CN1726952A - Extract product of fenugreek seeds, its extracting method, and treatment diabetes and complication purposes thereof - Google Patents
Extract product of fenugreek seeds, its extracting method, and treatment diabetes and complication purposes thereof Download PDFInfo
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- 235000001484 Trigonella foenum graecum Nutrition 0.000 title claims abstract description 22
- 244000250129 Trigonella foenum graecum Species 0.000 title claims abstract description 22
- 235000001019 trigonella foenum-graecum Nutrition 0.000 title claims abstract description 22
- 206010012601 diabetes mellitus Diseases 0.000 title claims abstract description 11
- 239000000284 extract Substances 0.000 title claims description 34
- 238000000034 method Methods 0.000 title abstract description 8
- 210000004369 blood Anatomy 0.000 claims abstract description 30
- 239000008280 blood Substances 0.000 claims abstract description 30
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 25
- 239000001917 trigonella foenum graecum l. absolute Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000003208 petroleum Substances 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 238000000605 extraction Methods 0.000 claims description 12
- 239000002021 butanolic extract Substances 0.000 claims description 9
- 230000001603 reducing effect Effects 0.000 claims description 9
- OMDQUFIYNPYJFM-XKDAHURESA-N (2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-[[(2r,3s,4r,5s,6r)-4,5,6-trihydroxy-3-[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@H](O)[C@H](O)O1 OMDQUFIYNPYJFM-XKDAHURESA-N 0.000 claims description 8
- 229920000926 Galactomannan Polymers 0.000 claims description 8
- 229920002678 cellulose Polymers 0.000 claims description 7
- 239000001913 cellulose Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000002024 ethyl acetate extract Substances 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000008103 glucose Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 9
- -1 saponins compound Chemical class 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 5
- 244000068988 Glycine max Species 0.000 description 5
- 229930182490 saponin Natural products 0.000 description 5
- 235000017709 saponins Nutrition 0.000 description 5
- 229930182493 triterpene saponin Natural products 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 4
- HIMXGTXNXJYFGB-UHFFFAOYSA-N alloxan Chemical compound O=C1NC(=O)C(=O)C(=O)N1 HIMXGTXNXJYFGB-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229930003944 flavone Natural products 0.000 description 4
- 235000011949 flavones Nutrition 0.000 description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229930002600 steroidal saponin Natural products 0.000 description 4
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 125000001033 ether group Chemical group 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 230000003914 insulin secretion Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229930182495 oleanane-type triterpene Natural products 0.000 description 3
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 3
- 150000007949 saponins Chemical class 0.000 description 3
- 210000000582 semen Anatomy 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000002791 soaking Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000004043 trisaccharides Chemical class 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 102000004877 Insulin Human genes 0.000 description 2
- 108090001061 Insulin Proteins 0.000 description 2
- 238000012449 Kunming mouse Methods 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- SIHHLZPXQLFPMC-UHFFFAOYSA-N chloroform;methanol;hydrate Chemical compound O.OC.ClC(Cl)Cl SIHHLZPXQLFPMC-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000002481 ethanol extraction Methods 0.000 description 2
- 238000003810 ethyl acetate extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000002212 flavone derivatives Chemical class 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 241000411851 herbal medicine Species 0.000 description 2
- 230000002218 hypoglycaemic effect Effects 0.000 description 2
- 229940125396 insulin Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 230000035764 nutrition Effects 0.000 description 2
- IUCHKMAZAWJNBJ-RCYXVVTDSA-N oleanolic acid 3-O-beta-D-glucosiduronic acid Chemical compound O([C@H]1CC[C@]2(C)[C@H]3CC=C4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@]1(CCC(C[C@H]14)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O IUCHKMAZAWJNBJ-RCYXVVTDSA-N 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000005773 FEN 560 (Fenugreek seed powder) Substances 0.000 description 1
- FOGVNFMUZXDMTR-UHFFFAOYSA-N [Mg].Cl Chemical compound [Mg].Cl FOGVNFMUZXDMTR-UHFFFAOYSA-N 0.000 description 1
- UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000002398 materia medica Substances 0.000 description 1
- 210000004279 orbit Anatomy 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 150000005856 steroid saponins Chemical class 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Medicines Containing Plant Substances (AREA)
Abstract
The present invention relates to extract product of fenugreek seeds, extracting method, diabetes and complication are treated in the pharmaceutical composition and the conduct thereof that contain them, especially as the purposes in blood sugar lowering and the blood fat-reducing product.
