Pleosporalone A, the first azaphilone characterized with aromatic A-ring from a marine-derived Pleosporales sp. fungus

Nat Prod Res. 2016 Nov;30(21):2448-52. doi: 10.1080/14786419.2016.1198352. Epub 2016 Jul 6.

Abstract

A fungal strain, Pleosporales sp. CF09-1, was isolated from marine sediment collected from the Bohai Sea. A novel azaphilone derivative, named pleosporalone A (1), along with two known analogues, cohaerins A and B (2 and 3), were obtained and identified from the culture extract of Pleosporales sp. CF09-1. Their planar structures were elucidated by detailed analysis of spectroscopic data and by comparison with related known compounds. Pleosporalone A (1) represents the first azaphilone derivative characterised with A-ring aromatisation. Compound 1 showed strong antifungal activity against three plant pathogenic fungi Botrytis cinerea, Rhizopus oryzae and Phytophthora capsici with the MIC values of 0.39, 0.78 and 0.78 μM, respectively.

Keywords: Marine sediment; Pleosporales sp; antifungal activity; azaphilone derivative.

MeSH terms

  • Ascomycota / metabolism*
  • Benzopyrans / chemistry
  • Benzopyrans / isolation & purification*
  • Benzopyrans / pharmacology
  • Botrytis / drug effects
  • Fungicides, Industrial / pharmacology
  • Geologic Sediments / microbiology*
  • Phytophthora / drug effects
  • Pigments, Biological / chemistry
  • Pigments, Biological / isolation & purification*
  • Pigments, Biological / pharmacology

Substances

  • Benzopyrans
  • Fungicides, Industrial
  • Pigments, Biological
  • azaphilone
  • pleosporalone A