Isolation, synthesis, and neurite outgrowth-promoting activity of illicinin A from the flowers of Illicium anisatum

被引：31

作者：

Takaoka, Shigeki ^{[1
]}

Takaoka, Noriko ^{[1
]}

Minoshima, Yuka ^{[1
]}

Huang, Jian-Mei ^{[2
]}

Kubo, Miwa ^{[1
]}

Harada, Kenichi ^{[1
]}

Hioki, Hideaki ^{[1
]}

Fukuyama, Yoshiyasu ^{[1
]}

机构：

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

[2] Beijing Univ Chinese Med, Fac Pharmaceut Sci, Beijing 100029, Peoples R China

来源：

TETRAHEDRON | 2009年 / 65卷 / 40期

关键词：

Illicium anisatum; Prenylated C-6-C-3 compound; Illicinin A; (4S)-Illicinone I; Neurotrophic activity; Synthesis; Stille reaction; NEUROTROPHIC ACTIVITY; HONOKIOL; FARGESII; NEURONS;

D O I：

10.1016/j.tet.2009.08.015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new prenylated C-6-C-3 compounds, illicinin A (1) and (4S)-illicinone 1 (2), were isolated from the flowers of Illicium anisatum. The structures of the new compounds were elucidated by spectroscopic methods. The absolute structure of (4S)-illicinone I was determined by comparing its CID spectrum and specific rotation with those of (4S)-illicinone A (4). Illicinin A (1) and 4-allyl-2,6-dimethoxy-3-(3-methylbut-2-enyl)phenol (3) were found to exhibit neurite outgrowth-promoting activity at concentrations ranging from 0.1 to 10 mu M in primary cultured rat cortical neurons. Illicinin A and its derivatives were synthesized for structure-activity relationship studies by employing sequential Stille reactions to introduce a prenyl and an allyl group to the benzene ring, thereby indicating that an allylphenyl moiety in the molecule of 1 is essential for its neurotrophic properties. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：8354 / 8361

页数：8

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