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. 2020 Mar 2:16:297-304.
doi: 10.3762/bjoc.16.29. eCollection 2020.

Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus

Amit Raj Sharma  1 , Enjuro Harunari  1 , Naoya Oku  1 , Nobuyasu Matsuura  2 , Agus Trianto  3 , Yasuhiro Igarashi  1
Affiliations

Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus

Amit Raj Sharma et al. Beilstein J Org Chem. .

Abstract

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 PPARα and PPARγ.

Keywords: Micrococcus; PPAR; antibacterial; coral; keto fatty acid.

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Figures

Figure 1
Figure 1
Structures of (6E,8Z)- and (6E,8E)-5-oxo-6,8-tetradecadienoic acids (1 and 2).
Figure 2
Figure 2
COSY and key HMBC correlations for 1 and 2.
Figure 3
Figure 3
Spin system simulation for the C8–C9 double bond of 2.
Figure 4
Figure 4
Natural keto fatty acids of various origins.
Figure 5
Figure 5
PPAR activation by 1 and 2.
See this image and copyright information in PMC

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