Phorone A and isophorbasone A, sesterterpenoids isolated from the marine sponge Phorbas sp

Org Lett. 2012 Sep 7;14(17):4486-9. doi: 10.1021/ol3019874. Epub 2012 Aug 24.

Abstract

A chemical investigation of a Korean marine sponge, Phorbas sp., yielded unprecedented sesterterpenoids phorone A (1) and isophorbasone A (2) along with ansellone B (3) and phorbasone A acetate (4). Their complete structures were elucidated by the combination of spectroscopic data and chemical manipulation. Phorone A (1) and isophorbasone A (2) have the new "phorane"(5) and "isophorbasane"(6) sesterterpenoid carbon skeletons, respectively. Ansellone B (3) and phorbasone A acetate (4) exhibited potent inhibitory activity on nitric oxide production in RAW 264.7 LPS-activated mouse macrophage cells with IC(50) values of 4.5 and 2.8 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Ketones
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Marine Biology
  • Mice
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Porifera / chemistry*
  • Sesterterpenes / chemistry
  • Sesterterpenes / isolation & purification*
  • Sesterterpenes / pharmacology

Substances

  • Ketones
  • Lipopolysaccharides
  • Sesterterpenes
  • isophorbasone A
  • phorone A
  • Nitric Oxide
  • phorone