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

Mechanism for conversion of spirosolane derivative into pregnane

Chem Pharm Bull (Tokyo). 2008 Jul;56(7):1015-7. doi: 10.1248/cpb.56.1015.

Authors

Toshihiro Nohara¹, Kahori Okamoto, Sayaka Matsushita, Yukio Fujiwara, Tsuyoshi Ikeda, Hiroyuki Miyashita, Masateru Ono, Hitoshi Yoshimitsu, Hisako Kansui, Takehisa Kunieda

Affiliation

¹ Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto, Japan. [email protected]

PMID: 18591823
DOI: 10.1248/cpb.56.1015

Abstract

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

Publication types

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

MeSH terms

Glycosides / chemistry*
Pregnanes / chemical synthesis*
Sapogenins / chemistry*
Solanum lycopersicum / chemistry*

Substances

Glycosides
Pregnanes
Sapogenins
isoesculeogenin A