Research Article

Cuticular waxes from Ivy leaves (Hedera helix L.): analysis of high-molecular-weight esters

  1. Sara Santos1,
  2. Lukas Schreiber2,
  3. José Graça1,*

Article first published online: 13 NOV 2006

DOI: 10.1002/pca.952

Issue

Phytochemical Analysis

Phytochemical Analysis

Volume 18, Issue 1, pages 60–69, January 2007

Additional Information

How to Cite

Santos, S., Schreiber, L. and Graça, J. (2007), Cuticular waxes from Ivy leaves (Hedera helix L.): analysis of high-molecular-weight esters. Phytochemical Analysis, 18: 60–69. doi: 10.1002/pca.952

Author Information

  1. 1

    Departamento de Engenharia Florestal, Instituto Superior de Agronomia, Universidade Técnica de Lisboa, Tapada da Ajuda, 1349-017, Lisboa, Portugal

  2. 2

    Institut für Zelluläre und Molekulare Botanik, Universität Bonn, Kirschallee 1, D-53115 Bonn, Germany

*Departamento de Engenharia Florestal, Instituto Superior de Agronomia, Universidade Técnica de Lisboa, Tapada da Ajuda, 1349-017, Lisboa, Portugal.

Publication History

  1. Issue published online: 12 DEC 2006
  2. Article first published online: 13 NOV 2006
  3. Manuscript Accepted: 24 SEP 2006
  4. Manuscript Revised: 7 SEP 2006
  5. Manuscript Received: 21 MAR 2006

Funded by

  • Portuguese MCES FCT. Grant Number: AGR/46419
  • Centro de Estudos Florestais (BioPol Group)
  • DFG (Deutsche Forschungsgemeinschaft)

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Keywords:

  • ESI-MS/MS;
  • high-molecular weight esters;
  • alkyl alkanoates;
  • alkyl coumarates;
  • cuticular waxes;
  • Hedera helix L

Abstract

Soluble waxes were extracted from the cuticle of ivy (Hedera helix L.) leaves with dichloromethane in a yield of ca. 13%. The cuticular waxes were directly analysed by GC-MS, high-temperature GC-MS and ESI-MS/MS. The GC-MS analysis showed mostly n-alkanols (45.3%), monoacids (18.8%), triterpenes (9.7%), n-aldehydes (8.7%) and n-alkanes (7.7%). The high-temperature GC-MS and the ESI-MS/MS analyses showed the presence of ester waxes, namely alkyl alkanoates and alkyl coumarates. Alkyl alkanoates comprised esters of the hexadecanoic acid with n-alkanols ranging from C16 to C34. Alkyl coumarates included esters of coumaric acid with n-alkanols ranging from C16 to C32. The cuticular waxes were hydrolysed and the resulting organic and aqueous phases analysed by GC-MS. The hydrolysate showed a major increase in the quantities of n-alkanols, hexadecanoic acid and coumaric acid derived from the alkyl and acyl moieties from the ester waxes. A content of ester waxes of 38% was estimated based on the results from the GC-MS analysis of the non-hydrolysed and hydrolysed cuticular waxes. Alkyl alkanoates were analysed by ESI-MS/MS as [M + Li]+ adduct ions and the alkyl coumarates as [M − H]− deprotonated ions. The ESI-MS/MS analysis allowed the detection of a wider range of ester waxes than high-temperature GC-MS, and was shown to be a useful technique for the qualitative analysis of ester waxes from plant cuticles. Copyright © 2006 John Wiley & Sons, Ltd.

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