Microbial transformation of ginsenoside Rb1 by Acremonium strictum

被引:99
作者
Chen, Guang-Tong [1 ,2 ]
Yang, Min [1 ]
Song, Yan [2 ]
Lu, Zhi-Qiang [1 ]
Zhang, Jin-Qiang [1 ]
Huang, Hui-Lian [1 ]
Wu, Li-Jun [2 ]
Guo, De-An [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai Inst Biol Sci, Shanghai Res Inst Modernizat Tradit Chinese Med, Shanghai 201203, Peoples R China
[2] Shenyang Pharmaceut Univ, Coll Tradit Chinese Mat Med, Shenyang 110016, Peoples R China
关键词
ginsenoside Rb-1; biotransformation; Acremonium strictum;
D O I
10.1007/s00253-007-1258-4
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
Preparative-scale fermentation of ginsenoside Rb-1 (1) with Acremonium strictum AS 3.2058 gave three new compounds, 12 beta-hydroxydammar-3-one-20 (S)-O-beta-D-glucopyranoside (7), 12 beta, 25-dihydroxydammar-(E)-20(22)-ene-3-O-beta-D-glucopyranosyl-(1 -> 2)-beta-D-glucopyranoside (8), and 12 beta, 20 (R), 25-trihydroxydammar-3-O-beta-D-glucopyranosyl-(1 -> 2)-beta-D-glucopyranoside (9), along with five known compounds, ginsenoside Rd (2), gypenoside XVII (3), ginsenoside Rg(3) (4), ginsenoside F-2 (5), and compound K (6). The structural elucidation of these metabolites was based primarily on one- and two-dimensional nuclear magnetic resonance and high-resolution electron spray ionization mass spectra analyses. Among these compounds, 2-6 are also the metabolites of ginsenoside Rb-1 in mammals. This result demonstrated that microbial culture parallels mammalian metabolism; therefore, A. strictum might be a useful tool for generating mammalian metabolites of related analogs of ginsenosides for complete structural identification and for further use in pharmaceutical research in this series of compounds. In addition, the biotransformation kinetics was also investigated.
引用
收藏
页码:1345 / 1350
页数:6
相关论文
共 20 条
[11]  
Rao GP, 1997, DRUG METAB DISPOS, V25, P709
[12]   MICROBIAL MODELS OF MAMMALIAN METABOLISM - AROMATIC HYDROXYLATION [J].
SMITH, RV ;
ROSAZZA, JP .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1974, 161 (02) :551-558
[13]   MICROBIAL MODELS OF MAMMALIAN METABOLISM [J].
SMITH, RV ;
ROSAZZA, JP .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1975, 64 (11) :1737-1759
[14]   STUDIES ON THE PHARMACODYNAMICS OF GINSENOSIDE-RG(1), GINSENOSIDE-RB-1 AND GINSENOSIDE-RB-2 IN RATS [J].
TAKINO, Y .
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1994, 114 (08) :550-564
[15]  
Teng R. W., 2000, CHIN J MAGN RESON, V17, P461
[16]  
[滕荣伟 Teng Rongwei], 2002, [波谱学杂志, Chinese Journal of Microwave & Radio-frequency Spectroscopy], V19, P25
[17]  
Wang John Q., 2003, Current Neuropharmacology, V1, P1, DOI 10.2174/1570159033360548
[18]   Specific 12β-hydroxylation of cinobufagin by filamentous fungi [J].
Ye, M ;
Qu, GQ ;
Guo, HZ ;
Guo, D .
APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2004, 70 (06) :3521-3527
[19]   Structures of new dammarane-type triterpene saponins from the flower buds of Panax notoginseng and hepatoprotective effects of principal ginseng saponins [J].
Yoshikawa, M ;
Morikawa, T ;
Kashima, Y ;
Ninomiya, K ;
Matsuda, H .
JOURNAL OF NATURAL PRODUCTS, 2003, 66 (07) :922-927
[20]   Minor dammarane saponins from Panax notoginseng [J].
Zhao, P ;
Liu, YQ ;
Yang, CR .
PHYTOCHEMISTRY, 1996, 41 (05) :1419-1422