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

Conversion of esculeoside A into esculeogenin B

Chem Pharm Bull (Tokyo). 2008 Jul;56(7):926-9. doi: 10.1248/cpb.56.926.

Authors

Mona El Aasr¹, Yukino Oshiro, Yukio Fujiwara, Hiroyuki Miyashita, Tsuyoshi Ikeda, Masateru Ono, Hitoshi Yoshimitsu, Toshihiro Nohara

Affiliation

¹ Faculty of Medical and Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan.

PMID: 18591803
DOI: 10.1248/cpb.56.926

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, (5alpha,22S,23R,25S)-22,26-epimino-16beta,23-epoxy-3beta,23,27-trihydroxycholestane, and esculeogenin B-1, (5alpha,22R,23S,25S)-22,26-epimino-16beta,23-epoxy-3beta,23,27-trihydroxycholestane, which are rare naturally occurring compounds was attained by acid hydrolysis with 2 N HCl in dioxane and water (1 : 1).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Magnetic Resonance Spectroscopy
Sapogenins / chemistry*
Solanum lycopersicum / chemistry*

Substances

Sapogenins
esculeogenin B
esculeoside A