CN1263102A - New saponin compound and its preparation method and application - Google Patents

New saponin compound and its preparation method and application Download PDF

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Publication number
CN1263102A
CN1263102A CN99100721A CN99100721A CN1263102A CN 1263102 A CN1263102 A CN 1263102A CN 99100721 A CN99100721 A CN 99100721A CN 99100721 A CN99100721 A CN 99100721A CN 1263102 A CN1263102 A CN 1263102A
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saponin compound
new saponin
compound
new
preparation
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CN99100721A
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CN1108306C (en
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叶文才
戴岳
丛晓东
朱兴祥
赵守训
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Guilin Ji Qi Pharmaceutical Co Ltd
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Shandong Luye Pharmaceutical Co Ltd
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Priority to CN99100721A priority Critical patent/CN1108306C/en
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Priority to JP2000598513A priority patent/JP4903309B2/en
Priority to AU20909/00A priority patent/AU2090900A/en
Priority to CA2362864A priority patent/CA2362864C/en
Priority to US09/913,322 priority patent/US6833443B1/en
Priority to EP00901035A priority patent/EP1176149B1/en
Priority to KR1020017010217A priority patent/KR100625222B1/en
Priority to PCT/CN2000/000010 priority patent/WO2000047594A1/en
Priority to DE60004353T priority patent/DE60004353T2/en
Publication of CN1263102A publication Critical patent/CN1263102A/en
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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Abstract

The present invention relates to a new saponin compound, its preparation method and application in preparation of medicine for curing diabetes. Said new saonin compound possesses the functions of reducing blood sugar, reducing blood fat and resisting platelet aggregation,

