CN101406498A - Effective hypoglycemic component of may flower and preparation method and use thereof - Google Patents
Effective hypoglycemic component of may flower and preparation method and use thereof Download PDFInfo
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- CN101406498A CN101406498A CNA2008102309654A CN200810230965A CN101406498A CN 101406498 A CN101406498 A CN 101406498A CN A2008102309654 A CNA2008102309654 A CN A2008102309654A CN 200810230965 A CN200810230965 A CN 200810230965A CN 101406498 A CN101406498 A CN 101406498A
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Abstract
The invention discloses a hypoglycemic effective position for sweet osmanthus, a preparation method and application thereof. The effective position is an ethyl acetate position and/or a normal butanol position which is obtained by taking sweet osmanthus as a raw material, and after extraction of condensate by crushing, cold soaking, filtration and vacuum recovery. The hypoglycemic effective position, namely ethyl acetate extract, has obvious activity in inhibiting alpha-glucosaccharase; and hypoglycemic effective constituents obtained from the effective position, namely an ursolic acid and an oleanolic acid, also have high activity in inhibiting the alpha-glucosaccharase, wherein the IC50 value (the half inhibition ratio) is 0.003Mug.m L <-1>, and the activity of the ursolic acid and the oleanolic acid in inhibiting the alpha-glucosaccharase is better than that of a hypoglycemic medicine - acarbose (the IC50 value is 1,081.27 Mug.m L <-1>) which is commonly used on clinic under the same condition.
Description
Technical field
The present invention relates to a kind of effective hypoglycemic component of may flower and preparation method thereof and extract effective ingredient that obtains and preparation method thereof by this effective site, simultaneously, also relate to the application of this effective site and effective ingredient.
Background technology
Diabetes be a kind of be feature with the hyperglycemia, metabolism disorder for the performance, with the closely-related systemic disease of insulin secretion, be the clinical syndrome that causes owing to the h and E factor interaction.Absolute or relative deficiency and target tissue reduce insulin sensitivity because of insulin secretion, cause a series of metabolism disorders such as sugar, albumen, fat, power and water Xie Zhi.Diabetes mainly are divided into two types: type i diabetes (being insulin dependent diabetes mellitus (IDDM)) and type ii diabetes (being non-insulin-dependent diabetes mellitus), the latter accounts for the 99%-95% of patient's sum.The clinical manifestation of diabetes is more than three (polyphagia, polydipsia, polyurias), few (weight loss) and a hyperglycemia symptom.The complication that diabetes cause (as acute complicationses such as cardiovascular, kidney, retina and neural chronic complicating diseases, diabetic ketoacidosis, hyperosmolar nonketotic diabetic comas) is the main cause that causes death, all diabetic complications can be by strict glycemic control, from preventing to the full extent, the blood sugar level of oneself can be controlled near in the normal range of blood sugar as the fructosuria patient, then diabetic complication just can not occur, and perhaps occurs than later and degree is also lighter.At present, China's diabetics is about 1,200 ten thousand, and the whole world is about 1.5 hundred million, has become to threaten human No. 3 " healthy killer ", and therefore prevention and treatment diabetes have become global problem.Treatment of diabetes is a target with the control fasting glucose mainly for many years, and medicine mainly concentrates on sulphanylureas and biguanides for a long time.Recent study is found, post-prandial glycemia also is the main hazard factor that diabetic complication takes place, post-prandial glycemia is the highest stage of blood sugar level in one day, its persistent period can be for 8 hour or is longer, long-time high-caliber post-prandial glycemia can increase the weight of diabetes itself, blood glucose is further raise, if at table with regard to energy better controlled hyperglycemia, then can avoid its after the meal the sugar in the blood circulation pile up, therefore, the control post-prandial glycemia is the control hyperglycemia, prevents and treats the important behave of diabetes.In the existing treatment diabetes medicament, sulfonylurea drugs is blood sugar lowering by stimulating secretion of insulin; Biguanides then is by increasing peripheral tissues to the utilization of glucose and blood sugar lowering, and both all have better curative effect to reducing type ii diabetes patient fasting glucose, but very limited to the effect that reduces post-prandial glycemia.
