some embodiments, the C18 flash chromatography column is a C18 flash chromatography column (e.g., Daiso ODS, 40 ~ 70 μm, 100 x 490 mm). In some embodiments, the column is eluted with a 26% aqueous solution of ACN at a flow rate of 70 mL/min. Next, in some embodiments, the eluate is applied to a Sephadex LH-20 column (e.g., 55 x 1500mm) and eluted with ACN. In some embodiments, the column is eluted using an 18% aqueous solution of ACN at a flow rate of 0.3 to 1.5 mL/min. In some embodiments, the eluate from the Sephadex LH-20 column is applied to a preparative HPLC column (e.g., YMC ODS, 5 μm, 10X 250mm) and eluted with ACN to purify at least one compound according to the morphology presented herein. In some embodiments, the column is eluted using a 14-21% aqueous solution of ACN at a flow rate of 4.5 mL/min.

Referring to fig. 2-4, in some embodiments, at least one compound according to the morphology presented herein is (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-mogroside IVa, compound 1 a).

Referring to fig. 5-7, in some embodiments, at least one compound according to the modalities set forth herein is (1S,4R,9 β,11 α,24R) -1- (β -D-glucopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-mogroside III, compound 2 a).

Referring to fig. 8-10, in some embodiments, at least one compound according to the modalities set forth herein is (1S,4R,9 β,11 β,24R) -1- (β -D-glucopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-11-epi-mogroside III, compound 2 b).

Referring to fig. 11-13, in some embodiments, at least one compound according to the morphology presented herein is (1S,4R,9 β,11 α,24R) -24- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-1-yl 4-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-isomogroside IVa, compound 3 a).

Referring to fig. 14-16, in some embodiments, at least one compound according to the morphology proposed herein is (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -7,11, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (7-hydroxy-mogroside V, compound 4 a).

Referring to fig. 17-19, in some embodiments, at least one compound according to the modalities set forth herein is (1S,4R,9 β,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-9- (hydroxymethyl) -10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (19-hydroxy-11-oxomogroside V, compound 5 a).

Referring to fig. 22-22, in some embodiments, at least one compound according to the modalities set forth herein is (1S,4R,9 β,24R) -9-formyl-1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (19-formyl-11-oxomogroside V, compound 6 a).

Referring to fig. 23-25, in some embodiments, at least one compound according to the morphology proposed herein is (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,20, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (20-hydroxy-mogroside V, compound 7 a).

Referring to fig. 26-28, in some embodiments, at least one compound according to the modalities set forth herein is (1S,4R,9 β,24R) -1- (β -D-glucopyranosyloxy) -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (20-hydroxy-11-oxomogroside III, compound 8 a).

Referring to fig. 29 to fig. 31, in some embodiments, at least one compound according to the modalities set forth herein is (1S,4R,9 β,24R) -24- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-ring-9, 10-ring-opened cholest-5-en-1-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (compound 9 a).

Referring to fig. 32-34, in some embodiments, at least one compound according to the modalities set forth herein is [ (1S,4R,9 β,10R,24R) -24- { [ β -D-glucopyranosyl- (1 → 6) - β -D-glucopyranosyl ] oxy } -1, 25-dihydroxy-9, 14-dimethyl-11-oxo-4, 9-ring-9, 10-ring-opened cholest-5-en-10-yl ] methyl β -D-glucopyranosyl- (1 → 6) - [ β -D-glucopyranosyl- (1 → 4) - β -D-glucopyranosyl- (1 → 2) ] - β -D-glucopyranosyl [ (1S,4R, 9R) -24- { [ β -D-glucopyranosyl- (1 → 6) } -D-glucopyranosyl [ -beta-D-glucopyranosyl [ ] Compound 10 a).

Referring to fig. 35-37, in some embodiments, at least one compound according to the morphology proposed herein is (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 6) - [ β -D-glucopyranosyl- (1 → 4) - β -D-glucopyranosyl- (1 → 2) ] - β -D-glucopyranoside (compound 12 a).

Referring to fig. 38-40, in some embodiments, at least one compound according to the morphology proposed herein is (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (compound 13 a).

Referring to figures 41 to 43, in some embodiments, at least one compound according to the modalities set forth herein is (1S,4R,9 β,11 β,24R) -1- { [ β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (11-epi-mogroside VI, compound 14 a).

Referring to figures 44 to 46, in some embodiments, at least one compound according to the modalities set forth herein is (1S,4S,9 β,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl 2-O- β -D-glucopyranosyl- β -D-glucopyranoside (11-deoxymogroside IV, compound 15 a).

Sweetener and/or sweetness enhancer

At least one compound according to some of the modalities presented herein may be used as a sweetness enhancer, flavor enhancer, taste masking agent, and/or sweetener in a variety of flavored articles.

In certain forms, the present disclosure provides a method of enhancing sweetness of a flavored article, the method comprising: providing a flavored article and incorporating a mogroside compound in any of the foregoing forms or embodiments thereof into a flavored article, such as a flavored food or beverage product. In some such embodiments, the compound is introduced in an amount effective to enhance the sweetness of the flavored article.

In certain related forms, the present disclosure provides the use of a mogroside compound of any one of the foregoing forms or embodiments thereof for enhancing the sweetness of a flavored article, such as a flavored food or beverage product.

In some embodiments of the foregoing methods and uses, the mogroside compound can be used at any suitable concentration. In some embodiments, the concentration of mogroside compounds in the flavored article is from 1ppm to 1000ppm, or from 5ppm to 1000ppm, or from 10ppm to 750ppm, or from 10ppm to 500ppm, or from 10ppm to 400ppm, or from 10ppm to 300 ppm. In some other embodiments, the concentration of mogroside compounds in the flavored article is from 1ppm to 50ppm, or from 1ppm to 40ppm, or from 1ppm to 30ppm, or from 5ppm to 50ppm, or from 5ppm to 40ppm, or from 5ppm to 30 ppm. In some other embodiments, the concentration of mogroside compounds in the flavored article is 1ppm, 5ppm, 10ppm, 20ppm, 30ppm, 40ppm, 50ppm, 60ppm, 70ppm, 80ppm, 90ppm, 100ppm, 150ppm, 200ppm, 250ppm, 300ppm, 350ppm, 400ppm, 450ppm, 500ppm, 600ppm, 700ppm, 800ppm, 900ppm, 1000 ppm.

In certain forms, the present disclosure provides compositions, such as edible compositions, comprising a mogroside compound of any one of the foregoing forms or embodiments thereof. In some embodiments thereof, the edible composition comprises a carrier, such as a bulking agent (e.g., erythritol, a rare sugar, a cellulosic material, or any combination thereof) or water. In some related forms, the edible composition is incorporated into or made into a flavored article, such as a flavored food or beverage product.

In some embodiments of the foregoing composition forms, the mogroside compound can be used in the composition at any suitable concentration. In some embodiments, the concentration of mogroside compounds in the edible composition is from 1ppm to 1000ppm, or from 5ppm to 1000ppm, or from 10ppm to 750ppm, or from 10ppm to 500, or from 10ppm to 400ppm, or from 10ppm to 300 ppm. In some other embodiments, the concentration of mogroside compounds in the edible composition is from 1ppm to 50ppm, or from 1ppm to 40ppm, or from 1ppm to 30ppm, or from 5ppm to 50ppm, or from 5ppm to 40ppm, or from 5ppm to 30 ppm. In some other embodiments, the concentration of mogroside compounds in the edible composition is 1ppm, 5ppm, 10ppm, 20ppm, 30ppm, 40ppm, 50ppm, 60ppm, 70ppm, 80ppm, 90ppm, 100. ppm, 150ppm, 200ppm, 250ppm, 300ppm, 350ppm, 400ppm, 450ppm, 500ppm, 600ppm, 700ppm, 800ppm, 900ppm, 1000 ppm.

