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The identification of new triterpenoids in eucalyptus globulus wood

2021-06-08Journal article Open access
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dc.contributor.authorLourenço, Ana
dc.contributor.authorV Marques, A
dc.contributor.authorGominho, Jorge
dc.date.accessioned2021-07-13T13:42:47Z
dc.date.available2021-07-13T13:42:47Z
dc.date.issued2021-06-08
dc.description.abstractEight 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.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationLOURENÇO, Ana; MARQUES, António Velez; GOMINHO, Jorge – The identification of new triterpenoids in eucalyptus globulus wood. Molecules. ISSN 1420-3049. Vol. 26, N.º 12 (2021), pp. 1-13pt_PT
dc.identifier.doi10.3390/molecules26123495pt_PT
dc.identifier.issn1420-3049
dc.identifier.urihttp://hdl.handle.net/10400.21/13547
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherMDPIpt_PT
dc.relationUID/AGR/00239/2019 - FCTpt_PT
dc.relationUIDB/00239/2020 - FCTpt_PT
dc.relationPTDC/AGRCFL/110419/2009 - FCTpt_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.citation.endPage13pt_PT
oaire.citation.issue12pt_PT
oaire.citation.startPage1pt_PT
oaire.citation.titleMoleculespt_PT
oaire.citation.volume26pt_PT
person.familyNameLourenço
person.familyNameMarques
person.familyNameGominho
person.givenNameAna
person.givenNameAntónio
person.givenNameJorge
person.identifierA-5901-2011
person.identifierB-4816-2009
person.identifier.ciencia-id411B-FD38-7C96
person.identifier.ciencia-idE21C-1B36-77F6
person.identifier.orcid0000-0003-4896-344X
person.identifier.orcid0000-0001-7421-6363
person.identifier.orcid0000-0003-3419-6075
person.identifier.scopus-author-id36877743000
person.identifier.scopus-author-id7202134785
person.identifier.scopus-author-id57195915156
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublication7a4a5157-6b59-49fb-8a41-47d9f4a0e0cb
relation.isAuthorOfPublicationb3d0c7ab-dc57-45a9-a86b-6f99a6232f34
relation.isAuthorOfPublication93f6372e-fa94-467e-8d7c-8a014f0f6e66
relation.isAuthorOfPublication.latestForDiscovery93f6372e-fa94-467e-8d7c-8a014f0f6e66

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