Acylated pregnane glycosides from Caralluma sinaica

Caralluma sinaica is sold on local markets of Saudi Arabia for various health benefits however no phytochemical study has specifically been performed on this species. NMR and UHPLC-ESI-TOF-MS profilings of the ethanolic extract of the whole plant reveal a very complex phytochemical composition dominated by pregnanes. Detailed information on its constituents was obtained after isolation. Six pregnane glycosides were obtained and characterized based on the extensive spectroscopic analysis (including IR, H-1 NMR, C-13 NMR and MS data), in addition to ten known compounds (seven pregnanes and three flavonoids). The compounds were identified as 12 beta-O-benzoyl-20-O-acetyl boucerin-3-O-6-deoxy-3-O-methyl-beta-D-glucopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-cymaropyranoside, 12 beta-O-tigloyl-20-O-acetyl boucerin-3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-cymaropyranoside, 12 beta-O-benzoyl-20-O-acetyl boucerin-3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-digitalopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-cymaropyranoside, 12 beta-O-benzoyl-20-O-acetyl boucerin-3-O-beta-D-glucopyranosyl-(1 -> 4)-thevetopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-cymaropyranoside, 12 beta-O-benzoyl-20-O-tigloyl boucerin-3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-cymaropyranoside, 12 beta-20-O-dibenzoyl boucerin-3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-cymaropyranoside. Finally, the isolated compounds were evaluated for their quinone reductase induction. (C) 2012 Elsevier Ltd. All rights reserved.