Biocatalytic and semisynthetic optimization of the anti-invasive tobacco (1S,2E,4R,6R,7E,11E)-2,7,11-cembratriene-4,6-diol
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- 作者：Khalid A. El Sayed ; Surat Laphookhieo ; Hany N. Baraka ; Muhammad Yousaf ; Anne Hebert ; Danielle Bagaley ; Frederick A. Rainey ; A. Muralidharan ; Shibu Thomas ; Girish V. Shah
- 关键词：Tobacco cembranoids ; Biocatalysis ; Symbiotic marine microbials ; Semisynthesis ; Anti-invasive
- 刊名：Bioorganic and Medicinal Chemistry
- 出版年：2008
- 出版时间：15 March 2008
- 年：2008
- 卷：16
- 期：6
- 页码：2886-2893
- 全文大小：273 K
文摘
Tobacco cembranoids were reported to inhibit tumorigenesis. Biocatalysis of (1S,2E,4R,6R,7E,11E)-2,7,11-cembratriene-4,6-diol (1) using the symbiotic Bacillus sp. NC5, Bacillus sp. NK8, and Bacillus sp. NK7, isolated from the Red Sea sponge Negombata magnifica, afforded two new and four known hydroxylated metabolites 3–8. The use of symbiotic marine bacteria as biocatalysts for bioactive natural product scaffolds is very rare. Cembranoid 1 carbamate analogs 9–11 were prepared by its reaction with corresponding isocyanates. Cembranoid 1 and its bioconversion and carabamate products show anti-invasive activity against the human highly metastatic prostate PC-3M cancer cell line at 10–50 nM doses in Matrigel assay.