VIEW ARTICLE    http://dx.doi.org/10.1094/ASBCJ-2012-0627-01

Structures in the Hordatine Family with cis-Cinnamoyl Moieties. Norihiko Kageyama (1) and Takako Inui, Beer Development Department, Suntory Liquors Limited, Osaka, Japan; Harukazu Fukami, Department of Bioscience and Biotechnology, Faculty of Bioenvironmental Science, Kyoto Gakuen University, Kyoto, Japan; and Hajime Komura, Suntory Foundation for Life Sciences, Bioorganic Research Institute, Osaka, Japan. (1) Corresponding author. E-mail: <Norihiko_Kageyama@suntory.co.jp> J. Am. Soc. Brew. Chem. 70(3):133-136, 2012.

Three hordatine derivatives (4′-O-beta-D-glucopyranosyl hordatine A, 4′-O-beta-D-glucopyranosyl hordatine B, and 4′-O-beta-D-maltosyl hordatine A) have already been isolated from acrospires in barley malt as astringent substances. All of these substances possess a common trans-cinnamoyl moiety. In the astringent fraction, we have now also identified the corresponding cis-cinnamoyl derivatives: 4′-O-beta-D-glucopyranosyl (1″Z)-hordatine A, 4′-O-beta-D-glucopyranosyl (1″Z)-hordatine B, and 4′-O-beta-D-maltosyl (1″Z)-hordatine A. Their chemical structures were elucidated by mass and NMR spectrometry.

Tres derivados de hordatine, 4′-O-beta-D-glucopiranosil hordatine A, 4′-O-beta-D-glucopiranosil hordatine B y 4′-O-beta-D-maltosil hordatine A, ya han sido aislados de plúmulas de malta de cebada como sustancias astringentes. Todas estas sustancias poseen un común trans cinamoílo resto. En la fracción astringente, ahora hemos identificado también los correspondientes derivados de cis-cinamoilo: 4′-O-beta-D-glucopiranosil (1″Z)-hordatine A, 4′-O-beta-D-glucopiranosil (1″Z)-hordatine B, y 4′-O-beta-D-maltosil (1″Z)-hordatine A. Sus estructuras químicas fueron determinadas por espectrometría de masas y RMN.