CN109180484A - A kind of 2,4 disubstituted benzenes amphyl class compounds, its extracting method and purposes extracted from the beautiful ferment of promise - Google Patents
A kind of 2,4 disubstituted benzenes amphyl class compounds, its extracting method and purposes extracted from the beautiful ferment of promise Download PDFInfo
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- CN109180484A CN109180484A CN201810940470.4A CN201810940470A CN109180484A CN 109180484 A CN109180484 A CN 109180484A CN 201810940470 A CN201810940470 A CN 201810940470A CN 109180484 A CN109180484 A CN 109180484A
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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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 present invention relates to Natural Medicine Chemistry technical field, in particular to a kind of 2,4 disubstituted benzenes amphyl class compounds extracted from the beautiful ferment of promise, preparation method and in the purposes prepared in hypoglycemic drug.Phenol derivative species compound structure provided by the invention is novel, has that good therapeutic effect, source be natural, Small side effects to hypoglycemic；Meanwhile preparation method simple process, low in cost, raw material sources are extensive.
Description
Technical field
The present invention relates to Natural Medicine Chemistry technical field, in particular to a kind of 2,4 two extracted from the beautiful ferment of promise take
Substituting phenol derivatives quasi-compound, its extracting method and purposes.
Background technique
Diabetes are a kind of to generate and act on abnormal chronic disease related, characterized by blood glucose increases to insulin.With
Chinese society expanding economy, the change of people's dietary structure, the continuous improvement of living standard, the illness rate of diabetes is in fast
Violent ascendant trend, the sum of whole world diabetic is more than 1.2 hundred million people at present.The diabetes status very severe in China, hair
Sick rate is up to 9.6%, it has also become the fastest-rising country of diabetes number of patients in world wide.In recent decades, China
Diabetes prevalence is continuously increased, nineteen ninety-five whole nation Diabetes Epidemiological Investigation, 25 years old to the 64 years old crowd's diabetes in China
Illness rate is 2.5%.In August, 2010-in December, 2010 Chinese Center for Disease Control and Prevention and Medical College, Shanghai Communication Univ. are total
Diabetes investigation has been carried out with to the whole nation 18 years old and 98658 people of the above inhabitant, and investigation result shows China in 2010 18 years old
And above diabetic's illness rate is 9.65%.Currently, in the adult in China 18 years old or more, the number with diabetes
92,400,000 are had reached, No. 1 in the world is occupied, at the same time, the disease condition of China's adolescent diabetes also allows of no optimist, sugar
Urine disease prevention and treatment has become one of the most important public health problem that China faces.Long-standing hyperglycemia, leads when diabetes
Cause various tissues, especially eye, kidney, heart, blood vessel, the chronic lesion of nerve, dysfunction.
Existing hypoglycemic agent species are still not abundant enough, and drug-resistant effect, a large amount of patients can usually occur for long-term use
Have to that the insulin injection that cost is higher, risk is bigger is selected to treat due to drug-resistant effect, it would therefore be highly desirable to further develop
The novel blood sugar lowing drug to work well.
Noni fruit (Noni) is the fruit of beach wood Morinda offcinalis How.Shrub is 1-5 meters high to dungarunga；Stem is straight, the nearly quadrangular of branch
Shape.To life, oblong, ellipse or oval are 12-25 centimetres long for leaf interaction, and both ends are tapering or anxious point, usually have gloss, nothing
Hair, full edge.The beautiful ferment of promise has blood pressure lowering, Adjust-blood lipid, improves osteoporosis and hearing ability, antifatigue, enhancing memory, wound
The effects of wound reparation, expelling parasite.By literature search, there is not been reported in hypoglycemic application for the beautiful ferment of promise at present and its extract.
Summary of the invention
The first object of the present invention is to provide a kind of 2,4 disubstituted benzenes phenol of brand new extracted from the beautiful ferment of promise
Derivatives quasi-compound, structure are as follows:
The second object of the present invention is to provide the extracting method of above compound, include the following steps:
(1) Noni fruit is fermented to obtain the beautiful ferment of promise；
(2) the beautiful ferment of promise is extracted with ethyl acetate；
(3) after extract liquor concentration, through column chromatography, thin-layer chromatography and gel filtration chromatography, above compound is obtained.
