Molecular modeling of flavonoids that inhibits xanthine oxidase

Chun Mao Lin, Chien Shu Chen, Chien Tsu Chen, Yu Chih Liang, Jen Kun Lin

Research output: Contribution to journalArticle

185 Citations (Scopus)

Abstract

The inhibition of xanthine oxidase activity by various flavonoids was assessed. All of the tested flavonoids were competitive inhibitors, and from the kinetic analysis suggested that flavonoids bind to the reactive site. To further understand the stereochemistry between these flavonoids and xanthine oxidase, structure-based molecular modeling was performed. Apigenin was the most potent inhibitor which showed the most favorable interaction in the reactive site. The bicyclic benzopyranone ring of apigenin stacked with phenyl of Phe 914, and the phenolic group stretched to the space surrounding with several hydrophobic residues. Quercetin and myricetin composed a 3-hydroxyl group on benzopyranone which resulting in reduction of binding affinity. The phenolic group of genistein positioned in opposite orientation comparison with apigenin, and resulted in a weaker interaction with xanthine oxidase. Isovitexin showed the weakest inhibitory effect among the compounds tested. The bulky group of sugar in isovitexin may hamper its interaction with xanthine oxidase.

Original languageEnglish
Pages (from-to)167-172
Number of pages6
JournalBiochemical and Biophysical Research Communications
Volume294
Issue number1
DOIs
Publication statusPublished - 2002

Fingerprint

Molecular modeling
Xanthine Oxidase
Apigenin
Flavonoids
Catalytic Domain
Stereochemistry
Genistein
Quercetin
Molecular Structure
Sugars
Hydroxyl Radical
Kinetics
isovitexin

Keywords

  • Flavonoids
  • Molecular modeling
  • Xanthine oxidase

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics
  • Molecular Biology

Cite this

Molecular modeling of flavonoids that inhibits xanthine oxidase. / Lin, Chun Mao; Chen, Chien Shu; Chen, Chien Tsu; Liang, Yu Chih; Lin, Jen Kun.

In: Biochemical and Biophysical Research Communications, Vol. 294, No. 1, 2002, p. 167-172.

Research output: Contribution to journalArticle

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