Terpene isocyanides, isocyanates, and isothiocyanates from the Okinawan marine sponge Stylissa sp

J Nat Prod. 2004 May;67(5):833-7. doi: 10.1021/np030458p.

Abstract

Seven new nitrogenous terpenoids, (1R,6R,7S,10S)-10-isothiocyanatocadin-4-ene (1), (1S,2S,5S,6S,7R,8S)-13-isothiocyanatocubebane (2), (1R,3S,4R,7S,8S,12S,13S)-7-isocyanoamphilecta-10,14-diene (3), (1S,3S,4R,7S,8S,12S,13S)-8-isocyanoamphilecta-11(20),14-diene (4), (3S,4R,7S,8S,11S,13S)-8-isocyanoamphilecta-1(12),14-diene (5), 8-isocyanatocycloamphilect-10-ene (6), and 8-isothiocyanatocycloamphilect-10-ene (7), were isolated from the Okinawan sponge Stylissasp., along with 12 known related compounds. Structural determinations of these compounds were made by spectroscopic analysis, and assessment was made of their cytotoxicity toward HeLa cells.

MeSH terms

  • Animals
  • Crystallography, X-Ray
  • Cyanates / chemistry*
  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • Humans
  • Japan
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Porifera / chemistry*
  • Stereoisomerism
  • Terpenes / chemistry
  • Terpenes / isolation & purification*
  • Terpenes / pharmacology
  • Tumor Cells, Cultured

Substances

  • Cyanates
  • Terpenes