Saliniketals A and B, bicyclic polyketides from the marine actinomycete Salinispora arenicola
Saliniketals A and B, bicyclic polyketides from the marine actinomycete Salinispora arenicola
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DOI：
10.1021/np0604580
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发表时间：
2007-01-01
影响因子：
5.1
通讯作者：
Fenical, William
中科院分区：
文献类型：
--
作者：
Williams, Philip G.;Asolkar, Ratnakar N.;Fenical, William
对海洋放线菌Salinispora arenicola的几种菌株产生的次级代谢产物进行了广泛的研究，分离出两种不寻常的双环聚酮化合物，saliniketals A和B（1，2）。主要通过二维核磁共振波谱方法对化合物的结构进行了归属，其中含有一个新的1，4-二甲基-2，8-二氧杂双环[3.2.1]辛烷-3-基环。出乎意料的是，Saliniketal A与Mosher酰基氯的化学衍生化导致不饱和伯酰胺在异常温和的条件下以定量产率向相应腈的官能团互变。发现Saliniketals A和B抑制鸟氨酸脱羧酶诱导，这是癌症化学预防的重要靶点，IC 50值分别为1.95 +/- 0.37和7.83 +/- 1.2 μ g/mL。
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.