Preferably, the beautiful ferment of the promise specific the preparation method is as follows:
A. the epidermis of mature Noni fruit is cleaned with brush, is cut into the thin slice with a thickness of 1~5mm；
B. by Noni fruit according to white granulated sugar: Noni fruit: water=1:2~4:8~20 are put into clean round, fermentation
There are 20~30% spaces for its fermentation in container；
C. In Shade fermentation three months, wherein first month opens stirring daily or shakes round, and three months
After the beautiful ferment of promise is obtained by filtration.
Preferably, the volume ratio of the beautiful ferment of promise and ethyl acetate is 1:1~5 in step (2) extraction.
Preferably, extract liquor is concentrated into the 1/20~1/100 of original volume in the step (3).
Preferably, the column chromatography condition in the step (3) is specific as follows: column chromatography column is loaded with 300 mesh silica gel, with second
The ethyl acetate-light petrol mixed solvent that acetoacetic ester percentage by volume is 10~20% is eluant, eluent.
Preferably, the thin-layer chromatography condition in the step (3) is specific as follows: with ethyl acetate percentage by volume for 10%
~20% ethyl acetate-light petrol mixed solvent is solvent, or with volume ratio is petroleum ether-acetone mixed solvent of 4:1
For solvent, or using volume ratio for 10:1 chloroform-acetone mixed solvent as solvent.
Preferably, the gel filtration chromatography condition in the step (3) is specific as follows: gel is Sephadex LH-20, with
The chloroform-methanol mixed solvent that chloroform percentage by volume is 20%-40% is eluant, eluent.
The third aspect of the present invention is to improve purposes of the above compound in preparation treatment hypoglycemic drug.
The beneficial effects of the present invention are: provided by the invention 2,4 disubstituted benzenes amphyl class compound structures are novel, right
Hypoglycemic have that good therapeutic effect, source be natural, Small side effects；Meanwhile preparation method simple process, it is low in cost,
Raw material sources are extensive.
Specific embodiment
Illustrate technical solution of the present invention below by way of specific embodiment, but the scope of the present invention is not limited thereto.
Embodiment 1
(1) preparation of the beautiful ferment of promise
A. the epidermis of mature Noni fruit is cleaned with brush, is cut into the thin slice with a thickness of 1~5mm；
B. by Noni fruit according to white granulated sugar: Noni fruit: water=1:2:20 is put into clean round, in round
There are 20~30% spaces for its fermentation；
C. In Shade fermentation three months, wherein first month opens stirring daily or shakes round, and three months
After the beautiful ferment of promise is obtained by filtration.
(2) it extracts
The resulting beautiful ferment of promise is extracted with ethyl acetate twice, and the dosage of each ethyl acetate is the beautiful ferment body of promise to be extracted
Long-pending 2.5 times collect extract liquor；
(3) it separates
The extract liquor that step (2) obtains is concentrated into the 1/50 of original volume, successively through column chromatography, thin-layer chromatography, gel column
Chromatography；The condition of column chromatography are as follows: chromatographic column is 300 mesh silicagel columns, the ethyl acetate-for being 20% with ethyl acetate percentage by volume
Petroleum ether mixed solvent is eluant, eluent, collects eluent concentration and enters thin-layer chromatography；Thin-layer chromatography condition are as follows: with ethyl acetate body
The ethyl acetate-light petrol mixed solvent that product percentage is 25% is solvent, collects the maximum product of area on thin-layer chromatography
Point；Gel filtration chromatography condition are as follows: gel is Sephadex LH-20, mixed with the chloroform-methanol that chloroform percentage by volume is 40%
Bonding solvent is eluant, eluent, collects eluent and is concentrated to get target compound.
Embodiment 2
(1) preparation of the beautiful ferment of promise
A. the epidermis of mature Noni fruit is cleaned with brush, is cut into the thin slice with a thickness of 1~5mm；
B. by Noni fruit according to white granulated sugar: Noni fruit: water=1:4:8 is put into clean round, in round
There are 20~30% spaces for its fermentation；
C. In Shade fermentation three months, wherein first month opens stirring daily or shakes round, and three months
After the beautiful ferment of promise is obtained by filtration.
