Synthesis of a natural gamma-butyrolactone from nerylacetone by Acremonium roseum and Fusarium oxysporum cultures

Nat Prod Commun. 2011 Mar;6(3):367-70.

Abstract

Natural gamma-butyrolactone - (4R, 5R)-5-(4'-methyl-3'pentenyl)-4-hydroxy-5-methyl-dihydrofuran-2-one (2) was isolated as the product of microbial transformation of nerylacetone (1) by fungal strains. This product was obtained as the enantiomer (+) in high yields 24% and 61% with ee=94% and 82% by the biotransformation in the cultures of Acremonium roseum AM336 and Fusarium oxysporum AM13 respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / metabolism*
  • Acetone / analogs & derivatives*
  • Acetone / chemistry
  • Acremonium / chemistry
  • Acremonium / metabolism*
  • Biotransformation
  • Cell Line, Tumor
  • Chromatography, Gas
  • Drug Screening Assays, Antitumor
  • Fusarium / chemistry
  • Fusarium / metabolism*
  • Humans
  • Magnetic Resonance Spectroscopy
  • Spectrophotometry, Infrared
  • Tetrazolium Salts
  • Thiazoles

Substances

  • Tetrazolium Salts
  • Thiazoles
  • Acetone
  • thiazolyl blue
  • nerylacetone
  • 4-Butyrolactone