Linear Aliphatic Dimeric Esters from Cork Suberin

TitleLinear Aliphatic Dimeric Esters from Cork Suberin
Publication TypeJournal Article
Year of Publication2006
AuthorsGraça, J., & Santos S.
JournalBiomacromolecules
Volume7
Pagination2003-2010
Accession Number16768426
Keywordscork suberin, dimeric esters, Dimerization, Electrospray Ionization, Electrospray Ionization: metho, Esters, Esters: chemistry, GC-MS (voyant), Lipids, Mass, Membrane Lipids, Membrane Lipids: chemistry, Molecular Structure, Sensitivity and Specificity, Spectrometry, Trees, Trees: chemistry
Abstract

Cork suberin was partially depolymerized by methanolysis catalyzed by calcium hydroxide. Analysis by GC-MS of the methanolysate showed suberin monomers, including glycerol and long-chain α,?-diacids and ?-hydroxyacids. ESI-MS analysis of the methanolysate showed, besides the aliphatic monomers, suberin oligomers, including linear dimeric esters of α,?-diacids and ?-hydroxyacids. Two types of dimeric esters were identified:? a α,?-diacid linked to a ?-hydroxyacid and two inter-linked ?-hydroxyacids. The α,?-diacids and ?-hydroxyacids found as monomer residues in the dimeric esters were mainly the C18 monomers with midchain substituents. The identification of these dimeric esters was based in their CID-MS/MS spectra and confirmed after synthesis of model compounds. The occurrence of inter-esterified long-chain monomers in suberin brings a new insight in the understanding of the polyester structure of this biopolymer.