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Studies On The Constituents Of The Degradation Products Of Ginsen Panaxadiol Saponins In Leaves And Stems Of Panax Quinquefolium L. In Acidic Condition

Posted on:2010-09-04Degree:MasterType:Thesis
Country:ChinaCandidate:Z B YuFull Text:PDF
GTID:2144360272997508Subject:Organic Chemistry
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Panax quinquefolium L. is placed in the genus of panax,araliaceae In our country it was the first documented in "Compendium of Materia Medica theft by finding", and has more than 200 years of medicine history .As a kind of traditional chinese medicine, Panax quinquefolium L. is famous all over the world.Our country since the 70's start the introduction and cultivation of Panax quinquefolium L. and has been successful. At present, four major Panax quinquefolium L. have become ecoclimatic cultivation areas, that is, north-east, north, central and district Kangdian cultivation.The chemical constituents of Panax quinquefolium L., ginsenosides is a landmark composition, and also the main active ingredient. So far, 50 kinds of ginsenosides isolated from stems and leaves of Panax quinquefolium L.were identified, according to the structure of its mother it is divided into 3 categories: Dammarane ginsenosides, Ocotillol and Sidechain-changed-Protopanaxadiol ginsenosides. The dammarane-type ginsenosides of quinquefolium L.includ protopan-axadiol type ginsenosides which is referred to as PPD and protopan-axatriol type saponins which is referred to as PPT.Dammarane-skeleton is a result of anti-tumor activity have an important structural unit,it has been reported, Various ginsenosides have its own unique multiple pharmacological activities, especially the quantity of low content ginsenosides. Thus the development of sub- ginsenosides have an important theoretical and applied significance.As a result of sub-ginseng saponins and sapogenin are extremely low in Panax plants, Therefore not conducive to the development and application . It has been reported in the literature ,that it can be obtained a large number of minor ginsenosides through degradation of which content was high, easily to get.In order to prepare quantity of low content and high pharmacological activity ginseno-sides ,ten compounds were isolated from the products of ginsen panaxadiol saponins in leaves and stems of panax quinquefolium L. degradation in acidic condition by using the chromatography and recrystallization etc.Nine of the ten compounds were identified by the spectral methods including 1H-NMR,13C-NMR and IR etc.They are 20(S)-PD(Ⅰ),20(S)-PPD(Ⅱ),3-O-β-D-glucopyranosyl-3β,12β,25-trihydroxyl dammar-20(22)-ene(Ⅲ),20(S)-ginsenoside-Rh2(Ⅳ),20(R)-ginsenoside-Rh2(Ⅴ),3-O-β-D-glucopyranosyl-3β,12β, 20(R),25-tetrahydroxy dammarane(Ⅵ),20(S)-ginsenoside-Rg3(Ⅶ),20(R)-ginsenoside- Rg3(Ⅷ),3-O-(β-D-glucopyranosyl(2→1)-β-D-glucopyranosyl)-3β,12β,20(R),25-tetrahydroxyl dammarane(Ⅸ).The optimal condition in ethanol solution of sulfuric acid was established by orthognol experiments. The optimal conditions of degradation to prepare 20(R)-Rh2 are as follows: the ginsen panaxadiol saponins in leaves and stems of panax quinquefolium L.and ethanol solution of 5% sulfuric acid (the ratio is 1:50, saponins/ ethanol solution of sulfuric acid, w/v), then the solution was heated up to 80℃and was keeped for 4h at the temperature, the transformation rate was 6.13%; the ginsen panaxadiol saponins in leaves and stems of panax quinquefolium L. and ethanol solution of 3% sulfuric acid (the ratio is 1:50, saponins/ ethanol solution of sulfuric acid, w/v), then the solution was heated up to 90℃and was keeped for 4h at the temperature, the transformation rate was 6.34%; The results showed that ginsenosides can be degraded and become minor ginsenosides.In conclusion,all the results of the study can offer credible foundation for the development of new drugs.
Keywords/Search Tags:the ginsen panaxadiol saponins in leaves and stems of panax quinquefolium L., acidic degradation, structure identification, orthognol experiment
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