Most carbohydrates in the food are starch and sucrose etc., starch earlier after in saliva and the pancreatic juice α-Dian Fenmei be decomposed into oligosaccharide, oligosaccharide is decomposed into glucose at intestinal epithelial cell brush border place by alpha-glucosidase and after being absorbed, cause the post-prandial glycemia peak, therefore, the activity of inhibition alpha-glucosidase becomes an effective way that reduces post-prandial glycemia.Alpha-glucosidase inhibitor is a class new oral hypoglycemic drug of researching and developing out in the seventies later stage, has been recommended as a line medicine that falls post-prandial glycemia for three times by Asian-Pacific area Remedies for diabetes guide.Its mechanism of action is: emulative inhibition alpha-glucosidase, delay and hinder the digestion of carbohydrate, delay is from the absorption of the glucose of disaccharidase, oligosaccharide and polysaccharide, effectively postpone and alleviate the time and the degree of post-prandial glycemia rising, take for a long time and can also reduce fasting blood glucose level, this type of medicine all is suitable for I, type ii diabetes.Alpha-glucosidase inhibitor not only has definite curative effect to diabetes, and for obesity, chronic viral hepatitis B, acquired immune deficiency syndrome (AIDS) and tumor certain therapeutical effect is arranged all.Be used for this type of clinical medicine at present acarbose, voglibose and miglitol are arranged.
Diabetes are chronic diseases, positive health preserving in Drug therapy, health care are particularly important to the raising of the control of conditions of patients and quality of life, thereby the health food of developing medicine and having a specific function is the important channel of diabetes mellitus prevention and auxiliary treatment.The existing medicine cost that is used for the treatment of diabetes is higher, and has significant side effects: as borborygmus, abdominal distention, feel sick, vomiting etc.Chinese medicine and natural plant have comparatively safe and cheap characteristics, and exploitation Chinese medicine and natural plant can provide Remedies for diabetes source widely as the phlorose enzyme inhibitor; Simultaneously, the most of Chinese medicine of China all has the effect of medicine-food two-purpose, can be developed as health food diabetes are prevented and auxiliary treatment.
Flos Osmanthi Fragrantis has another name called sweet-scented osmanthus, Folium Et Cacumen Murrayae, Jin Su, is the Oleaceae aiphyllium.The various plants that " Flos Osmanthi Fragrantis " general reference Oleaceae sweet-scented osmanthus that is commonly called as among the people belongs to.China is the world distribution center of this platymiscium.Add up according to " Chinese Plants will ", totally 25 kinds of China osmanthus, account for more than 80% of 30 kinds in the whole world, at the existing cultivation history in 2500 of China, be distributed in to the north of the southern mountain range on the south the Basin of Huaihe River of the Qinling Mountains, north has formed historic five big Flos Osmanthi Fragrantis producing regions such as Suzhou, Jiangsu, xianning,hubei, Chengdu, Sichuan, Zhejiang Hangzhou and Guilin to the Shandong Peninsula and other places, produces 1000000 kilograms of dry flowers per year.Flos Osmanthi Fragrantis is as the famous flower and tree of China, and its fragrance of a flower is elegant, gladdens the heart and refresh the mind, and except that having very high ornamental value, still can eat, medicinal.Ming Dynasty's Li Shizhen (1518-1593 A.D.) Compendium of Material Medica is carried: " that Flos Osmanthi Fragrantis is promoted the production of body fluid, wards off is smelly, reduce phlegm, and controls acute toothache." modern study shows that Flos Osmanthi Fragrantis still contains higher nutritive value, its total amino acids content also is usually used in beauty treatment and dietetic therapy up to 3.78%.Flos Osmanthi Fragrantis is mainly used in the production of traditional Flos Osmanthi Fragrantis food and high-grade spice, and the application of Flos Osmanthi Fragrantis medical value aspect is not still reported.
Summary of the invention
The object of the present invention is to provide a kind of effective hypoglycemic component of may flower.
