Nasunin from eggplant consists of cis-trans isomers of delphinidin 3-[4-(p-coumaroyl)-L-rhamnosyl (1-->6)glucopyranoside]-5-glucopyranoside

J Agric Food Chem. 2005 Nov 30;53(24):9472-7. doi: 10.1021/jf051841y.

Abstract

Two major anthocyanins were isolated from the acidified methanolic extract of eggplant (Solanum melongena L.) by column chromatography and preparative high-performance liquid chromatography. These anthocyanins were interconvertible under room light illumination condition. By means of tandem time-of-flight mass spectrometry and nuclear magnetic resonance spectroscopy, their structures were identified and elucidated as delphinidin 3-[4-(cis-p-coumaroyl)-l-rhamnosyl(1-->6)glucopyranoside]-5-glucopyranoside (compound 1) and delphinidin 3-[4-(trans-p-coumaroyl)-l-rhamnosyl-(1-->6)glucopyranoside]-5-glucopyranoside (compound 2), respectively. The results indicated that nasunin comprised cis and trans isomers of the p-coumaric acid moiety in its structure.

MeSH terms

  • Anthocyanins / analysis*
  • Anthocyanins / chemistry
  • Chromatography, High Pressure Liquid
  • Coumaric Acids / analysis
  • Coumaric Acids / chemistry
  • Fruit / chemistry
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Propionates
  • Solanum melongena / chemistry*

Substances

  • Anthocyanins
  • Coumaric Acids
  • Propionates
  • nasunin
  • delphinidin
  • p-coumaric acid