Biocatalytic and semisynthetic optimization of the anti-invasive tobacco (1S,2E,4R,6R,7E,11E)-2,7,11-cembratriene-4,6-diol
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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DOI：
10.1016/j.bmc.2007.12.056
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发表时间：
2008-03-15
影响因子：
3.5
通讯作者：
Shah, Girish V.
中科院分区：
文献类型：
--
作者：
El Sayed, Khalid A.;Laphookhieo, Surat;Shah, Girish V.
烟草西松烷类化合物被报道抑制肿瘤发生。使用从红海海绵Negombata magnifica分离的共生芽孢杆菌属NC 5、芽孢杆菌属NK 8和芽孢杆菌属NK 7对（1 S，2 E，4 R，6 R，7 E，11 E）-2，7，11-西柏三烯4，6-二醇（1）进行生物催化，得到两种新的和四种已知的羟基化代谢物3-8。利用共生海洋细菌作为生物催化剂的生物活性天然产物支架是非常罕见的。西松烷类化合物1氨基甲酸酯类似物9-11通过其与相应的异氰酸酯反应制备。西松烷醇1及其生物转化产物和氨基甲酸酯产物在基质胶测定中以10-50 nM剂量显示出对人高转移性前列腺PC-3 M癌细胞系的抗侵袭活性。(C)2008爱思唯尔有限公司保留所有权利。
Tobacco cembranoids were reported to inhibit tumorigenesis. Biocatalysis of (1S,2E,4R,6R,7E, 11E)-2,7,11-cembratriene4,6-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. (C) 2008 Elsevier Ltd. All rights reserved.