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Facile conversion of 23-hydroxyspirosolane into pregnane
Authors:Sayaka Matsushita  Yukio Fujiwara  Masateru Ono  Toshihiro Nohara
Institution:a Faculty of Medical and Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan
b School of Agriculture, Kyushu Tokai University, 5435 Choyo, Kumamoto 869-1404, Japan
Abstract:Two novel reactions with regard to steroidal alkaloid sapogenols obtained from ripe tomato have been found. These reactions have been attained by simple facile method in only refluxing with pyridine and water. One is isomerization of a spirosolane derivative, isoesculeogenin A (2), into a rare solanocapsine derivative, esculeogenin B (3), disclosing a chemical correlation between isoesculeogenin A and esculeogenin B. Another is conversion of a 23-hydroxyspirosolane derivative, esculeogenin A (1), into a pregnane derivative (4), presenting an epoch-making method for derivation of steroidal hormone material.
Keywords:Lycopersicon esculentum  Tomato steroidal alkaloids sapogenol  Spirosolane  Isomerization  Solanocapsine  Pregnane
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