In certain particular embodiments, the ingestible composition comprises sucrose and a mogroside compound or any edible acceptable salt thereof. In some such embodiments, the introduction of the mogroside compound (or salt) allows one to use less sucrose (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieve the sweetness level of a comparable product using more sucrose. In some embodiments, the concentration of the mogroside compound or an edible acceptable salt thereof is no more than 1000ppm, or no more than 900ppm, or no more than 800ppm, or no more than 700ppm, or no more than 600ppm, or no more than 500ppm, or no more than 400ppm, or no more than 300ppm, or no more than 200ppm, or no more than 100ppm, or no more than 50ppm, or no more than 25ppm, or no more than 10 ppm. Such ingestible compositions may be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the food products specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as soda or the like. The sucrose may be introduced in any suitable form, such as natural syrup (cane syrup) and the like.

In certain particular embodiments, the ingestible composition comprises fructose and a mogroside compound or any edible acceptable salt thereof. In some such embodiments, the introduction of the mogroside compound (or salt) allows one to use less fructose (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieve the sweetness level of a comparable product using more fructose. In some embodiments, the concentration of the mogroside compound or an edible acceptable salt thereof is no more than 1000ppm, or no more than 900ppm, or no more than 800ppm, or no more than 700ppm, or no more than 600ppm, or no more than 500ppm, or no more than 400ppm, or no more than 300ppm, or no more than 200ppm, or no more than 100ppm, or no more than 50ppm, or no more than 25ppm, or no more than 10 ppm. In some embodiments, the ingestible composition is a food product, such as any of the food products specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as soda or the like. Fructose may be supplied in any suitable form, such as natural syrup, high fructose corn syrup, and the like.

In certain particular embodiments, the ingestible composition comprises high fructose corn syrup and a mogroside compound or any edible acceptable salt thereof. In some such embodiments, the introduction of the mogroside compound (or salt) allows one to use less high fructose corn syrup (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieve the sweetness level of a comparable product using more high fructose corn syrup. In some embodiments, the concentration of the mogroside compound or an edible acceptable salt thereof is no more than 1000ppm, or no more than 900ppm, or no more than 800ppm, or no more than 700ppm, or no more than 600ppm, or no more than 500ppm, or no more than 400ppm, or no more than 300ppm, or no more than 200ppm, or no more than 100ppm, or no more than 50ppm, or no more than 25ppm, or no more than 10 ppm. In some embodiments, the ingestible composition is a food product, such as any of the food products specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as soda or the like.

In certain particular embodiments, the ingestible composition comprises glucose (e.g., the alpha or beta forms of D-glucose, or a combination thereof) and a mogroside compound or any edible salt thereof. In some such embodiments, the introduction of the mogroside compound (or salt) allows one to use less glucose (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less), and still achieve the sweetness level of a comparable product using more glucose. In some embodiments, the concentration of the mogroside compound or an edible acceptable salt thereof is no more than 1000ppm, or no more than 900ppm, or no more than 800ppm, or no more than 700ppm, or no more than 600ppm, or no more than 500ppm, or no more than 400ppm, or no more than 300ppm, or no more than 200ppm, or no more than 100ppm, or no more than 50ppm, or no more than 25ppm, or no more than 10 ppm. Such ingestible compositions may be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the food products specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as soda or the like. Glucose may be introduced in any suitable form, such as natural syrups and the like.

In certain particular embodiments, the ingestible composition comprises sucralose and a mogroside compound or any edible acceptable salt thereof. In some such embodiments, the introduction of the mogroside compound (or salt) allows one to use less sucralose (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less), and still achieve the sweetness level of a comparable product using more sucralose. In some embodiments, the concentration of the mogroside compound or an edible acceptable salt thereof is no more than 1000ppm, or no more than 900ppm, or no more than 800ppm, or no more than 700ppm, or no more than 600ppm, or no more than 500ppm, or no more than 400ppm, or no more than 300ppm, or no more than 200ppm, or no more than 100ppm, or no more than 50ppm, or no more than 25ppm, or no more than 10 ppm. Such ingestible compositions may be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the food products specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as soda or the like.

In certain particular embodiments, the ingestible composition comprises a rebaudioside (e.g., rebaudioside a, rebaudioside D, rebaudioside E, rebaudioside M, or any combination thereof) and a mogroside compound or any edible salt thereof. In some such embodiments, the introduction of the mogroside compound (or salt) allows one to use less rebaudioside (e.g., by more than 10%, by more than 20%, by more than 30%, by more than 40%, by more than 50%, by more than 60%, or by more than 70%), and still achieve the sweetness level of a comparable product using more rebaudioside. In some embodiments, the concentration of the mogroside compound or an edible acceptable salt thereof is no more than 1000ppm, or no more than 900ppm, or no more than 800ppm, or no more than 700ppm, or no more than 600ppm, or no more than 500ppm, or no more than 400ppm, or no more than 300ppm, or no more than 200ppm, or no more than 100ppm, or no more than 50ppm, or no more than 25ppm, or no more than 10 ppm. Such ingestible compositions may be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the food products specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as soda or the like.

In certain particular embodiments, the ingestible composition comprises acesulfame potassium and a mogroside compound or any edible acceptable salt thereof. In some such embodiments, the introduction of the mogroside compound (or salt) allows one to use less acesulfame potassium (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieve the sweetness level of a comparable product using more acesulfame potassium. In some embodiments, the concentration of the mogroside compound or an edible acceptable salt thereof is no more than 1000ppm, or no more than 900ppm, or no more than 800ppm, or no more than 700ppm, or no more than 600ppm, or no more than 500ppm, or no more than 400ppm, or no more than 300ppm, or no more than 200ppm, or no more than 100ppm, or no more than 50ppm, or no more than 25ppm, or no more than 10 ppm. Such ingestible compositions may be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the food products specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as soda or the like.

In certain particular embodiments, the ingestible composition comprises a rare sugar and a mogroside compound or any edible acceptable salt thereof. In some such embodiments, the introduction of the mogroside compound (or salt) allows one to use less rare sugars (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less), and still achieve the sweetness level of a comparable product using more rare sugars. In some embodiments, the concentration of the mogroside compound or an edible acceptable salt thereof is no more than 1000ppm, or no more than 900ppm, or no more than 800ppm, or no more than 700ppm, or no more than 600ppm, or no more than 500ppm, or no more than 400ppm, or no more than 300ppm, or no more than 200ppm, or no more than 100ppm, or no more than 50ppm, or no more than 25ppm, or no more than 10 ppm. Such ingestible compositions may be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the food products specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as soda or the like.