Description
Technical field
The present invention relates to extract product of fenugreek seeds, extracting method, diabetes and complication are treated in the pharmaceutical composition and the conduct thereof that contain them, especially as the purposes in blood sugar lowering and the blood fat-reducing product.
Technical background
Fenugreek seed is a kind of traditional Chinese crude drug, has the effect of the kidney warming, cold relieving, pain relieving.Existing report is separated to multiple composition (Shang Mingying, Chinese herbal medicine, 1998,29 (10): 655 such as steroid saponin, flavone, alkaloid from Semen Trigonellae; Acta Pharmaceutica Sinica, 2001,36 (11): 837; CHINA JOURNAL OF CHINESE MATERIA MEDICA, 2002,27 (4): 277; Xu Xuemin, Chinese herbal medicine, 2003,34 (8): 678; I.P.Varshney, Indian J.Chem., 1978,16B:1134; M.Yoshikawa, Chem.Pharm.Bull., 1997,45 (1): 81-87).Relevant fenugreek seed has hypoglycemic activity early existing research report (G.Ribes, Proceedingsof the Society for Experimental Biology and Medicine, 1986,182:159-166 at home and abroad; M.A.Riyad, Planta Med., 1988,54:286; R.D.Sharma, Nutrition Res., 1996,16 (8): 1331; L.Ali, Planta Med., 1995,61:358; Zhu Zhenhai, the Sichuan traditional Chinese medical science, 2000,18 (11): 20; Chen Yiyu, Zhenjiang medical college journal, 2001,11 (2): 163), but wherein effective site and effective ingredient report seldom, not clear and definite as yet.G.Ribes finds that fiber is a blood-sugar decreasing active in kind of the skin.L.Ali finds that the solubility galactomannan has hypoglycemic activity in the seed.Bibliographical information fenugreek seed cholesterol reducing activity, wherein active component is saponins compound (G.Valette, Atherosclerosis, 1984,50:105; R.D.Sharma, Nutrition Reports International, 1986,33 (4): 669; Pierre R.P., Steroids, 1995,60:674).
Summary of the invention
The inventor has now found that after deliberation, the extract product of fenugreek seeds of polysaccharide component such as cellulose or galactomannan not, and this extract has strong blood sugar lowering and effect for reducing blood fat, can stimulate insulin secretion, and this result does not see identical research report.
One aspect of the present invention relates to a kind of extract product of fenugreek seeds, it is characterized in that: not cellulose and galactomannan.
The invention still further relates to the preparation method of extract product of fenugreek seeds, it comprises crude drug fenugreek seed drying and crushing, under room temperature, the normal pressure, obtains fenugreek seed with organic solvent, water-containing organic solvent or flooding and extracts extractum; Extractum reuse petroleum ether, ethyl acetate and n-butyl alcohol continuous extraction, the extract concentrating under reduced pressure obtains petroleum ether, ethyl acetate and n-butanol extract respectively, only keeps n-butanol extract.
The invention still further relates to the product that is used for the treatment of diabetes and complication and blood fat reducing, it comprises extract product of fenugreek seeds and harmless carrier, and wherein said extract product of fenugreek seeds is cellulose and galactomannan not.
The invention further relates to extract product of fenugreek seeds and be used for the treatment of purposes in the product of diabetes and complication and blood fat reducing in preparation, wherein said extract product of fenugreek seeds is cellulose and galactomannan not.
Further, in preparation method of the present invention, crude drug fenugreek seed powder is generally 1 with the w/v that soaks with organic solvent, water-containing organic solvent or water: 5-15 (kg/liter).Soak time is generally greater than 24 hours, general 0 ℃-60 ℃ of soaking temperature.Used organic solvent comprises methanol, ethanol, propanol, acetone.
Extraction, the extraction of extract extractum was divided into for three steps, and the first step adopts the low polar solvent extraction, comprises petroleum ether, carbon tetrachloride, cyclohexane extraction and benzene, preferably uses petroleum ether.Second step adopted the Semi-polarity solvent to comprise ethyl acetate, and chloroform, ether are preferably used ethyl acetate.The 3rd step adopted than the high polarity solvent, n-butanol.
Extract product of fenugreek seeds extractum weight and extractant volume ratio 1: 5～15 (grams per milliliter).With petroleum ether room temperature extraction 2 times, petroleum ether extraction liquid concentrating under reduced pressure obtains petroleum ether part earlier.Extraction residue ethyl acetate extraction 2 times, the acetic acid ethyl acetate extract concentrating under reduced pressure obtains ethyl acetate extract.Ethyl acetate extraction residue reuse n-butanol extraction 2 times, the butanol extraction liquid concentrating under reduced pressure obtains n-butanol portion or n-butanol extract.
