Effects of Interaction of Tannins with Co-existing Substances: VII: Inhibitory Effects of Tannins and Related Polyphenois on Xanthine Oxidase

Tsutomu Hatano, Taeko Yasuhara, Rieko Yoshihara, Takuo Okuda

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Abstract

The inhibitory effects of hydrolyzable tannins, condensed tannins and related polyphenols on the activity of xanthine oxidase (XOD), catalyzing uric acid formation from xanthine, were investigated. Marked differences in the strength of the inhibition were observed. Some of the differences among the monomeric hydrolyzable tannins were due to their molecular weights, reflecting the number of phenolic hydroxyl groups in the molecule. However, the inhibitory activity of several oligomeric hydrolyzable tannins seemed particularly low in spite of their large molecular size. It was also observed that differences in location of acyl groups on the carbohydrate cores caused differences in the inhibitory activity among monomeric and oligomeric hydrolyzable tannins. A caffeic acid derivative (caffeetannin), 3,5-di-O-caffeoylquinic acid (24), also inhibited this enzyme. Galloylation and the degree of polymerization in proanthocyanidins were also shown to affect remarkably the strength of the inhibition. Among the compounds tested in the present study, valoneic acid dilactone (29), isolated from Mallotus japonicus, inhibited the enzyme most effectively. A kinetic study showed that this dilactone inhibited XOD non-competitively. Comparison of the inhibitory effect on XOD, with the binding activity to hemoglobin, for each tannin, suggests that their inhibition of XOD is not based on non-specific binding to the protein. Similar comparison of the inhibitory effect on XOD with the inhibitory effect on the generation of superoxide anion radical (02“) from the hypoxanthine-XOD system revealed that the inhibition of 027 generation by tannins is due to their radical-scavenging activity, and not due to their inhibitory activity upon the enzyme.

Original languageEnglish
Pages (from-to)1224-1229
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume38
Issue number5
DOIs
Publication statusPublished - Jan 1 1990

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Keywords

  • Mallotus japonicus
  • ellagitannin
  • galloylglucose
  • inhibition
  • proanthocyanidin
  • superoxide anion
  • tannin
  • valoneic acid dilactone
  • xanthine oxidase

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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