CN105434509A - Preparation method of trifolium pratense linn extract and application thereof in reduction of blood glucose - Google Patents
Preparation method of trifolium pratense linn extract and application thereof in reduction of blood glucose Download PDFInfo
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- CN105434509A CN105434509A CN201510991333.XA CN201510991333A CN105434509A CN 105434509 A CN105434509 A CN 105434509A CN 201510991333 A CN201510991333 A CN 201510991333A CN 105434509 A CN105434509 A CN 105434509A
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- extract
- trifolium pratense
- preparation
- petroleum ether
- ethyl acetate
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- HKQYGTCOTHHOMP-UHFFFAOYSA-N COc(cc1)ccc1C1=COc2cc(O)ccc2C1=O Chemical compound COc(cc1)ccc1C1=COc2cc(O)ccc2C1=O HKQYGTCOTHHOMP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/39—Complex extraction schemes, e.g. fractionation or repeated extraction steps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/55—Liquid-liquid separation; Phase separation
Abstract
The invention provides an extraction preparation method of a trifolium pratense linnhypoglycemic component which can obviously reduce activity of glucosaccharase and is expected to be applied to prevention and treatment of diabetes. The trifolium pratense linn extract prepared by the method provided by the invention, serving as a plant source medicine, has small side effects while effectively reducing the activity of glucosaccharase, and provides a new treatment means for patients with hyperglycemia and diabetes. According to the method provided by the invention, main functional components are subjected to separation and identification and are determined as isoflavone compounds, thereby providing a premise for further development and utilization with high added values. The preparation process provided by the invention is simple, quick and environment-friendly, and as plant resources are rich, the development is low, sustainable development can be achieved, and the economic benefit is obvious.
Description
Technical field
The invention belongs to biological pharmacy technical field, be specifically related to a kind of Trifolium pratense extract and preparation method thereof and the application in treating diabetes.
Background technology
Diabetes be a kind of produce to insulin and act on abnormal relevant, take hyperglycemia as the metabolic disease of principal character, there is no radical cure way.Recent research finds, diabetes disease is sent out process and often first occurred postprandial hyperglycemia, and then develop into diabetes, namely the former is the sign in advance of the latter.For diabetics, particularly II type patient, postprandial hyperglycemia to the harm of body considerably beyond hyperglycemia, a large amount of excreting insulin of appearance stimulating pancreas of postprandial hyperglycemia, multiple Developmental and Metabolic Disorder and vascular lesion can be caused, make pancreatic function suffer damage further simultaneously.Therefore, reduce post-prandial glycemia for treatment type Ⅱdiabetes mellitus and this disease of prevention, reduce one of complication and the important measures reducing mortality rate.
Alpha-glucosidase inhibitor is the antidiabetic medicine that a class of the appearance 1980s is new, it is by suppressing the degraded being used for reducing saccharide of the glycosidase on intestinal villi film, delay the absorption and digestion of saccharide, thus effectively reduce the peak value of after-dinner blood sugar of diabetes patients concentration.This inhibitor has been the first-line drug falling post-prandial glycemia by third time Asian-Pacific area Remedies for diabetes Guidelines recommend, is classified as the 3rd class oral antidiabetic drug by medical circle.But this product such as acarbose, the voglibose etc. that have gone on the market at present mostly are sintetics, though good drug efficacy is comparatively large to human body toxic and side effects, as gastrointestinal reaction, anaphylaxis etc.Taking Chinese herbal medicine as raw material, find and take safety for treating and preventing diabetes significant, is also a focus of research alpha-glucosidase inhibitor both at home and abroad at present.
Trifolium pratense (TrifoliumpratenseLinn) has another name called Herba Trifolii Pratentis, red clover, red Holland Astragalus sinicuses, and is integrate multi-functional good forage that is ecological, feeding and medical value.This plant has adaptability widely, is distributed in global most countries and area, and resource is very abundant.This patent is furtherd investigate for Trifolium pratense function of polysaccharide, and technique is simple, and production cost is low, is easy to industrialization, and the prevention and therapy for global diabetes is significant.
