Journal
JOURNAL OF NATURAL PRODUCTS
Volume 65, Issue 11, Pages 1715-1718Publisher
AMER CHEMICAL SOC
DOI: 10.1021/np0202576
Keywords
-
Funding
- NCRR NIH HHS [G12RR03641] Funding Source: Medline
- NIGMS NIH HHS [S06GM08102] Funding Source: Medline
Ask authors/readers for more resources
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available