Microbial Transformation of 20(S)-Protopanaxatriol-Type Saponins by Absidia coerulea
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- 作者：Guangtong Chen ; Min Yang ; Zhiqiang Lu ; Jinqiang Zhang ; Huilian Huang ; Yan Liang ; Shuhong Guan ; Yan Song ; Lijun Wu ; De-an Guo
- 刊名：Journal of Natural Products
- 出版年：2007
- 出版时间：July 2007
- 年：2007
- 卷：70
- 期：7
- 页码：1203 - 1206
- 全文大小：66K
- 年卷期：v.70,no.7(July 2007)
- ISSN：1520-6025
文摘
Three 20(S)-protopanaxatriol-type saponins, ginsenoside-Rg1 (1), notoginsenoside-R1 (2), and ginsenoside-Re (3), weretransformed by the fungus Absidia coerulea (AS 3.3389). Compound 1 was converted into five metabolites, ginsenoside-Rh4 (4), 3
,2,25-trihydroxydammar-(E)-20(22)-ene-6-O--D-glucopyranoside (5), 20(S)-ginsenoside-Rh1 (6), 20(R)-ginsenoside-Rh1 (7), and a mixture of 25-hydroxy-20(S)-ginsenoside-Rh1 and its C-20(R) epimer (8). Compound 2 wasconverted into 10 metabolites, 20(S)-notoginsenoside-R2 (9), 20(R)-notoginsenoside-R2 (10), 3,12,25-trihydroxydammar-(E)-20(22)-ene-6-O--D-xylopyranosyl-(1
2)--D-glucopyranoside (11), 3,12-dihydroxydammar-(E)-20(22),24-diene-6-O--D-xylopyranosyl-(12)--D-glucopyranoside (12), 3,12,20,25-tetrahydroxydammaran-6-O--D-xylopyranosyl-(12)--D-glucopyranoside (13), and compounds 4-8. Compound 3 was metabolized to 20(S)-ginsenoside-Rg2 (14),20(R)-ginsenoside-Rg2 (15), 3,12,25-trihydroxydammar-(E)-20(22)-ene-6-O-
-L-rhamnopyranosyl-(12)--D-glucopyranoside (16), 3,12-dihydroxydammar-(E)-20(22),24-diene-6-O--L-rhamnopyranosyl-(12)--D-glucopyranoside(17), 3,12,20,25-tetrahydroxydammaran-6-O--L-rhamnopyranosyl-(12)--D-glucopyranoside (18), and compounds4-8. The structures of five new metabolites, 10-13 and 16, were established by spectroscopic methods.
,2,25-trihydroxydammar-(E)-20(22)-ene-6-O--D-glucopyranoside (5), 20(S)-ginsenoside-Rh1 (6), 20(R)-ginsenoside-Rh1 (7), and a mixture of 25-hydroxy-20(S)-ginsenoside-Rh1 and its C-20(R) epimer (8). Compound 2 wasconverted into 10 metabolites, 20(S)-notoginsenoside-R2 (9), 20(R)-notoginsenoside-R2 (10), 3,12,25-trihydroxydammar-(E)-20(22)-ene-6-O--D-xylopyranosyl-(12)--D-glucopyranoside (11), 3,12-dihydroxydammar-(E)-20(22),24-diene-6-O--D-xylopyranosyl-(12)--D-glucopyranoside (12), 3,12,20,25-tetrahydroxydammaran-6-O--D-xylopyranosyl-(12)--D-glucopyranoside (13), and compounds 4-8. Compound 3 was metabolized to 20(S)-ginsenoside-Rg2 (14),20(R)-ginsenoside-Rg2 (15), 3,12,25-trihydroxydammar-(E)-20(22)-ene-6-O--L-rhamnopyranosyl-(12)--D-glucopyranoside (16), 3,12-dihydroxydammar-(E)-20(22),24-diene-6-O--L-rhamnopyranosyl-(12)--D-glucopyranoside(17), 3,12,20,25-tetrahydroxydammaran-6-O--L-rhamnopyranosyl-(12)--D-glucopyranoside (18), and compounds4-8. The structures of five new metabolites, 10-13 and 16, were established by spectroscopic methods.