Literature DB >> 17629326

Microbial transformation of 20(S)-protopanaxatriol-type saponins by Absidia coerulea.

Guangtong Chen1, Min Yang, Zhiqiang Lu, Jinqiang Zhang, Huilian Huang, Yan Liang, Shuhong Guan, Yan Song, Lijun Wu, De-an Guo.   

Abstract

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.

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Year:  2007        PMID: 17629326     DOI: 10.1021/np070053v

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  11 in total

Review 1.  Genome sequencing of strain Cellulosimicrobium sp. TH-20 with ginseng biotransformation ability.

Authors:  Fei Zheng; Wei Zhang; Xiaodan Chu; Yulin Dai; Jing Li; Huanxi Zhao; Liankui Wen; Hao Yue; Shanshan Yu
Journal:  3 Biotech       Date:  2017-07-11       Impact factor: 2.406

Review 2.  Ginsenosides from American ginseng: chemical and pharmacological diversity.

Authors:  Lian-Wen Qi; Chong-Zhi Wang; Chun-Su Yuan
Journal:  Phytochemistry       Date:  2011-03-09       Impact factor: 4.072

3.  New dammarane-type triterpenoid saponins from Panax notoginseng saponins.

Authors:  Qian Li; Mingrui Yuan; Xiaohui Li; Jinyu Li; Ming Xu; Di Wei; Desong Wu; Jinfu Wan; Shuangxi Mei; Tao Cui; Jingkun Wang; Zhaoyun Zhu
Journal:  J Ginseng Res       Date:  2018-12-13       Impact factor: 6.060

4.  Bioactivity and bioavailability of ginsenosides are dependent on the glycosidase activities of the A/J mouse intestinal microbiome defined by pyrosequencing.

Authors:  Tao Niu; Diane L Smith; Zhen Yang; Song Gao; Taijun Yin; Zhi-Hong Jiang; Ming You; Richard A Gibbs; Joseph F Petrosino; Ming Hu
Journal:  Pharm Res       Date:  2012-12-20       Impact factor: 4.200

Review 5.  Current evaluation of the millennium phytomedicine- ginseng (II): Collected chemical entities, modern pharmacology, and clinical applications emanated from traditional Chinese medicine.

Authors:  Lee Jia; Yuqing Zhao; Xing-Jie Liang
Journal:  Curr Med Chem       Date:  2009       Impact factor: 4.530

6.  Complete (1)H-NMR and (13)C-NMR spectral analysis of the pairs of 20(S) and 20(R) ginsenosides.

Authors:  Heejung Yang; Jeom Yong Kim; Sun Ok Kim; Young Hyo Yoo; Sang Hyun Sung
Journal:  J Ginseng Res       Date:  2014-05-27       Impact factor: 6.060

7.  Efficacy and Safety of Panax notoginseng Saponin Therapy for Acute Intracerebral Hemorrhage, Meta-Analysis, and Mini Review of Potential Mechanisms of Action.

Authors:  Dongying Xu; Ping Huang; Zhaosheng Yu; Daniel H Xing; Shuai Ouyang; Guoqiang Xing
Journal:  Front Neurol       Date:  2015-01-07       Impact factor: 4.003

8.  Highly Regioselective Biotransformation of Protopanaxadiol-type and Protopanaxatriol-type Ginsenosides in the Underground Parts of Panax notoginseng to 18 Minor Ginsenosides by Talaromyces flavus.

Authors:  Ying-Zhong Liang; Min Guo; Yin-Fei Li; Lin-Jiao Shao; Xiu-Ming Cui; Xiao-Yan Yang
Journal:  ACS Omega       Date:  2022-04-22

9.  Cordyceps sinensis-mediated biotransformation of notoginsenoside R1 into 25-OH-20(S/R)-R2 with elevated cardioprotective effect against DOX-induced cell injury.

Authors:  Jishuang Liu; Yu Xin; Zhidong Qiu; Qi Zhang; Tianzhu He; Ye Qiu; Weinan Wang
Journal:  RSC Adv       Date:  2022-04-28       Impact factor: 4.036

Review 10.  Advances in the chemistry, pharmacological diversity, and metabolism of 20(R)-ginseng saponins.

Authors:  Chaoming Wang; Juan Liu; Jianqiang Deng; Jiazhen Wang; Weizhao Weng; Hongxia Chu; Qingguo Meng
Journal:  J Ginseng Res       Date:  2019-01-31       Impact factor: 6.060

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