Conversion of tomato saponins to pregnane derivatives.
Here reports new conversions methods of tomato saponins, esculeoside A (1) and a mixture of esculeosides B-1 (2) and B-2 (3), (the latter two were obtained from tomato cans) into pregnane derivative (5) by an alkal treatment followed by acid treatment. Compound 1 or a mixture of 2 and 3 were each refluxed with 1 N KOH to afford a characteristic pyridine steroidal glycoside (4), which was then treated with 2 N HCl-MeOH to afford a pregnane derivative, 3β-hydroxy-5α-pregn-16-en-20-one (5). The results of the above two reactions indicated that tomato saponins are chemically closely related to pregnane hormones. We assume that the assimilated tomato saponins via the small intestine are metabolized into pregnane derivatives, demonstrating various bioactivities such as anti-cancer, anti-osteoporosis, and anti-menopausal disorder activities.
Faculty of Pharmaceutical Sciences, Sojo University.
Toshihiro
T
Nohara
Hideyuki
H
Manabe
Yukio
Y
Fujiwara
Tsuyoshi
T
Ikeda
Masateru
M
Ono
Kotaro
K
Murakami
Daisuke
D
Nakano
Junei
J
Kinjo
Tetsuya
T
Kajimoto
D018551:Solanum lycopersicum / Q000737:chemistry*; D008968:Molecular Conformation; D011278:Pregnanes / Q000138:chemical synthesis* / Q000737:chemistry; D012503:Saponins / Q000737:chemistry*
D011278:Pregnanes; D012503:Saponins