(2) it extracts
The resulting beautiful ferment of promise is extracted with ethyl acetate twice, and the dosage of each ethyl acetate is the beautiful ferment body of promise to be extracted
Extract liquor is collected in long-pending 1/2；
(3) it separates
The extract liquor that step (2) obtains is concentrated into the 1/100 of original volume, successively through column chromatography, thin-layer chromatography, gel column
Chromatography；The condition of column chromatography are as follows: chromatographic column is 300 mesh silicagel columns, the ethyl acetate-for being 10% with ethyl acetate percentage by volume
Petroleum ether mixed solvent is eluant, eluent, collects eluent concentration and enters thin-layer chromatography；Thin-layer chromatography condition are as follows: with ethyl acetate body
The ethyl acetate-light petrol mixed solvent that product percentage is 10% is solvent, collects the maximum product of area on thin-layer chromatography
Point；Gel filtration chromatography condition are as follows: the chloroform-methanol mixed solvent for being 20% using chloroform percentage by volume as eluant, eluent, wash by collection
De- liquid is concentrated to get target compound.
Embodiment 3
The physicochemical property of target compound, hydrogen are composed and Mass Spectrometer Method data are as follows:
Target compound is clear crystal, is soluble in methanol, DMSO, is in black blackening under 254nm ultraviolet lamp.HRESI-MS
It is 240 that [m/z 263.0, calculated value 240.10], which releases the compound molecular weight, molecular formula C12H16O5, degree of unsaturation 5.1H
NMR(400MHz in CD3OD) and13C NMR(100MHz in CD3OD it) is shown in Table.
Embodiment 4
Target compound is subjected to the test of alpha-glucosaccharase enzyme inhibition activity:
Target compound is configured to 0.6,0.3,0.15mg/mL stock solution with PBS (phosphate buffer).
The substrate PNPG of enzyme solutions and 2.5mmol/L that compound concentration is 2U is stand-by
Experimental procedure: taking one piece of 96 orifice plate, and 58 μ l 0.1M PBS buffer solution are added；Compound is (total after 20 μ l dilution is added
4 groups, 3 groups of parallel 1 group of controls) the parallel group 10 prepared enzyme solutions of μ l of addition, control group addition same volume 0.01M PBS buffering
20 μ l substrate PNPG are added in liquid after mixing, blank control is separately arranged, and 20 μ l DMSO are added, remaining operation is same as above.After mixing
It is placed on 15min in 37 DEG C of constant incubators, 150 μ l terminate liquid (Na are added after taking-up2CO3Solution), using acarbose as mark
Quasi- control, microplate reader measure its absorbance.
Judge that 2,4 disubstituted benzenes amphyl class compounds are to α-grape in the beautiful ferment of promise with alpha-glucosaccharase enzyme inhibition rate
The influence of glycosidase calculates inhibiting rate (Inhibitory rate)=(monomeric compound group OD value-control according to following formula
Group OD value/control group OD value) × 100%, IC is calculated by inhibiting rate50Value, experimental result are shown in Table 1.
Phenol derivative species close object alpha-glucosaccharase enzyme inhibition activity IC in the beautiful ferment of 1 promise of table50Value
The experimental results showed that target compound is higher than reference substance acarbose to alpha-glucosaccharase enzyme inhibition activity.
Taking the above-mentioned ideal embodiment according to the present invention as inspiration, through the above description, relevant staff is complete
Various changes and amendments can be carried out without departing from the scope of the technological thought of the present invention' entirely.The technology of this invention
Property range is not limited to the contents of the specification, it is necessary to which the technical scope thereof is determined according to the scope of the claim.
Claims (8)
1. a kind of 2,4 disubstituted benzenes amphyl class compounds extracted from the beautiful ferment of promise, structure are as follows:
2. a kind of extracting method of compound as described in claim 1, it is characterised in that include the following steps:
(1) Noni fruit is fermented to obtain the beautiful ferment of promise；
(2) the beautiful ferment of promise is extracted with ethyl acetate；
(3) after extract liquor concentration, through column chromatography, thin-layer chromatography and gel filtration chromatography, above compound is obtained.
3. the extracting method of compound as claimed in claim 2, it is characterised in that the specific preparation method of the step (1) is such as
Under:
A. the epidermis of mature Noni fruit is cleaned with brush, is cut into the thin slice with a thickness of 1~5mm；
B. by Noni fruit according to white granulated sugar: Noni fruit: water=1:2~4:8~20 are put into clean round, round
In there are 20~30% space for its fermentation；
C. In Shade fermentation three months, wherein first month opens stirring daily or shakes round, mistake after three months
Filter obtains the beautiful ferment of promise.
