Efficient Conversion of Tomatidine into Neuritogenic Pregnane Derivative

Sayaka Matsushita; Yoshihiro Yanai; Asami Fusyuku; Yukio Fujiwara; Tsuyoshi Ikeda; Masateru Ono; Chunguang Han; Makoto Ojika; Toshihiro Nohara

doi:10.1248/cpb.55.1077

Notes

Efficient Conversion of Tomatidine into Neuritogenic Pregnane Derivative

Sayaka Matsushita, Yoshihiro Yanai, Asami Fusyuku, Yukio Fujiwara, Tsuyoshi Ikeda, Masateru Ono, Chunguang Han, Makoto Ojika, Toshihiro Nohara

Author information

Sayaka Matsushita
Faculty of Medical and Pharmaceutical Sciences, Kumamoto University
Yoshihiro Yanai
Faculty of Medical and Pharmaceutical Sciences, Kumamoto University
Asami Fusyuku
Faculty of Medical and Pharmaceutical Sciences, Kumamoto University
Yukio Fujiwara
Faculty of Medical and Pharmaceutical Sciences, Kumamoto University
Tsuyoshi Ikeda
Faculty of Medical and Pharmaceutical Sciences, Kumamoto University
Masateru Ono
School of Agriculture, Kyushu Tokai University
Chunguang Han
Graduate School of Bioagricultural Sciences, Nagoya University
Makoto Ojika
Graduate School of Bioagricultural Sciences, Nagoya University
Toshihiro Nohara
Faculty of Medical and Pharmaceutical Sciences, Kumamoto University

Keywords: tomatidine, acetylation, δ²⁰⁽²²⁾-pseudo compound, ozonolysis, pregnane derivative, neuritogenic activity

JOURNAL FREE ACCESS

2007 Volume 55 Issue 7 Pages 1077-1078

DOI https://doi.org/10.1248/cpb.55.1077

Details

Abstract

Moderate acetylation of tomatidine with anhydrous acetic acid and pyridine for 20 h at r.t., followed by pseudomerization in ice-water, gave a δ²⁰⁽²²⁾-pseudo compound, which was then subjected to ozonolysis to provide a pregnane derivative in a total 54% yield showing neuritogenic and NGF-enhancing activities.

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