In certain particular embodiments, the ingestible composition comprises erythritol and a mogroside compound or any edible acceptable salt thereof. In some such embodiments, the introduction of the mogroside compound (or salt) allows one to use less erythritol (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieve the sweetness level of a comparable product using more erythritol. In some embodiments, the concentration of the mogroside compound or an edible acceptable salt thereof is no more than 1000ppm, or no more than 900ppm, or no more than 800ppm, or no more than 700ppm, or no more than 600ppm, or no more than 500ppm, or no more than 400ppm, or no more than 300ppm, or no more than 200ppm, or no more than 100ppm, or no more than 50ppm, or no more than 25ppm, or no more than 10 ppm. Such ingestible compositions may be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the food products specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as soda or the like.

In certain particular embodiments, the ingestible composition comprises aspartame and a mogroside compound or any edible acceptable salt thereof. In some such embodiments, the introduction of the mogroside compound (or salt) allows one to use less aspartame (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieve the sweetness level of a comparable product using more aspartame. In some embodiments, the concentration of the mogroside compound or an edible acceptable salt thereof is no more than 1000ppm, or no more than 900ppm, or no more than 800ppm, or no more than 700ppm, or no more than 600ppm, or no more than 500ppm, or no more than 400ppm, or no more than 300ppm, or no more than 200ppm, or no more than 100ppm, or no more than 50ppm, or no more than 25ppm, or no more than 10 ppm. Such ingestible compositions may be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the food products specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as soda or the like.

In certain particular embodiments, the ingestible composition comprises a cyclamate (cyclamate) and a mogroside compound, or any edible acceptable salt thereof. In some such embodiments, the introduction of the mogroside compound (or salt) allows one to use less cyclamate (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less), and still achieve the sweetness level of a comparable product using more cyclamate. In some embodiments, the concentration of the mogroside compound or an edible acceptable salt thereof is no more than 1000ppm, or no more than 900ppm, or no more than 800ppm, or no more than 700ppm, or no more than 600ppm, or no more than 500ppm, or no more than 400ppm, or no more than 300ppm, or no more than 200ppm, or no more than 100ppm, or no more than 50ppm, or no more than 25ppm, or no more than 10 ppm. Such ingestible compositions may be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the food products specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as soda or the like.

In certain particular embodiments, the ingestible composition comprises mogrosides (e.g., mogroside III, mogroside IV, mogroside V, siamenoside I, isomogroside V, mogroside IV)_EMogroside III_E11-oxo-mogroside V, the α -1, 6-isomer of siamenoside I, and any combination thereof) and mogroside compounds or any edible salt thereof. In some such embodiments, the introduction of the mogroside compound (or salt) allows one to use less mogroside (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less), and still achieve the sweetness level of a comparable product using more mogroside. In some embodiments, the concentration of the mogroside compound or a food acceptable salt thereof is no more than 1000ppm, or no more than 900ppm, or no more than 800ppm, or no more than 700ppm, or no more than 600ppm, or no more than 500ppm, or no more than 400ppm, or no more than 300ppm, or no more than 200ppm, or no more than 100ppm, or no more than 50ppm, or no more than25ppm, or not more than 10 ppm. Such ingestible compositions may be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the food products specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as soda or the like. Additional mogroside compounds that can be suitably used are described in U.S. patent application publication No. 2017/0119032.

The ingestible composition of any one of the preceding embodiments, in certain embodiments, further comprises one or more additional flavor modifying compounds, such as a sweet taste enhancing compound (e.g., hesperetin, naringenin, glucosylated steviol glycosides, etc.), a bitter taste blocking compound, an umami taste enhancing compound, an acidic or licorice taste reducing compound, a salty taste enhancing compound, a cooling effect enhancing compound, or any combination of the preceding.

Thus, in some embodiments, the ingestible compositions disclosed herein comprise a mogroside compound, or any edible acceptable salt thereof, in combination according to any embodiment or embodiments described above, in combination with one or more other sweet taste enhancing compounds. Such sweetness enhancing compounds include, but are not limited to, naturally derived compounds such as hesperetin, naringenin, glucosylated steviol glycosides, or synthetic compounds such as those described in U.S. patent nos. 8,541,421; 8,815,956, respectively; 9,834,544, respectively; 8,592,592, respectively; 8,877,922, respectively; 9,000,054, respectively; and 9,000,051, and any of the compounds described in U.S. patent application publication No. 2017/0119032. The mogroside compound (or edible salt thereof) may be combined with such other sweetness enhancers in any suitable ratio (w/w) in the range of 1:1000 to 1000:1, or 1:100 to 100:1, or 1:50 to 50:1, or 1:25 to 25:1, or 1:10 to 10:1, e.g., 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 1: 15:1, 1:17, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1 or 25: 1. In some embodiments of any of the preceding embodiments, a mogroside compound (or any edible salt thereof) is combined with a glucosylated steviol glycoside in any of the ratios described above. As used herein, the term "glucosylated steviol glycosides" refers to the products of enzymatically glucosylating natural steviol glycoside compounds. Glycosylation typically occurs through glycosidic linkages, such as alpha-1, 2 linkages, alpha-1, 4 linkages, alpha-1.6 linkages, beta-1, 2 linkages, beta-1, 4 linkages, beta-1, 6 linkages, and the like.

In some further embodiments, the ingestible compositions disclosed herein comprise a mogroside compound, or any edible acceptable salt thereof, in combination according to any embodiment or embodiments described above, in combination with one or more other umami enhancing compounds. Such umami taste enhancing compounds include, but are not limited to, naturally derived compounds such as (E) -3- (3, 4-dimethoxyphenyl) -N- (4-methoxyphenethyl) acrylamide (ericamide), or synthetic compounds such as those described in U.S. patent nos. 8,735,081; 8,124,121, respectively; and 8,968,708. The mogroside compound (or a pharmaceutically acceptable salt thereof) may be combined with such umami enhancing agent in any suitable ratio (w/w) in the range of 1:1000 to 1000:1, or 1:100 to 100:1, or 1:50 to 50:1, or 1:25 to 25:1, or 1:10 to 10:1, e.g., 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 1: 13:1, 1: 15:1, 1:1, 9:1, 10:1, 11:1, 12, 1:1, 1: 15:1, 1: 15:1, 1: 17:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1: 17:1, 1:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1 or 25: 1.

In some further embodiments, the ingestible compositions disclosed herein comprise a mogroside compound, or any edible acceptable salt thereof, in combination according to any embodiment or embodiments described above, in combination with one or more cooling enhancing compounds. Such cooling enhancing compounds include, but are not limited to, naturally derived compounds such as menthol or analogs thereof, or synthetic compounds such as any of the compounds described in U.S. patent nos. 9,394,287 and 10,421,727. The mogroside compound (or a pharmaceutically acceptable salt thereof) may be combined with such umami enhancing agent in any suitable ratio (w/w) in the range of 1:1000 to 1000:1, or 1:100 to 100:1, or 1:50 to 50:1, or 1:25 to 25:1, or 1:10 to 10:1, e.g., 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 1: 13:1, 1: 15:1, 1:1, 9:1, 10:1, 11:1, 12, 1:1, 1: 15:1, 1: 15:1, 1: 17:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1: 17:1, 1:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1 or 25: 1.

