دورية أكاديمية
Electrospray ionization tandem mass spectrometry of monoketone curcuminoids.
العنوان: | Electrospray ionization tandem mass spectrometry of monoketone curcuminoids. |
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المؤلفون: | Vieira TM; Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Av. Bandeirantes, 3900, Monte Alegre, CEP 14040-901, Ribeirão Preto, SP, Brazil., Orenha RP; Núcleo de Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, CEP 14404-600, Franca, SP, Brazil., Crevelin EJ; Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Av. Bandeirantes, 3900, Monte Alegre, CEP 14040-901, Ribeirão Preto, SP, Brazil., Furtado SSP; Núcleo de Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, CEP 14404-600, Franca, SP, Brazil., Vessecchi R; Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Av. Bandeirantes, 3900, Monte Alegre, CEP 14040-901, Ribeirão Preto, SP, Brazil., Parreira RLT; Núcleo de Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, CEP 14404-600, Franca, SP, Brazil., Crotti AEM; Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Av. Bandeirantes, 3900, Monte Alegre, CEP 14040-901, Ribeirão Preto, SP, Brazil. |
المصدر: | Rapid communications in mass spectrometry : RCM [Rapid Commun Mass Spectrom] 2020 Sep; Vol. 34 Suppl 3, pp. e8699. Date of Electronic Publication: 2020 Feb 11. |
نوع المنشور: | Journal Article |
اللغة: | English |
بيانات الدورية: | Publisher: John Wiley And Sons Ltd Country of Publication: England NLM ID: 8802365 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1097-0231 (Electronic) Linking ISSN: 09514198 NLM ISO Abbreviation: Rapid Commun Mass Spectrom Subsets: MEDLINE |
أسماء مطبوعة: | Publication: Chichester : John Wiley And Sons Ltd Original Publication: London, UK : Heyden, c1987- |
مواضيع طبية MeSH: | Diarylheptanoids/*chemistry, Chemical Fractionation ; Deuterium Exchange Measurement ; Diarylheptanoids/chemical synthesis ; Ions/chemistry ; Molecular Structure ; Spectrometry, Mass, Electrospray Ionization/methods ; Tandem Mass Spectrometry/methods |
مستخلص: | Rationale: Although monoketone curcuminoids (MKCs) have been largely investigated due to their biological activities, data on the gas-phase fragmentation reactions of protonated MKCs under collision-induced dissociation (CID) conditions are still scarce. Here, we combined electrospray ionization tandem mass spectrometry (ESI-MS/MS) data, multiple-stage mass spectrometry (MS n ), deuterium exchange experiments, accurate-mass data, and thermochemical data estimated by computational chemistry to elucidate and to rationalize the fragmentation pathways of eleven synthetic MKCs. Methods: The MKCs were synthesized by Claisen-Schmidt condensation under basic (1-9) or acidic (10-11) conditions. ESI-CID-MS/MS analyses and deuterium-exchange experiments were carried out on a triple quadrupole mass spectrometer. MS n analyses on an ion trap mass spectrometer helped to elucidate the fragmentation pathways. Accurate-mass data and thermochemical data, obtained at the B3LYP/6-31+G(d,p) level of theory, were used to support the ion structures. Results: The most intense product ions were the benzyl ions ([C Conclusions: Our results reinforce some aspects of the fragmentation pathways previously published for 1,5-bis-(2-methoxyphenyl)-1,4-pentadien-3-one and 1,5-bis-(2-hydroxyphenyl)-1,4-pentadien-3-one. The alternative fragmentation mechanism proposed herein can explain the fragmentation of a wider diversity of monoketone curcuminoids. (© 2019 John Wiley & Sons, Ltd.) |
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معلومات مُعتمدة: | 313648/2018-2 Conselho Nacional de Desenvolvimento Científico e Tecnológico; Finance Code 001 Coordenação de Aperfeiçoamento de Pessoal de Nível Superior; 2011/07623-8 Fundação de Amparo à Pesquisa do Estado de São Paulo; 2016/19272-9 Fundação de Amparo à Pesquisa do Estado de São Paulo; 2017/24856-2 Fundação de Amparo à Pesquisa do Estado de São Paulo |
المشرفين على المادة: | 0 (Diarylheptanoids) 0 (Ions) |
تواريخ الأحداث: | Date Created: 20191218 Date Completed: 20210705 Latest Revision: 20210705 |
رمز التحديث: | 20231215 |
DOI: | 10.1002/rcm.8699 |
PMID: | 31845428 |
قاعدة البيانات: | MEDLINE |
تدمد: | 1097-0231 |
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DOI: | 10.1002/rcm.8699 |