Description

A kind of new saponin compound and its production and use
The present invention relates to a kind of new saponin compound, this compound has hypoglycemic, lipopenicillinase and anti-platelet aggregation effect, the invention still further relates to the preparation method and its usage of this compound, especially the purposes aspect preparation treatment diabetes medicament.
Largeleaf Gymnema is Asclepiadaceae plant Gymnema sylvestre R.Br.Since it India among the people be used for anti-pyogenic infections, snakebite, separate malaria, diuresis and hypoglycemic etc., so people have carried out many researchs and report to its contained composition, find that wherein contained gymnemic acid has hypoglycemic activity.The contriver is further research on the basis of forefathers' research, finds to also have a kind of new saponin compound in Largeleaf Gymnema, up to the present, does not still find to have reported in literature.This new saponin compound also has hypoglycemic activity.
The purpose of this invention is to provide a kind of new saponin compound.
Another object of the present invention provides the preparation method of this saponin.
Another purpose of the present invention provides the purposes of this saponin.
New saponin compound of the present invention has following general formula (I):
Figure A9910072100031
Or
Figure A9910072100032
Work as R 1For The time, R 2For hydrogen atom or
Figure A9910072100034
New saponin compound of the present invention can obtain by following method:
A) Largeleaf Gymnema cured leaf is pulverized, with the alcohol reflux of 60-95% 3 times, and each 2 hours, united extraction liquid, reclaim under reduced pressure obtains concentrated solution to there not being the alcohol flavor, and is standby;
B) resulting concentrated solution is extracted 3-6 time with hexanaphthene, and then use n-butanol extraction,, standby propyl carbinol part reclaim under reduced pressure to dry extract;
C) admix thick silica gel in the dry extract that step b) is obtained, treat upper prop after the processing; Using the thin-layer chromatography of silica gel H to separate, is 90 with the chloroform-methanol ratio: 10-50: 50 mixed solution pressurized column chromatography behind sample on the sample obtains the new saponin compound of formula (I) respectively.
Wherein work as R 1Be hydrogen atom and R 2For The time, this new saponin compound (calling compd A in the following text) has following physicochemical data:
Amorphous powder; Mp 206-209 ℃; [α] 20 D-16.0 ° (c 0.11, MeOH); IR ν Max3424 (OH), 1735 (COOR), 1636 (C=C), 1457,1034cm -1, 1H NMR (400MHz, pyridine-d 5) δ 0.82 (3H, s, Me), 0.87 (3H, s, Me), 0.91 (3H, s, Me), 0.97 (3H, s, Me), 1.07 (3H, s, Me), 1.20 (3H, s, Me), 1.23 (3H, s, Me), 3.17 (1H, dd, J=3.5 and 10.2Hz, H-18), 3.30 (1H, dd, J=3.9 and 11.7Hz, H-3 α), 5.37 (1H, br s, H-12); 13C NMR (100 MHz, pyridine-d 5) see Table 1 with table 2; FABMS m/z 943[M+H] +
Work as R 1For , R 2During for hydrogen atom, this new saponin compound (calling compd B in the following text) has following physicochemical data:
Amorphous powder; Mp 202-204 ℃; [α] 20 D-3.2 ° (c0.15, MeOH); IR ν Max3410 (OH), 1710 (COOH), 1638 (C=C), 1458,1036cm -1, 1H NMR (400MHz, pyridine-d 5) δ 0.87 (3H, s, Me), 0.91 (3H, s, Me), 0.96 (3H, s, Me), 1.02 (3H, s, Me), 1.10 (3H, s, Me), 1.24 (3H, s, Me), 1.29 (3H, s, Me), 3.30 (1H, dd, J=4.5 and 11.5Hz, H-3 α), 5.38 (1H, brs, H-12); 13C NMR (100MHz, pyridine-d 5) see Table 1 with table 2; FABMS m/z 935[M+Na] +
Work as R 1For
Figure A9910072100043
, R 2For
Figure A9910072100044
The time, this new saponin compound (calling Compound C in the following text) has following physicochemical data:
Amorphous powder; Mp 212-215 ℃; [α] 20 D-9.6 ° (c 0.20, MeOH); IR ν Max3414 (OH), 1740 (COOR), 1636 (C=C), 1460,1364,1044,896cm -1, 1H NMR (500MHz, pyridine-d 5) δ 0.85 (3H, s, Me), 0.90 (3H, s, Me), 0.94 (3H, s, Me), 1.00 (3H, s, Me), 3.19 (1H, dd, J=4.0 and 13.7Hz, H-18), 3.32 (1H, dd, J=4.4 and 11.7Hz, H-3 α), 5.40 (1H, br s, H-12); 13C NMR (125 MHz, pyridine-d 5) see Table 1 with table 2; FABMS m/z 1097[M+Na] +
Work as R 1Be hydrogen atom, R 2For The time, this new saponin compound (calling Compound D in the following text) has following physicochemical data:
Amorphous powder; Mp 209-211 ℃; [α] 20 D-12.1 ° (c 0.12, MeOH); IR ν Max3424 (OH), 1734 (COOR), 1636 (C=C), 1458,1074cm -1, 1H NMR (500MHz, pyridine-d 5) δ 0.87 (3H, s, Me), 0.90 (3H, s, Me), 0.92 (3H, s, Me), 1.00 (3H, s, Me), 1.09 (3H, s, Me), 1.22 (3H, s, Me), 1.26 (3H, s, Me), 3.20 (1H, dd, J=3.5 and 13.6Hz, H-18), 3.33 (1H, dd, J=4.4 and 11.5Hz, H-3 α), 5.39 (1H, br s, H-12); 13C NMR (125 MHz, pyridine-d 5) see Table 1 with table 2; FABMS m/z 1127[M+Na] +
