CN109053451B - Phenol derivative compound extracted from noni ferment, and extraction method and application thereof - Google Patents
Phenol derivative compound extracted from noni ferment, and extraction method and application thereof Download PDFInfo
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- CN109053451B CN109053451B CN201810941410.4A CN201810941410A CN109053451B CN 109053451 B CN109053451 B CN 109053451B CN 201810941410 A CN201810941410 A CN 201810941410A CN 109053451 B CN109053451 B CN 109053451B
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- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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Abstract
The invention relates to the technical field of natural medicinal chemistry, in particular to a phenol derivative compound extracted from noni ferment, a preparation method thereof and application thereof in preparing hypoglycemic drugs. The phenol derivative compound provided by the invention has a novel structure, has a good treatment effect on reducing blood sugar, is natural in source and small in side effect; meanwhile, the preparation method has the advantages of simple process, low cost and wide raw material source.
Description
Technical Field
The invention relates to the technical field of natural pharmaceutical chemistry, and particularly relates to a phenol derivative compound extracted from noni ferment, and an extraction method and application thereof.
Background
Diabetes mellitus is a chronic disease characterized by elevated blood sugar associated with abnormal insulin production and action. With the development of socioeconomic in China, the change of dietary structure and the continuous improvement of living standard of people, the prevalence rate of diabetes is on the rapid rising trend, and the total number of diabetes patients in the world is more than 1.2 hundred million people at present. The current situation of diabetes in China is very severe, the incidence rate is as high as 9.6%, and the situation becomes the country with the fastest increase of the number of people suffering from diabetes worldwide. The prevalence of diabetes in our country has increased since decades, and the prevalence of diabetes in people 25 to 64 years in our country is 2.5% by national diabetes epidemiological investigation in 1995. The Chinese disease prevention and control center between 8 months 2010 and 12 months 2010 and Shanghai medical college of transportation university jointly carry out diabetes investigation on 98658 people living in 18 years and above all over China, and the investigation result shows that the prevalence rate of diabetes of the 18 years and above all over China is 9.65% in 2010. At present, the number of people with diabetes among adults 18 years old and older in China reaches 9240 ten thousands, and the people are the first in the world, meanwhile, the disease condition of diabetes of teenagers in China is not optimistic, and the diabetes prevention and treatment becomes one of the most major public health problems in China. Hyperglycemia occurring in the long term of diabetes results in chronic damage to, and dysfunction of, various tissues, particularly the eyes, kidneys, heart, blood vessels, nerves.
The existing hypoglycemic drugs are not abundant enough, and often have drug resistance after long-term administration, and a large number of patients have to select injection insulin therapy with higher cost and higher risk due to the drug resistance, so that a new hypoglycemic drug with good effect is urgently needed to be further developed.
Noni (Noni) is the fruit of morinda citrifolia. Shrubs to small trees, 1-5 meters high; the stem is straight and the branch is close to the quadrangular shape. The leaves are alternately opposite, and are long round, oval or oval, 12-25 cm long, tapered or sharp at both ends, generally glossy, hairless and complete. Noni ferment has effects of lowering blood pressure, regulating blood lipid, improving osteoporosis and auditory ability, relieving fatigue, improving memory, repairing wound, and expelling parasites. Through literature search, the application of noni ferment and the extract thereof in reducing blood sugar is not reported at present.
Disclosure of Invention
The first objective of the present invention is to provide a phenol derivative compound with a novel structure extracted from noni ferment, which has the following structure:
the second purpose of the invention is to provide an extraction method of the compound, which comprises the following steps:
(1) fermenting noni fruits to obtain noni ferment;
(2) extracting noni ferment with ethyl acetate;
(3) concentrating the extractive solution, and performing column chromatography, thin layer chromatography and gel column chromatography to obtain the above compound.
Preferably, the preparation method of the noni ferment is as follows:
a. cleaning the skin of mature noni fruits by using a brush, and cutting into slices with the thickness of 1-5 mm;
b. mixing noni fruits according to the proportion of white granulated sugar: and (3) noni fruits: putting water in a clean fermentation container in a ratio of 1: 2-4: 8-20, and leaving 20-30% of space in the fermentation container for fermentation;
c. fermenting in shade for three months, wherein the first month is that the fermentation container is opened or shaken every day, and filtering after three months to obtain noni ferment.
