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红藻角叉菜中溴代二萜的结构及体外抗肿瘤活性评价。

Structure and in vitro antitumor activity evaluation of brominated diterpenes from the red alga Sphaerococcus coronopifolius.

机构信息

Department of Pharmacognosy and Chemistry of Natural Products, School of Pharmacy, University of Athens, Panepistimiopolis Zografou, Athens 15771, Greece.

出版信息

Bioorg Med Chem. 2010 Feb;18(3):1321-30. doi: 10.1016/j.bmc.2009.12.025. Epub 2009 Dec 16.

DOI:10.1016/j.bmc.2009.12.025
PMID:20045651
Abstract

A novel bromoditerpene methyl ketone (1), two new bromoditerpene alcohols featuring a neodolastane (2), and a bromocorodienol skeleton (3), along with 13 previously reported metabolites (4-16) were isolated from the organic extract of Sphaerococcus coronopifolius collected from the rocky coasts of Corfu island in the Ionian Sea. The structures of the new natural products, as well as their relative stereochemistry, were elaborated on the basis of extensive spectral analysis, including 2D NMR experiments. The absolute stereochemistry of metabolite 3 was determined using the modified Mosher's method. The isolated metabolites were evaluated for their antitumoral activity against four human apoptosis-resistant (U373, A549, SKMEL-28, OE21) and two human apoptosis-sensitive (PC-3, LoVo) cancer cell lines with IC(50) in vitro growth inhibitory concentrations in the range 3-100 microM.

摘要

从科孚岛(位于爱奥尼亚海)的岩质海岸采集的冠状球腔菌(Sphaerococcus coronopifolius)的有机提取物中分离得到了一种新型溴二萜甲酮(1)、两种具有尼奥多拉坦(neodolastane)骨架的新溴二萜醇(2)和一种溴科罗迪烯醇骨架(3),以及 13 种先前报道的代谢产物(4-16)。新天然产物的结构及其相对立体化学通过广泛的光谱分析,包括 2D NMR 实验进行了阐述。采用改良的 Mosher 法确定了代谢产物 3 的绝对立体化学。用体外生长抑制浓度(IC50)为 3-100 μM 的范围内,评估了分离得到的代谢产物对四种人类抗凋亡(U373、A549、SKMEL-28、OE21)和两种人类凋亡敏感(PC-3、LoVo)癌细胞系的抗肿瘤活性。

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