Hydrophilic ester-bearing chlorogenic acid binds to a novel domain to inhibit xanthine oxidase

Shwu Huey Wang, Chien Shu Chen, Shih Hao Huang, Szu Hsu Yu, Zhi Yang Lai, Sheng Tung Huang, Chun Mao Lin

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Caffeic acid is a xanthine oxidase (XO) inhibitor that binds to the molybdopterin region of its active site. Caffeic acid phenethyl ester (CAPE) has higher hydrophobicity and exhibits stronger inhibition potency toward XO. Chlorogenic acid is a quinyl ester of caffeic acid that has increased hydrophilicity and also shows stronger XO inhibitory activity compared with caffeic acid. Caffeic acid and CAPE showed competitive inhibition against XO, whereas chlorogenic acid displayed mixed-type inhibition, implying that it binds to sites other than the active site. Structure-based molecular modeling was performed to account for the different binding characteristics of the hydrophobic and hydrophilic esters of caffeic acid. Chlorogenic acid showed weak binding to the molybdopterin region of XO, while it more strongly bound the flavin adenine dinucleotide region than it did the molybdopterin region. These results provide the basis for interactions of caffeic acid analogues with XO via various binding domains.

Original languageEnglish
Pages (from-to)1237-1240
Number of pages4
JournalPlanta Medica
Volume75
Issue number11
DOIs
Publication statusPublished - 2009

Fingerprint

Bearings (structural)
Chlorogenic Acid
Xanthine Oxidase
Esters
Hydrophobic and Hydrophilic Interactions
Catalytic Domain
Flavin-Adenine Dinucleotide
Molecular modeling
Hydrophilicity
Hydrophobicity
Molecular Structure
caffeic acid

Keywords

  • Caffeic acid
  • Chlorogenic acid
  • FAD
  • Molecular modeling
  • Olybdopterin
  • Xanthine oxidase

ASJC Scopus subject areas

  • Complementary and alternative medicine
  • Molecular Medicine
  • Organic Chemistry
  • Analytical Chemistry
  • Pharmaceutical Science
  • Pharmacology
  • Drug Discovery

Cite this

Wang, S. H., Chen, C. S., Huang, S. H., Yu, S. H., Lai, Z. Y., Huang, S. T., & Lin, C. M. (2009). Hydrophilic ester-bearing chlorogenic acid binds to a novel domain to inhibit xanthine oxidase. Planta Medica, 75(11), 1237-1240. https://doi.org/10.1055/s-0029-1185521

Hydrophilic ester-bearing chlorogenic acid binds to a novel domain to inhibit xanthine oxidase. / Wang, Shwu Huey; Chen, Chien Shu; Huang, Shih Hao; Yu, Szu Hsu; Lai, Zhi Yang; Huang, Sheng Tung; Lin, Chun Mao.

In: Planta Medica, Vol. 75, No. 11, 2009, p. 1237-1240.

Research output: Contribution to journalArticle

Wang, Shwu Huey ; Chen, Chien Shu ; Huang, Shih Hao ; Yu, Szu Hsu ; Lai, Zhi Yang ; Huang, Sheng Tung ; Lin, Chun Mao. / Hydrophilic ester-bearing chlorogenic acid binds to a novel domain to inhibit xanthine oxidase. In: Planta Medica. 2009 ; Vol. 75, No. 11. pp. 1237-1240.
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