Stereochemical determination and bioactivity assessment of (S)-(+)-curcuphenol dimers isolated from the marine sponge Didiscus aceratus and synthesized through laccase biocatalysis
Stereochemical determination and bioactivity assessment of (S)-(+)-curcuphenol dimers isolated from the marine sponge Didiscus aceratus and synthesized through laccase biocatalysis
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DOI：
10.1016/j.bmc.2005.06.020
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发表时间：
2005-10-01
影响因子：
3.5
通讯作者：
Crews, P
中科院分区：
文献类型：
--
作者：
Cichewicz, RH;Clifford, LJ;Crews, P
电喷雾离子化质谱引导的双盘藻提取物的分离导致了生物活性红没药烯型海绵代谢物（S）-（+）-姜黄酚（1）的几种新衍生物的发现。通过该方法获得的化合物包括已知的（2）和新的（3）二羟基化类似物的混合物以及二聚衍生物的新家族，二姜黄酚A-E（4-8）和二姜黄酚醚F（9）。二聚体4-9也随后通过半合成方法获得，其中1与漆酶一起孵育。对阻转异构二聚体5和6进行振动圆二色性分析，从而分别确定它们的绝对联芳基轴向手性为P和M。与1相反，代谢物2-9表现出弱的或没有细胞毒性或脂氧合酶抑制作用。(c)2005 Elsevier Ltd.保留所有权利。
Electrospray ionization mass spectrometry-guided isolation of extracts from Didiscus aceratus led to the discovery of several new derivatives of the bioactive bisabolene-type sponge metabolite (S)-(+)-curcuphenol (1). The compounds obtained by this method included a mixture of known (2) and new (3) dihydroxylated analogs as well as a novel family of dimeric derivatives, dicurcuphenols A-E (4-8), and dicurcuphenol ether F (9). Dimers 4-9 were also subsequently obtained through a hemisynthetic method in which 1 was incubated with the enzyme laccase. Atropisomeric dimers 5 and 6 were subjected to vibrational circular dichroism analysis thereby establishing their absolute biaryl axial chirality as P and M, respectively. In contrast to 1, metabolites 2-9 exhibited weak or no cytotoxic or lipoxygenase inhibitory effects. (c) 2005 Elsevier Ltd. All rights reserved.