Natural zinniol derivatives from Alternaria tagetica. Isolation, synthesis, and structure-activity correlation

J Agric Food Chem. 2002 Feb 27;50(5):1053-8. doi: 10.1021/jf010641t.

Abstract

Two novel phytotoxins, 8-zinniol methyl ether (5) and 8-zinniol acetate (6), in addition to 6-(3',3'-dimethylallyloxy)-4-methoxy-5-methylphthalide (2), 5-(3',3'-dimethylallyloxy)-7-methoxy-6-methylphthalide (3), and the novel metabolites 8-zinniol 2-(phenyl)ethyl ether (4) and 7-zinniol acetate (7) have been identified as natural zinniol derivatives from the organic crude extract of Alternaria tagetica culture filtrates. Using zinniol as the starting material, phytotoxin 5 was synthesized, together with a number of synthetic intermediates (8-13). Both natural and synthetic zinniol derivatives were evaluated in the leaf-spot bioassay against marigold leaves (Tagetes erecta).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alternaria / chemistry*
  • Alternaria / metabolism
  • Hydrolysis
  • Magnetic Resonance Spectroscopy
  • Methylation
  • Molecular Conformation
  • Mycotoxins / chemical synthesis
  • Mycotoxins / chemistry
  • Mycotoxins / isolation & purification*
  • Mycotoxins / metabolism
  • Structure-Activity Relationship
  • Xylenes / chemical synthesis
  • Xylenes / chemistry
  • Xylenes / isolation & purification*
  • Xylenes / metabolism

Substances

  • Mycotoxins
  • Xylenes
  • zinniol