Niphateolide A: isolation from the marine sponge Niphates olemda and determination of its absolute configuration by an ECD analysis
Niphateolide A: isolation from the marine sponge Niphates olemda and determination of its absolute configuration by an ECD analysis
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DOI：
10.1016/j.tet.2015.07.009
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发表时间：
2015-09-23
期刊：
影响因子：
2.1
通讯作者：
Tsukamoto, Sachiko
中科院分区：
文献类型：
--
作者：
Kato, Hikaru;Nehira, Tatsuo;Tsukamoto, Sachiko
从海绵中分离得到一种新骨架的二萜类化合物niphatetamine A（1），它是p53-Hdm 2相互作用的抑制剂。用核磁共振谱确定了其结构，用电子捕获检测器（ECD）在真空紫外区确定其绝对构型为10 R，11 R。观察到化合物1在C-17处为不可分离的立体异构体混合物，随后通过采用简化的两种形式10 R，11 R，17 R-和10 R，11 R，17 S-1a之间的虚拟平衡进行ECD分析，其中将计算的ECD光谱与理论推导的内能和自由能进行校正积分。(C)2015爱思唯尔有限公司版权所有。
A diterpene with a new skeleton, niphateolide A (1), was isolated from the marine sponge, Niphates olemda, as an inhibitor of the p53-Hdm2 interaction. Its structure was elucidated by NMR spectroscopy and its absolute configuration was established as 10R, 11R by ECD at the vacuum-ultraviolet region with a theoretical calculation. Compound 1 was observed as an inseparable stereoisomeric mixture at C-17 and an ECD analysis was subsequently performed by adopting a virtual equilibrium between the simplified two forms, 10R,11R,17R- and 10R,11R,17S-1a, in which the calculated ECD spectra were correctively integrated with the theoretically-derived internal and free energies. (C) 2015 Elsevier Ltd. All rights reserved.