In some further embodiments, the ingestible compositions disclosed herein comprise a mogroside compound, or any edible acceptable salt thereof, in combination according to any embodiment or embodiments described above, in combination with one or more bitter blocking compounds. Such bitter blocking compounds include, but are not limited to, naturally derived compounds, such as menthol or analogs thereof, or synthetic compounds, such as those described in U.S. patent nos. 8,076,491; 8,445,692, respectively; and 9,247,759. The mogroside compound (or a pharmaceutically acceptable salt thereof) may be combined with such bitter taste blocker in any suitable ratio (w/w) in the range of 1:1000 to 1000:1, or 1:100 to 100:1, or 1:50 to 50:1, or 1:25 to 25:1, or 1:10 to 10:1, e.g., 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 1: 13:1, 1: 15:1, 1:1, 9:1, 10:1, 11:1, 12, 1:1, 1:1, 1:1, 1:1, 1: 15:1, 1:1, 1: 15:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1: 17:1, 1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1 or 25: 1.

In some other embodiments, the ingestible compositions disclosed herein comprise a mogroside compound, or any edible acceptable salt thereof, in combination according to any embodiment or embodiments described above, in combination with one or more acidity-regulating compounds. The mogroside compound (or a pharmaceutically acceptable salt thereof) may be combined with such acidity-modulating compounds in any suitable ratio (w/w) within the range of 1:1000 to 1000:1, or 1:100 to 100:1, or 1:50 to 50:1, or 1:25 to 25:1, or 1:10 to 10:1, e.g., 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 1: 13:1, 1: 17:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1 or 25: 1.

In some other embodiments, the ingestible compositions disclosed herein comprise a mogroside compound, or any edible acceptable salt thereof, in combination according to any embodiment or embodiments described above, in combination with one or more mouthfeel improving compounds. Such taste modifying compounds include, but are not limited to, tannins, cellulosic materials, bamboo powder, and the like. The mogroside compounds (or edible salts thereof) may be combined with such mouthfeel enhancing agents in any suitable ratio (w/w) within the range of 1:1000 to 1000:1, or 1:100 to 100:1, or 1:50 to 50:1, or 1:25 to 25:1, or 1:10 to 10:1, e.g., 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 1: 13:1, 1: 15:1, 1:17, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1 or 25: 1.

In some further embodiments, the ingestible compositions disclosed herein comprise a mogroside compound, or any edible acceptable salt thereof, in combination according to any embodiment or embodiments described above, in combination with one or more flavor masking compounds. Such flavor masking compounds include, but are not limited to, cellulosic materials, materials extracted from fungi, materials extracted from plants, citric acid, carbonic acid (or carbonates), and the like. The mogroside compounds (or edible salts thereof) may be combined with such mouthfeel enhancing agents in any suitable ratio (w/w) within the range of 1:1000 to 1000:1, or 1:100 to 100:1, or 1:50 to 50:1, or 1:25 to 25:1, or 1:10 to 10:1, e.g., 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:15, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 1: 13:1, 1: 15:1, 1:17, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 1:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1 or 25: 1.

In some of the foregoing embodiments, the edible composition further comprises a food base.

For the purposes of this disclosure, "food base" refers to an edible product, such as a food or beverage. Thus, the flavoured articles provided herein comprise a functional formula, and optionally additional benefit agents, corresponding to a desired edible product, such as a savory cube, and a flavouring effective amount of at least one compound according to the modalities set forth herein.

The compositions and methods provided herein can be used in food or beverage products. When the food product is a granular or powdered food, the dry particles can be easily added by dry blending. Typical food products are selected from the group consisting of instant soups or sauces, breakfast cereals, milk powders, baby foods, powdered beverages, powdered chocolate beverages, spreads, powdered cereal beverages, chewing gums, effervescent tablets, cereal bars and chocolate bars. The powdered food or beverage may be intended for consumption after reconstitution of the product with water, milk and/or fruit juice or another aqueous liquid.

The food product may be selected from the group consisting of a condiment, a baked good, a powdered food, a bread filling, and a fluid dairy product.

Condiments include, but are not limited to, ketchup, mayonnaise, salad dressing, worthler sauce, fruit dressing, chocolate sauce, tomato sauce, chili sauce, and mustard.

Baked goods include, but are not limited to, cakes, biscuits, pastries, breads, donuts, and the like.

Bread fillings include, but are not limited to, low or neutral pH fillings, high, medium or low solids fillings, fruit or milk (pudding or mousse type) based fillings, hot or cold complementary fillings and non-fat to full fat fillings.

Fluid dairy products include, but are not limited to, non-frozen, partially frozen, and frozen fluid dairy products such as milk, ice cream, sorbets, and yogurt. Beverage products include, but are not limited to, carbonated soft drinks including cola, lemon-lime, root beer, citrus maxima ("cooling"), fruit flavored and cream sodas; powdered soft drinks, as well as liquid concentrates such as fountain syrups and fruit juices concentrates (cordials); coffee and coffee-based beverages, coffee substitutes and cereal beverages; tea, including dry blended products and ready-to-drink tea (herbal and tea based); fruit and vegetable juices and fruit juice flavored beverages as well as fruit juice beverages, nectars, concentrates, punch and various fruit drinks ("ads"); carbonated and non-foaming sweet and flavored waters; sports/energy/health drinks; alcoholic beverages plus non-alcoholic and other low-alcoholic products including beer and malt beverages, cider and wine (non-foaming, fortified wine and wine fruit drinks (wine cooler)); other beverages in hot processed (infusion, pasteurization, ultra high temperature, electric heating or commercial aseptic sterilization) and hot-fill packages; and cold-filled products made by filtration or other freshness-preserving techniques.

The nature and type of the food or beverage ingredients do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the nature of the product.

The proportions in which at least one compound according to the modalities set forth herein can be incorporated into the various aforementioned articles or compositions vary within a wide range of values. These values, when the compounds according to the invention are mixed with flavouring co-ingredients, solvents or additives commonly used in the art, depend on the nature of the article to be flavoured and on the desired organoleptic effect as well as on the nature of the co-ingredients in a given base.

In the case of the flavouring composition, typical concentrations are from about 0.0001 wt% to 1 wt%, or even higher levels, based on the weight of the consumer product into which it is incorporated, of at least one compound according to the morphology set forth herein. When at least one compound according to the morphology proposed herein is incorporated into a flavoured article, concentrations lower than these may be used, for example in amounts of 0.001% to 0.5% by weight, the percentages being relative to the weight of the article.

Examples

Example 1: purification of (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-secocholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-mogroside IVa, Compound 1a) from extracts of Lo Han Guo

60kg of Lo Han Guo (Siraitia grosvenor rriii) extract from Gui Lin Layn Natural Ingredients Corp. (pale yellow liquid, 3.5% mogroside V) was dissolved in 150L of deionized water and loaded onto XDA macroporous resin. The resin was then eluted with water, 5% aqueous EtOH and 95% aqueous EtOH and the final fraction enriched in mogroside was collected as Frac 1(5.0 kg). Frac 1 was further separated on a C18 flash column (Daiso ODS, 40-70 μm, 100X 490 mm). After the sample was loaded, the column was eluted with water, 10%, 20%, 25%, 30%, 40%, 50% ACN aqueous solution and 100% ACN at a flow rate of 70mL/min, and 16 fractions were collected (Frac. 35-50). Frac.45(412g) was further purified by passing through a C18 flash column (Daiso ODS, 40-70 μm, 100X 490mm, 26% aqueous ACN, 70mL/min), Sephadex LH-20 column (55X 1500mm, 18% aqueous ACN, 0.3 to 1.5mL/min) and preparative HPLC (YMC ODS, 5 μm, 10X 250mm, 14-21% aqueous ACN, 4.5mL/min) to give (1S,4R,9 β,11 α,24R) -1- { [6-O- (. beta. -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl 6-O-. beta. -D-pyranyl- β -D-pyranyl-p-E-p-n-p-n-p-O-n-p-n-p-O-p-O-n-p-n-p-O-p-O-p-n-O-n-p-O-n-O-p-O-n-O-n-p-O-n-p-O-n-p-n-p-n-O-n-p-n-p-n Glucopyranoside (22-hydroxy-mogroside IVa, Compound 1a) (50mg, purity: 97%).

