New polyaromatic metabolites from a marine-derived fungus Penicillium sp

Org Lett. 2013 Mar 15;15(6):1286-9. doi: 10.1021/ol4002174. Epub 2013 Feb 22.

Abstract

Herqueiazole (1), herqueioxazole (2), and herqueidiketal (3), polyaromatic metabolites with a novel skeletal class, were isolated from the marine-derived fungus Penicillium sp. Based on the combined spectroscopic analyses, the structures of 1 and 2 were determined to be the first examples of pyrrole- and oxazole-containing phenalenone compounds, respectively, whereas 3 possessed a novel skeleton with a highly oxidized naphthoquinone moiety. Compound 3 exhibited moderate cytotoxicity and significant inhibitory activity against sortase A.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Heterocyclic Compounds, 4 or More Rings / isolation & purification*
  • Heterocyclic Compounds, 4 or More Rings / pharmacology
  • Marine Biology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Penicillium / chemistry*
  • Staphylococcus aureus / drug effects

Substances

  • Anti-Bacterial Agents
  • Heterocyclic Compounds, 4 or More Rings
  • herqueiazole
  • herqueidiketal
  • herqueioxazole