阅读说明：本技术 一种顺式-阿魏酸戊酯化合物及其制备方法和应用 (Cis-ferulic acid amyl ester compound and preparation method and application thereof ) 是由 张华� 张君生 曹欣欣 徐德峰 于 2020-07-31 设计创作，主要内容包括：本发明属于食品和天然药物化学领域,提供了一种顺式-阿魏酸戊酯化合物,其结构式如图1所示。上述阿魏酸戊酯化合物从食用菌杏鲍菇(<I>Pleurotus eryngii</I>)中通过溶剂提取、萃取、柱层析和高效液相色谱等方法分离得到。药理实验表明该化合物能够显著淬灭DPPH自由基的活性；可用于制备保健食品,以及预防和/或治疗因自由基产生导致的炎症、癌症相关疾病的组合物、药物。(The invention belongs to the field of food and natural pharmaceutical chemistry, and provides a cis-ferulic acid amyl ester compound, the structural formula of which is shown in figure 1. The above ferulic acid amyl ester compound is prepared from edible mushroom Pleurotus eryngii (Pleurotus eryngii) Pleurotus eryngii ) Middle-pass dissolvingExtracting with solvent, extracting, performing column chromatography, and separating with high performance liquid chromatography. Pharmacological experiments show that the compound can obviously quench the activity of DPPH free radicals; can be used for preparing health food, and composition and medicine for preventing and/or treating inflammation and cancer related diseases caused by free radical generation.)

1. A cis-ferulic acid amyl ester compound with a structure shown in figure 1.

2. A process for the preparation of a cis-amyl ferulate compound as claimed in claim 1 comprising the steps of:

drying fruiting bodies of pleurotus eryngii, crushing, extracting with ethanol, and concentrating the extract under reduced pressure until no alcohol smell exists to obtain a crude extract;

will be described in detail

will be described in detail

3. The process for preparing a cis-amyl ferulate compound of claim 2, wherein: step (ii) ofApricot kernelThe material-liquid ratio of the pleurotus eryngii to the ethanol is 1: 2-1: 4 (w/v).

4. The process for preparing a cis-amyl ferulate compound of claim 2, wherein: step (ii) of

5. The process for preparing a cis-amyl ferulate compound of claim 2, wherein: step (ii) ofThe leaching times are 3-4 times, and each time is 7-10 days.

6. The process for preparing a cis-amyl ferulate compound of claim 2, wherein: step (ii) ofThe concentration of the intermediate is 1/50-1/70 of the original volume.

7. The process for preparing a cis-amyl ferulate compound of claim 2, wherein: step (ii) of

8. The process for preparing a cis-amyl ferulate compound of claim 2, wherein: step (ii) of

9. Use of the cis-amyl ferulate compound of claim 1 as a food additive.

10. Use of the cis-amyl ferulate compound of claim 1 in the preparation of compositions and medicaments for treating inflammation, cancer and related diseases caused by free radical production.

Technical Field

The invention belongs to the field of food and natural pharmaceutical chemistry, and relates to a preparation method of a cis-ferulic acid amyl ester compound and application of the cis-ferulic acid amyl ester compound as a free radical scavenger/antioxidant.

Background

The radical is also referred to as "radical" chemically, and refers to an atom or a group having an unpaired electron formed by homolytic cleavage of a covalent bond in a molecule of a compound under external conditions such as photo-thermal conditions. In general, life is not isolated from free radical activity. There are also free radicals in the body, controlled radicals being beneficial to the body, which can help deliver energy to sustain life vitality, can be used to kill bacteria and parasites, and can also participate in toxin elimination; however, when the amount of free radicals in human body exceeds a certain amount, the control is lost, and the human body is hurt to our life. Free radicals in living bodies are inherent, and the life continues to the present, which shows that the life has the capability of balancing the free radicals or eliminating redundant free radicals. However, as the rapid development of human civilization continues to destroy the ecological environment, more free radicals are produced, which exceeds the standard of normal balance of life, and thus human health faces an unprecedented serious challenge. With the development of radical research, it is becoming clear that the measures for scavenging excess radicals are beneficial for the prevention and treatment of certain diseases, and the significance of the research on radical scavengers in human health is very important. Therefore, the development and utilization of natural antioxidants, free radical scavengers, which are highly effective and nontoxic, have become important research directions in the research and development fields of food and medicine; especially, the novel free radical scavenger is searched and developed from edible resources, and the research value and the development prospect are greater.

