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

Two new prenylated C 6–C 3 compounds, illicinin A ( 1) and (4 S)-illicinone I ( 2), were isolated from the flowers of Illicium anisatum. The structures of the new compounds were elucidated by spectroscopic methods. The absolute structure of (4 S)-illicinone I was determined by comparing its CD spect...

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Bibliographic Details
Published in:Tetrahedron 2009-10, Vol.65 (40), p.8354-8361
Main Authors: Takaoka, Shigeki, Takaoka, Noriko, Minoshima, Yuka, Huang, Jian-Mei, Kubo, Miwa, Harada, Kenichi, Hioki, Hideaki, Fukuyama, Yoshiyasu
Format: Article
Language:English
Subjects:
(4 S)-Illicinone I
Aroma and flavouring agent industries
Biological and medical sciences
Chemistry
Exact sciences and technology
Food industries
Fundamental and applied biological sciences. Psychology
Illicinin A
Illicium
Illicium anisatum
Neurotrophic activity
Noncondensed benzenic compounds
Organic chemistry
Prenylated C 6–C 3 compound
Preparations and properties
Stille reaction
Synthesis
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Summary:Two new prenylated C 6–C 3 compounds, illicinin A ( 1) and (4 S)-illicinone I ( 2), were isolated from the flowers of Illicium anisatum. The structures of the new compounds were elucidated by spectroscopic methods. The absolute structure of (4 S)-illicinone I was determined by comparing its CD spectrum and specific rotation with those of (4 S)-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 μM 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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.08.015