Crellasterones A and B: A-Norsterol Derivatives from the New Caledonian Sponge Crella incrustans

Mar Drugs. 2017 Jun 15;15(6):177. doi: 10.3390/md15060177.

Abstract

Two new steroids, crellasterones A (1) and B (2), together with the previously reported compound chalinasterol (3) and several nucleosides (4-7), were isolated from the sponge Crella incrustans, collected in New Caledonia. The structures of the new compounds were established by extensive NMR and mass spectroscopic analysis and revealed unprecedented marine natural products with a ring-contracted A-norsterone nucleus and 2-hydroxycyclopentenone chromophore. The absolute configurations were derived from electronic circular dichroism (ECD) measurements in conjunction with high-level density functional theory (DFT) calculations.

Keywords: Crella; DFT; crellasterone; marine natural products; sponge; steroid.

MeSH terms

  • Animals
  • Magnetic Resonance Spectroscopy
  • Norsteroids / chemistry
  • Norsteroids / isolation & purification*
  • Porifera / chemistry*

Substances

  • Norsteroids
  • crellasterone