Referring to the mass spectra and NMR analyses shown in fig. 2 to 4, the following structures were derived:

when a sample of the purified compound was tasted at a concentration of 250ppm, no taste was perceived.

Example 2: purification of (1S,4R,9 β,11 α,24R) -1- (β -D-glucopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-mogroside III, Compound 2a) from extracts of Lo Han Guo

60kg of Lo Han Guo (Siraitia grosvenor rriii) extract from Gui Lin Layn Natural Ingredients Corp. (pale yellow liquid, 3.5% mogroside V) was dissolved in 150L of deionized water and loaded onto XDA macroporous resin. The resin was then eluted with water, 5% aqueous EtOH and 95% aqueous EtOH and the final fraction enriched in mogroside was collected as Frac 1(5.0 kg). Frac 1 was further separated on a C18 flash column (Daiso ODS, 40-70 μm, 100X 490 mm). After the sample was loaded, the column was eluted with water, 10%, 20%, 25%, 30%, 40%, 50% ACN aqueous solution and 100% ACN at a flow rate of 70mL/min, and 16 fractions were collected (Frac. 35-50). Frac.45(412g) was further purified by column chromatography on C18 flash chromatography (Daiso ODS, 40-70 μm, 100X 490mm, 26% aqueous ACN, 70mL/min), Sephadex LH-20 column (55X 1500mm, 18% aqueous ACN, 0.3 to 1.5mL/min) and preparative HPLC (YMC ODS, 5 μm, 10X 250mm, 14-21% aqueous ACN, 4.5mL/min) to give (1S,4R,9 β,11 α,24R) -1- (. beta. -D-glucopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholesteric-5-en-24-yl 6-O-. beta. -D-glucopyranosyl-. beta. -D-glucopyranoside (22-hydroxy-mogroside III, compound 2a) (200mg, purity: 94%).

Referring to the mass spectra and NMR analyses shown in fig. 5 to 7, the following structures were derived:

when a sample of the purified compound was tasted at a concentration of 500ppm in the aqueous base, a weak sweet taste was perceived, about 20 to 50 times the sweetness of sucrose.

Example 3: (1S,4R,9 β,11 β,24R) -1- (β -D-glucopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-Ring-opened cholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-11-epi-mogroside III, Compound 2b) purification from Luo Han Guo extract

60kg of Lo Han Guo (Siraitia grosvenor rriii) extract from Gui Lin Layn Natural Ingredients Corp. (pale yellow liquid, 3.5% mogroside V) was dissolved in 150L of deionized water and loaded onto XDA macroporous resin. The resin was then eluted with water, 5% aqueous EtOH and 95% aqueous EtOH and the final fraction enriched in mogroside was collected as Frac 1(5.0 kg). Frac 1 was further separated on a C18 flash column (Daiso ODS, 40-70 μm, 100X 490 mm). After the sample was loaded, the column was eluted with water, 10%, 20%, 25%, 30%, 40%, 50% ACN aqueous solution and 100% ACN at a flow rate of 70mL/min, and 16 fractions were collected (Frac. 35-50). Frac.45(412g) was further purified by passing through a C18 flash column (Daiso ODS, 40-70 μm, 100X 490mm, 26% aqueous ACN, 70mL/min), a Sephadex LH-20 column (55X 1500mm, 18% aqueous ACN, 0.3 to 1.5mL/min) and preparative HPLC (YMC ODS, 5 μm, 10X 250mm, 14-21% aqueous ACN, 4.5mL/min) to give (1S,4R,9 β,11 β,24R) -1- (. beta. -D-glucopyranosyloxy) -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O-. beta. -D-glucopyranosyl-. beta. -D-glucopyranoside (22-hydroxy-11-epi-mogroside III, compound 2b) (50mg, purity: 95%).

Referring to the mass spectra and NMR analyses shown in fig. 8-10, the following structures were derived:

when a sample of the purified compound was tasted at a concentration of 250ppm, no taste was perceived.

Example 4: purification of (1S,4R,9 β,11 α,24R) -24- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-secocholest-5-en-1-yl 4-O- β -D-glucopyranosyl- β -D-glucopyranoside (22-hydroxy-isomogroside IVa, Compound 3a) from extracts of Lo Han Guo

60kg of Lo Han Guo (Siraitia grosvenor rriii) extract from Gui Lin Layn Natural Ingredients Corp. (pale yellow liquid, 3.5% mogroside V) was dissolved in 150L of deionized water and loaded onto XDA macroporous resin. The resin was then eluted with water, 5% aqueous EtOH and 95% aqueous EtOH and the final fraction enriched in mogroside was collected as Frac 1(5.0 kg). Frac 1 was further separated on a C18 flash column (Daiso ODS, 40-70 μm, 100X 490 mm). After the sample was loaded, the column was eluted with water, 10%, 20%, 25%, 30%, 40%, 50% ACN aqueous solution and 100% ACN at a flow rate of 70mL/min, and 16 fractions were collected (Frac. 35-50). Frac.45(412g) was further purified by passing through a C18 flash column (Daiso ODS, 40-70 μm, 100X 490mm, 26% aqueous ACN, 70mL/min), Sephadex LH-20 column (55X 1500mm, 18% aqueous ACN, 0.3 to 1.5mL/min) and preparative HPLC (YMC ODS, 5 μm, 10X 250mm, 14-21% aqueous ACN, 4.5mL/min) to give (1S,4R,9 β,11 α,24R) -24- { [6-O- (. beta. -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,22, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-1-yl 4-O-. beta. -D-glucopyranosyl- β -D-pyridone-p-D-pyridone-D-p-n-p-n-O-p-n-p-n-p-n-O-n-p-O-n-O-p-n-O-p-n-O-n-p-n-O-n-p-O-p-O-n-e-n-p-n-p-n-p-n-p-n-p-n-p-n-p-n-p-n-p-n- Glucopyranoside (22-hydroxy-isomogroside IVa, Compound 3a) (50mg, purity: 97%).

Referring to the mass spectra and NMR analyses shown in fig. 11 to 13, the following structures were derived:

when a sample of the purified compound was tasted at a concentration of 250ppm, no taste was perceived.

Example 5: (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -7,11, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (7-hydroxy-mogroside V, Compound 4a) purification from an extract of Lo Han Guo

60kg of Lo Han Guo (Siraitia grosvenor rriii) extract from Gui Lin Layn Natural Ingredients Corp. (pale yellow liquid, 3.5% mogroside V) was dissolved in 150L of deionized water and loaded onto XDA macroporous resin. The resin was then eluted with water, 5% aqueous EtOH and 95% aqueous EtOH and the final fraction enriched in mogroside was collected as Frac 1(5.0 kg). Frac 1 was further separated on a C18 flash column (Daiso ODS, 40-70 μm, 100X 490 mm). After the sample was loaded, the column was eluted with water, 10%, 20%, 25%, 30%, 40%, 50% ACN aqueous solution and 100% ACN at a flow rate of 70mL/min, and 16 fractions were collected (Frac. 35-50). Frac.45(412g) was further purified by passing through a C18 flash column (Daiso ODS, 40-70 μm, 100X 490mm, 26% aqueous ACN, 70mL/min), a Sephadex LH-20 column (55X 1500mm, 18% aqueous ACN, 0.3 to 1.5mL/min) and preparative HPLC (YMC ODS, 5 μm, 10X 250mm, 14-21% aqueous ACN, 4.5mL/min) to give (1S,4R,9 β,11 α,24R) -1- { [6-O- (. beta. -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -7,11, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholesteric-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D- ] -glucopyranosyl-) Glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (7-hydroxy-mogroside V, Compound 4a) (200mg, purity: 99%).

