Biotransformation of 20(S)-protopanaxadiol by Aspergillus niger AS 3.1858

Fitoterapia. 2013 Dec:91:256-260. doi: 10.1016/j.fitote.2013.09.019. Epub 2013 Oct 3.

Abstract

The biotransformation of 20(S)-protopanaxadiol (1) by Aspergillus niger AS 3.1858 was conducted. Seven metabolites 26-hydroxyl-20(S)-protopanaxadiol (2); 23, 24-en-25-hydroxyl-20(S)-protopanaxadiol (3); 25, 26-en-20(S)-protopanaxadiol (4); (E)-20, 22-en-25-hydroxyl-20(S)-protopanaxadiol (5); 25, 26-en-24(R)-hydroxyl-20(S)-protopanaxadiol (6); 25, 26-en-24(S)-hydroxyl-20(S)-protopanaxadiol (7); and 23, 24-en-25-ethoxyl-20(S)-protopanaxadiol (8) were afforded. Among them, 6, 7, and 8 are new compounds. The chemical structures of these metabolites were elucidated based on extensive spectral data including 2D NMR and HRMS. In addition, the cytotoxicity of substrate and all transformed products was evaluated by MTT assay using a panel of seven human tumor cell lines (Du-145, Hela, K562, K562/ADR, SH-SY5Y, HepG2, and MCF-7 cells) and one normal cell line Vero.

Keywords: 20(S)-Protopanaxadiol; Aspergillus niger AS 3.1858; Biotransformation; Cytotoxic activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Antineoplastic Agents, Phytogenic / therapeutic use*
  • Aspergillus niger / metabolism*
  • Biological Products / chemistry
  • Biological Products / pharmacology
  • Biological Products / therapeutic use*
  • Biotransformation
  • Chlorocebus aethiops
  • HeLa Cells
  • Hep G2 Cells
  • Humans
  • MCF-7 Cells
  • Molecular Structure
  • Neoplasms / drug therapy*
  • Panax / chemistry*
  • Phytotherapy*
  • Sapogenins / metabolism*
  • Vero Cells

Substances

  • Antineoplastic Agents, Phytogenic
  • Biological Products
  • Sapogenins
  • protopanaxadiol