Simultaneously, the present invention also aims to provide a kind of preparation method of this blood-sugar-lowering effective parts.
The present invention also aims to provide a kind of blood sugar lowering effective ingredient that extracts from effective hypoglycemic component of may flower; Simultaneously, also related to this extraction of effective components.
Further, the present invention also aims to provide the application aspect blood sugar lowering of a kind of Flos Osmanthi Fragrantis and effective site and effective ingredient thereof.
To achieve these goals, technical scheme of the present invention has adopted a kind of effective hypoglycemic component of may flower, this effective site is for (general reference Oleaceae sweet-scented osmanthus belongs to the flower of Flos Osmanthi Fragrantis by Flos Osmanthi Fragrantis, the position flower that comprises Flos Osmanthi Fragrantis such as Osmanthus fragrans var.thunbergii. in four strains group silver osmanthus class, Osmanthus fragrans var.thunbergii. class, Osmanthus tragranscv.Aurantiacu class, the four seasons osmanthus class, Osmanthus tragranscv.Aurantiacu, four seasons osmanthus, the Buddhist decorative pearl on top of an official cap) is raw material, get concentrate through pulverizing, merceration, filtration and through reclaim under reduced pressure, the ethyl acetate extract and/or the n-butanol portion that obtain after the concentrate extraction.
Described effective site is preferably ethyl acetate extract.
Technical scheme of the present invention has also adopted a kind of preparation method of effective hypoglycemic component of may flower, specifically comprise and following step: (general reference Oleaceae sweet-scented osmanthus belongs to the flower of Flos Osmanthi Fragrantis to get dry Flos Osmanthi Fragrantis Osmanthus fragrans Lour., comprise four strains group silver osmanthus class, the Osmanthus fragrans var.thunbergii. class, the Osmanthus tragranscv.Aurantiacu class, Osmanthus fragrans var.thunbergii. in the four seasons osmanthus class, Osmanthus tragranscv.Aurantiacu, four seasons osmanthus, the position flower of Flos Osmanthi Fragrantis such as the Buddhist decorative pearl on top of an official cap), pulverize, with acetone and water or pure merceration 2-4 time, each 5-9 days, filter, merging filtrate, decompression and solvent recovery gets concentrate, spissated extract is dispersed in the water, use petroleum ether successively, ethyl acetate, n-butyl alcohol respectively extracts 2-4 time, gets corresponding petroleum ether part, ethyl acetate extract and n-butanol portion.
The volume ratio of described acetone and water is: acetone: water=(6-8): (2-4).
Described alcohol is any one in methanol, ethanol, propanol or the butanols.
In addition, technical scheme of the present invention has also adopted a kind of Flos Osmanthi Fragrantis blood sugar lowering effective ingredient and preparation method thereof, this effective ingredient is with effective site---ethyl acetate extract is through 200～300 order silica gel column chromatographies, with chloroform: methanol (100: 1 → 8: 2) carries out gradient elution, obtains having the part that suppresses alpha-glucosidase activity; Through the silica gel H column chromatography, petroleum ether-acetone (20: 1) eluting detects merging with TLC with this part, and through Sephadex LH-20 column chromatography, the acetone eluting obtains chemical compound 1 ursolic acid and chemical compound 2 oleanolic acid are the blood sugar lowering effective ingredient.
Say that further technical scheme of the present invention has also adopted the application of a kind of Flos Osmanthi Fragrantis aspect blood sugar lowering.
Technical scheme of the present invention has also adopted the application of a kind of effective hypoglycemic component of may flower aspect blood sugar lowering.
Technical scheme of the present invention has also adopted the application of a kind of Flos Osmanthi Fragrantis blood sugar lowering effective ingredient aspect blood sugar lowering.
