Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2017 (2017), Article ID 3535148, 11 pages
https://doi.org/10.1155/2017/3535148
Research Article

Effect of Constituent Units, Type of Interflavan Bond, and Conformation on the Antioxidant Properties of Procyanidin Dimers: A Computational Outlook

Coordinación de Tecnología de Alimentos de Origen Vegetal, CIAD, A.C., Carretera a la Victoria Km 0.6, 83304 Hermosillo, SON, Mexico

Correspondence should be addressed to Ana María Mendoza-Wilson

Received 1 December 2016; Accepted 23 January 2017; Published 21 February 2017

Academic Editor: Artur M. S. Silva

Copyright © 2017 Ana María Mendoza-Wilson and René Renato Balandrán-Quintana. 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.

Linked References

  1. O. Dangles, “Antioxidant activity of plant phenols: chemical mechanisms and biological significance,” Current Organic Chemistry, vol. 16, no. 6, pp. 692–714, 2012. View at Publisher · View at Google Scholar · View at Scopus
  2. T. Enomoto, Y. Nagasako-Akazome, T. Kanda, M. Ikeda, and Y. Dake, “Clinical effects of apple polyphenols on persistent allergic rhinitis: a randomized double-blind placebo-controlled parallel arm study,” Journal of Investigational Allergology and Clinical Immunology, vol. 16, no. 5, pp. 283–289, 2006. View at Google Scholar · View at Scopus
  3. J. M. R. Da Silva, N. Darmon, Y. Fernandez, and S. Mitjavila, “Oxygen free radical scavenger capacity in aqueous models of different procyanidins from grape seeds,” Journal of Agricultural and Food Chemistry®, vol. 39, no. 9, pp. 1549–1552, 1991. View at Publisher · View at Google Scholar · View at Scopus
  4. I. Tarascou, M.-A. Ducasse, E. J. Dufourc et al., “Structural and conformational analysis of two native procyanidin trimers,” Magnetic Resonance in Chemistry, vol. 45, no. 2, pp. 157–166, 2007. View at Publisher · View at Google Scholar · View at Scopus
  5. Y. Wang, S.-J. Chung, W. O. Song, and O. K. Chun, “Estimation of daily proanthocyanidin intake and major food sources in the U.S. diet,” The Journal of Nutrition, vol. 141, no. 3, pp. 447–452, 2011. View at Publisher · View at Google Scholar · View at Scopus
  6. K. Ou and L. Gu, “Absorption and metabolism of proanthocyanidins,” Journal of Functional Foods, vol. 7, no. 1, pp. 43–53, 2014. View at Publisher · View at Google Scholar · View at Scopus
  7. V. A. P. De Freitas, Y. Glories, and M. Laguerre, “Incidence of molecular structure in oxidation of grape seed procyanidins,” Journal of Agricultural and Food Chemistry, vol. 46, no. 2, pp. 376–382, 1998. View at Publisher · View at Google Scholar · View at Scopus
  8. K. Klausen, A. G. Mortensen, B. Laursen, K. F. Haselmann, B. M. Jespersen, and I. S. Fomsgaard, “Phenolic compounds in different barley varieties: identification by tandem mass spectrometry (QStar) and NMR; quantification by liquid chromatography triple quadrupole-linear ion trap mass spectrometry (Q-Trap),” Natural Product Communications, vol. 5, no. 3, pp. 407–414, 2010. View at Google Scholar · View at Scopus
  9. A. M. Mendoza-Wilson, S. I. Castro-Arredondo, A. Espinosa-Plascencia, M. Del Refugio Robles-Burgueño, R. R. Balandrán-Quintana, and M. Del Carmen Bermúdez-Almada, “Chemical composition and antioxidant-prooxidant potential of a polyphenolic extract and a proanthocyanidin-rich fraction of apple skin,” Heliyon, vol. 2, no. 2, Article ID e00073, 2016. View at Publisher · View at Google Scholar · View at Scopus
  10. P.-G. Pietta, “Flavonoids as antioxidants,” Journal of Natural Products, vol. 63, no. 7, pp. 1035–1042, 2000. View at Publisher · View at Google Scholar · View at Scopus
  11. M. J. Frisch, G. W. Trucks, H. B. Schlegel et al., Gaussian 09, Revision A.1-SMP, Gaussian Inc, Wallingford, Conn, USA, 2009.
  12. Y. Zhao, N. E. Schultz, and D. G. Truhlar, “Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions,” Journal of Chemical Theory and Computation, vol. 2, no. 2, pp. 364–382, 2006. View at Publisher · View at Google Scholar · View at Scopus
  13. L. A. Burns, Á. Vázquez-Mayagoitia, B. G. Sumpter, and C. D. Sherrill, “Density-functional approaches to noncovalent interactions: a comparison of dispersion corrections (DFT-D), exchange-hole dipole moment (XDM) theory, and specialized functionals,” Journal of Chemical Physics, vol. 134, no. 8, Article ID 084107, 2011. View at Publisher · View at Google Scholar · View at Scopus
