Facile conversion of 23-hydroxyspirosolane into pregnane |
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Authors: | Sayaka Matsushita Yukio Fujiwara Masateru Ono Toshihiro Nohara |
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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 |
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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. |
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Keywords: | Lycopersicon esculentum Tomato steroidal alkaloids sapogenol Spirosolane Isomerization Solanocapsine Pregnane |
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