Concentrate the temperature that reaches the extract concentrating under reduced pressure and generally be equal to or less than 60 ℃.
N-butanol portion in the extract product of fenugreek seeds of the present invention mainly contains flavone, triterpene saponin and steroidal saponin.As contain tricin-7-O-β-D-glycoside, the oleanane-type triterpene saponin of trisaccharide (soybean saponin I), soybean saponin I methyl ester, compositions such as Semen Trigonellae steroidal saponin.
Product of the present invention comprises the product that orally uses with non-intestinal use, as oral liquid, and tablet, granule, capsule or injection.Product of the present invention also can be understood functional food or health product.Further, harmless carrier is meant that pharmacy or field of food allow the known carrier that uses among the present invention.
Further, extract product of fenugreek seeds can be regarded as the n-butanol extract of fenugreek seed among the present invention.
The specific embodiment
Embodiment 1
Fenugreek seed 2kg pulverizes, and sieve (20 order) added 95% medical ethanol 16L soaking at room temperature 72 hours, constantly stirs.Four layers of filtered through gauze, residue continue to soak 48 hours with 95% ethanol 8L, filter.Merging filtrate, centrifugal, 45 ℃ of concentrating under reduced pressure of supernatant obtain ethanol extract 155.6 grams, and yield is 7.8%.Fenugreek seed alcohol-extracted extract 500g adds 100ml water and grinds to form emulsion, uses 5000ml petroleum ether extraction three times, collects ether layer solution decompression and concentrates, and obtains petroleum ether part.Debris extracts three times with ethyl acetate 2000ml, and the extract concentrating under reduced pressure obtains ethyl acetate extract.Debris reuse 3000ml n-butanol extraction three times, the extract concentrating under reduced pressure obtains n-butanol portion or n-butanol extract 69.17 grams, and yield is 1.8%.
Semen Trigonellae 95% ethanol extraction residue 1kg constantly stirs with distilled water 8L soaking at room temperature 72h.Soak filters, and residue continues to soak 24h again with distilled water 4L, filtration, merging filtrate, concentrating under reduced pressure, 55 ℃ dry the water extracted immersing paste 177.4g, yield is 17.7%.
Embodiment 2
The n-butanol portion of the fenugreek seed that embodiment is obtained a little, be dissolved in the methanol, carry out thin layer chromatography.
Chromatoplate: the G254 silica gel plate,
Developing solvent condition (1) ethyl acetate: methanol=1: 3 (2) ethyl acetate: methanol: water=1: 2: 1
Color condition: fluorescence, λ=254,365.
The iodine fumigation
Method (1) Rf value: 0.55 (λ
365, I
2) method (2) Rf value: 0.83 (λ
365)
0.47(I
2) 0.79(I
2)
0.43(λ
254，I
2) 0.58(λ
254，I
2)
0.39(I
2) 0.37(I
2)
0.20(I
2) 0.28(λ
254，I
2)
0.09(λ
254，I
2) 0.20(λ
365，I
2)
0.06(I
2) 0.09(I
2)
Adopt hydrochloric acid-magnesium powder method of inspection to identify n-butanol portion and be positive, show and contain flavone compound; Acetic anhydride-strong sulfuric acid response is positive, and shows to contain saponins compound; Chloroform-strong sulfuric acid response is positive, and shows to contain terpenoid and steroid compound; The alpha-Naphthol strong sulfuric acid response is positive, and shows to contain the reducing sugar glycosides compound.
Polysaccharide in concentrated sulphuric acid-phynol method check water extract is positive.
Embodiment 3
The n-butanol portion of the extract product of fenugreek seeds that embodiment 1 is obtained is through D
101Macroporous resin column chromatography, respectively with water, 30%, 50%, 70%, 95% ethanol elution, 50% ethanol part is separated chloroform-methanol-water gradient elution through silica gel chromatographic column, obtaining a flavone compound is tricin-7-O-β-D-glycoside, be characterized as: yellow needle, fusing point 246-248 ℃, IR (KBr) cm
-1: 3378,1655,1598,1491.
