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Lipoxazolidinones A, B, and C: Antibacterial 4-Oxazolidinones from a Marine Actinomycete Isolated from a Guam Marine Sediment

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journal contribution
posted on 28.09.2007 by Venkat R. Macherla, Jehnan Liu, Michelle Sunga, Donald J. White, Jennifer Grodberg, Sy Teisan, Kin S. Lam, Barbara C. M. Potts
Marine actinomycete strain NPS008920, a member of the new genus Marinispora, was isolated from a sediment sample collected in Cocos Lagoon, Guam. In natural sea water containing media, the strain produced a series of novel 2-alkylidene-5-alkyl-4-oxazolidinones, lipoxazolidinone A (1), B (2), and C (3). Compounds 13 showed broad spectrum antimicrobial activity similar to that of the commercial antibiotic linezolid (Zyvox), a 2-oxazolidinone. Hydrolysis of the amide bond of the 4-oxazolidinone ring of 1 resulted in loss of antibacterial activity. The 2-alkylidene-4-oxazolidinone represents a new antibiotic pharmacophore and is unprecedented in nature.