Caffeoyl triterpenes from pear (Pyrus pyrifolia Nakai) fruit peels and their antioxidative activities against oxidation of rat blood plasma

J Agric Food Chem. 2013 May 15;61(19):4563-9. doi: 10.1021/jf400524b. Epub 2013 May 6.

Abstract

Six triterpenes, including three caffeoyl triterpenes, were purified and isolated from pear fruit ( Pyrus pyrifolia Nakai cv. Chuwhangbae) peel extracts using various column chromatography techniques with a guided 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assay. The isolated compounds were identified as betulinic aldehyde (1), lupeol (2), betulinic acid (3), 3-O-cis-caffeoylbetulinic acid (4), 3-O-trans-caffeoylbetulinic acid (5), and 3-O-trans-caffeoyloleanolic acid (6) on the basis of nuclear magnetic resonance spectroscopy and electrospray ionization mass spectrometry. Four compounds (1, 4-6) were identified from Asian pear fruit for the first time. In addition, compounds 4-6, containing a caffeic acid moiety, showed higher DPPH radical-scavenging and suppression effects against copper ion-induced oxidation of rat blood plasma than other compounds without a caffeic acid moiety.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antioxidants / pharmacology*
  • Betulinic Acid
  • Biphenyl Compounds / pharmacology
  • Caffeic Acids / pharmacology
  • Cholesterol Esters / antagonists & inhibitors
  • Cholesterol Esters / metabolism
  • Fruit / chemistry*
  • Lipid Peroxidation / drug effects
  • Oxidation-Reduction
  • Pentacyclic Triterpenes
  • Picrates / pharmacology
  • Pyrus / chemistry*
  • Rats
  • Rats, Sprague-Dawley
  • Spectrometry, Mass, Electrospray Ionization
  • Triterpenes / pharmacology*

Substances

  • Antioxidants
  • Biphenyl Compounds
  • Caffeic Acids
  • Cholesterol Esters
  • Pentacyclic Triterpenes
  • Picrates
  • Triterpenes
  • cholesteryl ester hydroperoxide
  • betulin
  • 1,1-diphenyl-2-picrylhydrazyl
  • caffeic acid
  • Betulinic Acid