Illudalane sesquiterpenoids from the soft coral Alcyonium paessleri: the first natural nitrate esters

J Org Chem. 2000 Jul 28;65(15):4482-6. doi: 10.1021/jo991740x.

Abstract

Fifteen illudalane sesquiterpenoids, alcyopterosins A-O (1-15) have been isolated from the subAntarctic soft coral Alcyonium paessleri which was collected at a depth of 200 m near the South Georgia Islands, and their structures were elucidated by spectroscopic techniques. Eight of these compounds (2, 3, 5-8, 10, and 13) are the first natural nitrate esters, while the other four (1, 4, 11, and 12) are chlorinated. These compounds are as well the first illudalane sesquiterpenoids to be isolated from the marine environment. Compounds 1, 3, 5, and 8 showed mild cytotoxicity toward human tumor cell lines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antarctic Regions
  • Cell Line
  • Cnidaria / chemistry*
  • Esters / chemistry*
  • Esters / isolation & purification
  • Esters / toxicity
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nitrates / chemistry*
  • Nitrates / isolation & purification*
  • Nitrates / toxicity
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / toxicity
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Esters
  • Nitrates
  • Sesquiterpenes