4. the extracting method of compound as claimed in claim 2, it is characterised in that the beautiful ferment of promise and second in step (2) extraction
The volume ratio of acetoacetic ester is 1:1~5.
5. the extracting method of compound as claimed in claim 2, it is characterised in that the column chromatography condition in the step (3) is specific
It is as follows: to load column chromatography column with 300 mesh silica gel, the ethyl acetate-light petrol for being 10~20% with ethyl acetate percentage by volume
Mixed solvent is eluant, eluent.
6. the extracting method of compound as claimed in claim 2, which is characterized in that the thin-layer chromatography condition in the step (3)
It is specific as follows: the ethyl acetate-light petrol mixed solvent for being 10%~20% using ethyl acetate percentage by volume as solvent, or
It for petroleum ether-acetone mixed solvent of 4:1 as solvent, or with volume ratio is chloroform-acetone mixing of 10:1 using volume ratio
Solvent is solvent.
7. the extracting method of compound as claimed in claim 2, which is characterized in that the gel filtration chromatography item in the step (3)
Part is specific as follows: using chloroform percentage by volume for 20%-40% chloroform-methanol mixed solvent as eluant, eluent.
8. the use of 2,4 disubstituted benzenes amphyl class compounds as claimed in claim in preparation treatment hypoglycemic drug
On the way.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810940470.4A CN109180484B (en) | 2018-08-17 | 2018-08-17 | 2, 4-disubstituted phenol derivative compounds extracted from noni ferment, and extraction method and application thereof |
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| CN201810940470.4A CN109180484B (en) | 2018-08-17 | 2018-08-17 | 2, 4-disubstituted phenol derivative compounds extracted from noni ferment, and extraction method and application thereof |
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| CN109180484B CN109180484B (en) | 2021-04-20 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112645950A (en) * | 2020-12-28 | 2021-04-13 | 海南师范大学 | Indole alkaloid compound in noni ferment as well as preparation method and application thereof |
| CN116063262A (en) * | 2021-10-29 | 2023-05-05 | 海南师范大学 | Kojic acid compound in noni fruits and preparation method and application thereof |
Citations (2)
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|---|---|---|---|---|
| WO2003020296A1 (en) * | 2001-08-31 | 2003-03-13 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | INHIBITION OF ANGIOGENESIS AND DESTRUCTION OF ANGIOGENIC VESSELS WITH EXTRACTS OF NONI JUICE $i(MORINDA CITRIFOLIA) |
| CN104374854A (en) * | 2014-08-21 | 2015-02-25 | 中国食品发酵工业研究院 | Method for simultaneously detecting content of multiple phenolic acids in Noni juice by HPLC (high performance liquid chromatography) wavelength switching technology |
-
2018
- 2018-08-17 CN CN201810940470.4A patent/CN109180484B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003020296A1 (en) * | 2001-08-31 | 2003-03-13 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | INHIBITION OF ANGIOGENESIS AND DESTRUCTION OF ANGIOGENIC VESSELS WITH EXTRACTS OF NONI JUICE $i(MORINDA CITRIFOLIA) |
| CN104374854A (en) * | 2014-08-21 | 2015-02-25 | 中国食品发酵工业研究院 | Method for simultaneously detecting content of multiple phenolic acids in Noni juice by HPLC (high performance liquid chromatography) wavelength switching technology |
Non-Patent Citations (3)
| Title |
|---|
| Y. W. CHIN ET AL.: ""Novel Oxooxepane Derivatives and New Phorbic Acid Derivative from Paederia scandens"", 《BULL. KOREAN CHEM. SOC.》 * |
| 张伟敏等: ""诺丽叶降血压、降血糖和抗氧化活性的研究"", 《食品研究与开发》 * |
| 晏永球等: ""诺丽的化学成分及药理活性研究进展"", 《中草药》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112645950A (en) * | 2020-12-28 | 2021-04-13 | 海南师范大学 | Indole alkaloid compound in noni ferment as well as preparation method and application thereof |
| CN116063262A (en) * | 2021-10-29 | 2023-05-05 | 海南师范大学 | Kojic acid compound in noni fruits and preparation method and application thereof |
| CN116063262B (en) * | 2021-10-29 | 2024-02-20 | 海南师范大学 | Kojic acid compound in noni fruits and preparation method and application thereof |
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