The present invention extracts from Flos Osmanthi Fragrantis (comprising other osmanthus cultivars that sweet-scented osmanthus belongs to) has the method that alpha-glucosidase suppresses active substance, and Flos Osmanthi Fragrantis extract is disclosed and the chemical compound that therefrom obtains is used to suppress this new purposes of alpha-glucosidase activity, for enlarging the screening scope of blood sugar lowering class medicine, exploitation plant class blood sugar lowering medicine provides new approach.Blood-sugar-lowering effective parts-ethyl acetate extract of the present invention has the activity of obvious suppression alpha-glucosidase; The blood sugar lowering effective ingredient that obtains from this effective site---ursolic acid and oleanolic acid also has very high alpha-glucosidase and suppresses active, IC
50Value (half suppression ratio) is 0.003 μ gm L
-1, under the same conditions than clinical antidiabetic drug acarbose (IC commonly used
50Be 1081.27 μ gm L
-1) alpha-glucosidase suppress active will be good many.The Flos Osmanthi Fragrantis effective ingredient is accredited as ursolic acid and oleanolic acid through structure, from any crude drug that contains ursolic acid and oleanolic acid.Oleanolic acid and ursolic acid are widely distributed and be easy to get in plant, and this just makes raw material of the present invention be easy to get, and cost is very low.Flos Osmanthi Fragrantis is as the distinctive plant of China, effect with medicine-food two-purpose, experimentation shows that Flos Osmanthi Fragrantis extract has good α-glucoside enzyme inhibition activity, itself both can be used as health product diabetes had been carried out auxiliary treatment, can further research and develop it again, prepare natural alpha-glucosidase inhibitor.
Experimentation shows: Flos Osmanthi Fragrantis is used to can be used for suppressing alpha-glucosidase activity in field of medicaments, Flos Osmanthi Fragrantis extract has alpha-glucosidase and suppresses active, and the activity intensity and the present widely used hypoglycemic drug acarbose of particularly fat-soluble extractive part of its extract and the effective ingredient chemical compound that therefrom obtains thereof are higher.
The specific embodiment
Embodiment 1
Present embodiment is the extracting method and the preliminary screening active ingredients of each effective site of Flos Osmanthi Fragrantis
The extracting method of effective site is specially: gets dry Osmanthus fragrans var.thunbergii. (1.9kg), pulverizes, and with acetone and water (volume ratio is 7: 3)/pure merceration 3 times, each 7 days, filtration, merging filtrate, decompression and solvent recovery gets concentrate; Spissated extract is dispersed in the water, respectively extracts 3 times with petroleum ether, ethyl acetate, n-butyl alcohol successively, get corresponding extract 10g, 33.4g, 400g.Extract used alcohol in the present embodiment and be preferably ethanol.
Determination of activity:
Method: microwell plate method
Principle: alpha-D-glucose glycosides enzymatic hydrolysis 4-Nitrobenzol-α-D-pyranglucoside (PNP-G), produce nitrophenol (PNP, yellow substance has absorption maximum about 400m), thereby can suppressing alpha-glucosidase, alpha-glucosidase inhibitor combines the burst size that reduces PNP with substrate.Calculate the enzyme inhibition activity of extract with the changes of contents of PNP in the certain hour internal reaction system.
Instrument: Multiskan MK3 microplate reader (thermoelectric Shanghai Instr Ltd.), 96 microwell plates, all size pipettor, the biochemical incubator (Shanghai one permanent Science and Technology Ltd.) of LRH-150.
Reagent: alpha-glucosidase (Sigma company, EC 3.2.1.20, from baker ' s yeast, lot number: 105K1313), right-nitrobenzophenone-α-D-pyranglucoside (PNPG, Sigma company, lot number: 026K1516), phosphate buffer (PH 6.8), acarbose (acarbose, Sigma company, lot number: 16869), other reagent are analytical pure.
Detection method:
112L kaliumphosphate buffer (pH 6.8) adds 20 μ L (concentration is 0.2U/mL) alpha-glucosidase, 8 μ L sample solutions, and 37 ℃ of constant temperature 15min add 20 μ L 2.5mmol/L PNPG, 37 ℃ of isothermal reaction 15min.The terminator Na that adds 80 μ L (concentration is 0.2mol/L) again
2CO
3Solution is surveyed the OD value down in the 405nm wavelength.4 groups are established in experiment altogether, and every group three hole is respectively: a. negative control group; B. blank group; C. sample determination group; D. sample matched group.Calculate suppression ratio by following method, and obtain corresponding IC with Origin software
50Value.
