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Abstract
Three hordatine derivatives (4′-O-β-D-glucopyranosyl hordatine A, 4′-O-β-D-glucopyranosyl hordatine B, and 4′-O-β-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-β-D-glucopyranosyl (1″Z)-hordatine A, 4′-O-β-D-glucopyranosyl (1″Z)-hordatine B, and 4′-O-β-D-maltosyl (1″Z)-hordatine A. Their chemical structures were elucidated by mass and NMR spectrometry.
RESUMEN
Tres derivados de hordatine, 4′-O-β-D-glucopiranosil hordatine A, 4′-O-β-D-glucopiranosil hordatine B y 4′-O-β-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-β-D-glucopiranosil (1″Z)-hordatine A, 4′-O-β-D-glucopiranosil (1″Z)-hordatine B, y 4′ -O-β-D-maltosil (1″Z)-hordatine A. Sus estructuras químicas fueron determinadas por espectrometría de masas y RMN.