Spectral and Chromatographic Analyses of Tannins. I. 13C Nuclear Magnetic Resonance Spectra of Hydrolyzable Tannins

Takashi Yoshida, Tsutomu Hatano, Takuo Okuda, M. Usman Memon, Tetsuro Shingu, Kenichiro Inoue

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Abstract

The 13C nuclear magnetic resonance (13C-NMR) spectra of hydrolyzable tannins, in which D-glucopyranose takes the 4C1 conformation, have been analyzed and the 13C resonances of the glucose carbons fully assigned. The peak sequences of carbons in glucose are different among several types of hydrolyzable tannins, reflecting differences of the acyl (galloyl, hexahydroxy-diphenoyl and dehydrohexahydroxydiphenoyl) groups, as found upon comparison of penta-O-galloyl-β-D-glucose (1), casuarictin (7), tellimagrandin II (13) and isoterchebin (15). 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-l and C-2 of glucose in these tannins can be deduced from the diagnostic 13C chemical shift of the anomeric carbon. The 13C resonances of the dimeric hydrolyzable tannins were assigned on the basis of the data for their monomeric units.

Original languageEnglish
Pages (from-to)1790-1799
Number of pages10
JournalChemical and Pharmaceutical Bulletin
Volume32
Issue number5
DOIs
Publication statusPublished - 1984

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Keywords

  • assignment of glucose carbon signal
  • dimeric hydrolyzable tannin
  • ellagitannin C-NMR
  • galloylation shift
  • galloylglucose
  • hexahydroxydiphenoylation shift
  • hydrolyzable tannin

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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