Sesquiterpenes from the red alga Laurencia tristicha

J Nat Prod. 2005 Jun;68(6):915-9. doi: 10.1021/np050096g.

Abstract

Seven new sesquiterpenes (1-7), together with seven known sesquiterpenes, aplysin (8), aplysinol (9), gossonorol (10), 7,10-epoxy-ar-bisabol-11-ol (11), 10-epi-7,10-epoxy-ar-bisabol-11-ol (12), johnstonol (13), and laurebiphenyl (14), have been isolated from the red alga Laurencia tristicha. The structures of new compounds were established as laur-11-en-2,10-diol (1), laur-11-en-10-ol (2), laur-11-en-1,10-diol (3), 4-bromo-1,10-epoxylaur-11-ene (4), cyclolauren-2-ol (5), laurentristich-4-ol (6), and ar-bisabol-9-en-7,11-diol (7) by means of spectroscopic methods including IR, HRMS, and 1D and 2D NMR techniques. Compound 6 possessed a novel rearranged skeleton. All compounds were tested against several human cancer cell lines including lung adenocarcinoma (A549), stomach cancer (BGC-823), hepatoma (Bel 7402), colon cancer (HCT-8), and HELA cell lines. Laurebiphenyl (14) showed moderate cytotoxicity against all tested cell lines, with IC(50) values of 1.68, 1.22, 1.91, 1.77, and 1.61 microg/mL, respectively. Other compounds were inactive (IC(50) > 10 microg/mL).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Drug Screening Assays, Antitumor
  • Humans
  • Laurencia / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Stereoisomerism
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Sesquiterpenes