Brominated metabolites from an Okinawan Laurencia intricata

Phytochemistry. 2002 Aug;60(8):861-7. doi: 10.1016/s0031-9422(02)00151-6.

Abstract

Two halogenated C(15) acetogenins, itomanallenes A and B, with a terminal bromoallene moiety along with a halogenated sesquiterpene, itomanol, have been isolated from the red alga Laurencia intricata collected in Okinawan waters. Their structures were deduced from 1D and 2D NMR experiments including (1)H-(1)H COSY, HSQC, HMBC, and NOESY methods. The alcohol corresponding to itomanallene B seems to be a plausible precursor of itomanallene A, which has an unusual 2,10-dioxabicyclo[7.3.0]dodecene skeleton. Itomanol was found to be a selinane-type bromosesquiterpenoid, and is the first example of a selinane to be isolated from Japanese Laurencia species.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bromine / metabolism*
  • Heterocyclic Compounds, 2-Ring / chemistry
  • Heterocyclic Compounds, 2-Ring / isolation & purification*
  • Molecular Structure
  • Rhodophyta / metabolism*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Spectrum Analysis

Substances

  • Heterocyclic Compounds, 2-Ring
  • Sesquiterpenes
  • itomanallene A
  • itomanallene B
  • itomanol
  • Bromine