Conversion of Esculeoside A into Esculeogenin B

Mona El Aasr; Yukino Oshiro; Yukio Fujiwara; Hiroyuki Miyashita; Tsuyoshi Ikeda; Masateru Ono; Hitoshi Yoshimitsu; Toshihiro Nohara

doi:10.1248/cpb.56.926

Regular Articles

Conversion of Esculeoside A into Esculeogenin B

Mona El Aasr, Yukino Oshiro, Yukio Fujiwara, Hiroyuki Miyashita, Tsuyoshi Ikeda, Masateru Ono, Hitoshi Yoshimitsu, Toshihiro Nohara

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Keywords: tomato, solanocapsine-type, esculeogenin B

JOURNAL FREE ACCESS

2008 Volume 56 Issue 7 Pages 926-929

DOI https://doi.org/10.1248/cpb.56.926

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Abstract

Conversion of the spirosolane-type glycoside, esculeoside A, a major component contained in the ripe tomato Lycopersicon esculentum fruits, into a solanocapsine-type sapogenol, esculeogenin B-2, (5α,22S,23R,25S)-22,26-epimino-16β,23-epoxy-3β,23,27-trihydroxycholestane, and esculeogenin B-1, (5α,22R,23S,25S)-22,26-epimino-16β,23-epoxy-3β,23,27-trihydroxycholestane, which are rare naturally occurring compounds was attained by acid hydrolysis with 2 N HCl in dioxane and water (1 : 1).

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