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

页码：6956 / 6960

页数：5

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