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. 2008 Apr;71(4):570-5.
doi: 10.1021/np0705155. Epub 2008 Mar 6.

Salinipyrones and pacificanones, mixed-precursor polyketides from the marine actinomycete Salinispora pacifica

Dong-Chan Oh  1 , Erin A Gontang, Christopher A Kauffman, Paul R Jensen, William Fenical
Affiliations

Salinipyrones and pacificanones, mixed-precursor polyketides from the marine actinomycete Salinispora pacifica

Dong-Chan Oh et al. J Nat Prod. 2008 Apr.

Abstract

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.

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Figures

Figure 1
Figure 1
1D NOE correlations used to assign the double-bond geometries in 1 (a) and 2 (b).
Figure 2
Figure 2
Comparison of 13C NMR chemical shifts (in CDCl3) of salinipyrone A (1) with two synthetic model compounds (a and b) to establish the relative configurations at C-10 and C-11 in 1.
Figure 3
Figure 3
1H NMR ΔδS–R values in ppm for the S- and R-MTPA esters of 1 (a) and 2 (b) in CD3OD.
Figure 4
Figure 4
CD spectra of salinipyrones A and B (1 and 2).
Figure 5
Figure 5
Key NOE correlations that defined the relative configurations for substituents on the chair cyclohexanone rings in 3 (a) and 4 (b).
Figure 6
Figure 6
1H NMR ΔδS–R values in ppm for the bis-S- and R-MTPA esters of alcohol 5 in CD3OD.
See this image and copyright information in PMC

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