期刊
JOURNAL OF NATURAL PRODUCTS
卷 65, 期 11, 页码 1715-1718出版社
AMER CHEMICAL SOC
DOI: 10.1021/np0202576
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资金
- NCRR NIH HHS [G12RR03641] Funding Source: Medline
- NIGMS NIH HHS [S06GM08102] Funding Source: Medline
The naturally occurring (5Z,9Z)-5,9-hexadecadienoic acid was synthesized stereochemically pure in six steps starting with commercially available 1,5-hexadiyne. The title compound was antimicrobial against the Gram-positive bacteria Staphylococcus aureus (MIC 80 muM) and Streptococcus faecalis (MIC 200 muM), but inactive against Gram-negative bacteria such as Pseudomonas aeruginosa. In addition, the (5Z,9Z)5,9-hexadecadienoic acid completely inhibits human topoisomerase I at a concentration of 800 muM, while 5,9-hexadecadiynoic acid and hexadecanoic acid do not inhibit topoisomerase I (> 1000 muM). This comparison reveals that the cis double bond geometry in the title compound is required for topoisomerase I inhibition. Moreover, these results suggest that the antimicrobial activity of (5Z,9Z)-5,9-hexadecadienoic acid against either S. aureus or S. faecalis could be a result, at least in part, of the inhibitory activity of the acid against topoisomerases.
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