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EnglishResveratrol is a polyphenolic compound found in plants and human foods which has shown biological activities including chemoprevention, acting through a mechanism which involves the reduction of Cu(II) species. By electrospray ionization (ESI) mass spectrometry we have produced and detected the resveratrol-copper complexes [ResvRCu]+, [ResvRCuRH2O]+ and [2ResvRCu]+ by using a resveratrol/CuSO4 solution in CH3CN/H2O. The most stable structures of the detected complexes have been calculated at the B3LYP/6-311G(d) level of theory. Resveratrol interacts with the copper ion through nucleophilic carbon atoms on the aromatic ring and the alkenyl group. The fact that only singly charged ions were observed implies that Cu(II) is reduced to Cu(I) in the ESI process. For investigating the structure-reactivity correlation, we have carried out a similar study on the synthetic analogue dihydroresveratrol (DHResv). For the latter only the [DHResvRCu]+ complex has been detected.
| Titolo: | A study of resveratrol-copper complexes by electrospray ionization mass spectrometry and density functional theory calculations |
| Autori: | Tamboli, Vajir; Defant, Andrea; Mancini, Ines; Tosi, Paolo |
| Autori Unitn: | |
| Titolo del periodico: | RAPID COMMUNICATIONS IN MASS SPECTROMETRY |
| Anno di pubblicazione: | 2011 |
| Codice identificativo Scopus: | 2-s2.0-79251500007 |
| Codice identificativo Pubmed: | 21259361 |
| Codice identificativo ISI: | WOS:000287338500009 |
| Digital Object Identifier (DOI): | 10.1002/rcm.4883 |
| Handle: | http://hdl.handle.net/11572/85712 |
| Citazione: | A study of resveratrol-copper complexes by electrospray ionization mass spectrometry and density functional theory calculations / Tamboli, Vajir; Defant, Andrea; Mancini, Ines; Tosi, Paolo. - In: RAPID COMMUNICATIONS IN MASS SPECTROMETRY. - ISSN 0951-4198. - STAMPA. - 25(2011), pp. 526-532. |
| Appare nelle tipologie: | 03.1 Articolo su rivista (Journal article) |
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