Summary of the invention
The invention provides a kind of preparation method of Trifolium pratense extract.Trifolium pratense is as one of pulse family Dominant Species of Forage Grass, extensive in distribution on global, aboundresources.The technology of the present invention raw material is sufficient, and technique is simple, is easy to realize industrialization.
Another object of the present invention is to provide Trifolium pratense extract in treatment and the application in preventing diabetes, provide fundamental basis for finding safe and reliable alpha-glucosidase inhibitor, science integration is developed Trifolium pratense resource and had very important significance.Through checking, this extract can reduce the activity of alpha-glucosidase effectively, thus has positive effect for the treatment of diabetes.
Utilize active means such as tracking separation method and Spectral Identification etc., specifying blood sugar lowering main active is formononetin genistein simultaneously.
Above-mentioned with the preparation technology of Trifolium pratense extract, comprise the steps:
1) preparation of Trifolium pratense extract;
Gather fresh Trifolium pratense plant tissue (blade or root or flower), dry in the shade after pulverizing, add ethanol water, ultrasonic or heating and refluxing extraction, repeats to extract 2-4 time, extracting solution concentrating under reduced pressure, then air-dry at ventilation lucifugal place, obtained Trifolium pratense extract.
Preferably, described ethanol water, addition is 5-50 times of dry powder volume, and ethanol water concentration is 20-100wt%; Ultrasonic or heating and refluxing extraction 10-90 minute.
2) preparation at Trifolium pratense different activities position
A. the preparation of Trifolium pratense petroleum ether part extract (hereinafter referred to as petroleum ether part): by Trifolium pratense extract water dissolution, add petroleum ether again, thermal agitation, stratification, supernatant is petroleum ether layer, and lower aqueous solution petroleum ether re-extract 2-5 time, merges petroleum ether layer, concentrating under reduced pressure, obtained Trifolium pratense petroleum ether part;
B. the preparation of Trifolium pratense ethyl acetate extract extract (hereinafter referred to as ethyl acetate extract): add ethyl acetate in the aqueous solution after petroleum ether extraction, thermal agitation, stratification, supernatant is ethyl acetate layer, lower aqueous solution ethyl acetate re-extract 2-5 time, combined ethyl acetate layer, concentrating under reduced pressure, obtained Trifolium pratense ethyl acetate extract;
Preferably, described step 2) step a in, the Trifolium pratense extract distilled water of its 2-50 times volume dissolves.
Preferably, described step 2) step a in, add the petroleum ether of Trifolium pratense extract solution 2-10 times of volume.
Preferably, described step 2) step b in, add the ethyl acetate of this solution 2-10 times of volume in the aqueous solution after petroleum ether extraction.
Detailed description of the invention
Following embodiment is convenient to understand the present invention better, but does not limit the present invention.Experimental technique in following embodiment, if no special instructions, is conventional method.Test material used in following embodiment, if no special instructions, is and purchases available from routine biochemistry reagent shop.
The preparation at embodiment 1 Trifolium pratense different activities position
1, the preparation of Trifolium pratense extract: the position, ground gathering fresh Trifolium pratense plant, dries in the shade, and pulverizes.Add 20 times of volume ethanol, supersound extraction 30 minutes, repeat extraction 3 times.By Extraction solvent concentrating under reduced pressure, at ventilation lucifugal, place is air-dry, obtains Trifolium pratense extract.
2, the preparation at Trifolium pratense different activities position: get obtained Trifolium pratense extract 20g, dissolves with the distilled water 100mL of 5 times of volumes, and add 3 times in aqueous to the petroleum ether 300mL of aqueous solution volume, thermal agitation, stratification, supernatant is petroleum ether layer; Re-extract 3 times, merges petroleum ether layer, concentrating under reduced pressure, obtained Trifolium pratense petroleum ether part.To add the ethyl acetate 300mL of 3 times of volumes in remaining aqueous solution after petroleum ether extraction, thermal agitation, stratification, supernatant is ethyl acetate layer, re-extract 3 times, combined ethyl acetate layer, concentrating under reduced pressure, obtained Trifolium pratense ethyl acetate extract.Remaining aqueous solution after extracting, concentrating under reduced pressure, obtained Trifolium pratense aqueous phase position.
