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The identification of new triterpenoids in Eucalyptus globulus wood

2021Artigo científico Acesso aberto
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dc.contributor.authorLourenço, Ana
dc.contributor.authorMarques, António Velez
dc.contributor.authorGominho, Jorge
dc.date.accessioned2021-07-05T10:35:52Z
dc.date.available2021-07-05T10:35:52Z
dc.date.issued2021
dc.description.abstractEight polyhydroxy triterpenoid acids, hederagenin, (4 )-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 (2 )-2- hydroxybetulinic acid and (2 ,4 )-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 -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 189pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationLourenço, A.; Marques, A.V.; Gominho, J. The Identification of New Triterpenoids in Eucalyptus globulusWood. Molecules 2021, 26, 3495pt_PT
dc.identifier.doihttps://doi.org/10.3390/ molecules26123495pt_PT
dc.identifier.urihttp://hdl.handle.net/10400.5/21590
dc.language.isoengpt_PT
dc.publisherMDPIpt_PT
dc.relationPTDC/AGRCFL/ 110419/2009pt_PT
dc.relationForest Research Centre
dc.relationForest Research Centre
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.subjectextractivespt_PT
dc.subjectpentacyclic triterpenoidspt_PT
dc.subjectoleanane triterpenespt_PT
dc.subjectursane triterpenespt_PT
dc.subjecttriterpene distributionpt_PT
dc.subjectGC-MSpt_PT
dc.subjection trappt_PT
dc.subjectbiorefinerypt_PT
dc.titleThe identification of new triterpenoids in Eucalyptus globulus woodpt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleForest Research Centre
oaire.awardTitleForest Research Centre
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UID%2FAGR%2F00239%2F2019/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F00239%2F2020/PT
oaire.citation.titleMoleculespt_PT
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
person.familyNameGominho
person.givenNameJorge
person.identifierc-OdG5gAAAAJ
person.identifier.ciencia-idE21C-1B36-77F6
person.identifier.orcid0000-0003-3419-6075
person.identifier.scopus-author-id57195915156
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublicationfe9fa41e-219f-4a80-8131-4cccb07c3a6a
relation.isAuthorOfPublication.latestForDiscoveryfe9fa41e-219f-4a80-8131-4cccb07c3a6a
relation.isProjectOfPublication6a9ac754-44c8-4fda-854c-879148c1ac4e
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