Experimental result is as shown in table 1: Flos Osmanthi Fragrantis ethyl acetate and n-butanol extract all than the alpha-glucosidase of clinical antidiabetic drug acarbose commonly used suppress active will be good many, and half suppression ratio IC
50More definite demonstration ethyl acetate extract can be used as the effective site that Dian clove suppresses alpha-glucosidase.
The alpha-glucosidase of the different extracts of table 1 Flos Osmanthi Fragrantis suppresses active
Annotate: ND is a undetermined
Embodiment 2
Present embodiment is under activity instructs, and prepares the method for blood sugar lowering effective ingredient reactive compound from Flos Osmanthi Fragrantis ethyl acetate effective site
The preparation method of blood sugar lowering effective ingredient is specific as follows: with ethyl acetate part 33.4g through 200～300 order silica gel column chromatographies, with chloroform: methanol (100: 1 → 8: 2) carries out gradient elution, obtains having the part that suppresses alpha-glucosidase activity; Through the silica gel H column chromatography, petroleum ether-acetone (20: 1) eluting detects merging with TLC with this part, and through Sephadex LH-20 column chromatography, the acetone eluting obtains chemical compound 1 (100.2mg), 2 (11.2mg).
Embodiment 3
Present embodiment suppresses the determination of activity of alpha-glucosidase for the chemical compound that obtains from Flos Osmanthi Fragrantis.
Assay method: with embodiment 1.
Measurement result: experimental result sees Table 2.The activity of the inhibition alpha-glucosidase of ursolic acid and oleanolic acid is up to 107.0%, and the half suppression ratio only is 0.003 μ gm L
-1, than the alpha-glucosidase of clinical antidiabetic drug acarbose commonly used suppress active will be good many, can be used as the main pharmacodynamics composition that Flos Osmanthi Fragrantis suppresses alpha-glucosidase activity and develop.And can further inquire into the hypoglycemic activity of active component and the relation of chemical constitution in detail, have important function to finding efficient, safe reduction post-prandial glycemia novel drugs.
The alpha-glucosidase of chemical compound suppresses active in table 2 Flos Osmanthi Fragrantis
Annotate: the primary dcreening operation final concentration of Acarbose is 1.5mgm L
-1
Embodiment 4
Present embodiment is that the structure that has the inhibiting active component of alpha-glucosidase in the Flos Osmanthi Fragrantis is identified.
Chemical compound 1: white powder, 305～308 ℃ of mp.EIMS?m/z(％)：456[M]
+(20)，410(8)，248(100)，233(30)，213(75)，175(33)，131(30)，119(40)，105(45)，91(35)。
1H NMR (400MHz, C
5D
5N) and
13C NMR (100MHz, C
5D
5N) data are consistent with bibliographical information, determine that chemical compound 1 is ursolic acid (ursolic acid)
Chemical compound 2: white powder,
1H-NMR (400MHz, C
5D
5N) there are δ 5.49 (1H, brs) ethylene linkage proton signal in the collection of illustrative plates; δ 0.88 (3H, s), 0.95 (3H, s), 0.98 (3H, s), 1.05 (3H, s), 1.22 (3H, s), 1.24 (3H, s) 7 methyl signals.
13C-NMR (400 MHz, C
5D
5N) there are 30 carbon signals in the collection of illustrative plates, demonstrate the pentacyclic triterpene structure type.Wherein, 1 carbonyl signal (δ 179.9), 1 pair of double key carbon signal (δ 144.7 and 122.4), the chemical shift of this pair key shows that this chemical compound is an oleanolic acid type triterpene skeleton.Its POP data are consistent with document, and authenticating compound is oleanolic acid (Oleanolic acid).
Claims (10)
1, a kind of effective hypoglycemic component of may flower is characterized in that: this effective site is for being raw material by Flos Osmanthi Fragrantis, gets concentrate, the ethyl acetate extract and/or the n-butanol portion that obtain after the concentrate extraction through pulverizing, merceration, filtration and through reclaim under reduced pressure.
