Electrospray ionization tandem mass spectrometry of monoketone curcuminoids.

التفاصيل البيبلوغرافية
العنوان:	Electrospray ionization tandem mass spectrometry of monoketone curcuminoids.
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 7 H 2 R 1 R 2 R 3 R 4 R 5 ] ⁺ ) and the acylium ions ([M + H - C 8 H 3 R 1 R 2 R 3 R 4 R 5 ] ⁺ ), which originated directly from the precursor ion as a result of two competitive hydrogen rearrangements. Product ions [M + H - H 2 O] ⁺ and [M + H - C 6 HR 1 R 2 R 3 R 4 R 5 ] ⁺ , which are formed after Nazarov cyclization, were also common to all the analyzed compounds. In addition, •Br and •Cl eliminations were diagnostic for the presence of these halogen atoms at the aromatic ring, whereas •CH 3 eliminations were useful to identify the methyl and methoxy groups attached to this same ring. Nazarov cyclization in the gas phase occurred for all the investigated MKCs and did not depend on the presence of the hydroxyl group at the aromatic ring. However, the presence and the position of a hydroxyl group at the aromatic rings played a key role in the Nazarov cyclization mechanism. 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

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