Salinipyrones and pacificanones, mixed-precursor polyketides from the marine actinomycete Salinispora pacifica.
Chemical examination of a phylogenetically unique strain of the obligate marine actinomycete Salinispora pacifica led to the discovery of four new polyketides, salinipyrones A and B ( 1, 2) and pacificanones A and B ( 3, 4). These compounds appear to be derived from a mixed-precursor polyketide biosynthesis involving acetate, propionate, and butyrate building blocks. Spectral analysis, employing NMR, IR, UV, and CD methods and chemical derivatization, was used to assign the structures and absolute configurations of these new metabolites. Salinipyrones A and B displayed exactly opposite CD spectra, indicating their pseudoenantiomeric relationship. This relationship was shown to be a consequence of the geometric isomerization of one double bond. The phenomenon of polyketide module skipping is proposed to explain the unusual biosynthesis of the salinipyrones and the pacificanones.
Oh
Dong-Chan
DC
Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California, San Diego, La Jolla, California 92093-0204, USA.
Gontang
Erin A
EA
Kauffman
Christopher A
CA
Jensen
Paul R
PR
Fenical
William
W
D039903:Actinobacteria / Q000737:chemistry*; D003512:Cyclohexanones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008386:Marine Biology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011753:Pyrones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013329:Structure-Activity Relationship
D003512:Cyclohexanones; D011753:Pyrones; C529468:pacificanone A; C529469:pacificanone B; C529466:salinipyrone A; C529467:salinipyrone B