Mechanism for Conversion of Spirosolane Derivative into Pregnane

Toshihiro Nohara; Kahori Okamoto; Sayaka Matsushita; Yukio Fujiwara; Tsuyoshi Ikeda; Hiroyuki Miyashita; Masateru Ono; Hitoshi Yoshimitsu; Hisako Kansui; Takehisa Kunieda

doi:10.1248/cpb.56.1015

Notes

Mechanism for Conversion of Spirosolane Derivative into Pregnane

Toshihiro Nohara, Kahori Okamoto, Sayaka Matsushita, Yukio Fujiwara, Tsuyoshi Ikeda, Hiroyuki Miyashita, Masateru Ono, Hitoshi Yoshimitsu, Hisako Kansui, Takehisa Kunieda

著者情報

キーワード: tomato, spirosolane, pregnane

ジャーナルフリー

2008 年 56 巻 7 号 p. 1015-1017

DOI https://doi.org/10.1248/cpb.56.1015

詳細

抄録

Previously, we reported an interesting reaction by which esculeogenin A [(5α,22S,23S,25S)-3β,23,27-trihydroxyspirosolane], a sapogenol of tomato-saponin, esculeoside A, was easily converted into a pregnane derivative, 5α-pregn-16-en-3β-ol-20-one, merely by refluxing with pyridine and water. Its chemical mechanism including air oxidation is here described.

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