Referring to the mass spectra and NMR analyses shown in fig. 14 to 16, the following structures were derived:

when a sample of the purified compound was tasted at a concentration of 500ppm in the aqueous base, a weak sweet taste was perceived, about 30 to 60 times the sweetness of sucrose.

Example 6: (1S,4R,9 β,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-9- (hydroxymethyl) -10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - β -D-glucopyranosyl- (1 → 6) ] - β -D-D-glucopyranoside (19-hydroxy-11-oxomogroside V, Compound 5a) purification from an extract of Lo Han Guo

60kg of Lo Han Guo (Siraitia grosvenor rriii) extract from Gui Lin Layn Natural Ingredients Corp. (pale yellow liquid, 3.5% mogroside V) was dissolved in 150L of deionized water and loaded onto XDA macroporous resin. The resin was then eluted with water, 5% aqueous EtOH and 95% aqueous EtOH and the final fraction enriched in mogroside was collected as Frac 1(5.0 kg). Frac 1 was further separated on a C18 flash column (Daiso ODS, 40-70 μm, 100X 490 mm). After the sample was loaded, the column was eluted with water, 10%, 20%, 25%, 30%, 40%, 50% ACN aqueous solution and 100% ACN at a flow rate of 70mL/min, and 16 fractions were collected (Frac. 35-50). Frac.45(412g) was further purified by passing through a C18 flash column (Daiso ODS, 40-70 μm, 100X 490mm, 26% aqueous ACN, 70mL/min), Sephadex LH-20 column (55X 1500mm, 18% aqueous ACN, 0.3 to 1.5mL/min) and preparative HPLC (YMC ODS, 5 μm, 10X 250mm, 14-21% aqueous ACN, 4.5mL/min) to give (1S,4R,9 β,24R) -1- { [6-O- (. beta. -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-9- (hydroxymethyl) -10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholesteric-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ beta-D-glucopyranosyl- (1 → 6) ] -beta-D-glucopyranoside (19-hydroxy-11-oxomogroside V, Compound 5a) (50mg, purity: 94%).

Referring to the mass spectra and NMR analyses shown in fig. 17 to 19, the following structures were derived:

when a sample of the purified compound was tasted at a concentration of 250ppm, no taste was perceived.

Example 7: (1S,4R,9 β,24R) -9-formyl-1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-ring-opening cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (19-formyl-11-oxomogroside V, Compound 6a) purification from an extract of Lo Han Guo

60kg of Lo Han Guo (Siraitia grosvenor rriii) extract from Gui Lin Layn Natural Ingredients Corp. (pale yellow liquid, 3.5% mogroside V) was dissolved in 150L of deionized water and loaded onto XDA macroporous resin. The resin was then eluted with water, 5% aqueous EtOH and 95% aqueous EtOH and the final fraction enriched in mogroside was collected as Frac 1(5.0 kg). Frac 1 was further separated on a C18 flash column (Daiso ODS, 40-70 μm, 100X 490 mm). After the sample was loaded, the column was eluted with water, 10%, 20%, 25%, 30%, 40%, 50% ACN aqueous solution and 100% ACN at a flow rate of 70mL/min, and 16 fractions were collected (Frac. 35-50). Frac.45(412g) was further purified by passing through a C18 flash column (Daiso ODS, 40-70 μm, 100X 490mm, 26% aqueous ACN, 70mL/min), Sephadex LH-20 column (55X 1500mm, 18% aqueous ACN, 0.3 to 1.5mL/min) and preparative HPLC (YMC ODS, 5 μm, 10X 250mm, 14-21% aqueous ACN, 4.5mL/min) to give (1S,4R,9 β,24R) -9-formyl-1- { [6-O- (. beta. -D-pyranosyl) - β -D-pyranosyl ] oxy } -25-hydroxy-10, 14-dimethyl-11-oxo-4, 9-cyclo-9, 10-secocholesteric-5-en-24-yl β -D-pyranosyl- (1 → 2) - [ beta-D-glucopyranosyl- (1 → 6) ] -beta-D-glucopyranoside (19-formyl-11-oxomogroside V, Compound 6a) (200mg, purity: 95%).

Referring to the mass spectra and NMR analyses shown in fig. 20 to 22, the following structures were derived:

when a sample of the purified compound was tasted at a concentration of 500ppm in the aqueous base, an intense sweet taste was perceived, about 100 to 200 times the sweetness of sucrose.

Example 8: (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,20, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (20-hydroxy-mogroside V, Compound 7a) purification from an extract of Lo Han Guo

60kg of Lo Han Guo (Siraitia grosvenor rriii) extract from Gui Lin Layn Natural Ingredients Corp. (pale yellow liquid, 3.5% mogroside V) was dissolved in 150L of deionized water and loaded onto XDA macroporous resin. The resin was then eluted with water, 5% aqueous EtOH and 95% aqueous EtOH and the final fraction enriched in mogroside was collected as Frac 1(5.0 kg). Frac 1 was further separated on a C18 flash column (Daiso ODS, 40-70 μm, 100X 490 mm). After the sample was loaded, the column was eluted with water, 10%, 20%, 25%, 30%, 40%, 50% ACN aqueous solution and 100% ACN at a flow rate of 70mL/min, and 16 fractions were collected (Frac. 35-50). Frac.45(412g) was further purified by passing through a C18 flash column (Daiso ODS, 40-70 μm, 100X 490mm, 26% aqueous ACN, 70mL/min), a Sephadex LH-20 column (55X 1500mm, 18% aqueous ACN, 0.3 to 1.5mL/min) and preparative HPLC (YMC ODS, 5 μm, 10X 250mm, 14-21% aqueous ACN, 4.5mL/min) to give (1S,4R,9 β,11 α,24R) -1- { [6-O- (. beta. -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11,20, 25-trihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholesteric-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D- ] -glucopyranosyl-) Glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (20-hydroxy-mogroside V, Compound 7a) (50mg, purity: 98%).

Referring to the mass spectra and NMR analyses shown in fig. 23 to 25, the following structures were derived:

when a sample of the purified compound was tasted at a concentration of 250ppm, no taste was perceived.

