4.4 Article

Tomato steroidal alkaloid glycosides, esculeosides A and B, from ripe fruits

Journal

TETRAHEDRON
Volume 60, Issue 22, Pages 4915-4920

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2004.03.088

Keywords

tomato : Lycopersicon esculentum; steroidal alkaloid glycoside; spirosolane-type; solanocapsine-type; cytotoxicity; anti-herpes activity

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Major novel steroidal alkaloid glycosides, named esculeoside A (1) and esculeoside B (2), have been isolated from the pink color-type and the red color-type, respectively, of the ripe tomato fruits of Lycopersicon esculentum MILL. for the first time. The structures of 1 and 2 have been characterized as 3-O-beta-lycotetraosyl (5S,22S,23S,25S)-23-acetoxy-3beta,27-dihydroxyspirosolane 27-O-beta-D-glucopyranoside and 3-O-beta-lycotetraosyl (5S,22S,23R,25S)-22,26-epimino-16beta,23-epoxy-3beta,23,27-trihydroxycholestane 27-O-beta-D-glucopyranoside, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

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