Embodiment 2 Trifolium pratense difference extraction position is to alpha-glucosaccharase enzyme inhibition activity
2.1 experimental technique
Alpha-glucosaccharase enzyme inhibition activity is that alpha-glucosidase (0.1 unit/mL) and substrate (p-NPG, 1.0mM) are dissolved in phosphate buffer (0.1M, pH6.7).All test specimen DMSO dissolve.Sample cultivates 10min with alpha-glucosidase together with 37 DEG C, adds substrate reactions 30min.Add Na
2cO
3cessation reaction, is determined at the ultraviolet absorption value OD under 405nm.5 variable concentrations got by all samples, repeat 3 times respectively, and calculate IC
50value.With commercially available hypoglycemic medicine acarbose for contrast.
2.2 date processing
Suppression ratio is by following formulae discovery:
Suppression ratio %=(OD
contrast-OD
sample)/OD
contrast× 100
2.3 active testing results
Table 1 different parts Inhibiting α-glucosidase IC
50value
The tracking of embodiment 3 hypoglycemic activity compound is separated
Activity Results shows, Trifolium pratense ethyl acetate extract activity is the strongest.Therefore, further separation and purification has been carried out to ethyl acetate extract.Get ethyl acetate extract 10g, sample is mixed with silica gel 10g, upper 100g silicagel column, use petroleum ether 300mL successively, petroleum ether: acetone (100:1) solution 300mL, petroleum ether: acetone (50:1) solution 300mL, petroleum ether: acetone (10:1) solution 500mL, petroleum ether: acetone (2:1) solution 300mL, petroleum ether: acetone (1:1) solution 300mL, acetone 100mL eluting, is compared by thin-layer chromatographic analysis, merge similar compositions, obtain A-H8 component.Carry out repeatedly continuous print silica gel column chromatography to wherein component D to be separated, utilize polydextran gel to carry out purification, recrystallization obtains compound formononetin.Carry out repeatedly continuous print silica gel column chromatography to wherein component E to be separated, utilize polydextran gel to carry out purification, obtain compound genistein.
Utilize nuclear magnetic resonance technique and mass spectrum, identify that these two active component are respectively formononetin (Formononetin) and genistein (Genistein), chemical structural formula is:
Its spectral configuration data are as follows:
Formononetin: colourless acicular crystal.ESI-MS provides [M+H]
+m/z269.0805.
1H-NMR(400M，DMSO-d
6)δ：8.34(1H,s,H-2),7.97(1H,d,J＝8.0Hz,H-5),7.51(2H,d,J＝8.0Hz,H-2’,H-6’),6.98(2H,d,J＝8.0Hz,H-3’,H-5’),6.93(1H,dd,J＝8.0,4.0Hz,H-6),6.87(1H,d,J＝4.0Hz,H-8),3.79(3H,s,4’-OCH
3)。
Genistein: colourless acicular crystal.ESI-MS provides [M+H]
+m/z271.0440.
1H-NMR(400M，DMSO-d
6)δ：12.96(1H,s,5-OH),10.88(1H,s,7-OH),9.58(1H,s,4’-OH),8.32(1H,s,H-2),7.38(2H,d,J＝12.0Hz,H-2’,H-6’),6.82(2H,d,J＝12.0Hz,H-3’,H-5’),6.39(1H,brs,H-8),6.23(1H,brs,H-6)。
Reactive compound is carried out hypoglycemic activity test, and method is with example 2, and Activity Results is in table 2.
Table 2 reactive compound Inhibiting α-glucosidase IC
50value
Carbohydrate in diet is under the effect of glucosidase, and release glucose also enters blood through intestinal absorption, is the main cause that post-prandial glycemia raises.Post-prandial glycemia raises and insulin sensitivity can be caused to reduce and cause serious complication.Therefore, the regulable control of alpha-glucosidase activity, can delay the absorption and digestion of carbohydrate, plays and reduces post-prandial glycemia and glycolated hemoglobin, reduces blood glucose fluctuation, the effect of control diabetic complication.
As can be known from Table 1, it is active that the different extract of the Trifolium pratense prepared by the present invention all has obvious Inhibiting α-glucosidase.Wherein ethyl acetate extract activity is the highest.Follow the tracks of to be separated by activity and find, Trifolium pratense hypoglycemic activity composition is formononetin and genistein (table 2), and wherein the activity of genistein is higher than contrast more than 20 times.
