Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Open Chemistry

formerly Central European Journal of Chemistry


IMPACT FACTOR 2017: 1.425
5-year IMPACT FACTOR: 1.511

CiteScore 2018: 1.58

SCImago Journal Rank (SJR) 2018: 0.345
Source Normalized Impact per Paper (SNIP) 2018: 0.684

ICV 2017: 165.27

Open Access
Online
ISSN
2391-5420
See all formats and pricing
More options …
Volume 10, Issue 1

Issues

Volume 13 (2015)

Ab initio study regarding the evaluation of the antioxidant character of cyanidin, delphinidin and malvidin

Raluca Pop / Mariana Ştefănut / Adina Căta / Cristian Tănasie / Mihai Medeleanu
Published Online: 2011-11-24 | DOI: https://doi.org/10.2478/s11532-011-0128-1

Abstract

A theoretical study regarding the evaluation of the antioxidant character of three of the most wide-spread anthocyanidins (cyanidin, delphinidin and malvidin) was carried out at ab initio level. Different parameters (bond dissociation enthalpy, ionization potential, proton affinity, and electron transfer enthalpy) were computed for each OH group of the compounds in order to predict their antioxidant capacity. Several molecular descriptors based on frontier molecular orbital theory (hardness, electrophilicity, frontier charge density) were also calculated, as well as the atomic charges corresponding to the O atoms of the hydroxyl groups.

Keywords: Anthocyanidins; Antioxidant character; Ab initio

  • [1] M. Andersen, K.R. Markham, Flavonoids. Chemistry, Biochemistry and Applications (CRC Press, Boca Raton, Florida, 2006) Google Scholar

  • [2] M. de Lorgeril, P. Salen, In: M.G. Bourassa, J.-C. Tardif, (Eds.), Antioxidants and Cardiovascular disease, 2nd edition (Springer Science+Business Media, Inc., New York, 2006) Google Scholar

  • [3] L. Packer, P. Rosen, H.J. Tritschler, G.L. King, A. Azzi, In: C.A Rice-Evans, L. Packer, (Eds.), Oxidative Stress and Disease, 2nd edition (Marcel Dekker, Inc., New York, 2003) Google Scholar

  • [4] J.S. Wright, E.R. Johnson, G.A. DiLabio, J. Am. Chem. Soc. 123(6), 1173 (2001) http://dx.doi.org/10.1021/ja002455uCrossrefGoogle Scholar

  • [5] M. Musialik, G. Litwinienko, Org. Lett. 7(22), 4951 (2005) http://dx.doi.org/10.1021/ol051962jCrossrefGoogle Scholar

  • [6] A.P. Vafiadis, E.G. Bakalbassis, Chem. Phys. 316(1–3), 195 (2005) http://dx.doi.org/10.1016/j.chemphys.2005.05.015CrossrefGoogle Scholar

  • [7] E. Migliavacca, P.-A. Carrupt, B. Testa, Helv. Chim. Acta 80(5), 1613 (1997) http://dx.doi.org/10.1002/hlca.19970800519CrossrefGoogle Scholar

  • [8] H.Y. Zhang, D.Z. Chen, Chin. Chem. Lett. 11(8), 727 (2000) Google Scholar

  • [9] L.F. Wang, X.L. Wang, H.Y. Zhang, Dyes and Pigments 67, 161 (2005) http://dx.doi.org/10.1016/j.dyepig.2004.11.007CrossrefGoogle Scholar

  • [10] H.-Y. Zhang, Current Computer-Aided Drug Design 1(3), 257 (2005) http://dx.doi.org/10.2174/1573409054367691CrossrefGoogle Scholar

  • [11] M. Wolniak, I. Waver, Solid State Nuclear Magnetic Resonance 34, 44 (2008) http://dx.doi.org/10.1016/j.ssnmr.2008.06.003CrossrefGoogle Scholar

  • [12] K. Sakata, N. Saito, T. Honda, Tetrahedron 62, 3721 (2006) http://dx.doi.org/10.1016/j.tet.2006.01.081CrossrefGoogle Scholar

  • [13] J.N. Woodford, Chemical Physics Letters 410, 182 (2005) http://dx.doi.org/10.1016/j.cplett.2005.05.067CrossrefGoogle Scholar

  • [14] T. Borkowski, H. Szymusiak, A. Gliszczynska-Swiglo, B. Tyrakowska, Food Research International 38, 1031 (2005) http://dx.doi.org/10.1016/j.foodres.2005.02.020CrossrefGoogle Scholar

  • [15] L. Estevez, N. Otero, R. A. Mosquera, J. Phys. Chem. B 114, 9706 (2010) http://dx.doi.org/10.1021/jp1041266CrossrefGoogle Scholar