Example 9: purification of (1S,4R,9 β,24R) -1- (β -D-glucopyranosyloxy) -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl 6-O- β -D-glucopyranosyl- β -D-glucopyranoside (20-hydroxy-11-oxo mogroside III, Compound 8a) from extracts of Lo Han Guo

60kg of Lo Han Guo (Siraitia grosvenor rriii) extract from Gui Lin Layn Natural Ingredients Corp. (pale yellow liquid, 3.5% mogroside V) was dissolved in 150L of deionized water and loaded onto XDA macroporous resin. The resin was then eluted with water, 5% aqueous EtOH and 95% aqueous EtOH and the final fraction enriched in mogroside was collected as Frac 1(5.0 kg). Frac 1 was further separated on a C18 flash column (Daiso ODS, 40-70 μm, 100X 490 mm). After the sample was loaded, the column was eluted with water, 10%, 20%, 25%, 30%, 40%, 50% ACN aqueous solution and 100% ACN at a flow rate of 70mL/min, and 16 fractions were collected (Frac. 35-50). Frac.45(412g) was further purified by passing through a C18 flash column (Daiso ODS, 40-70 μm, 100X 490mm, 26% aqueous ACN, 70mL/min), Sephadex LH-20 column (55X 1500mm, 18% aqueous ACN, 0.3 to 1.5mL/min) and preparative HPLC (YMC ODS, 5 μm, 10X 250mm, 14-21% aqueous ACN, 4.5mL/min) to give 1S,4R,9 β,24R) -1- (. beta. -D-glucopyranosyloxy) -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 6-O-. beta. -D-glucopyranosyl-. beta. -D-glucopyranoside (20-hydroxy-11-oxomogroside III) Compound 8a) (50mg, purity: 96%).

Referring to the mass spectra and NMR analyses shown in fig. 26 to 28, the following structures were derived:

when a sample of the purified compound was tasted at a concentration of 250ppm, no taste was perceived.

Example 10: (1S,4R,9 β,24R) -24- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-ring-9, 10-ring-opening cholest-5-en-1-yl β -D-glucopyranosyl- (1 → 2) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (Compound 9a) purification from an extract of Lo Han Guo

60kg of Lo Han Guo (Siraitia grosvenor rriii) extract from Gui Lin Layn Natural Ingredients Corp. (pale yellow liquid, 3.5% mogroside V) was dissolved in 150L of deionized water and loaded onto XDA macroporous resin. The resin was then eluted with water, 5% aqueous EtOH and 95% aqueous EtOH and the final fraction enriched in mogroside was collected as Frac 1(5.0 kg). Frac 1 was further separated on a C18 flash column (Daiso ODS, 40-70 μm, 100X 490 mm). After the sample was loaded, the column was eluted with water, 10%, 20%, 25%, 30%, 40%, 50% ACN aqueous solution and 100% ACN at a flow rate of 70mL/min, and 16 fractions were collected (Frac. 35-50). Frac.45(412g) was further purified by passing through a C18 flash column (Daiso ODS, 40-70 μm, 100X 490mm, 26% aqueous ACN, 70mL/min), a Sephadex LH-20 column (55X 1500mm, 18% aqueous ACN, 0.3 to 1.5mL/min) and preparative HPLC (YMC ODS, 5 μm, 10X 250mm, 14-21% aqueous ACN, 4.5mL/min) to give (1S,4R,9 β,24R) -24- { [6-O- (. beta. -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -20, 25-dihydroxy-9, 10, 14-trimethyl-11-oxo-4, 9-cyclo-9, 10-secocholesteric-5-en-1-yl β -D-glucopyranosyl- (1 → 2) - [ β - D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (Compound 9a) (50mg, purity: 95%).

Referring to the mass spectra and NMR analyses shown in fig. 29 to 31, the following structures were derived:

when a sample of the purified compound was tasted at a concentration of 250ppm, no taste was perceived.

Example 11: purification of [ (1S,4R,9 β,10R,24R) -24- { [ β -D-glucopyranosyl- (1 → 6) - β -D-glucopyranosyl ] oxy } -1, 25-dihydroxy-9, 14-dimethyl-11-oxo-4, 9-ring-9, 10-ring-opened cholest-5-en-10-yl ] methyl β -D-glucopyranosyl- (1 → 6) - [ β -D-glucopyranosyl- (1 → 4) - β -D-glucopyranosyl- (1 → 2) ] - β -D-glucopyranoside (compound 10a) from an extract of Momordica grosvenori Swingle.

60kg of Lo Han Guo (Siraitia grosvenor rriii) extract from Gui Lin Layn Natural Ingredients Corp. (pale yellow liquid, 3.5% mogroside V) was dissolved in 150L of deionized water and loaded onto XDA macroporous resin. The resin was then eluted with water, 5% aqueous EtOH and 95% aqueous EtOH and the final fraction enriched in mogroside was collected as Frac 1(5.0 kg). Frac 1 was further separated on a C18 flash column (Daiso ODS, 40-70 μm, 100X 490 mm). After the sample was loaded, the column was eluted with water, 10%, 20%, 25%, 30%, 40%, 50% ACN aqueous solution and 100% ACN at a flow rate of 70mL/min, and 16 fractions were collected (Frac. 35-50). Frac.45(412g) was further purified by passing through a C18 flash column (Daiso ODS, 40-70 μm, 100X 490mm, 26% aqueous ACN, 70mL/min), a Sephadex LH-20 column (55X 1500mm, 18% aqueous ACN, 0.3 to 1.5mL/min) and preparative HPLC (YMC ODS, 5 μm, 10X 250mm, 14-21% aqueous ACN, 4.5mL/min) to give [ (1S,4R,9 β,10R,24R) -24- { [ β -D-glucopyranosyl- (1 → 6) - β -D-glucopyranosyl ] oxy } -1, 25-dihydroxy-9, 14-dimethyl-11-oxo-4, 9-ring-9, 10-Ring-opened cholest-5-en-10-yl ] methyl β -D-glucopyranosyl- (1 → 6) - [ β -D-glucopyranosyl- (1 → 4) - β -D-glucopyranosyl- (1 → 2) ] - β -D-glucopyranoside (Compound 10a) (50mg, purity: 93%).

Referring to the mass spectra and NMR analyses shown in fig. 32 to 34, the following structures were derived:

when a sample of the purified compound was tasted at a concentration of 250ppm, no taste was perceived.

Example 12: (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-ring-opening cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 6) - [ β -D-glucopyranosyl- (1 → 4) - β -D-glucopyranosyl- (1 → 2) ] - β -D-glucopyranoside (Compound 12a) purification from an extract of Lo Han Guo

60kg of Lo Han Guo (Siraitia grosvenor rriii) extract from Gui Lin Layn Natural Ingredients Corp. (pale yellow liquid, 3.5% mogroside V) was dissolved in 150L of deionized water and loaded onto XDA macroporous resin. The resin was then eluted with water, 5% aqueous EtOH and 95% aqueous EtOH and the final fraction enriched in mogroside was collected as Frac 1(5.0 kg). Frac 1 was further separated on a C18 flash column (Daiso ODS, 40-70 μm, 100X 490 mm). After the sample was loaded, the column was eluted with water, 10%, 20%, 25%, 30%, 40%, 50% ACN aqueous solution and 100% ACN at a flow rate of 70mL/min, and 16 fractions were collected (Frac. 35-50). Frac.45(412g) was further purified by passing through a C18 flash column (Daiso ODS, 40-70 μm, 100X 490mm, 26% aqueous ACN, 70mL/min), Sephadex LH-20 column (55X 1500mm, 18% aqueous ACN, 0.3 to 1.5mL/min) and preparative HPLC (YMC ODS, 5 μm, 10X 250mm, 14-21% aqueous ACN, 4.5mL/min) to give 1S,4R,9 β,11 α,24R) -1- { [6-O- (. beta. -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 6) - β -D-glucopyranosyl-) Base- (1 → 4) - β -D-glucopyranosyl- (1 → 2) ] - β -D-glucopyranoside (Compound 12a) (50mg, purity: 96%).