The aglycone part of table 1: compd A-D 13The data of C NMR
Carbon atom Compd A Compd B Compound C Compound D
??????1 ????38.8 ????38.7 ????38.7 ????38.7
??????2 ????26.6 ????26.7 ????26.7 ????26.7
??????3 ????88.9 ????89.0 ????89.0 ????89.0
??????4 ????39.4 ????39.5 ????39.5 ????39.5
??????5 ????55.7 ????55.8 ????55.8 ????55.8
??????6 ????18.4 ????18.3 ????18.5 ????18.5
??????7 ????33.0 ????33.1 ????33.1 ????33.1
??????8 ????39.8 ????39.9 ????39.9 ????39.9
??????9 ????47.9 ????48.0 ????48.0 ????48.0
?????10 ????36.9 ????37.0 ????37.0 ????37.0
?????11 ????23.7 ????23.7 ????23.8 ????23.7
?????12 ????122.9 ????122.8 ????123.0 ????122.9
???13 ????144.0 ????144.4 ????144.0 ????144.1
???14 ????42.0 ????42.1 ????42.1 ????42.1
???15 ????28.2 ????28.2 ????28.2 ????28.2
???16 ????23.3 ????23.4 ????23.4 ????23.4
???17 ????46.9 ????46.5 ????47.0 ????47.0
???18 ????41.6 ????41.9 ????41.7 ????41.7
???19 ????46.2 ????46.1 ????46.2 ????46.3
???20 ????30.7 ????30.9 ????30.8 ????30.8
???21 ????33.9 ????34.4 ????34.0 ????34.0
???22 ????32.5 ????33.1 ????32.5 ????32.5
???23 ????28.1 ????28.2 ????28.2 ????28.3
???24 ????17.0 ????17.0 ????17.0 ????17.0
???25 ????15.5 ????15.8 ????15.6 ????15.6
???26 ????17.4 ????17.3 ????17.5 ????17.5
???27 ????26.0 ????26.1 ????26.1 ????26.1
???28 ????176.4 ????180.2 ????176.5 ????176.5
???29 ????33.1 ????33.2 ????33.2 ????33.2
???30 ????23.6 ????23.7 ????23.7 ????23.7
The sugar moieties of table 2: compd A-D 13C NMR data
????C-3 Compd A Compd B Compound C Compound D
????Glc1 ????106.9 ????107.0 ????107.0 ????106.9
????Glc2 ????75.1 ????75.0 ????75.0 ????75.2
????Glc3 ????78.4 ????78.3 ????78.3 ????78.4
????Glc4 ????71.6 ????71.5 ????71.5 ????71.5
????Glc5 ????77.0 ????77.0 ????77.0 ????77.0
????Glc6 ????70.4 ????70.4 ????70.4 ????70.5
????Glc’1 ????105.4 ????105.4 ????105.4 ????105.4
????Glc’2 ????75.5 ????75.6 ????75.6 ????75.6
????Glc’3 ????78.5 ????78.5 ????78.5 ????78.6
????Glc’4 ????71.7 ????71.6 ????71.6 ????71.7
????Glc’5 ????78.4 ????76.9 ????76.9 ????78.5
????Glc’6 ????62.7 ????69.8 ????69.8 ????62.6
????Xyl1 ????106.0 ????106.0
????Xyl2 ????74.9 ????74.9
?????Xyl3 ???78.0 ????78.1
?????Xyl4 ???71.1 ????71.1
?????Xyl5 ???67.0 ????67.1
?????C-28
?????Glc”1 ???95.7 ????95.8 ????95.7
?????Glc”2 ???74.1 ????74.1 ????73.9
?????Glc”3 ???78.8 ????78.9 ????78.7
?????Glc”4 ???71.0 ????71.1 ????70.9
?????Glc”5 ???79.3 ????79.3 ????78.0
?????Glc”6 ???62.1 ????62.2 ????69.3
?????Glc1 ????105.3
?????Glc2 ????75.2
?????Glc3 ????78.5
?????Glc4 ????71.7
?????Glc5 ????78.4
?????Glc6 ????62.7
Evidence, the new saponin compound that contains general formula (I) has the effect of hypoglycemic, lipopenicillinase and anti-platelet aggregation.
With the test example new saponin compound of the present invention is elaborated by the following examples.Embodiment 1
Gymnema latifolium Wall. ex Wight meal 1000g, alcohol reflux with 75% three times, each volume is 6.0L, each 2 hours time merged ethanol extract, and this ethanol extract reclaim under reduced pressure is not extremely had the alcohol flavor, the hexanaphthene butanols of concentrated solution with 0.5L extracted 3 times, merge butanol extraction liquid, reclaim under reduced pressure obtains dry extract shape thing 72.0g.Get 36.0g dry extract shape thing, admix the thick silica gel 60g of 60-100 purpose, be evaporated to driedly with water-bath, treat sample.The 200-400 purpose silica gel H of using with the 400g thin-layer chromatography, wet method dress post, on the sample behind the sample, with 90: 10-50: chloroform-methyl alcohol mixed liquor of 50 carries out pressurized column chromatography, obtains new saponin compound A (130mg), compd B (115mg), Compound C (160mg) and Compound D (195mg) respectively.Test example 1
The influence that new saponin compound of the present invention raises to mouse blood sugar
Male mice in kunming, be divided into experimental group at random, the oral new saponin compound 50 of the present invention of difference, 100,200mg/kg, positive controls is oral glyburide 50mg/kg respectively, the oral equivalent distilled water of blank group and normal control group, and the administration volume is 20ml/kg, continuous 7 days, fasting 10h before the last administration, except that the normal control group, each organizes orally give glucose solution 2.5g/kg (10ml/kg), respectively at before the glucose and glucose after 30min, by eye socket blood sampling 100ul, press the notatin method, measure the glucose content in the serum.
