New polyoxygenated farnesylcyclohexenones, deacetoxyyanuthone A and its hydro derivative from the marine-derived fungus Penicillium sp

J Nat Prod. 2003 Nov;66(11):1499-500. doi: 10.1021/np030231u.

Abstract

New polyoxygenated farnesylcyclohexenones, 7-deacetoxyyanuthone A (1) and its 2,3-hydro derivative (2), were isolated together with the known farnesylquinones (3, 4) from a marine isolate of the genus Penicillium. The structures of the new deacetoxyyanuthone A (1) and its 2,3-hydro derivative (2) were assigned by spectroscopic methods, including 2D NMR and CD for the Cotton effect of alpha-epoxyketone experiments. Compounds 1 and 3 showed moderate in vitro cytotoxicity in a panel of five human tumor cell lines, and 1 also exhibited mild in vitro antibacterial activity against methicillin-resistant and multidrug-resistant Staphylococcus aureus (MIC, 50 microg/mL).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Cyclohexanes / chemistry
  • Cyclohexanes / isolation & purification*
  • Cyclohexanes / pharmacology
  • Farnesol / analogs & derivatives
  • Farnesol / chemistry
  • Farnesol / isolation & purification*
  • Farnesol / pharmacology
  • Korea
  • Methicillin Resistance
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Penicillium / chemistry*
  • Staphylococcus aureus / drug effects*

Substances

  • Anti-Bacterial Agents
  • Cyclohexanes
  • deacetoxyyanuthone A
  • Farnesol