Ikeda Tsuyoshi
   Department   SOJO UNIVERSITY  Department of Pharmaceutical Sciences, FACULTY OF PHARMACEUTICAL SCIENCES
     /(DC)Division of Pharmaceutical Sciences,
Language English
Publication Date 2014/05
Peer Review Peer reviewed
Title Conversion of tomato saponins to pregnane derivatives.
Contribution Type
Journal Chemical & pharmaceutical bulletin
Journal TypeAnother Country
Volume, Issue, Page 62(5),pp.483-7
Author and coauthor Nohara Toshihiro, Manabe Hideyuki, Fujiwara Yukio, Ikeda Tsuyoshi, Ono Masateru, Murakami Kotaro, Nakano Daisuke, Kinjo Junei, Kajimoto Tetsuya
Details 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.
DOI 10.1248/cpb.c14-00004
ISSN 1347-5223
PMID 24789931