Referring to the mass spectra and NMR analyses shown in fig. 35 to 37, the following structures were derived:

when a sample of the purified compound was tasted at a concentration of 250ppm in the aqueous base, a moderate sweetness was perceived, about 50 to 100 times the sweetness of sucrose. The perceived intensity of sweetness is weaker than that perceived from mogroside V. However, the perception and long-lasting residual (lingering) profile (profile) of licorice of isomogroside IVe was weaker than that of mogroside V (see table below).

Dosage (250ppm)	Sweet taste	Licorice root flavor	Residue is remained
				Mogroside V	6.0	3.8	4.9
Compound 12a	3.4	3.1	3.0

Example 13: (1S,4R,9 β,11 α,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-ring-opening cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) - β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (Compound 13a) purification from an extract of Lo Han Guo

60kg of Lo Han Guo (Siraitia grosvenor rriii) extract from Gui Lin Layn Natural Ingredients Corp. (pale yellow liquid, 3.5% mogroside V) was dissolved in 150L of deionized water and loaded onto XDA macroporous resin. The resin was then eluted with water, 5% aqueous EtOH and 95% aqueous EtOH and the final fraction enriched in mogroside was collected as Frac 1(5.0 kg). Frac 1 was further separated on a C18 flash column (Daiso ODS, 40-70 μm, 100X 490 mm). After the sample was loaded, the column was eluted with water, 10%, 20%, 25%, 30%, 40%, 50% ACN aqueous solution and 100% ACN at a flow rate of 70mL/min, and 16 fractions were collected (Frac. 35-50). Frac.45(412g) was further purified by passing through a C18 flash column (Daiso ODS, 40-70 μm, 100X 490mm, 26% aqueous ACN, 70mL/min), Sephadex LH-20 column (55X 1500mm, 18% aqueous ACN, 0.3 to 1.5mL/min) and preparative HPLC (YMC ODS, 5 μm, 10X 250mm, 14-21% aqueous ACN, 4.5mL/min) to give (1S,4R,9 β,11 α,24R) -1- { [6-O- (. beta. -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-ring-9, 10-ring-opened cholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - β -D-glucopyranosyl- → E → 1 Glycosyl- (1 → 6) -beta-D-glucopyranosyl- (1 → 6) ] -beta-D-glucopyranoside (Compound 13a) (50mg, purity: 99%).

Referring to the mass spectra and NMR analyses shown in fig. 38 to 40, the following structures were derived:

when a sample of the purified compound was tasted at a concentration of 250ppm in the aqueous base, a moderate sweetness was perceived, about 100 to 150 times the sweetness of sucrose, with a sensory profile similar to mogroside V (see table below).

Dosage (250ppm)	Sweet taste	Licorice root flavor	Residue is remained
				Mogroside V	6.0	3.8	4.9
Compound 13a	4.6	4.4	4.2

Example 14: (1S,4R,9 β,11 β,24R) -1- { [ β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranoside (11-epi-mogroside VI, Compound 14a) purification from Lo Han Guo extract

60kg of Lo Han Guo (Siraitia grosvenor rriii) extract from Gui Lin Layn Natural Ingredients Corp. (pale yellow liquid, 3.5% mogroside V) was dissolved in 150L of deionized water and loaded onto XDA macroporous resin. The resin was then eluted with water, 5% aqueous EtOH and 95% aqueous EtOH and the final fraction enriched in mogroside was collected as Frac 1(5.0 kg). Frac 1 was further separated on a C18 flash column (Daiso ODS, 40-70 μm, 100X 490 mm). After the sample was loaded, the column was eluted with water, 10%, 20%, 25%, 30%, 40%, 50% ACN aqueous solution and 100% ACN at a flow rate of 70mL/min, and 16 fractions were collected (Frac. 35-50). Frac.45(412g) was further purified by passing through a C18 flash column (Daiso ODS, 40-70 μm, 100X 490mm, 26% aqueous ACN, 70mL/min), a Sephadex LH-20 column (55X 1500mm, 18% aqueous ACN, 0.3 to 1.5mL/min) and preparative HPLC (YMC ODS, 5 μm, 10X 250mm, 14-21% aqueous ACN, 4.5mL/min) to give (1S,4R,9 β,11 β,24R) -1- { [ β -D-glucopyranosyl- (1 → 2) - [ β -D-glucopyranosyl- (1 → 6) ] - β -D-glucopyranosyl ] oxy } -11, 25-dihydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-open-ring-cholest-5-en-24-yl β -D-glucopyranosyl-L-p-D-glucopyranosyl) Glycosyl- (1 → 2) - [ beta-D-glucopyranosyl- (1 → 6) ] -beta-D-glucopyranoside (11-epi-mogroside VI, compound 14a) (50mg, purity: 96%).

Referring to the mass spectra and NMR analyses shown in fig. 41 to 43, the following structures were derived:

when a sample of the purified compound was tasted at a concentration of 250ppm, no taste was perceived.

Example 15: (1S,4S,9 β,24R) -1- { [6-O- (β -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholest-5-en-24-yl 2-O- β -D-glucopyranosyl- β -D-glucopyranoside (11-deoxymogroside IV, Compound 15a) purification from an extract of Lo Han Guo

60kg of Lo Han Guo (Siraitia grosvenor rriii) extract from Gui Lin Layn Natural Ingredients Corp. (pale yellow liquid, 3.5% mogroside V) was dissolved in 150L of deionized water and loaded onto XDA macroporous resin. The resin was then eluted with water, 5% aqueous EtOH and 95% aqueous EtOH and the final fraction enriched in mogroside was collected as Frac 1(5.0 kg). Frac 1 was further separated on a C18 flash column (Daiso ODS, 40-70 μm, 100X 490 mm). After the sample was loaded, the column was eluted with water, 10%, 20%, 25%, 30%, 40%, 50% ACN aqueous solution and 100% ACN at a flow rate of 70mL/min, and 16 fractions were collected (Frac. 35-50). Frac.37(114g) was further purified by passing through a C18 flash column (Daiso ODS, 40-70 μm, 100X 490mm, 41% aqueous ACN solution, 70mL/min), a Sephadex LH-20 column (55X 1500mm, 30% aqueous ACN solution, 0.3 to 1.5mL/min) and preparative HPLC (YMC ODS, 5 μm, 10X 250mm, 22-30% aqueous ACN solution, 4.5mL/min) to give (1S,4S,9 β,24R) -1- { [6-O- (. beta. -D-glucopyranosyl) - β -D-glucopyranosyl ] oxy } -25-hydroxy-9, 10, 14-trimethyl-4, 9-cyclo-9, 10-secocholesteric-5-en-24-yl 2-O-. beta. -D-glucopyranosyl-. beta. -D-glucopyranoside (11- Deoxymogroside IV, compound 15a) (200mg, purity: 93%).

Referring to the mass spectra and NMR analyses shown in fig. 44 to 46, the following structures were derived:

when a sample of the purified compound was tasted at a concentration of 500ppm in the water base, an intense sweet taste was perceived, about 150 to 300 times the sweetness of sucrose, with a sensory profile similar to mogroside V (see table below).

Dosage (500ppm)	Sweet taste	Licorice root flavor	Residue is remained
				Mogroside V	7.2	4.2	5.2
Compound 15a	7.0	6.8	6.3

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