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dc.creatorNicolaus, Christoph
dc.creatorSievers Engler, Adrian
dc.creatorMurillo Masis, Renato
dc.creatorD’Ambrosio, Michele
dc.creatorLämmerhofer, Michael
dc.creatorMerfort, Irmgard
dc.date.accessioned2018-04-06T20:34:22Z
dc.date.available2018-04-06T20:34:22Z
dc.date.issued2016-01-25
dc.identifier.citationhttps://www.sciencedirect.com/science/article/pii/S0731708515301989?via%3Dihubes_ES
dc.identifier.issn0731-7085
dc.identifier.urihttp://hdl.handle.net/10669/74424
dc.description.abstractPentacyclic triterpene mono- and diesters have been isolated from Calendula officinalis flowers. GC–MS, APCI-Exactive Orbitrap HR-MS and NMR allowed to identify the triterpene skeleton in various samples (different triterpene mixtures from Calendula n-hexane extract). NMR provided evidence that triterpene diesters are present in the samples as well. However, the corresponding quasi-molecular ions could not be detected by APCI-Exactive Orbitrap HR-MS. Instability of triterpene diesters and loss of a fatty acid residue, respectively, in the ion-source made their MS detection challenging. Thus, a set of new APCI-QTOF-MS methods (using the TripleTOF 5600+ mass spectrometer) were developed which made it eventually possible to solve this problem and confirm the diester structures by MS via quasi-molecular ion [M + H]+ detection. Direct infusion APCI-QTOF MS experiments in MS/MS high sensitivity scan mode with low collision energy and multi-channel averaging acquisition (MCA) allowed the detection of quasi-molecular ions of triterpene diesters for the first time and unequivocally confirmed the presence of faradiol 3,16-dimyristate and -dipalmitate, as well as the corresponding mixed diesters faradiol 3-myristate,16-palmitate and faradiol 3-palmitate,16-myristate. Preferential loss of the fatty acid in 16-position made it possible to distinguish the mixed diesters by MS/MS spectra. Their chromatographic separations turned out to be challenging due to their bulkiness and extended molecular dimensions. However, separation could be achieved by an uncommon non-aqueous RPLC mode with an in-house synthesized C30 phase. Finally, two (U)HPLC-APCI-QTOF-MS methods with C18- and C30-based non-aqueous RPLC provided suitable, sensitive assays to monitor the presence of monoesters and diesters of various triterpenes (faradiol, maniladiol, arnidiol, arnitriol A and lupane-3β,16β,20-triol esters) in the n-hexane extract of C. officinalis with high mass resolution and good mass accuracy.es_ES
dc.description.sponsorshipStruktur- und Innovationsfonds Baden-Württemberg/[INST 37/821-1 FUGG]/SI-BW/Alemaniaes_ES
dc.description.sponsorshipGerman Research Foundation/[INST 37/821-1 FUGG]/DFG/Alemaniaes_ES
dc.language.isoen_USes_ES
dc.sourceJournal of Pharmaceutical and Biomedical Analysis, Vol. 118, 2016es_ES
dc.subjectCalendula officinalises_ES
dc.subjectTriterpene mono- and novel diesterses_ES
dc.subject(U)HPLC-APCI-QTOF-MSes_ES
dc.subjectnon-aqueous RPLCes_ES
dc.subjectC30 stationary phasees_ES
dc.titleMastering analytical challenges for the characterization of pentacyclic triterpene mono- and diesters of Calendula officinalis flowers by non-aqueous C30 HPLC and hyphenation with APCI-QTOF-MSes_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.identifier.doi10.1016/j.jpba.2015.10.025
dc.description.procedenceUCR::Investigación::Unidades de Investigación::Ciencias Básicas::Centro de Investigaciones en Productos Naturales (CIPRONA)es_ES
dc.description.procedenceUCR::Docencia::Ciencias Básicas::Facultad de Ciencias::Escuela de Químicaes_ES


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