Niphateolide A: isolation from the marine sponge Niphates olemda and determination of its absolute configuration by an ECD analysis

被引：16
|
作者：
Kato, Hikaru [1 ]
Nehira, Tatsuo [2 ]
Matsuo, Koichi [3 ]
Kawabata, Tetsuro [1 ]
Kobashigawa, Yoshihiro [4 ]
Morioka, Hiroshi [4 ]
Losung, Fitje [5 ]
Mangindaan, Remy E. P. [5 ]
de Voogd, Nicole J. [6 ]
Yokosawa, Hideyoshi [7 ]
Tsukamoto, Sachiko [1 ]
机构：
[1] Kumamoto Univ, Grad Sch Pharmaceut Sci, Dept Nat Med, Kumamoto 8620973, Japan
[2] Hiroshima Univ, Grad Sch Integrated Arts & Sci, Higashihiroshima 7398521, Japan
[3] Hiroshima Univ, Hiroshima Synchrotron Radiat Ctr, Higashihiroshima 7390046, Japan
[4] Kumamoto Univ, Grad Sch Pharmaceut Sci, Dept Analyt & Biophys Chem, Kumamoto 8620973, Japan
[5] Sam Ratulangi Univ, Fac Fisheries & Marine Sci, Manado 95115, Indonesia
[6] Naturalis Biodivers Ctr, NL-2300 RA Leiden, Netherlands
[7] Aichi Gakuin Univ, Sch Pharm, Chikusa Ku, Nagoya, Aichi 4648650, Japan
来源：
TETRAHEDRON | 2015年 / 71卷 / 38期
关键词：
Diterpene; Marine sponge; Niphates olemda; ECD analysis; CONTACT SEX-PHEROMONE; GOMADALACTONE-A; DERIVATIVES;
D O I：
10.1016/j.tet.2015.07.009
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：6956 / 6960
页数：5
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