Disclosure of Invention

In order to further develop the economic and medicinal values of pleurotus eryngii, the invention provides a cis-ferulic acid amyl ester compound extracted from pleurotus eryngii, which has obvious activity of removing DPPH free radicals.

Another object of the present invention is to provide a process for preparing the above cis-ferulic acid pentyl ester compound.

It is still another object of the present invention to provide a use of the above cis-ferulic acid pentyl ester compound as a DPPH free-agent scavenger/antioxidant.

In order to achieve the purpose, the invention adopts the following technical scheme.

A cis-ferulic acid amyl ester compound has a structural formula shown in figure 1.

The preparation method of the cis-ferulic acid amyl ester compound comprises the following steps:

drying fruiting bodies of pleurotus eryngii, crushing, extracting with ethanol, and concentrating the extract under reduced pressure until no alcohol smell exists to obtain a crude extract;

will be described in detailSuspending the obtained crude extract in distilled water, extracting with ethyl acetate, mixing ethyl acetate extractive solutions, and concentrating under reduced pressure to obtain ethyl acetate extract;

will be described in detailSubjecting the ethyl acetate extract obtained in the step (a) to D101 macroporous resin column chromatography, and sequentially eluting with 30%, 50%, 70% and 95% ethanol-water to obtain four components Fr A1-A4;

will be described in detail

The fraction Fr A3 obtained in (1) is passed through normal phase silica gelPerforming column chromatography, and performing gradient elution by using petroleum ether-ethyl acetate of 99:1 to 4:1 to obtain eight components Fr B1-B8;

will be described in detailSubjecting the obtained component Fr B5 to RP-18 reverse phase silica gel column chromatography, and performing gradient elution with 70% to 100% methanol-water to obtain five components Fr C1-C5;

will be described in detail

The fraction Fr C3 obtained in (1) is purified by Agilent SB-C₁₈Performing column high performance liquid chromatography, isocratically eluting with 80% acetonitrile-water solution, detecting wavelength at 254 nm, and collecting components with retention time of 18.2 min to obtain cis-amyl ferulate compound shown in figure 1.

Step (ii) of

The material-liquid ratio of the pleurotus eryngii to the ethanol is 1: 2-1: 4 (w/v).

Step (ii) of

The dried pleurotus eryngii fruiting body is crushed to the particle size diameter of less than 3 mm.

Step (ii) ofThe leaching times are 3-4 times, and each time is 7-10 days.

Step (ii) ofThe concentration of the intermediate is 1/50-1/70 of the original volume.

Step (ii) of

The volume ratio of the crude extract to water is 1: 1-1: 2.

Step (ii) of

The volume ratio of the ethyl acetate to the water is 1: 1-1: 1.5.

Step (ii) of

Wherein the extraction times of the ethyl acetate are 3-4 times.

Step (ii) ofThe flow rate was 3.0 mL/min.

An application of the cis-ferulic acid amyl ester compound in the aspects of being used as a free agent scavenger and an antioxidant.

Drawings

FIG. 1 is a structural formula of a compound;

FIG. 2 is hydrogen (600 MHz) and carbon (151 MHz) (CD 3 OD) spectra data for compounds;

FIG. 3 is a high resolution mass spectrum of a compound;

FIG. 4 is a hydrogen spectrum of a compound;

FIG. 5 is a carbon spectrum of a compound;

FIG. 6 is a two-dimensional COSY spectrum of a compound;

FIG. 7 is a two-dimensional HSQC spectrum of a compound;

fig. 8 is a two-dimensional HMBC spectrum of a compound.

Detailed Description

The present invention will be further described with reference to the following examples and drawings, but the present invention is not limited to the following examples.