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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, 00:00 authored 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.