As a result, the oral glucose 30min of mouse, blood sugar obviously raises, new saponin compound 100 of the present invention, 200mg/kg and glyburide 50mg/kg all significantly suppress mouse blood sugar and raise, and the blood sugar reducing function of new saponin compound 200mg/kg of the present invention is close with glyburide 50mg/kg, sees the following form 3.
Table 3
Group Dosage (mg/kg) Blood glucose value (mmol/L)
?????0(min) ??????30(min)
Normal group ????6.20±1.01 ???6.64±1.04
Control group ????6.55±1.16 ???13.94±3.22 ΔΔ
New saponin compound of the present invention ??????50 ????6.79±1.16 ???12.01±1.88
?????100 ????6.09±1.34 ????9.59±2.25 **
?????200 ????6.42±0.99 ????9.16±1.08 **
Glyburide ??????50 ????4.48±0.83 ** ????8.18±1.72 **
The Δ ΔCompare with normal group P＜0.01; *Compare with control group P＜0.01.Test example 2
New saponin compound of the present invention is to the influence of hyperlipidemia rats serum triglyceride, cholesterol level
Male SD rat, body weight 130-170g, normal group gives normal diet, and other each group gives high lipid food (1% cholesterol, 10% lard, 0.3% cholic acid, 0.2% thiamazole and 88.5% normal diet are made cubed feed certainly).Continuous 14 days, the rat fasting was pressed the test kit method and is measured rat blood serum triglyceride level and cholesterol level after 12 hours, then, carried out random packet by the blood fat value.Experimental group orally give 50,100,200mg/kg, positive controls is oral clofibrate 100mg/kg respectively, control group gives distilled water, the administration volume is 10ml/kg, continuous 10 days, each group was still raised with high lipid food in administration in preceding 5 days, raised with normal diet in back 5 days, fasting is 11 hours before the last administration, and triglyceride level and cholesterol level in the serum surveyed in blood sampling in 1 hour after the administration.
The result, rat gave high lipid food after 10 days, serum triglyceride and cholesterol level obviously raise, new saponin compound 50,100 of the present invention, 200mg/kg and clofibrate 100mg/kg all make hyperlipidemia rats serum triglyceride and cholesterol levels obviously descend, the reducing blood lipid of new saponin compound 200mg/kg of the present invention is close with clofibrate 100mg/kg, sees Table 4.Table 4: The compounds of this invention to the influence of hyperlipidemia rats lipids contents (X ± SD,
n＝9-10)
Group Dosage (mg/kg) Triglyceride level (mmol/L) Total cholesterol (mmol/L)
Before the administration After the administration Before the administration After the administration
Normal group ???1.02±0.22 ????1.04±0.15 ????2.43±0.41 ?????1.99±0.47
Control group ???2.64±0.82 ????3.04±0.93 ??4.10±0.51 ΔΔ ????4.77±0.63 ΔΔ
New saponin compound of the present invention ?????50 ???2.72±0.61 ????2.41±0.44 ????4.29±0.60 ????3.92±0.58 **
????100 ???2.54±0.90 ????1.75±0.53 ** ????4.02±0.59 ????2.94±0.66 **
????200 ???2.72±0.76 ????1.37±0.40 ** ????4.18±0.61 ????2.31±0.74 **
Clofibrate ????100 ???2.51±0.77 ????2.72±0.74 ????4.33±0.51 ????2.15±0.76 **
The Δ ΔCompare with normal group P＜0.01; *P＜0.01 is with control group comparison test example 3
New saponin compound of the present invention is to the influence of external rabbit platelet aggregation
The rabbit heart puncturing extracting blood, the centrifugal 5min of 3.8% Potassium Citrate anti-freezing (1: 9) 1000rpm gets the upper strata as platelet rich plasma (PRP), and again with the centrifugal 10min of 4000rpm, supernatant is platelet poor plasma (PPP).Final concentration is respectively 250,500,1000ug/ml, the positive control pipe adds Asprin normal saline solution 10ul, final concentration is 250 ug/ml, the blank pipe adds physiological saline 10ul, and final concentration is 1.0 * 10-5M, observes the MA in the 3min on PAM-1 type platelet aggregation instrument.
As a result, new saponin compound 500 of the present invention, 1000ug/ml, Asprin 250ug/ml significantly suppresses the rabbit platelet aggregation, the results are shown in Table 5.Table 5: new saponin compound of the present invention to the influence of external rabbit platelet aggregation (X ± SD,
n＝8)
Group Final concentration (ug/ml) MA (%) Inhibiting rate (%)
Control group ?????47.9±5.2
?????250 ?????43.6±7.0 ????9.0
?????500 ?????35.9±4.5 ** ????25.1
????1000 ?????27.8±4.8 ** ????42.0
Asprin ?????250 ?????23.7±6.0 ** ????50.3
*Compare with control group P＜0.01.

