Brominated labdane-type diterpenoids from an Okinawan Laurencia sp

J Nat Prod. 2002 Jun;65(6):801-4. doi: 10.1021/np010596j.

Abstract

From an unidentified species of Laurencia collected from Okinawan waters two novel brominated metabolites, 1 and 2, along with known halogenated compounds, 2,10-dibromo-3-chloro-alpha-chamigrene (3) and microcladallene A (4), were isolated and identified. The structures of these new compounds were established as ent-labdane-type bromoditerpenes, (1S,3R,5S,6S,8S,9S,10R,13R)-1-acetoxy-3-bromo-6-hydroxy-8,13-epoxy-labd-14-ene (1) and (3R,5S,6S,8S,9S,10R,13R)-3-bromo-6-hydroxy-8,13-epoxylabd-14-en-1-one (2), by interpretation of their spectroscopic data as well as by X-ray crystallographic analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Escherichia coli / drug effects
  • Hydrocarbons, Brominated / chemistry*
  • Hydrocarbons, Brominated / isolation & purification*
  • Hydrocarbons, Brominated / pharmacology
  • Japan
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pseudomonas / drug effects
  • Rhodophyta / chemistry*
  • Salmonella / drug effects
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology
  • Spectrophotometry, Infrared
  • Staphylococcus / drug effects
  • Stereoisomerism

Substances

  • 1-acetoxy-3-bromo-6-hydroxy-8,13-epoxy-labd-14-ene
  • 2,10-dibromo-3-chloro-alpha-chamigrene
  • 3-bromo-6-hydroxy-8,13-epoxylabd-14-en-1-one
  • Diterpenes
  • Hydrocarbons, Brominated
  • Sesquiterpenes
  • microcladallene A