Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 16, Issue -, Pages 297-304Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.16.29
Keywords
antibacterial; coral; keto fatty acid; Micrococcus; PPAR
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Funding
- JSPS KAKENHI [24580156]
- Grants-in-Aid for Scientific Research [24580156] Funding Source: KAKEN
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A pair of geometrically isomeric unsaturated keto fatty acids, (6E,8Z)- and (6E,8E)-5-oxo-6,8-tetradecadienoic acids (1 and 2), were isolated from the culture broth of an actinomycete of the genus Micrococcus, which was associated with a stony coral, Catalaphyllia sp. Their chemical structures were elucidated by spectroscopic analysis including NMR and MS, with special assistance of spin system simulation studies for the assignment of an E geometry at C8 in 2. As metabolites of microbes, compounds 1 and 2 are unprecedented in terms of bearing a 2,4-dienone system. Both 1 and 2 showed antibacterial activity against the plant pathogen Rhizobium radiobacter and the fish pathogen Tenacibaculum maritimum, with a contrasting preference that 1 is more effective to the former strain while 2 is so to the latter. In addition, compounds 1 and 2 displayed agonistic activity against peroxisome proliferator-activated receptors (PPARs) with an isoform specificity towards PPAR alpha and PPAR gamma.
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