Glycerol and glyceryl esters of omega-hydroxyacids in cutins.
Cutins from the leaves and fruits of seven plant species were depolymerized by NaOCH(3)-methanolysis. The monomers that were released mostly included C16 and C18 omega-hydroxyacids with mid-chain oxygenated substitutions, namely epoxy and hydroxyl groups. Glycerol was also solubilized as a monomer in quantities that ranged from 1 to 14% of the methanolysates. Partial depolymerization of three cutins by CaO-methanolysis released the same monomers as had been obtained in the previous reaction, as well as small quantities of 1- and 2-monoacylglyceryl esters of omega-hydroxyacids. Molar proportions of glycerol permit the esterification of a significant part of the aliphatic omega-hydroxyacids, thereby possibly playing a major role in the polyester structure of cutin. Glycerol had not previously been known to form part of the cutin polymer.
Graça
José
J
Centro de Estudos Florestais, Departamento de Engenharia Florestal, Instituto Superior de Agronomia, Universidade Técnica de Lisboa, 1349-017, Lisbon, Portugal. jgraca@isa.utl.pt
Schreiber
Lukas
L
Rodrigues
José
J
Pereira
Helena
H
D004952:Esters / Q000032:analysis* / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D005990:Glycerol / Q000031:analogs & derivatives* / Q000032:analysis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008563:Membrane Lipids / Q000737:chemistry*; D015394:Molecular Structure; D010944:Plants / Q000737:chemistry*
D004952:Esters; D008563:Membrane Lipids; C000521:cutin; D005990:Glycerol