Probing sponge-derived terpenoids for human 15-lipoxygenase inhibitors

J Org Chem. 2001 Oct 19;66(21):6847-51. doi: 10.1021/jo015784t.

Abstract

A human 15-lipoxygenase (15-HLO) assay has been employed to discover new marine-sponge-derived bioactive compounds. Extracts from two different sponges, Jaspis splendens (order Choristida, family Jaspidae) and Suberea sp. (order Verongida, family Aplysinellidae), exhibited potent IC(50) values of 0.4 and 0.1 microg/mL, respectively. Both are sources of terpenoids, and the former is a known source of (+)-jasplakinolide (7), which is inactive as a 15-HLO inhibitor. The terpenoids included (+)-(5S,6S)-subersin (1, IC(50) > 100 microM), (-)-(5R,10R)-subersic acid (2, IC(50) = 15 microM), jaspaquinol (3, IC(50) = 0.3 microM), and (-)-jaspic acid (4, IC(50) = 1.4 microM). Structure elucidations and lipoxygenase activity studies of these compounds are reported.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Humans
  • Inhibitory Concentration 50
  • Lipoxygenase Inhibitors*
  • Molecular Structure
  • Porifera / chemistry*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Terpenes / pharmacology*

Substances

  • Lipoxygenase Inhibitors
  • Terpenes