Present invention process is simple, and the plant resources utilized enriches, and development cost is low, and successful is better than contrast, not easily develops immunity to drugs, and has good development prospect.
Last it is noted that the foregoing is only the preferred embodiments of the present invention, be not limited to the present invention, although with reference to previous embodiment to invention has been detailed description, for a person skilled in the art, it still can be modified to the technical scheme described in foregoing embodiments, or carries out equivalent replacement to wherein portion of techniques feature.Within the spirit and principles in the present invention all, any amendment done, equivalent replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (7)
1. a preparation method for Trifolium pratense extract, comprises ultrasonic for Trifolium pratense tissue organic solvent or heating and refluxing extraction.It is characterized in that, the preparation method of Trifolium pratense extract is completed by following steps:
1) preparation of Trifolium pratense extract;
Gather fresh Trifolium pratense plant tissue, dry in the shade after pulverizing, add ethanol water, ultrasonic or heating and refluxing extraction, repeat to extract 2-4 time, extracting solution concentrating under reduced pressure, then air-dry at ventilation lucifugal place, obtained Trifolium pratense extract.
2) preparation at Trifolium pratense different activities position
A. the preparation of Trifolium pratense petroleum ether part extract: by Trifolium pratense extract water dissolution, then add petroleum ether, thermal agitation, stratification, supernatant is petroleum ether layer, lower aqueous solution petroleum ether re-extract 2-5 time, merge petroleum ether layer, concentrating under reduced pressure, obtained Trifolium pratense petroleum ether part;
B. the preparation of Trifolium pratense ethyl acetate extract extract: add ethyl acetate in the aqueous solution after petroleum ether extraction, thermal agitation, stratification, supernatant is ethyl acetate layer, lower aqueous solution ethyl acetate re-extract 2-5 time, combined ethyl acetate layer, concentrating under reduced pressure, obtained Trifolium pratense ethyl acetate extract.
2. the preparation method of a kind of Trifolium pratense extract according to claim 1, is characterized in that, described ethanol water, and addition is 5-50 times of dry powder volume, and ethanol water concentration is 20-100wt%; Ultrasonic or heating and refluxing extraction 10-90 minute.
3. the preparation method of a kind of Trifolium pratense extract according to claim 1, is characterized in that:
Described step 2) step a in, the Trifolium pratense extract distilled water of its 2-50 times volume dissolves; Add the petroleum ether of Trifolium pratense extract solution 2-10 times of volume.
Described step 2) step b in, add the ethyl acetate of this solution 2-10 times of volume in the aqueous solution after petroleum ether extraction.
4. the preparation method of a kind of Trifolium pratense extract according to claim 1, it is characterized in that, during concentrating under reduced pressure, temperature is lower than 40 DEG C.
5. the application of a kind of Trifolium pratense extract according to claim 1, is characterized in that: this extract is effective for diabetes control.
6. the application of a kind of Trifolium pratense extract according to claim 5, is characterized in that: this extract hypoglycemic activity composition is formononetin and genistein.
7. the application of a kind of Trifolium pratense extract according to claim 1 and 5, is characterized in that: hypoglycemic activity composition is mainly present in ethyl acetate extract.
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Cited By (3)
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| CN106237315A (en) * | 2016-08-02 | 2016-12-21 | 马南行 | A kind of compositions of external curing diabetes and preparation method thereof |
| CN112972321A (en) * | 2019-12-16 | 2021-06-18 | 兰州大学 | Natural antioxidant for cosmetics and preparation method thereof |
| WO2021120506A1 (en) * | 2019-12-17 | 2021-06-24 | 兰州大学 | Natural food antioxidant and preparation method therefor |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106237315A (en) * | 2016-08-02 | 2016-12-21 | 马南行 | A kind of compositions of external curing diabetes and preparation method thereof |
| CN112972321A (en) * | 2019-12-16 | 2021-06-18 | 兰州大学 | Natural antioxidant for cosmetics and preparation method thereof |
| WO2021120506A1 (en) * | 2019-12-17 | 2021-06-24 | 兰州大学 | Natural food antioxidant and preparation method therefor |
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