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Linear aliphatic dimeric esters from cork suberin.

José Graça1, Sara Santos

  • 1Instituto Superior de Agronomia, Departamento de Engenharia Florestal, Universidade Técnica de Lisboa, Tapada da Ajuda, 1349-017 Lisboa, Portugal. jograca@isa.utl.pt

Biomacromolecules
|June 14, 2006
PubMed
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Cork suberin

Area of Science:

  • Biopolymer Chemistry
  • Plant Cell Wall Research
  • Natural Product Analysis

Background:

  • Cork suberin is a complex biopolymer found in plant tissues.
  • Its polyester structure is crucial for protective functions but remains incompletely understood.
  • Previous studies focused mainly on suberin monomers.

Purpose of the Study:

  • To investigate the presence and structure of suberin oligomers.
  • To gain a deeper understanding of the suberin polyester network.
  • To identify specific linkages and monomer compositions within oligomers.

Main Methods:

  • Partial depolymerization of cork suberin using methanolysis with calcium hydroxide catalysis.
  • Analysis of the methanolysate by Gas Chromatography-Mass Spectrometry (GC-MS) for monomers.

Related Experiment Videos

  • Analysis by Electrospray Ionization Mass Spectrometry (ESI-MS) and Collision-Induced Dissociation Mass Spectrometry/Mass Spectrometry (CID-MS/MS) for oligomers.
  • Synthesis of model compounds for confirmation.

    • Main Results:

    • Identified glycerol and long-chain alpha,omega-diacids and omega-hydroxyacids as suberin monomers.
    • Detected suberin oligomers, specifically linear dimeric esters, in the methanolysate.
    • Characterized two types of dimeric esters: alpha,omega-diacid linked to omega-hydroxyacid, and two inter-linked omega-hydroxyacids.
    • Found that C18 monomers with midchain substituents were predominant in these dimeric esters.

    Conclusions:

    • The study reveals the presence of inter-esterified long-chain monomers in cork suberin.
    • This finding provides new insights into the complex polyester structure of suberin.
    • Oligomeric structures contribute significantly to the suberin biopolymer network.