Biotransformation of 20(S)-protopanaxatriol by Mucor racemosus and the anti-cancer activities of some products

Biotechnol Lett. 2015 Oct;37(10):2005-9. doi: 10.1007/s10529-015-1877-2. Epub 2015 Jun 9.

Abstract

Objective: To produce new derivatives of 20(S)-protopanaxatriol by fungal biotransformation.

Result: Biotransformation of 20(S)-protopanaxatriol (1) by Mucor racemosus AS 3.205 afforded six products. Their structures were elucidated on the basis of extensive spectroscopic analyses. M. racemosus could selectively catalyze dehydrogenation at C-12 and further hydroxylation at C-7, C-11, and C-15, as well as rearrangement of double bond at C-26. Two of these new compounds exhibited potent inhibitory activity against SH-SY5Y and HepG2 cell lines.

Conclusion: Biotransformation by M. racemosus AS 3.205 was an effective approach to produce new derivatives of 20(S)-protopanaxatriol.

Keywords: 20(S)-Protopanaxatriol; Anti-cancer compounds; Biocatalysis; Biotransformation; Cytotoxic activity; Dehydrogenation; Mucor racemosus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / metabolism*
  • Antineoplastic Agents / pharmacology*
  • Biotransformation
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Humans
  • Mucor / metabolism*
  • Sapogenins / metabolism*
  • Spectrum Analysis

Substances

  • Antineoplastic Agents
  • Sapogenins
  • protopanaxatriol