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Spectral and chromatographic analyses of tannins 1. carbon 13 nmr spectra of hydrolyzable tannins


, : Spectral and chromatographic analyses of tannins 1. carbon 13 nmr spectra of hydrolyzable tannins. Chemical and Pharmaceutical Bulletin (Tokyo) 32(5): 1790-1799

The 13C-NMR spectra of hydrolyzable tannins, in which D-glucopyranose takes the 4C1 conformation, were analyzed and the 13C resonances of the glucose C fully assigned. The peak sequences of C in glucose are different among several types of hyrolyzable tannins, reflecting differences of the acyl (galloyl, hexahydroxydiphenoyl and dehydrohexahydroxydiphenoyl) groups, as found upon comparison of penta-O-galloyl-.beta.-D-glucose, casuarictin, tellimagrandin II and isoterchebin. The additive character of galloylation and hexahydroxydiphenoylation shifts can be used for locating the positions of the acyl groups. The substituents and substitution mode at C-1 and C-2 of glucose in these tannins can be deduced from the diagnostic 13C chemical shift of the anomeric C. The 13C resonances of the dimeric hydrolyzable tannins were assigned on the basis of the data for their monomeric units.

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