Hydroxycinnamoylmalic acids and their methyl esters from pear (Pyrus pyrifolia Nakai) fruit peel

J Agric Food Chem. 2011 Sep 28;59(18):10124-8. doi: 10.1021/jf2022868. Epub 2011 Aug 31.

Abstract

Two novel caffeoylmalic acid methyl esters, 2-O-(trans-caffeoyl)malic acid 1-methyl ester (6) and 2-O-(trans-caffeoyl)malic acid 4-methyl ester (7), were isolated from pear (Pyrus pyrifolia Nakai cv. Chuhwangbae) fruit peels. In addition, 5 known hydroxycinnamoylmalic acids and their methyl esters were identified: 2-O-(trans-coumaroyl)malic acid (1), 2-O-(cis-coumaroyl)malic acid (2), 2-O-(cis-coumaroyl)malic acid 1-methyl ester (3), 2-O-(trans-coumaroyl)malic acid 1-methyl ester (4), and 2-O-(trans-caffeoyl)malic acid (phaselic acid, 5). The chemical structures of these compounds were determined by spectroscopic data from ESI MS and NMR. Of all the isolated compounds, five hydroxycinnamoylmalic acids and their methyl esters (2-4, 6, 7) were identified in the pear for the first time.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Caffeic Acids / chemistry
  • Caffeic Acids / isolation & purification
  • Coumaric Acids / chemistry
  • Coumaric Acids / isolation & purification*
  • Esters / isolation & purification
  • Fruit / chemistry*
  • Malates / chemistry
  • Malates / isolation & purification*
  • Molecular Structure
  • Pyrus / chemistry*

Substances

  • Caffeic Acids
  • Coumaric Acids
  • Esters
  • Malates
  • caffeoylmalic acid