How glucosylation triggers physical-chemical properties of Curcumin: an experimental and theoretical study

Rois Benassi (1) , Erika Ferrari (1) , Sandra Lazzari (1) , Francesca Pignedoli (1) , Ferdinando Spagnolo (1) , Monica Saladini (1)

1 Department of Chemical and Geological Sciences [Modena]

In the present study we investigate the structures of glucosylated curcumin derivatives with DFT at B3LYP/6-31G* level. A conformational analysis is performed in order to determine the GS (conformational minimum) and TS (rotational transition state) of curcumin derivatives and then their electronic features are evaluated. HOMO and LUMO frontier orbitals and Maps of Electron Density Potential (MEPs) are plotted and compared. In order to correlate their predicted spectroscopic properties with IR, UV-vis and NMR experimental data we extended the theoretical study on electronic properties to different solvents (H2O, MeOH, ACN, DMSO). The main finding is that the curcuminic core maintains the same geometrical and electronic structure in all compounds miming the metal coordination capability showed by curcumin, therefore we may confirm that the presence of glucose does not affect electronic properties of the derivatives.

Mots clés: Physical Sciences

Rois Benassi, Erika Ferrari, Sandra Lazzari, Francesca Pignedoli, Ferdinando Spagnolo, et al.. How glucosylation triggers physical-chemical properties of Curcumin: an experimental and theoretical study. Journal of Physical Organic Chemistry, 2010, 24 (4), pp.299. ⟨10.1002/poc.1750⟩. ⟨hal-00599802⟩