Microbial transformation of ginsenoside Rb₁ by Acremonium strictum

Preparative-scale fermentation of ginsenoside Rb₁ (1) with Acremonium strictum AS 3.2058 gave three new compounds, 12β-hydroxydammar-3-one-20 (S)-O-β-d-glucopyranoside (7), 12β, 25-dihydroxydammar-(E)-20(22)-ene-3-O-β-d-glucopyranosyl-(1[rightward arrow]2)-β-d-glucopyranoside (8), and 12β, 20 (R), 2...

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Published in:Applied microbiology and biotechnology 2008, Vol.77 (6), p.1345-1350
Main Authors: Chen, Guang-Tong, Yang, Min, Song, Yan, Lu, Zhi-Qiang, Zhang, Jin-Qiang, Huang, Hui-Lian, Wu, Li-Jun, Guo, De-An
Format: Article
Language:English
Subjects:
Acremonium strictum
Applied Microbial and Cell Physiology
Biological and medical sciences
Biotechnology
Biotransformation
Chinese medicine
Chromatography
Fermentation
Fundamental and applied biological sciences. Psychology
Ginsenoside Rb
Ionization
Kinetics
Laboratories
Life Sciences
Mammals
Mass spectra
Metabolism
Metabolites
Microbial Genetics and Genomics
Microbiology
Microorganisms
NMR
Nuclear magnetic resonance
Pallets
Pharmaceuticals
Studies
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Summary:Preparative-scale fermentation of ginsenoside Rb₁ (1) with Acremonium strictum AS 3.2058 gave three new compounds, 12β-hydroxydammar-3-one-20 (S)-O-β-d-glucopyranoside (7), 12β, 25-dihydroxydammar-(E)-20(22)-ene-3-O-β-d-glucopyranosyl-(1[rightward arrow]2)-β-d-glucopyranoside (8), and 12β, 20 (R), 25-trihydroxydammar-3-O-β-d-glucopyranosyl-(1[rightward arrow]2)-β-d-glucopyranoside (9), along with five known compounds, ginsenoside Rd (2), gypenoside XVII (3), ginsenoside Rg₃ (4), ginsenoside F₂ (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 Rb₁ 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.
ISSN:0175-7598
1432-0614
DOI:10.1007/s00253-007-1258-4