Antibiotic activity and absolute configuation of 8S-heptadeca-2(Z),9(Z)-diene-4,6-diyne-1,8-diol from Bupleurum salicifolium

J Nat Prod. 1994 Aug;57(8):1178-82. doi: 10.1021/np50110a009.

Abstract

A polyacetylene has been isolated from Bupleurum salicifolium. Its structure and absolute configuration were determined to be 8S-heptadeca-2(Z),9(Z)-diene-4,6-diyne-1,8-diol [1] by means of 1H- and 13C-nmr spectroscopic studies, including 1H-13C heteronuclear correlation (HMQC) and long-range correlation spectra with inverse detection (HMBC). Its absolute configuration was determined by application of the Horeau method. This compound exhibited significant antibiotic activity against the Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis. Also isolated during this investigation were the known compounds; betulin, herniarin, 6,7,8-trimethoxycoumarin, p-hydroxyphenethyl alcohol, pluviatolide, guamaroline, bursehernin, guayadequiol, kaerophyllin, and matairesinol dimethyl ether.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology*
  • Bacillus subtilis / drug effects
  • Enediynes
  • Fatty Alcohols / chemistry
  • Fatty Alcohols / pharmacology
  • Gram-Negative Bacteria / drug effects
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Spain
  • Staphylococcus aureus / drug effects

Substances

  • Alkynes
  • Anti-Bacterial Agents
  • Enediynes
  • Fatty Alcohols
  • heptadeca-2,9-diene-4,6-diyne-1,8-diol