  14. A. V. Marenich, C. J. Cramer, and D. G. Truhlar, “Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions,” Journal of Physical Chemistry B, vol. 113, no. 18, pp. 6378–6396, 2009. View at Publisher · View at Google Scholar · View at Scopus
  15. E. F. Pettersen, T. D. Goddard, C. C. Huang et al., “UCSF Chimera—a visualization system for exploratory research and analysis,” Journal of Computational Chemistry, vol. 25, no. 13, pp. 1605–1612, 2004. View at Publisher · View at Google Scholar · View at Scopus
  16. J. W. Ochterski, Thermochemistry in Gaussian, Gaussian, Inc., 2000.
  17. E. Lewars, Computacional Chemistry. Introduction to the Theory and Applications of Molecular and Quantum Mechanics, Kluwer Academic, Dordrecht, The Netherlands, 1st edition, 2003.
  18. P. Geerlings, F. De Proft, and W. Langenaeker, “Conceptual density functional theory,” Chemical Reviews, vol. 103, no. 5, pp. 1793–1873, 2003. View at Publisher · View at Google Scholar · View at Scopus
  19. J. W. Ochterski, G. A. Petersson, and K. B. Wiberg, “A comparison of model chemistries,” Journal of the American Chemical Society, vol. 117, no. 45, pp. 11299–11308, 1995. View at Publisher · View at Google Scholar · View at Scopus
  20. R. G. Parr and W. Yang, Density-Functional Theory of Atoms and Molecules, Oxford University Press, New York, NY, USA, 1989.
  21. W. Yang and W. J. Mortier, “The use of global and local molecular parameters for the analysis of the gas-phase basicity of amines,” Journal of the American Chemical Society, vol. 108, no. 19, pp. 5708–5711, 1986. View at Publisher · View at Google Scholar · View at Scopus
  22. M. L. Khan, E. Haslam, and M. P. Williamson, “Structure and conformation of the procyanidin B-2 dimer,” Magnetic Resonance in Chemistry, vol. 35, no. 12, pp. 854–858, 1997. View at Publisher · View at Google Scholar · View at Scopus
  23. D. Lin-Vien, N. B. Colthup, W. G. Fateley, and J. G. Grasselli, “Alcohols and phenols,” in The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules, chapter 4, pp. 45–60, Academic Press, 1st edition, 1991. View at Google Scholar
  24. A. M. Mendoza-Wilson, S. I. Castro-Arredondo, and R. R. Balandrán-Quintana, “Computational study of the structure-free radical scavenging relationship of procyanidins,” Food Chemistry, vol. 161, pp. 155–161, 2014. View at Publisher · View at Google Scholar · View at Scopus
  25. A. M. Mendoza-Wilson, F. J. Carmelo-Luna, H. Astiazarán-García, B. I. Pacheco-Moreno, I. Anduro-Corona, and M. L. Rascón-Durán, “DFT study of the physicochemical properties of A- and B-type procyanidin oligomers,” Journal of Theoretical and Computational Chemistry, vol. 15, no. 8, Article ID 1650069, 18 pages, 2016. View at Publisher · View at Google Scholar
  26. I. Tarascou, K. Barathieu, C. Simon et al., “A 3D structural and conformational study of procyanidin dimers in water and hydro-alcoholic media as viewed by NMR and molecular modeling,” Magnetic Resonance in Chemistry, vol. 44, no. 9, pp. 868–880, 2006. View at Publisher · View at Google Scholar · View at Scopus
  27. H. M. Awad, M. G. Boersma, S. Boeren, P. J. Van Bladeren, J. Vervoort, and I. M. C. M. Rietjens, “The regioselectivity of glutathione adduct formation with flavonoid quinone/quinone methides is pH-dependent,” Chemical Research in Toxicology, vol. 15, no. 3, pp. 343–351, 2002. View at Publisher · View at Google Scholar · View at Scopus
  28. D. R. Roy, U. Sarkar, P. K. Chattaraj et al., “Analyzing toxicity through electrophilicity,” Molecular Diversity, vol. 10, no. 2, pp. 119–131, 2006. View at Publisher · View at Google Scholar
  29. A. M. Mendoza-Wilson and D. Glossman-Mitnik, “CHIH-DFT study of the electronic properties and chemical reactivity of quercetin,” Journal of Molecular Structure: THEOCHEM, vol. 716, no. 1-3, pp. 67–72, 2005. View at Publisher · View at Google Scholar · View at Scopus
  30. A. M. Mendoza-Wilson, M. E. Armenta-Vázquez, S. I. Castro-Arredondo et al., “Potential of polyphenols from an aqueous extract of apple peel as inhibitors of free radicals: an experimental and computational study,” Journal of Molecular Structure, vol. 1035, pp. 61–68, 2013. View at Publisher · View at Google Scholar · View at Scopus
  31. F. L. Hirshfeld, “Bonded-atom fragments for describing molecular charge densities,” Theoretica Chimica Acta, vol. 44, no. 2, pp. 129–138, 1977. View at Publisher · View at Google Scholar · View at Scopus