The marinopyrroles, antibiotics of an unprecedented structure class from a marine Streptomyces sp.
Cultivation of an obligate marine Streptomyces strain has furnished the marinopyrroles A and B, densely halogenated, axially chiral metabolites that contain an uncommon bispyrrole structure. X-ray analysis of marinopyrrole B showed that the natural product exists as an atropo-enantiomer with the M-configuration. Though configurationally stable at room temperature, M-(-)-marinopyrrole A can be racemized at elevated temperatures to yield the non-natural P-(+)-atropo-enantiomer. The marinopyrroles possess potent antibiotic activities against methicillin-resistant Staphylococcus aureus.
Hughes
Chambers C
CC
Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California-San Diego, La Jolla, California 92093-0204, USA.
Prieto-Davo
Alejandra
A
Jensen
Paul R
PR
Fenical
William
W
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D024881:Drug Resistance, Bacterial / Q000187:drug effects; D008386:Marine Biology; D016106:Methicillin Resistance / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D011758:Pyrroles; C528298:marinopyrrole A; C528299:marinopyrrole B