Biphenyl glycosides from the fruit of Pyracantha fortuneana

J Nat Prod. 2006 Jul;69(7):1022-4. doi: 10.1021/np0600853.

Abstract

Five new biphenyl glycosides, fortuneanosides A (1), B (2), C (3), D (4), and E (5), were isolated from the fruit of Pyracantha fortuneana. Their structures were established as 3,3'-dihydroxy-5'-methoxy-(1,1'-biphenyl)-4-O-beta-d-glucoside, 4'-hydroxy-2,3',5'-trimethoxy-(1,1'-biphenyl)-2'-O-beta-d-glucoside, 4'-hydroxy-3',5'-dimethoxy-(1,1'-biphenyl)-2-O-beta-d-glucoside, 2,4'-dihydroxy-3',5'-dimethoxy-(1,1'-biphenyl)-3-O-beta-d-glucoside, and 3,4'-dihydroxy-3',5'-dimethoxy-(1,1'-biphenyl)-4-O-beta-d-glucoside by spectroscopic analysis. All compounds were evaluated for inhibitory activity against tyrosinase. Compared with arbutin (IC(50) = 0.23 mM), fortuneanoside D possessed more potency, with an IC(50) value of 0.07 mM.

MeSH terms

  • Biphenyl Compounds / chemistry
  • Biphenyl Compounds / isolation & purification*
  • Biphenyl Compounds / pharmacology
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • Fruit / chemistry
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Inhibitory Concentration 50
  • Molecular Structure
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Plants, Medicinal / chemistry*
  • Pyracantha / chemistry*

Substances

  • Biphenyl Compounds
  • Drugs, Chinese Herbal
  • Glycosides
  • Monophenol Monooxygenase