Dactylomelatriol, a biogenetically intriguing omphalane-derived marine sesquiterpene

J Nat Prod. 2012 Jan 27;75(1):115-8. doi: 10.1021/np200845f. Epub 2012 Jan 5.

Abstract

Dactylomelatriol (1), obtained from the sea hare Aplysia dactylomela, is the first naturally occurring omphalane-derived sesquiterpene from the marine environment. From this species the known chamigrene and modified bisabolene sesquiterpenes 2-6 were also isolated. The structure and relative configuration of 1 were established by spectroscopic evidence. Its chemical structure is related to omphalic acid, the unique terrestrial-derived omphalane sesquiterpene isolated from a liverwort. A biogenetic route for this compound is proposed. The antimicrobial activities of compounds 1-6 were evaluated against a panel of microorganisms.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / isolation & purification*
  • Anti-Infective Agents / pharmacology
  • Aplysia / chemistry*
  • Bacillus cereus / drug effects
  • Candida albicans / drug effects
  • Feeding Behavior
  • Laurencia / chemistry
  • Marine Biology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology

Substances

  • Anti-Infective Agents
  • Sesquiterpenes
  • dactylomelatriol