期刊
JOURNAL OF NATURAL PRODUCTS
卷 70, 期 1, 页码 83-88出版社
AMER CHEMICAL SOC
DOI: 10.1021/np0604580
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资金
- NATIONAL CANCER INSTITUTE [P01CA048112] Funding Source: NIH RePORTER
- NATIONAL CENTER FOR RESEARCH RESOURCES [S10RR017768] Funding Source: NIH RePORTER
- NCI NIH HHS [P01 CA48112] Funding Source: Medline
- NCRR NIH HHS [S10RR017768] Funding Source: Medline
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 mu g/mL, respectively.
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