Preferably, the volume ratio of the noni ferment to the ethyl acetate in the step (2) is 1: 1 to 5.
Preferably, the extract liquid in the step (3) is concentrated to 1/20-1/100 of the original volume.
Preferably, the column chromatography conditions in step (3) are as follows: and filling a column chromatographic column with 300-mesh silica gel, and taking an ethyl acetate-petroleum ether mixed solvent with ethyl acetate volume percentage of 30-50% as an eluent.
Preferably, the thin layer chromatography conditions in step (3) are specifically as follows: the developing solvent is ethyl acetate-petroleum ether mixed solvent with ethyl acetate volume percentage of 30-50%.
Preferably, the gel column chromatography conditions in step (3) are as follows: using chloroform-methanol mixed solvent with 10-40% chloroform volume percentage as eluent.
A third aspect of the present invention is to improve the use of the above compounds for the preparation of a medicament for the treatment of hypoglycemia.
The invention has the beneficial effects that: the phenol derivative compound provided by the invention has a novel structure, has a good treatment effect on reducing blood sugar, is natural in source and small in side effect; meanwhile, the preparation method has the advantages of simple process, low cost and wide raw material source.
Detailed Description
The technical solutions of the present invention are described below by way of specific examples, but the scope of the present invention is not limited thereto.
Example 1
(1) Preparation of noni enzyme
a. Cleaning the skin of mature noni fruits by using a brush, and cutting into slices with the thickness of 1-5 mm;
b. mixing noni fruits according to the proportion of white granulated sugar: and (3) noni fruits: putting water in a ratio of 1:2:20 into a clean fermentation container, and leaving 20-30% of space in the fermentation container for fermentation;
c. fermenting in shade for three months, wherein the first month is that the fermentation container is opened or shaken every day, and filtering after three months to obtain noni ferment.
(2) Extraction of
Extracting the obtained noni ferment twice by using ethyl acetate, wherein the using amount of the ethyl acetate is 2.5 times of the volume of the noni ferment to be extracted each time, and collecting extract liquor;
(3) separation of
Concentrating the extract obtained in the step (2) to 1/50 of the original volume, and sequentially carrying out column chromatography, thin layer chromatography and gel column chromatography; the column chromatography conditions were: the chromatographic column is a 300-mesh silica gel column, an ethyl acetate-petroleum ether mixed solvent with the volume percentage of ethyl acetate being 30% is taken as an eluent, and the eluent is collected, concentrated and enters thin-layer chromatography; the thin layer chromatography conditions were: collecting the product point with the largest area on the thin-layer chromatography by taking an ethyl acetate-petroleum ether mixed solvent with the ethyl acetate volume percentage of 50% as a developing solvent; the gel column chromatography conditions are as follows: the gel is Sephadex LH-20, a chloroform-methanol mixed solvent with the chloroform volume percentage of 40 percent is used as an eluent, and the eluent is collected and concentrated to obtain the target compound.
Example 2
(1) Preparation of noni enzyme
a. Cleaning the skin of mature noni fruits by using a brush, and cutting into slices with the thickness of 1-5 mm;
b. mixing noni fruits according to the proportion of white granulated sugar: and (3) noni fruits: putting water in a ratio of 1:4:8 into a clean fermentation container, and leaving 20-30% of space in the fermentation container for fermentation;
c. fermenting in shade for three months, wherein the first month is that the fermentation container is opened or shaken every day, and filtering after three months to obtain noni ferment.
(2) Extraction of
Extracting the obtained noni ferment twice by using ethyl acetate, wherein the using amount of the ethyl acetate is 1/2 of the volume of the noni ferment to be extracted each time, and collecting extract liquor;
(3) separation of
Concentrating the extract obtained in the step (2) to 1/100 of the original volume, and sequentially carrying out column chromatography, thin layer chromatography and gel column chromatography; the column chromatography conditions were: the chromatographic column is a 300-mesh silica gel column, an ethyl acetate-petroleum ether mixed solvent with the ethyl acetate volume percentage of 50% is used as an eluent, and the eluent is collected, concentrated and enters thin-layer chromatography; the thin layer chromatography conditions were: collecting the product point with the largest area on the thin-layer chromatography by taking an ethyl acetate-petroleum ether mixed solvent with the ethyl acetate volume percentage of 30% as a developing solvent; the gel column chromatography conditions are as follows: and (3) taking a chloroform-methanol mixed solvent with the chloroform volume percentage of 10% as an eluent, collecting the eluent and concentrating to obtain the target compound.