2, effective hypoglycemic component of may flower according to claim 1 is characterized in that: described effective site is preferably ethyl acetate extract.
3, a kind of preparation method of effective hypoglycemic component of may flower as claimed in claim 1, it is characterized in that: comprise and following step: get dry Flos Osmanthi Fragrantis, pulverize, use acetone and water or pure merceration 2-4 time, each 5-9 days, filter, merging filtrate, decompression and solvent recovery gets concentrate, and spissated extract is dispersed in the water, respectively extract 2-4 time with petroleum ether, ethyl acetate, n-butyl alcohol successively, get corresponding petroleum ether part, ethyl acetate extract and n-butanol portion.
4, the preparation method of effective hypoglycemic component of may flower according to claim 3 is characterized in that: the volume ratio of described acetone and water is acetone: water=(6-8): (2-4).
5, the preparation method of effective hypoglycemic component of may flower according to claim 4 is characterized in that: described alcohol is any one in methanol, ethanol, propanol or the butanols.
6, a kind of Flos Osmanthi Fragrantis blood sugar lowering effective ingredient, it is characterized in that: this effective ingredient is with effective site---ethyl acetate extract is through 200～300 order silica gel column chromatographies, with chloroform: methanol (100: 1 → 8: 2) carries out gradient elution, obtains having the part that suppresses alpha-glucosidase activity; Through the silica gel H column chromatography, petroleum ether-acetone (20: 1) eluting detects merging with TLC with this part, and through Sephadex LH-20 column chromatography, the acetone eluting obtains chemical compound 1 ursolic acid and chemical compound 2 oleanolic acid are the blood sugar lowering effective ingredient.
7, a kind of preparation method of Flos Osmanthi Fragrantis blood sugar lowering effective ingredient as claimed in claim 6, it is characterized in that: the preparation method of this effective ingredient specifically may further comprise the steps: with effective site---and ethyl acetate extract is through 200～300 order silica gel column chromatographies, with chloroform: methanol (100: 1 → 8: 2) carries out gradient elution, obtains having the part that suppresses alpha-glucosidase activity; Through the silica gel H column chromatography, petroleum ether-acetone (20: 1) eluting detects merging with TLC with this part, and through Sephadex LH-20 column chromatography, the acetone eluting obtains chemical compound 1 ursolic acid and chemical compound 2 oleanolic acid are the blood sugar lowering effective ingredient.
8, the application of a kind of Flos Osmanthi Fragrantis aspect blood sugar lowering.
9, a kind of by the prepared effective hypoglycemic component of may flower of Flos Osmanthi Fragrantis in the application aspect the blood sugar lowering.
10, a kind of Flos Osmanthi Fragrantis blood sugar lowering effective ingredient that is prepared by effective hypoglycemic component of may flower is in the application aspect the blood sugar lowering.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103751269A (en) * | 2014-01-09 | 2014-04-30 | 黄河科技学院 | Application of herba rabdosiae rubescentis extract to alpha-glucosidase inhibitor |
| CN111248440A (en) * | 2020-02-25 | 2020-06-09 | 广西壮族自治区农业科学院 | Functional jasmine flower oligosaccharide oral liquid and application thereof |
-
2008
- 2008-11-20 CN CNA2008102309654A patent/CN101406498A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103751269A (en) * | 2014-01-09 | 2014-04-30 | 黄河科技学院 | Application of herba rabdosiae rubescentis extract to alpha-glucosidase inhibitor |
| CN103751269B (en) * | 2014-01-09 | 2016-08-17 | 黄河科技学院 | Rabdosia rubescens extract application in alpha-glucosidase inhibitor |
| CN111248440A (en) * | 2020-02-25 | 2020-06-09 | 广西壮族自治区农业科学院 | Functional jasmine flower oligosaccharide oral liquid and application thereof |
| CN111248440B (en) * | 2020-02-25 | 2023-04-07 | 广西壮族自治区农业科学院 | Functional jasmine flower oligosaccharide oral liquid and application thereof |
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Open date: 20090415 |