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How glucosylation triggers physical–chemical properties of curcumin: an experimental and theoretical study
Author(s) -
Benassi Rois,
Ferrari Erika,
Lazzari Sandra,
Pignedoli Francesca,
Spagnolo Ferdinando,
Saladini Monica
Publication year - 2011
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1750
Subject(s) - curcumin , chemistry , atomic orbital , computational chemistry , electronic structure , electronic effect , homo/lumo , stereochemistry , electron , steric effects , organic chemistry , molecule , physics , biochemistry , quantum mechanics
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 conformational minimum (GS) and rotational transition state (TS) 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 (H 2 O, MeOH, ACN, DMSO). The main finding is that the curcuminic core maintains the same geometrical and electronic structures in all compounds miming the metal coordination capability showed by curcumin. Therefore, we may confirm that the presence of glucose does not affect the electronic properties of the derivatives. Copyright © 2010 John Wiley & Sons, Ltd.