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Paper | Regular issue | Vol 75, No. 7, 2008, pp.1639-1650
Published online, 7th March, 2008
DOI: 10.3987/COM-08-11332
Medicinal Foodstuffs. XXXIII. Gastroprotective Principles from Boesenbergia rotunda (Zingiberaceae) - Absolute Stereostructures of Diels-Alder Type Addition Prenylchalcones

Masayuki Yoshikawa,* Toshio Morikawa, Kanako Funakoshi, Momotaro Ochi, Yutana Pongpiriyadacha, and Hisashi Matsuda

*Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan

Abstract

The methanolic extract from the rhizomes of Boesenbergia rotunda (Zingiberaceae) was found to exhibit potent inhibitory activities on ethanol- or indomethacin-induced gastric mucosal lesions in rats. Through the bioassay-guided separation, six new optically active Diels-Alder type addition prenylcalcones, (+)-panduratin A (1a), (-)-panduratin A (1b), (+)-4-hydroxypanduratin A (2a), (-)-4-hydroxypanduratin A (2b), (+)-isopanduratin A (3a), and (-)-isopanduratin A (3b) were isolated together with 12 known compounds [(4-14) and geraniol]. The absolute stereostrucutures of six new compounds were elucidated on the basis of physicochemical evidence including CD spectra. Among them, the enantiomeric mixtures of panduratin A (1a, 1b) and 4-hydroxypanduratin A (2a, 2b), and pinocembrin (4) showed gastroprotective effects on ethanol- or indomethacin-induced gastric mucosal in rats.