New anti-bacterial halogenated tricyclic sesquiterpenes from Bornean Laurencia majuscula (Harvey) Lucas

Nat Prod Res. 2019 Feb;33(4):464-471. doi: 10.1080/14786419.2017.1396593. Epub 2017 Nov 2.

Abstract

Three new halogenated tricyclic sesquiterpenes, omphalaurediol (1), rhodolaurenones B (2) and C (3) were isolated together with nine known haloganated sesquiterpenes such as rhodolaurenone A (4), rhodolaureol (5), isorhodolaureol (6), (-)-laurencenone D (7), elatol (8), (+)-deschloroelatol (9), cartilagineol (10), (+)-laurencenone B (11) and 2-chloro-3-hydroxy-α-chamigren-9-one (12) from a population of Bornean red algae Laurencia majuscula. The structures of three new metabolites were determined based on their spectroscopic data (IR, 1D and 2D NMR, and MS). These compounds showed antibacterial activity against three human pathogenic bacteria (Escherichia coli, Salmonella typhi and Vibrio cholera).

Keywords: antibacterial activity; halogenated tricyclic sesquiterpene; omphalane; rhodolaurane.

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology*
  • Drug Evaluation, Preclinical / methods
  • Escherichia coli / drug effects
  • Laurencia / chemistry*
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Polycyclic Sesquiterpenes
  • Salmonella typhi / drug effects
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology*
  • Spiro Compounds / chemistry
  • Spiro Compounds / pharmacology
  • Vibrio cholerae / drug effects

Substances

  • Anti-Bacterial Agents
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes
  • Spiro Compounds
  • deschloroelatol
  • laurencenone B
  • elatol