Microbial transformation of some triterpenoids of Guayule resin by Chaetomium sp.

Marielle C. Inacio, Weimao Zhong, Ya Ming Xu, E. M.Kithsiri Wijeratne, Chandrashekhar Madasu, István Molnár, A. A.Leslie Gunatilaka

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Microbial biotransformation of argentatin A (1), isoargentatin A (2) and argentatin C (3), the triterpenoid constituents of guayule (Parthenium argentatum) resin was conducted with Chaetomium sp. PA001, an endophytic fungus of the same plant. The experiments yielded six new products (4–9) formed by: (i) nucleophilic oxygenation of the 3-ketone moiety resulting in Baeyer-Villiger oxidation; (ii) lactone ring opening of these oxidation products; (iii) rearrangement of the 9(10)-cyclopropane ring; and (iv) reduction of the 3-ketone moiety. The structures of all new biotransformation products were established by detailed analysis of their spectroscopic data. None of the products exhibited any antimicrobial activity. However, the hydroxy-carboxylic acid derivative 5 of argentatin A showed weak cytotoxic activity, but improved selectivity against human breast cancer cell line MCF-7 compared to the parent compound. This constitutes the first report of microbial biotransformation of isoargentatin A and argentatin C.

Original languageEnglish (US)
Pages (from-to)124-130
Number of pages7
JournalPhytochemistry Letters
Volume55
DOIs
StatePublished - Jun 2023

Keywords

  • Argentatins
  • Biotransformation
  • Chaetomium sp.PA001
  • Enzymatic Baeyer-Villiger oxidation
  • Guayule
  • Parthenium argentatum

ASJC Scopus subject areas

  • Biotechnology
  • Biochemistry
  • Agronomy and Crop Science
  • Plant Science

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