Four new compounds from Ligularia virgaurea: isolation of eremophilane and noreremophilane sesquiterpenoids and the absolute configuration of 2α-hydroxyeremophil-11-en-9-one by CD spectrum and DFT calculation

被引：23

作者：

Saito, Yoshinori ^{[1
]}

Taniguchi, Mizuho ^{[1
]}

Komiyama, Teppei ^{[2
]}

Ohsaki, Ayumi ^{[2
]}

Okamoto, Yasuko ^{[1
]}

Gong, Xun ^{[3
]}

Kuroda, Chiaki ^{[4
,5
]}

Tori, Motoo ^{[1
]}

机构：

[1] Tokushima Bunri Univ, Fac Pharmaceut Sci, Yamashiro, Tokushima 7708514, Japan

[2] Tokyo Med & Dent Univ, Inst Biomat & Bioengn, Chiyoda Ku, Tokyo 1010062, Japan

[3] Chinese Acad Sci, Kunming Inst Bot, Kunming 650204, Peoples R China

[4] Rikkyo Univ, Dept Chem, Toshima Ku, Tokyo 1718501, Japan

[5] Rikkyo Univ, Res Ctr Smart Mol, Toshima Ku, Tokyo 1718501, Japan

来源：

TETRAHEDRON | 2013年 / 69卷 / 39期

关键词：

Asteraceae; Ligularia virgaurea; Sesquiterpenoid; Absolute configuration; Circular dichroism; FAURIEI FR KOIDZ; SAN-SHION; PHOTOSENSITIZED OXYGENATION; ISOMERIC HYDROPEROXIDES; CHEMICAL-CONSTITUENTS; GENETIC DIVERSITY; YUNNAN PROVINCE; LACTONES; CHINA; FURANOEREMOPHILANES;

D O I：

10.1016/j.tet.2013.06.104

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four new compounds, rearranged noreremophilan-8,6-olide, rearranged dinoreremophilanone, epoxy gamma-lactone, and 2 alpha-hydroxyermophil-11-en-9-one, along with eremophilenolides related to ligularol and other known terpenoids, were isolated from Ligularia virgaurea (ligularol type) collected from the northern Sichuan Province of China. Three of the new compounds had degraded and unique structures. The absolute configuration of 2 alpha-hydroxyermophil-11-en-9-one was determined on the basis of density functional theory calculation. The back octant rule cannot be applied to this compound because of the contribution of the hydroxy group to the front octant. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：8505 / 8510

页数：6