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

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.