Claims (5)

1. new saponin compound that general formula is (1):
Figure A9910072100021
R 2For hydrogen atom or
2. the preparation method of the new saponin compound of claim 1 comprises the following steps:
A) Largeleaf Gymnema cured leaf is pulverized, with the alcohol reflux of 60-95% three times, and each 2 hours, united extraction liquid, reclaim under reduced pressure obtains concentrated solution to there not being the alcohol flavor, and is standby;
B) resulting concentrated solution is extracted 3-6 time with hexanaphthene, and then use n-butanol extraction,, standby propyl carbinol part reclaim under reduced pressure to dry extract;
C) admix thick silica gel in the dry extract that step b) is obtained, treat upper prop after the processing; Using the thin-layer chromatography of silica gel H to separate, is 90 with the chloroform-methanol ratio: 10-50: 50 mixed solution pressurized column chromatography behind sample on the sample obtains the new saponin compound of formula (I) respectively.
3. the new saponin compound of claim 1 is in the purposes of preparation aspect the medicine.
4. according to claim 3, wherein said medicine has the effect of hypoglycemic, lipopenicillinase or platelet aggregation-against.
5. according to claim 3, wherein said medicine can be treated diabetes.
CN99100721A 1999-02-11 1999-02-11 New saponin compound and its preparation method and application Expired - Fee Related CN1108306C (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
CN99100721A CN1108306C (en) 1999-02-11 1999-02-11 New saponin compound and its preparation method and application
AU20909/00A AU2090900A (en) 1999-02-11 2000-01-21 Novel gymnemic acid derivatives, process for the preparation thereof and use thereof as medicine
CA2362864A CA2362864C (en) 1999-02-11 2000-01-21 New gymnemic acid derivatives, their preparation, pharmaceutical composition containing them and their medical use
US09/913,322 US6833443B1 (en) 1999-02-11 2000-01-21 Gymnemic acid derivatives, process for the preparation thereof and use thereof as medicine
JP2000598513A JP4903309B2 (en) 1999-02-11 2000-01-21 Novel gymnemic acid derivatives, their production, pharmaceutical compositions containing them, and their pharmaceutical use
EP00901035A EP1176149B1 (en) 1999-02-11 2000-01-21 Novel gymnemic acid derivatives, process for the preparation thereof and use thereof as medicine
KR1020017010217A KR100625222B1 (en) 1999-02-11 2000-01-21 Novel gymnemic acid derivatives, process for the preparation thereof and use thereof as medicine
PCT/CN2000/000010 WO2000047594A1 (en) 1999-02-11 2000-01-21 Novel gymnemic acid derivatives, process for the preparation thereof and use thereof as medicine
DE60004353T DE60004353T2 (en) 1999-02-11 2000-01-21 DERIVATIVES OF GYMNEMIC ACID, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINES

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN99100721A CN1108306C (en) 1999-02-11 1999-02-11 New saponin compound and its preparation method and application

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5843909A (en) * 1997-06-13 1998-12-01 Kowa Chemical Industries Co., Ltd. (3-β), 4-α, 16-β)-16, -23, 28-trihdroxyolean-12-ene-3-yl-β-D-glucopyranuronic acid derivatives, as glucose absorption inhibiting agents

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Patentee before: Guilin Jiqi Pharmaceutical Industry Co., Ltd.

CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20030514

Termination date: 20160211

CF01 Termination of patent right due to non-payment of annual fee