Metabolites with nematicidal and antimicrobial activities from the ascomycete Lachnum papyraceum (Karst.) Karst. III. Production of novel isocoumarin derivatives, isolation, and biological activities

J Antibiot (Tokyo). 1995 Mar;48(3):261-6. doi: 10.7164/antibiotics.48.261.

Abstract

During investigations on the influence of CaBr2 on the secondary metabolism of Lachnum papyraceum, the production of mycorrhizins and lachnumon type antibiotics was strongly inhibited in bromide-containing culture media. Instead, six isocoumarin derivatives, 6-hydroymellein (6), 4-chloro-6-hydroxymellein (7), 4-bromo-6-hydroxymellein (9), 6-methoxymellein (10). 4-chloro-6-methoxymellein (11), and 4-chloro-6,7-dihydroxymellein (12) were isolated. Compounds 7, 9, 11, and 12 have never been isolated from natural sources. 6-Hydroxymellein has been isolated previously from many sources including Gilmaniella humicola and proposed to be a precursor of mycorrhizin A (see reference 6). In comparison to the mycorrhizins, the isocoumarin derivatives exhibited only weak antimicrobial, cytotoxic, phytotoxic, and nematicidal activities.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Infective Agents / isolation & purification*
  • Anti-Infective Agents / pharmacology
  • Antinematodal Agents / isolation & purification*
  • Antinematodal Agents / pharmacology
  • Ascomycota / metabolism*
  • Caenorhabditis elegans
  • Cell Line
  • Chromatography, High Pressure Liquid
  • Coumarins / isolation & purification*
  • Coumarins / pharmacology
  • Fermentation
  • HeLa Cells
  • Humans
  • Microbial Sensitivity Tests

Substances

  • Anti-Infective Agents
  • Antinematodal Agents
  • Coumarins
  • mycorrhizin A