蓝色犁头霉对20(S)-原人参三醇型皂苷的微生物转化
Microbial transformation of 20(S)-protopanaxatriol-type saponins by Absidia coerulea.
作者信息
Chen Guangtong, Yang Min, Lu Zhiqiang, Zhang Jinqiang, Huang Huilian, Liang Yan, Guan Shuhong, Song Yan, Wu Lijun, Guo De-an
机构信息
Shanghai Research Center for Modernization of Traditional Chinese Medicine, Shanghai Institute of Materia Medica, Shanghai Institute for Biological Sciences, Chinese Academy of Sciences, Guo Shoujing Road, Zhangjiang, Shanghai, People's Republic of China.
出版信息
J Nat Prod. 2007 Jul;70(7):1203-6. doi: 10.1021/np070053v. Epub 2007 Jul 13.
Three 20(S)-protopanaxatriol-type saponins, ginsenoside-Rg1 (1), notoginsenoside-R1 (2), and ginsenoside-Re (3), were transformed by the fungus Absidia coerulea (AS 3.3389). Compound 1 was converted into five metabolites, ginsenoside-Rh4 (4), 3beta,2beta,25-trihydroxydammar-(E)-20(22)-ene-6-O-beta-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 was converted into 10 metabolites, 20(S)-notoginsenoside-R2 (9), 20(R)-notoginsenoside-R2 (10), 3beta,12beta,25-trihydroxydammar-(E)-20(22)-ene-6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (11), 3beta,12beta-dihydroxydammar-(E)-20(22),24-diene-6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (12), 3beta,12beta,20,25-tetrahydroxydammaran-6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (13), and compounds 4-8. Compound 3 was metabolized to 20(S)-ginsenoside-Rg2 (14), 20(R)-ginsenoside-Rg2 (15), 3beta,12beta,25-trihydroxydammar-(E)-20(22)-ene-6-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (16), 3beta,12beta-dihydroxydammar-(E)-20(22),24-diene-6-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (17), 3beta,12beta,20,25-tetrahydroxydammaran-6-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (18), and compounds 4-8. The structures of five new metabolites, 10-13 and 16, were established by spectroscopic methods.
三种20(S)-原人参三醇型皂苷，人参皂苷-Rg1（1）、三七皂苷-R1（2）和人参皂苷-Re（3），被蓝色犁头霉（AS 3.3389）转化。化合物1被转化为五种代谢产物，人参皂苷-Rh4（4）、3β,2β,25-三羟基达玛-(E)-20(22)-烯-6-O-β-D-吡喃葡萄糖苷（5）、20(S)-人参皂苷-Rh1（6）、20(R)-人参皂苷-Rh1（7）以及25-羟基-20(S)-人参皂苷-Rh1及其C-20(R)差向异构体的混合物（8）。化合物2被转化为十种代谢产物，20(S)-三七皂苷-R2（9）、20(R)-三七皂苷-R2（10）、3β,12β,25-三羟基达玛-(E)-20(22)-烯-6-O-β-D-吡喃木糖基-(1→2)-β-D-吡喃葡萄糖苷（11）、3β,12β-二羟基达玛-(E)-20(22),24-二烯-6-O-β-D-吡喃木糖基-(1→2)-β-D-吡喃葡萄糖苷（12）、3β,12β,20,25-四羟基达玛烷-6-O-β-D-吡喃木糖基-(1→2)-β-D-吡喃葡萄糖苷（13）以及化合物4 - 8。化合物3被代谢为20(S)-人参皂苷-Rg2（14）、20(R)-人参皂苷-Rg2（15）、3β,12β,25-三羟基达玛-(E)-20(22)-烯-6-O-α-L-吡喃鼠李糖基-(1→2)-β-D-吡喃葡萄糖苷（16）、3β,12β-二羟基达玛-(E)-20(22),24-二烯-6-O-α-L-吡喃鼠李糖基-(1→2)-β-D-吡喃葡萄糖苷（17）、3β,12β,20,25-四羟基达玛烷-6-O-α-L-吡喃鼠李糖基-(1→2)-β-D-吡喃葡萄糖苷（18）以及化合物4 - 8。通过光谱方法确定了五种新代谢产物10 - 13和16的结构。
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