A study of resveratrol-copper complexes by electrospray ionization mass spectrometry and density functional theory calculations.
Resveratrol 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 [Resv+Cu](+), [Resv+Cu+H(2)O](+) and [2Resv+Cu](+) by using a resveratrol/CuSO(4) solution in CH(3)CN/H(2)O. 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 [DHResv+Cu](+) complex has been detected.
Department of Physics, University of Trento, via Sommarive 14, I-38123 Povo-Trento, Italy.
Vajir
V
Tamboli
Andrea
A
Defant
Ines
I
Mancini
Paolo
P
Tosi
D003300:Copper / Q000737:chemistry*; D019327:Copper Sulfate; D008956:Models, Chemical; D000077185:Resveratrol; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D013267:Stilbenes / Q000737:chemistry*; D013816:Thermodynamics
D013267:Stilbenes; C544754:dihydroresveratrol; D003300:Copper; D019327:Copper Sulfate; D000077185:Resveratrol