1H-NMR(DMSO)δ：12.96，9.40，3.88，6.46，6.87，7.08，7.36，5.05，3.24，-3.73。
13C-NMR(DMSO)δ：182.1，56.4，100.1，60.6-77.4。
30% ethanol part is separated through silica gel chromatographic column, and chloroform-methanol-water gradient elution obtains 3 triterpene saponin and 1 steroidal saponin.Triterpene saponin is oleanane-type triterpene saponin (soybean saponin I) and 1 soybean saponin I methyl ester of 2 trisaccharides.One of them triterpene saponin is characterized as: white powder, fusing point 228-231 ℃, IR (KBr) cm
-1: 3410,1625,1355-1392.
1H-NMR(C
5D
5N)δ：0.69，0.95，1.00，1.22，1.29，1.39，1.75，2.40，3.23，4.23，3.74，6.25。
13C-NMR(DMSO)δ：122.3，144.8，172.3，105.3，102.3，101.7。Another triterpene saponin feature: white powder, fusing point 280-282 ℃, Preliminary Identification is the trisaccharide oleanane-type triterpene saponin.Soybean saponin I methyl ester is characterized as: white powder, fusing point 247-249 ℃, IR (KBr) cm
-1: 3424,2926,1731,1619,1382,1050.
1H-NMR(DMSO)δ：0.75-1.14，3.67，4.74，4.95，5.16；
13C-NMR(DMSO)δ：169.2，144.1，121.5，103.7，100.2，100.0，51.7。Steroidal saponin is characterized as colourless acicular crystal, and fusing point 173-175 ℃, IR (KBr) cm
-1: 3390,1627,1033.
1H-NMR(DMSO)δ：4.96，4.83，4.97，3.94，3.62，3.95，3.68，1.62，1.03，0.73，0.70；
13C-NMR(DMSO)δ：152.3，104.8，103.6，105.3，17.3，14.4，13.2，11.7。
Embodiment 4
50 kunming mices are divided into normal control group (10) at random and treat modeling group (40).Treat that the fasting of modeling group mice (can't help water) after 24 hours, tail vein fast injection alloxan normal saline solution, dosage is 60mgkg
-1The tail point is got hematometry mouse blood sugar, blood glucose value＞20.0mmolL behind the 72h
-1Mice be chosen as diabetic mice, be divided into model group (10) and embodiment 1 n-butanol extract group (abbreviation group A from now on) 1g.kg
-1Group (10), water extract group 1g.kg
-1Group (10), gastric infusion is 20 days continuously, the 7th day mensuration blood glucose, the 20th day mensuration blood glucose.Data represent that with X ± SD two groups of mean differences are checked with t.
Table 1 fenugreek seed 95% ethanol extraction blood sugar lowering experimental result
| The 0th day blood glucose | The 7th day blood glucose | The 20th day blood glucose | |
| Matched group model group group A water extract group | 7.61±1.03 24.80±3.52 24.00±3.38 24.10±3.52 | 7.43±0.60 24.57±4.60 17.28±8.04 * 21.57±3.75 | 7.65±1.11 25.67±3.56 16.57±8.58 * 20.72±4.09 |
Annotate: compare with model group,
*P＜0.05.
Embodiment 5
100 kunming mices are divided into normal control group (10) at random and treat modeling group (90).Treat that the fasting of modeling group mice (can't help water) after 24 hours, tail vein fast injection alloxan normal saline solution, dosage is 60mgkg
-1The tail point is got hematometry mouse blood sugar, blood glucose value＞20.0mmolL behind the 72h
-1Mice be chosen as diabetic mice, be divided into model group (10) and petroleum ether part (10), ethyl acetate extract 1g.kg
-1Group (10), the n-butanol portion of embodiment 1 (10).Irritate stomach, dosage 800mg/kg, successive administration 20 days was measured blood glucose on the 7th day, and behind the 21st day mensuration blood glucose, eye socket is got blood, puts to death, and measures triglyceride and insulin level in the mice serum.Data represent that with X ± SD two groups of mean differences are checked with t.Experimental result shows that n-butanol portion has remarkable blood sugar lowering and effect for reducing blood fat, and diabetic mice is had the effect of the insulin secretion of promotion.
Table 2 fenugreek seed n-butanol portion blood sugar lowering experimental result
| The 0th day blood glucose | The 7th day blood glucose | The 21st day blood glucose | |
| Matched group model group petroleum ether group ethyl acetate group n-butyl alcohol group | 7.87±1.03 24.02±2.49 23.96±4.10 23.85±3.85 23.84±2.90 | 7.67±0.60 26.20±5.48 25.38±5.24 23.24±6.75 15.54±8.19 * | 6.81±1.11 23.36±5.00 20.20±5.76 16.38±8.64 13.65±7.69 ** |
Annotate: compare with model group,
*P＜0.05,
*P＜0.01.
