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Structure of Procyanidin Oligomers Isolated From Grape Seeds in Relation to Some of their Chemical Properties

  • Véronique Cheynier
  • Jacques Rigaud
  • Jorge M. Ricardo da Silva
Part of the Basic Life Sciences book series (BLSC, volume 59)

Abstract

A micro-method using thiolysis followed by HPLC monitoring of the degradation products was developed to determine the structure of procyanidin oligomers available in small quantities (≤ 0.1 mg). It was successfully applied to a series of procyanidins isolated from grape seeds, allowing the identification of procyanidins dimers B5 to B8 linked by C4 → C6 bonds, six procyanidin trimers with C4 → C8 and C4 → C6 linkages, and six galloylated dimers and trimers, along with the four C4 → C8 linked dimers, Bl to B4. The influence of procyanidin structural variations on their interactions with proteins, free radical scavenging effect, and oxidation was studied using these compounds. Protein-procyanidin interactions increased with the degree of polymerization, the number of galloyl substituents, and the extent of C4→ C6 linkages. Galloylation increased scavenger capacity of procyanidin dimers for Superoxide anion (O2 -•) and hydroxyl (su•OH) radicals. The type of C → C linkage and the esterification position were also important. None of the molecules tested was oxidizable by grape polyphenoloxidase, but they were all oxi-dized by the enzymically generated caffeoyl tartaric acid o-quinones. In addition, galloylated procyanidins seemed to undergo condensation reactions faster than the corresponding non-galloylated ones, even though their rate of oxidation was similar.

Keywords

Condensed Tannin Grape Seed Grape Seed Extract Raney Nickel Azuki Bean 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Springer Science+Business Media New York 1992

Authors and Affiliations

  • Véronique Cheynier
    • 1
  • Jacques Rigaud
    • 1
  • Jorge M. Ricardo da Silva
    • 2
  1. 1.Institute for Wine ProductsNational Institute for Agriculture ResearchMontpellierFrance
  2. 2.Institute of AgronomyTechnical University of LisboaLisboa CodexPortugal

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