Phytotoxic sesterterpene, 11-epiterpestacin, from Bipolaris sorokiniana NSDR-011

Biosci Biotechnol Biochem. 2002 Mar;66(3):685-8. doi: 10.1271/bbb.66.685.

Abstract

The structure of siccanol, a phytotoxic sesterterpene of fungal origin, was analyzed after chemical conversion by NMR spectroscopy. Siccanol was found to be an epimer of terpestacin that has been isolated from Arthrinium sp., and was thus renamed 11-epiterpestacin. Its stereochemistry was also identical with that of fusaproliferin, a structurally related mycotoxin from Fusarium proliferatum. Therefore, this sesterterpene may also be referred to as 24-deacetyl fusaproliferin. The phytotoxicity of 11-epiterpestacin was almost equal to that of terpestacin, but significantly higher than that of fusaproliferin.

MeSH terms

  • Ascomycota / chemistry*
  • Bridged Bicyclo Compounds / pharmacology*
  • Crystallography, X-Ray
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Molecular Sequence Data
  • Plant Diseases / microbiology
  • Plant Roots / drug effects
  • Plant Roots / growth & development
  • Secale / drug effects
  • Secale / growth & development

Substances

  • Bridged Bicyclo Compounds
  • terpestacin

Associated data

  • GENBANK/AB055799