Heptaketides from Corynespora sp. inhabiting the cavern beard lichen, Usnea cavernosa: first report of metabolites of an endolichenic fungus

J Nat Prod. 2007 Nov;70(11):1700-5. doi: 10.1021/np070466w. Epub 2007 Nov 8.

Abstract

Two new heptaketides, corynesporol (1) and 1-hydroxydehydroherbarin (2), along with herbarin (3) were isolated from an endolichenic fungal strain, Corynespora sp. BA-10763, occurring in the cavern beard lichen Usnea cavernosa. The structures of 1-3 were elucidated from their spectroscopic data. Aerial oxidation of corynesporol (1) yielded herbarin (3). Acetylation of 1 afforded the naphthalene derivative 4, whereas acetylation of 3 gave the corresponding naphthoquinone 6 and dehydroherbarin (5). All compounds were evaluated for their cytotoxicity and ability to inhibit migration of human metastatic breast and prostate cancer cell lines MDA-MB-231 and PC-3M, respectively. Dehydroherbarin (5) inhibited migration of both cell lines at concentrations not toxic to these cell lines. This is the first report of metabolites from an endolichenic fungus.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Arizona
  • Ascomycota / chemistry*
  • Drug Screening Assays, Antitumor
  • Female
  • Humans
  • Male
  • Molecular Structure
  • Naphthoquinones / chemistry
  • Naphthoquinones / isolation & purification*
  • Naphthoquinones / pharmacology
  • Usnea

Substances

  • 1-hydroxydehydroherbarin
  • Antineoplastic Agents
  • Naphthoquinones
  • corynesporol
  • herbarin