Lipoxazolidinones A, B, and C: antibacterial 4-oxazolidinones from a marine actinomycete isolated from a Guam marine sediment.
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 1- 3 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.
Macherla
Venkat R
VR
Nereus Pharmaceuticals, Inc., San Diego, California 92121, USA. vmacherla@nereuspharm.com
Liu
Jehnan
J
Sunga
Michelle
M
White
Donald J
DJ
Grodberg
Jennifer
J
Teisan
Sy
S
Lam
Kin S
KS
Potts
Barbara C M
BC
D039903:Actinobacteria / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006141:Guam; D006193:Haemophilus influenzae / Q000187:drug effects; D008386:Marine Biology; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D023303:Oxazolidinones; C524232:lipoxazolidinone A; C524233:lipoxazolidinone B; C524234:lipoxazolidinone C