An apigenin-derived xanthine oxidase inhibitor from Palhinhaea cernua

J Nat Prod. 2006 Jul;69(7):1089-91. doi: 10.1021/np060038a.

Abstract

Fractionation of the ethanol extract of Palhinhaea cernua afforded a new (1) and two known p-coumaroylated apigenin glycosides (2, 3) in addition to dillenetin, rhamnazin, alpha-onocerin, beta-sitosterol, and (E)-2-hydroxy-5-methoxycinnamic acid. The structure of compound 1 was elucidated as apigenin-4'-O-(2' '-O-p-coumaroyl)-beta-D-glucopyranoside by a combination of its spectroscopic data. The new glycoside 1 inhibits xanthine oxidase (IC(50): 23.95 +/- 0.43 microM) in a competitive-noncompetitive manner with K(i) and K(I) values of 14.35 and 93.68 microM, whereas compounds 2 and 3 were inactive. The distribution and significance of acylated flavonoid glycosides are discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Apigenin* / chemistry
  • Apigenin* / isolation & purification
  • Apigenin* / pharmacokinetics
  • China
  • Glucosides* / chemistry
  • Glucosides* / isolation & purification
  • Glucosides* / pharmacokinetics
  • Lycopodiaceae / chemistry*
  • Molecular Structure
  • Plants, Medicinal / chemistry*
  • Xanthine Oxidase / antagonists & inhibitors*

Substances

  • Glucosides
  • apigenin-4'-O-(2' '-O-p-coumaroyl)-beta-D-glucopyranoside
  • Apigenin
  • Xanthine Oxidase