Structures and biological activities of azaphilones produced by Penicillium sp. KCB11A109 from a ginseng field

Phytochemistry. 2016 Feb:122:154-164. doi: 10.1016/j.phytochem.2015.12.008. Epub 2015 Dec 19.

Abstract

Twelve metabolites, including five highly oxygenated azaphilones, geumsanols A-E, along with seven known analogues were isolated from Penicillium sp. KCB11A109, a fungus derived from a ginseng field. Their structures were assigned by spectroscopic means (NMR and MS), and stereochemistries were determined by extensive spectroscopic analyses ((1)H-(1)H coupling constants, NOESY, and HETLOC) and chemical derivatizations (modified Mosher's method and acetonide formation). The isolates were evaluated for their anticancer, antimicrobial, antimalarial activities, and phenotypic effects in zebrafish development. Of these compounds possessing no pyranoquinone core, only geumsanol E exhibited cytotoxic activities and toxic effects on zebrafish embryos, suggesting that a double bond at C-11 and C-12 is important for biological activity.

Keywords: Azaphilone; Geumsanol; Penicillium sp.; Structure elucidation; Trichocomaceae; Zebrafish screening.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Benzopyrans / chemistry
  • Benzopyrans / isolation & purification*
  • Benzopyrans / pharmacology*
  • Drug Screening Assays, Antitumor
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Panax / microbiology*
  • Penicillium / chemistry*
  • Pigments, Biological / chemistry
  • Pigments, Biological / isolation & purification*
  • Pigments, Biological / pharmacology*
  • Zebrafish / growth & development

Substances

  • Benzopyrans
  • Pigments, Biological
  • azaphilone
  • geumsanol E