New acyclic sesquiterpenes and norsesquiterpenes from the Caribbean Gorgonian Plexaurella grisea

J Nat Prod. 2001 Apr;64(4):401-5. doi: 10.1021/np000540+.

Abstract

The gorgonian Plexaurella grisea from Punta Cana, Dominican Republic, contains five new acyclic sesquiterpenes, (3E,5E)-3,7,11-trimethyl-9-oxododeca-1,3,5-triene (3), (3Z,5E)-3,7,11-trimethyl-9-oxododeca-1,3,5-triene (4), (3E)-6-acetoxy-3,11-dimethyl-7-methylidendodeca-1,3,10-triene (5), (3E,5E)-7-hydroxy-3,7,11-trimethyldodeca-1,3,5,10-tetraene (6), and (3E,5E,9E)-8,11-diacetoxy-3,7,11-trimethyldodeca-1,3,5,9-tetraene (7), and two new linear norsesquiterpenes, (2E,4E,7Z)-2,6,10-trimethylundeca-2,4,7,9-tetraenal (8) and (2E,4E)-2,6,10-trimethylundeca-2,4,9-trienal (9), in addition to the known compounds 1, 2, and 10. The structures of the new compounds 3-9 were elucidated by interpretation of spectroscopic data. In general, the new compounds are mildly cytotoxic against tumor cell lines, and although norsesquiterpene 8 was inactive, norsesquiterpene 9 exhibited the greatest and selective activity against the P-388 tumor cell line.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cnidaria
  • Drug Screening Assays, Antitumor
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Structure
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Tumor Cells, Cultured

Substances

  • Sesquiterpenes