UV/Visible spectra of natural polyphenols: A time-dependent density functional theory study

Food Chemistry

Volumn 131, Issue 1, 2012, Pages 79-89

  Anouar, El Hassane ^a   Gierschner, Johannes ^b   Duroux, Jean Luc ^a   Trouillas, Patrick ^a,c  

^a UNIVERSITY OF LIMOGES   (France)

^b INSTITUTO MADRILEÑO DE ESTUDIOS AVANZADOS EN NANOCIENCIA IMDEA NANOCIENCIA   (Spain)

^c UNIVERSITY OF MONS   (Belgium)

Author keywords

Colour; Flavonoid; Polyphenol; TD DFT; UV Vis absorption

Indexed keywords

BIOLOGICAL ACTIVITIES; FLAVONOID; HYDROXYL GROUPS; ISOFLAVONOIDS; LOCALISATION; POLYPHENOLS; QUANTUM-CHEMICAL CALCULATION; STRUCTURAL MODIFICATIONS; STRUCTURE PROPERTY RELATIONSHIPS; TD-DFT; TIME DEPENDENT DENSITY FUNCTIONAL THEORY; TIME-DEPENDENT DENSITY; UV/VIS ABSORPTION;

CHEMICAL COMPOUNDS; COLOR; MOLECULAR ORBITALS; PHENOLS; ULTRAVIOLET SPECTROSCOPY;

DENSITY FUNCTIONAL THEORY;

DIHYDROFLAVONOL; FLAVANONE DERIVATIVE; FLAVONOID; FLAVONOLIGNAN; HYDROXYL GROUP; ISOFLAVONOID; POLYPHENOL DERIVATIVE; QUERCETIN; TAXIFOLIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; FOOD COLOR; QUANTUM CHEMISTRY; RING OPENING; ULTRAVIOLET SPECTROSCOPY;

EID: 80054020584     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2011.08.034     Document Type: Article

References (24)

1. C. Amovilli, V. Barone, R. Cammi, E. Cancés, M. Cossi, and B. Mennucci Recent Advances in the Description of Solvent Effects with the Polarizable Continuum Model (Vol. 32, pp. 227-261) 1998 Academic Press
2. A.R. Ballester, J. Molthoff, R. de Vos, B.L. Hekkert, D. Orzaez, and J.P. Fernández-Moreno Biochemical and molecular analysis of pink tomatoes: Deregulated expression of the gene encoding transcription factor SlMYB12 leads to pink tomato fruit color Plant Physiology 152 2010 71 84
3. S.M. Beyhan, A.W. Götz, F. Ariese, L. Visscher, and C. Gooijer Computational study on the anomalous fluorescence behavior of isoflavones The Journal of Physical Chemistry A 115 9 2011 1493 1499
4. R. Brouillard Chemical structure of anthocyanins Pericles Markakis, Anthocyanins as Food Colors 1982 Academic Press Inc. New York pp. 1-38
5. R. Brouillard, and O. Dangles Anthocyanin molecular interactions: The first step in the formation of new pigments during wine aging? Food Chemistry 51 1994 365 371 (Pubitemid 24359025)
6. M.E. Casida Review: Time-dependent density-functional theory for molecules and molecular solids Journal of Molecular Structure (THEOCHEM) 914 1-3 2009 3 18
7. C.S. Cockell, and J. Knowland Ultraviolet radiation screening compounds Biological Revue 74 1999 311 345 (Pubitemid 29381273)
8. H.J. Egelhaaf, J. Gierschner, and D. Oelkrug Polarizability effects and energy transfer in quinquethiophene doped bithiophene and OPV films Synthetic Metals 127 1-3 2002 221 227 (Pubitemid 34201213)
9. A.A. Freitas, K. Shimizu, L.G. Dias, and F.H. Quina A computational study of substituted flavylium salts and their quinoidal conjugate-bass: S0 → S1 electronic transition, absolute pKa and reduction potential calculations by DFT and semiempirical ethods Journal Brazilian Chemistry Society 18 2007 1537 1546
10. Frisch, M. J., Trucks, G. W., Schlegel, H. B., et al., (Eds.) (2003) GAUSSIAN 03, Revision B.04. Pittsburgh, PA: Gaussian Inc.
11. J. Gierschner, J. Cornil, and H.-J. Egelhaaf Optical bandgaps of π-conjugated organic materials at the polymer limit: Experiment and theory Advanced Materials 19 2 2007 173 191 (Pubitemid 46160172)
12. M. Guerra, R. Amorati, and G.F. Pedulli Water effect on the O-H dissociation enthalpy of para-substituted phenols: A DFT study The Journal of Organic Chemistry 69 16 2004 5460 5467 (Pubitemid 39014382)
13. J.B. Harborne, T.J. Mabry, and H. Mabry The Flavonoids 1975 Chapman and Hall London
14. A. Kootstra Protection from UV-B-induced DNA damage by flavonoids Plant Molecular Biology 26 2 1994 771 774 (Pubitemid 2158300)
15. W.E. Kurtin, and P.-S. Song Electronic structures and spectra of some natural products of theoretical interest-I: Molecular orbital studies of anthocyanidins Tetrahedron 24 5 1968 2255 2267
16. Lattanzio,V., Lattanzio V.M.T., & Cardinal A. (2006). Role of phenolics in the resistance mechanisms of plants against fungal pathogens and insects. In: Phytochemistry: Advances in Research (pp. 23-67). Research Signpost: Kerala, India.
17. G.K. Pereira, and S.E. Galembeck Computational study of the electronic excitations of some anthocyanidins Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 54 2 1998 339 348 (Pubitemid 128408422)
18. E.A. Perpete, V. Wathelet, J. Preat, C. Lambert, and D. Jacquemin Toward a theoretical quantitative estimation of the λmax of anthraquinones-based dyes Journal of Chemical Theory and Computation 2 2 2006 434 440
19. C. Rice-Evans, N.J. Miller, and G. Paganga Structure-antioxidant activity relationships of flavonoids and phenolic acids Free Radical Biology & Medicine 20 7 1996 933 956 (Pubitemid 26157509)
20. C. Rice-Evans, N. Miller, and G. Paganga Antioxidant properties of phenolic compounds Trends in Plant Science 2 4 1997 152 159 (Pubitemid 27158898)
21. E. Runge, and E.K.U. Gross Density-functional theory for time-dependent systems Physical Revue Letter 52 1984 997 1000
22. K. Sakata, N. Saito, and T. Honda Ab initio study of molecular structures and excited states in anthocyanidins Tetrahedron 62 15 2006 3721 3731
23. Tomasi, J., Mennucci, B., & Cammi, R. (2005). Quantum Mechanical Continuum Solvation Models. Chemical Revue (Washington, DC, U. S.), 105(8), 2999-3093. (Pubitemid 41222791)
24. K. Yoshida, M. Mori, and T. Kondo Blue flower color development by anthocyanins: from chemical structure to cell physiology Natural Product Report 26 2009 857 964