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Molecules 2018, 23(7), 1587;

Theoretical Characterization by Density Functional Theory (DFT) of Delphinidin 3-O-Sambubioside and Its Esters Obtained by Chemical Lipophilization

Facultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Chihuahua 31125, Mexico
Technion-Israel Institute of Technology, Haifa 31096, Israel
Montpellier SupAgro, Montpellier 34060, France
Authors to whom correspondence should be addressed.
Academic Editors: M. Monica Giusti and Gregory T. Sigurdson
Received: 1 June 2018 / Revised: 26 June 2018 / Accepted: 27 June 2018 / Published: 29 June 2018
(This article belongs to the Special Issue Advances in Anthocyanin Research 2018)
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Anthocyanins are water-soluble phenolic pigments. However, their poor solubility in lipidic media limits their use. This hurdle can be overcome with the lipophilization of anthocyanins, which consists of adding an aliphatic chain to a hydrophilic compound, in order to increase its solubility in lipids. Still, the unspecific chemical lipophilization of anthocyanin-esters produces molecules with different properties from their precursors. In this work, experimental changes of anthocyanin-esters obtained by chemical lipophilization are investigated in silico aiming specifically at observing their molecular behavior and comparing it with their anthocyanin precursor. Thus, the analysis of delphinidin 3-O-sambubioside and its esters employing Density Functional Theory (DFT) methods, such as the hybrid functional B3LYP in combination with the 6-31++G(d,p) Pople basis set, provides the ground state properties, the local reactivity and the molecular orbitals (MOs) of these compounds. Excited states properties were analyzed by TD-DFT with the B3LYP functional, and the M06 and M06-2X meta-GGA functionals. Local reactivity calculations showed that the electrophilic site for all the anthocyanin-esters was the same as the one for the anthocyanin precursor, however the nucleophilic site changed depending localization of the esterification. TD-DFT results indicate that the place of esterification could change the electronic transitions and the MOs spatial distribution. View Full-Text
Keywords: anthocyanin; lipophilization; time-depending density functional theory anthocyanin; lipophilization; time-depending density functional theory

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Márquez-Rodríguez, A.S.; Grajeda-Iglesias, C.; Sánchez-Bojorge, N.-A.; Figueroa-Espinoza, M.-C.; Rodríguez-Valdez, L.-M.; Fuentes-Montero, M.E.; Salas, E. Theoretical Characterization by Density Functional Theory (DFT) of Delphinidin 3-O-Sambubioside and Its Esters Obtained by Chemical Lipophilization. Molecules 2018, 23, 1587.

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