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Highly regioselective biotransformation of ginsenoside Rg1 to 25-OH derivatives of 20(S/R)-Rh1 by Cordyceps Sinensis.

Authors
  • Sui, Xin1
  • Liu, Jishuang2
  • Xin, Yu2
  • Qu, Mo2
  • Qiu, Ye3
  • He, Tianzhu2
  • Luo, Haoming2
  • Wang, Weinan4
  • Qiu, Zhidong2
  • 1 Changchun University of Chinese Medicine, Changchun 130117, China; The Affiliated Hospital to Changchun University of Chinese Medicine, Changchun 130117, China. , (China)
  • 2 Changchun University of Chinese Medicine, Changchun 130117, China. , (China)
  • 3 Changchun University of Chinese Medicine, Changchun 130117, China; National Engineering Laboratory for Druggable Gene and Protein Screening, Northeast Normal University, Changchun 130117, China. , (China)
  • 4 Changchun University of Chinese Medicine, Changchun 130117, China. Electronic address: [email protected] , (China)
Type
Published Article
Journal
Bioorganic & medicinal chemistry letters
Publication Date
Aug 19, 2020
Volume
30
Issue
21
Pages
127504–127504
Identifiers
DOI: 10.1016/j.bmcl.2020.127504
PMID: 32827631
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

25-OH ginsenosides are potent and rare prodrugs in natural sources. However current strategies for such modification always end up in undesirable side products and unsatisfied yield that hinders them from further applications. Herein, ginsenoside Rg1 was thoroughly converted into 20(S/R)-Rh1 and 25-OH-20(S/R)-Rh1 by Cordyceps Sinensis in an optimum medium. The chemical correctness of either 25-OH-20(S/R)-Rh1 epimers was validated by LC-IT-TOF-MSn and 13C NMR spectrometry. The biocatalytic pathway was established as Rg1 → 20(S/R)-Rh1 → 25-OH-20(S/R)-Rh1. The molar bioconversion rate for total 25-OH-20(S/R)-Rh1 was calculated to be 82.5%, of which S-configuration accounted for 43.2% while R-configuration 39.3%. These two 25-OH derivatives are direct hydration products from 20(S/R)-Rh1 without other side metabolites, suggesting this is a highly regioselective process. In conclusion, this biocatalytic system could be harnessed to facilitate the preparation of diversified 25-OH ginsenosides with high yields of the target compound and simple chemical background in the reaction mixture. Copyright © 2020 Elsevier Ltd. All rights reserved.

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