Saliniketals A and B, Bicyclic Polyketides from the Marine Actinomycete Salinispora arenicola
- 13 December 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Natural Products
- Vol. 70 (1), 83-88
- https://doi.org/10.1021/np0604580
Abstract
An extensive study of the secondary metabolites produced by several strains of the marine actinomycete Salinispora arenicola has led to the isolation of two unusual bicyclic polyketides, saliniketals A and B (1, 2). The structures, which contain a new 1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-3-yl ring, were assigned mainly by 2D NMR spectroscopic methods. Unexpectedly, chemical derivatization of saliniketal A with Mosher's acid chloride resulted in a functional group interconversion of an unsaturated primary amide to the corresponding nitrile in a quantitative yield under unusually mild conditions. Saliniketals A and B were found to inhibit ornithine decarboxylase induction, an important target for the chemoprevention of cancer, with IC50 values of 1.95 +/- 0.37 and 7.83 +/- 1.2 microg/mL, respectively.Keywords
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