Sorbicillinol, a key intermediate of bisorbicillinoid biosynthesis in Trichoderma sp. USF-2690

Biosci Biotechnol Biochem. 2001 Oct;65(10):2271-9. doi: 10.1271/bbb.65.2271.

Abstract

In the course of our screening program for free radical scavengers from Trichoderma sp. USF-2690, we found an unidentified metabolite (1) that appeared by the method used for HPLC analysis. Metabolite 1 gradually decreased with the production of bisorbicillinoids and was easily missed during the general isolation procedure. The LC-ESI-MS (negative) analysis for 1 gave m/z 247 as the (M-1)- ion peak. The hydrolysis of synthetic 6-O-acetylsorbicillinol (+/- -2) by 0.05 M KOH and acetylation of product 1 in an aqueous solution indicated that the structure of 1 was (6S)-4-(2,4-hexadienoyl)-3,6-dihydroxy-2,6-dimethyl-2,4-cyclohexadien-1-one, designated sorbicillinol, a quinol that has been postulated to be important in bisorbicillinoid biosynthesis.

MeSH terms

  • Bepridil / analogs & derivatives*
  • Bepridil / chemistry
  • Biphenyl Compounds
  • Chromatography, High Pressure Liquid
  • Cyclohexanones / chemistry
  • Cyclohexanones / metabolism*
  • Fermentation
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / metabolism
  • Gas Chromatography-Mass Spectrometry
  • Kinetics
  • Picrates*
  • Trichoderma / metabolism*

Substances

  • Biphenyl Compounds
  • Cyclohexanones
  • Free Radical Scavengers
  • Picrates
  • sorbicillinol
  • Bepridil
  • 1,1-diphenyl-2-picrylhydrazyl