Production of phenylacetic acid derivatives and 4-epiradicinol in culture by Curvularia lunata

Phytochemistry. 2006 Sep;67(17):1925-30. doi: 10.1016/j.phytochem.2006.05.032. Epub 2006 Aug 1.

Abstract

Phenylacetic acid derivatives, methyl 2-acetyl-3,5-dihydroxyphenylacetate (1) and methyl 2-acetyl-5-hydroxy-3-methoxyphenylacetate (3); curvulin or ethyl 2-acetyl-3,5-dihydroxyphenylacetate (4), a known metabolite of Curvularia siddiqui, and 4-epiradicinol (5) have been isolated from the culture mycelia of Curvularia lunata grown on YMG, a medium consisting of yeast, malt extract and glucose. Compounds 1, 3 and 4 lack antimicrobial and antioxidant activity, but 4-epiradicinol (5) inhibited the growth of Escherichia coli, Staphylococcus aureus, Salmonella choleraesuis and Bacillus subtilis. The structures of compounds 1, 3-5 were determined by analyses of IR, MS, 1D and 2D NMR data, assisted by chemical shift comparison to related and model compounds. The relative stereochemistry of the vicinal diol in 5 was determined from the 1H NMR signals for the methyl protons of the resulting cyclic acetonide prepared from 5.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / metabolism
  • Anti-Bacterial Agents / pharmacology
  • Ascomycota / growth & development
  • Ascomycota / metabolism*
  • Bacillus subtilis / drug effects
  • Culture Media, Conditioned / chemistry
  • Culture Media, Conditioned / pharmacology
  • Escherichia coli / drug effects
  • Magnetic Resonance Spectroscopy / methods
  • Microbial Sensitivity Tests / methods
  • Molecular Structure
  • Phenylacetates / chemistry
  • Phenylacetates / metabolism*
  • Phenylacetates / pharmacology
  • Staphylococcus aureus / drug effects

Substances

  • Anti-Bacterial Agents
  • Culture Media, Conditioned
  • Phenylacetates
  • methyl 2-acetyl-3,5-dihydroxyphenylacetate
  • methyl 2-acetyl-5-hydroxy-3-methoxyphenylacetate
  • phenylacetic acid