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Article

The Identification of New Triterpenoids in Eucalyptus globulus Wood

by
Ana Lourenço
1,
António Velez Marques
1,2,* and
Jorge Gominho
1
1
Centro de Estudos Florestais, Instituto Superior de Agronomia, Universidade de Lisboa, Tapada da Ajuda, 1349-017 Lisboa, Portugal
2
Instituto Superior de Engenharia de Lisboa, Instituto Politécnico de Lisboa, Rua Conselheiro Emídio Navarro 1, 1959-007 Lisboa, Portugal
*
Author to whom correspondence should be addressed.
Molecules 2021, 26(12), 3495; https://doi.org/10.3390/molecules26123495
Submission received: 18 May 2021 / Revised: 2 June 2021 / Accepted: 5 June 2021 / Published: 8 June 2021

Abstract

Eight polyhydroxy triterpenoid acids, hederagenin, (4α)-23-hydroxybetulinic acid, maslinic acid, corosolic acid, arjunolic acid, asiatic acid, caulophyllogenin, and madecassic acid, with 2, 3, and 4 hydroxyl substituents, were identified and quantified in the dichloromethane extract of Eucalyptus globulus wood by comparing their GC-retention time and mass spectra with standards. Two other triterpenoid acids were tentatively identified by analyzing their mass spectra, as (2α)-2-hydroxybetulinic acid and (2α,4α)-2,23-dihydroxybetulinic acid, with 2 and 3 hydroxyl substituents. Two MS detectors were used, a quadrupole ion trap (QIT) and a quadrupole mass filter (QMF). The EI fragmentation pattern of the trimethylsilylated polyhydroxy structures of these triterpenoid acids is characterized by the sequential loss of the trimethylsilylated hydroxyl groups, most of them by the retro-Diels-Alder (rDA) opening of the C ring with a π-bond at C12-C13. The rDA C-ring opening produces ions at m/z 320 (or 318) and m/z 278 (or 277, 276, 366). Sequential losses of the hydroxyl groups produce ions with m/z from [M - 90] to [M - 90*y], where y is the number of hydroxyl substituents present (from 2 to 4). Moreover, specific cleavage in ring E was observed, passing from m/z 203 to m/z 133 and conducting other major fragments such as m/z 189.
Keywords: extractives; pentacyclic triterpenoids; oleanane triterpenes; ursane triterpenes; triterpene distribution; GC-MS; ion trap; biorefinery extractives; pentacyclic triterpenoids; oleanane triterpenes; ursane triterpenes; triterpene distribution; GC-MS; ion trap; biorefinery

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MDPI and ACS Style

Lourenço, A.; Marques, A.V.; Gominho, J. The Identification of New Triterpenoids in Eucalyptus globulus Wood. Molecules 2021, 26, 3495. https://doi.org/10.3390/molecules26123495

AMA Style

Lourenço A, Marques AV, Gominho J. The Identification of New Triterpenoids in Eucalyptus globulus Wood. Molecules. 2021; 26(12):3495. https://doi.org/10.3390/molecules26123495

Chicago/Turabian Style

Lourenço, Ana, António Velez Marques, and Jorge Gominho. 2021. "The Identification of New Triterpenoids in Eucalyptus globulus Wood" Molecules 26, no. 12: 3495. https://doi.org/10.3390/molecules26123495

APA Style

Lourenço, A., Marques, A. V., & Gominho, J. (2021). The Identification of New Triterpenoids in Eucalyptus globulus Wood. Molecules, 26(12), 3495. https://doi.org/10.3390/molecules26123495

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