IRMPD Spectroscopy of Bare Monodeprotonated Genistein, an Antioxidant Flavonoid.

Autor:	Paciotti R; Dipartimento di Farmacia, Università G. D'Annunzio Chieti-Pescara, Via dei Vestini 31, Chieti I-66100, Italy., Chiavarino B; Dipartimento di Chimica e Tecnologie del Farmaco, Università di Roma 'La Sapienza', Piazzale Aldo Moro, 5, I-00185 Roma, Italy., Coletti C; Dipartimento di Farmacia, Università G. D'Annunzio Chieti-Pescara, Via dei Vestini 31, Chieti I-66100, Italy., Scuderi D; Institut de Chimie Physique (UMR8000), CNRS, Université Paris-Saclay, 91405 Orsay, France., Re N; Dipartimento di Farmacia, Università G. D'Annunzio Chieti-Pescara, Via dei Vestini 31, Chieti I-66100, Italy., Corinti D; Dipartimento di Chimica e Tecnologie del Farmaco, Università di Roma 'La Sapienza', Piazzale Aldo Moro, 5, I-00185 Roma, Italy., Rotari L; Dipartimento di Chimica e Tecnologie del Farmaco, Università di Roma 'La Sapienza', Piazzale Aldo Moro, 5, I-00185 Roma, Italy., Fornarini S; Dipartimento di Chimica e Tecnologie del Farmaco, Università di Roma 'La Sapienza', Piazzale Aldo Moro, 5, I-00185 Roma, Italy., Crestoni ME; Dipartimento di Chimica e Tecnologie del Farmaco, Università di Roma 'La Sapienza', Piazzale Aldo Moro, 5, I-00185 Roma, Italy.
Jazyk:	angličtina
Zdroj:	ACS omega [ACS Omega] 2022 May 30; Vol. 7 (23), pp. 19535-19544. Date of Electronic Publication: 2022 May 30 (Print Publication: 2022).
DOI:	10.1021/acsomega.2c01236
Abstrakt:	Genistein is a naturally occurring polyphenol belonging to the family of flavonoids with estrogenic properties and proven antioxidant, anti-inflammatory, and hormonal effects. Genistein and its derivatives are involved in radical scavenging activity by way of mechanisms based on sequential proton-loss electron transfer. In view of this role, a detailed structural characterization of its bare deprotonated form, [geni-H] - , generated by electrospray ionization, has been performed by tandem mass spectrometry and infrared multiple photon dissociation (IRMPD) spectroscopy in the 800-1800 cm -1 spectral range. Quantum chemical calculations at the B3LYP/6-311+G(d,p) level of theory were carried out to determine geometries, thermochemical data, and anharmonic vibrational properties of low-lying isomers, enabling to interpret the experimental spectrum. Evidence is gathered that the conjugate base of genistein exists as a single isomeric form, which is deprotonated at the most acidic site (7-OH) and benefits from a strong intramolecular H-bond interaction between 5-OH and the adjacent carbonyl oxygen in the most stable arrangement. Competing Interests: The authors declare no competing financial interest. (© 2022 The Authors. Published by American Chemical Society.)
Databáze:	MEDLINE
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