Blood fat reducing of table 3 fenugreek seed n-butanol portion and promotion insulin secretion experimental result
| In the 21st day blood plasma | ||
| Triglyceride levels (mmol/L) | Insulin level (μ IU/ml) | |
| Matched group model group petroleum ether group ethyl acetate group n-butyl alcohol group | 1.802±0.215 1.884±0.577 1.672±0.436 1.680±0.686 1.396±0.144 *** | 26.36±10.73 13.26±6.64 16.07±4.40 14.73±3.09 20.93±8.19 * |
Annotate: compare with model group,
*P＜0.05,
* *P＜0.001.
Claims (5)
1. extract product of fenugreek seeds is characterized in that: not cellulose and galactomannan.
2. the preparation method of extract product of fenugreek seeds, it comprises crude drug fenugreek seed drying and crushing, under room temperature, the normal pressure, obtains fenugreek seed with organic solvent, water-containing organic solvent or flooding and extracts extractum; Extractum reuse petroleum ether, ethyl acetate and n-butyl alcohol continuous extraction, the extract concentrating under reduced pressure obtains petroleum ether, ethyl acetate and n-butanol extract respectively, only keeps n-butanol extract.
3. the product that is used for the treatment of diabetes and complication thereof and blood fat reducing, it comprises extract product of fenugreek seeds and harmless carrier, wherein said extract product of fenugreek seeds is cellulose and galactomannan not.
4. extract product of fenugreek seeds is used for the treatment of purposes in the product of diabetes and complication and blood fat reducing in preparation, and wherein said extract product of fenugreek seeds is cellulose and galactomannan not.
5. the extract product of fenugreek seeds of claim 1, wherein said extract is the n-butanol extract of fenugreek seed.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010140165A1 (en) | 2009-06-01 | 2010-12-09 | Kumar Pawan Goel | A novel antidiabetic furostanolic saponin rich (fsr) fraction from fenugreek seeds |
| CN101703208B (en) * | 2009-11-20 | 2012-02-08 | 天津农学院 | Preparation method of edible coriander powder |
| CN102670697A (en) * | 2012-05-14 | 2012-09-19 | 新疆医科大学 | Fenugreek aqueous extract, and preparation and application thereof |
| CN102988464A (en) * | 2008-05-13 | 2013-03-27 | 赛图彼奥有限公司 | Fenugreek extract for treating human and animal diseases involving flagellate parasites |
| JP2017210473A (en) * | 2016-05-23 | 2017-11-30 | アークレイ株式会社 | Oxidized protein hydrolase activity enhancing agent and glycation stress inhibitor |
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2004
- 2004-07-27 CN CN 200410071030 patent/CN1726952A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102988464A (en) * | 2008-05-13 | 2013-03-27 | 赛图彼奥有限公司 | Fenugreek extract for treating human and animal diseases involving flagellate parasites |
| CN102988464B (en) * | 2008-05-13 | 2014-10-22 | 赛图彼奥有限公司 | Application of Fenugreek extract in preparation of composition comprising Fenugreek water extract and excipient |
| WO2010140165A1 (en) | 2009-06-01 | 2010-12-09 | Kumar Pawan Goel | A novel antidiabetic furostanolic saponin rich (fsr) fraction from fenugreek seeds |
| CN102448479A (en) * | 2009-06-01 | 2012-05-09 | 库马尔·帕万·戈埃尔 | Novel antidiabetic furostanol saponin-rich (FSR) fraction from fenugreek seeds |
| CN102448479B (en) * | 2009-06-01 | 2014-07-23 | 库马尔·帕万·戈埃尔 | Novel antidiabetic Furostanolic Saponin Rich (FSR) fraction from fenugreek seeds |
| CN101703208B (en) * | 2009-11-20 | 2012-02-08 | 天津农学院 | Preparation method of edible coriander powder |
| CN102670697A (en) * | 2012-05-14 | 2012-09-19 | 新疆医科大学 | Fenugreek aqueous extract, and preparation and application thereof |
| JP2017210473A (en) * | 2016-05-23 | 2017-11-30 | アークレイ株式会社 | Oxidized protein hydrolase activity enhancing agent and glycation stress inhibitor |
| JP7007813B2 (en) | 2016-05-23 | 2022-01-25 | アークレイ株式会社 | Oxidizing proteolytic enzyme activity enhancer and glycation stress inhibitor |
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