Sesterterpenoids isolated from a northeastern Pacific Phorbas sp

J Org Chem. 2013 Sep 6;78(17):8267-73. doi: 10.1021/jo4014589. Epub 2013 Aug 20.

Abstract

Four new sesterterpenoids, ansellone B (4), phorbadione (5), secoepoxyansellone A (6), and alotaketal C (7), have been isolated from specimens of the sponge Phorbas sp. collected in British Columbia. Ansellone B (4) has an unprecedented heterocyclic skeleton featuring an oxocane ring, and secoepoxyansellone A (6) is the first example of the degraded "secoansellane" sesterterpenoid carbon skeleton. Alotaketal C (7) is an activator of cAMP signaling in HEK cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cyclic AMP / metabolism
  • Dose-Response Relationship, Drug
  • HEK293 Cells
  • Humans
  • Molecular Conformation
  • Porifera / chemistry*
  • Sesterterpenes / chemistry
  • Sesterterpenes / isolation & purification*
  • Sesterterpenes / pharmacology
  • Signal Transduction / drug effects
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Sesterterpenes
  • Cyclic AMP