Antibiotic Activity and Absolute Configuration of 8S-Heptadeca-2(Z),9(Z)-diene-4,6-diyne-1,8-diol from Bupleurum salicifolium

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 super(1)H- and super(13)C-nmr spectroscopic studies, including super(1)H- super(13)C heteronuclear correlation...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1994-08, Vol.57 (8), p.1178-1182
Main Authors: Estevez-Braun, A, Estevez-Reyes, R, Moujir, L. M, Ravelo, A. G, Gonzalez, A. G
Format: Article
Language:English
Subjects:
ANTIMICROBIAL PROPERTIES
BACILLUS SUBTILIS
CANARIAS
CANARIES (ILES)
CANARY ISLANDS
CHEMICAL COMPOSITION
COMPOSICION QUIMICA
COMPOSITION CHIMIQUE
ESPECTROMETRIA
HIDROCARBUROS
HYDROCARBONS
HYDROCARBURE
MOLECULAR CONFORMATION
MOLECULAR STRUCTURE
POLYACETYLENES
PROPIEDADES ANTIMICROBIANAS
PROPRIETE ANTIMICROBIENNE
SPECTRAL ANALYSIS
SPECTROMETRIE
SPECTROMETRY
STAPHYLOCOCCUS AUREUS
UMBELLIFERAE
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Summary: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 super(1)H- and super(13)C-nmr spectroscopic studies, including super(1)H- super(13)C 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.
ISSN:0163-3864
1520-6025
DOI:10.1021/np50110a009