Example 3
The physicochemical properties, hydrogen spectrum and mass spectrum detection data of the target compound are as follows:
the target compound is colorless crystal, is easily soluble in methanol and chloroform, and is black and dark spot under an ultraviolet lamp of 254 nm. Molecular formula C17H24O5The unsaturation degree was 6.1H NMR(400MHz in CDCl3) And13C NMR(100MHz in CDCl3) See table.
Example 4
The target compound was subjected to an α -glucosidase inhibitory activity test:
the target compounds were prepared into stock solutions of 0.6, 0.3, 0.15mg/mL with PBS (phosphate buffered saline).
Preparing an enzyme solution with the concentration of 2U and a substrate PNPG with the concentration of 2.5mmol/L for standby
The experimental steps are as follows: adding 58 μ l of 0.1M PBS buffer into a 96-well plate; mu.l of diluted compound (4 groups, 3 groups and 1 group as a control) was added to the mixed solution, 10. mu.l of the prepared enzyme solution was added to the control group, 0.01M PBS buffer solution was added to the control group, 20. mu.l of substrate PNPG was added after mixing, a blank control was set, 20. mu.l of DMSO was added, and the other operations were the same as above. Mixing, placing in 37 deg.C constant temperature incubator for 15min, taking out, adding 150 μ l stop solution (Na)2CO3Solution) and the absorbance is measured by a microplate reader with acarbose as a standard control.
The influence of phenol derivative compounds in noni ferment on alpha-glucosidase is judged according to alpha-glucosidase inhibition rate, and inhibition rate (inhibition rate) (monomer compound group OD value) is calculated according to the following formulaOD value of control group/OD value of control group). times.100%, and IC was calculated from the inhibition ratio50The values, experimental results are shown in table 1.
TABLE 1 phenol derivative compounds of noni ferment alpha-glucosidase inhibitory activity IC50Value of
The experimental result shows that the inhibiting activity of the target compound on alpha-glucosidase is higher than that of a reference product acarbose.
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.
Claims (5)
1. A phenol derivative compound extracted from noni ferment has the following structure:
2. a method for extracting a compound according to claim 1, comprising the steps of:
(1) fermenting noni fruits to obtain noni ferment;
(2) extracting noni ferment with ethyl acetate;
(3) concentrating the extractive solution, and performing column chromatography, thin layer chromatography and gel column chromatography to obtain the above compound;
the column chromatography conditions in the step (3) are as follows: filling a column chromatographic column with 300-mesh silica gel, and taking an ethyl acetate-petroleum ether mixed solvent with ethyl acetate volume percentage of 30-50% as an eluent;
the thin layer chromatography conditions in step (3) are as follows: taking ethyl acetate-petroleum ether mixed solvent with 30-50% of ethyl acetate volume percentage as developing agent;
the gel column chromatography conditions in the step (3) are as follows: using chloroform-methanol mixed solvent with 10-40% chloroform volume percentage as eluent.
3. The method for extracting the compound according to claim 2, wherein the specific preparation method in the step (1) is as follows:
a. cleaning the skin of mature noni fruits by using a brush, and cutting into slices with the thickness of 1-5 mm;
b. mixing noni fruits according to the proportion of white granulated sugar: and (3) noni fruits: putting water in a clean fermentation container in a ratio of 1: 2-4: 8-20, and leaving 20-30% of space in the fermentation container for fermentation;
c. fermenting in shade for three months, wherein the first month is that the fermentation container is opened or shaken every day, and filtering after three months to obtain noni ferment.
4. The method for extracting compounds according to claim 2, wherein the volume ratio of noni ferment to ethyl acetate in the extraction in the step (2) is 1: 1 to 5.
5. The use of the phenol derivative compounds according to claim 1 for the preparation of a medicament for lowering blood sugar.
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