Marinoquinolones and Marinobactoic Acid: Antimicrobial and Cytotoxic ortho-Dialkylbenzene-Class Metabolites Produced by a Marine Obligate Gammaproteobacterium of the …

MR Ul Karim, K Fukaya, Y In, AR Sharma… - Journal of Natural …, 2022 - ACS Publications
MR Ul Karim, K Fukaya, Y In, AR Sharma, E Harunari, N Oku, D Urabe, A Trianto, Y Igarashi
Journal of Natural Products, 2022ACS Publications
Chemical investigation of the culture extract of a marine obligate proteobacterium,
Marinobacterium sp. C17-8, isolated from scleractinian coral Euphyllia sp., led to the
discovery of three new o-dialkylbenzene-class metabolites, designated marinoquinolones A
(1) and B (2) and marinobactoic acid (3). Spectroscopic analysis using MS and NMR
revealed the structures of 1 and 2 to be 4-quinolones with an o-dialkylbenzene-containing
side chain at C3 and 3 to be a fatty acid bearing an o-dialkylbenzene substructure. The 4 …
Chemical investigation of the culture extract of a marine obligate proteobacterium, Marinobacterium sp. C17-8, isolated from scleractinian coral Euphyllia sp., led to the discovery of three new o-dialkylbenzene-class metabolites, designated marinoquinolones A (1) and B (2) and marinobactoic acid (3). Spectroscopic analysis using MS and NMR revealed the structures of 1 and 2 to be 4-quinolones with an o-dialkylbenzene-containing side chain at C3 and 3 to be a fatty acid bearing an o-dialkylbenzene substructure. The 4-quinolone form of 1 and 2 was unequivocally determined by comparison of the 1H, 13C, and 15N chemical shifts of 1 with those predicted for 2-methyl-4-quinolone A and its tautomer 2-methyl-4-quinolinol B by quantum chemical calculation. Compound 1 was proven to be racemic by X-ray crystallographic analysis and chiral-phase HPLC analysis of its chemical degradation product. Compounds 13 exhibited antimicrobial activity against bacteria and filamentous fungi at MIC of 6.3–50 μg/mL. In addition, all compounds showed cytotoxicity against P388 murine leukemia cells at micromolar ranges.
ACS Publications
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