  • [16] R. Guzman, C. Santiago, M. Sanchez, J. Mol. Struct. 935, 110 (2009) http://dx.doi.org/10.1016/j.molstruc.2009.06.048CrossrefGoogle Scholar

  • [17] P. Trouillas, P. Marsal, D. Siri, R. Lazzaroni, J.L. Duroux, Food Chemistry 97, 679 (2006) http://dx.doi.org/10.1016/j.foodchem.2005.05.042CrossrefGoogle Scholar

  • [18] E. Klein, V. Lukes, M. Ilcin, Chemical Physics 336, 51 (2007) http://dx.doi.org/10.1016/j.chemphys.2007.05.007CrossrefGoogle Scholar

  • [19] L.F. Wang, H.Y. Zhang, Bioorganic Chemistry 33, 108 (2005) http://dx.doi.org/10.1016/j.bioorg.2005.01.002CrossrefGoogle Scholar

  • [20] K. Sadasivam, R. Kumaresan, Computational and Theoretical Chemistry 963, 227 (2011) http://dx.doi.org/10.1016/j.comptc.2010.10.025CrossrefGoogle Scholar

  • [21] E.G. Bakalbassis, A. Chatzopolou, V.S. Melissas, M. Tsimidou, M. Tsolaki, A. Vafiadis, Lipids 36, 181 (2001) http://dx.doi.org/10.1007/s11745-001-0705-9CrossrefGoogle Scholar

  • [22] B. Rojano, J. Saez, G. Schinella, J. Quijano, E. Velez, A. Gil, R. Notario, J. Mol. Struc. 877, 1 (2008) http://dx.doi.org/10.1016/j.molstruc.2007.07.010CrossrefGoogle Scholar

  • [23] H. Wang, G. Cao, R.L. Prior, J. Agric. Food Chem. 45, 304 (1997) http://dx.doi.org/10.1021/jf960421tCrossrefGoogle Scholar

  • [24] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revision B.03 (Gaussian, Inc., Pittsburgh PA, 2003) Google Scholar

  • [25] J. Zhang, F. Du, B. Peng, R. Lu, H. Gao, Z. Zhou, J. Mol. Struct. (THEOCHEM) 955, 1 (2010) http://dx.doi.org/10.1016/j.theochem.2010.04.036CrossrefGoogle Scholar

  • [26] E. Klein, V. Lukes, J. Mol. Struct. (THEOCHEM) 805, 153 (2007) http://dx.doi.org/10.1016/j.theochem.2006.11.002CrossrefGoogle Scholar

  • [27] P.K. Chattaraj, H. Lee, R.G. Parr, J. Am. Chem. Soc. 113(5), 1855 (1991) http://dx.doi.org/10.1021/ja00005a073CrossrefGoogle Scholar

  • [28] X.M. Duan, G.L. Song, Z.H. Li, X.J. Wang, G.H. Chen, K.N. Fan, J. Chem. Phys. 121(15), 7086 (2004) http://dx.doi.org/10.1063/1.1786582CrossrefGoogle Scholar

About the article

Published Online: 2011-11-24

Published in Print: 2012-02-01


Citation Information: Open Chemistry, Volume 10, Issue 1, Pages 180–186, ISSN (Online) 2391-5420, DOI: https://doi.org/10.2478/s11532-011-0128-1.

Export Citation

© 2011 Versita Warsaw. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[1]
Qianyu Yue, Lili Xu, Guangqing Xiang, Xin Yu, and Yuxin Yao
Journal of Agricultural and Food Chemistry, 2018
[3]
D. Alejandro Hernandez and Francisco J. Tenorio
Structural Chemistry, 2017
[6]
Ganna Petruk, Anna Illiano, Rita Del Giudice, Assunta Raiola, Angela Amoresano, Maria Manuela Rigano, Renata Piccoli, and Daria Maria Monti
Journal of Photochemistry and Photobiology B: Biology, 2017, Volume 172, Page 42
[7]
Wuyang Huang, Yunming Zhu, Chunyang Li, Zhongquan Sui, and Weihong Min
Oxidative Medicine and Cellular Longevity, 2016, Volume 2016, Page 1
[8]
Wu-Yang Huang, Ya-Mei Liu, Jian Wang, Xing-Na Wang, and Chun-Yang Li
Molecules, 2014, Volume 19, Number 8, Page 12827
[9]
Ondřej Kurka, Jana Roithová, and Petr Bednář
Journal of Mass Spectrometry, 2014, Volume 49, Number 12, Page 1314
[10]
Yunhui Cheng, Fang Luo, Zhiyin Zeng, Li Wen, Zhongliang Xiao, Hanping Bu, Fei Lv, Zhou Xu, and Qinlu Lin
Structural Chemistry, 2015, Volume 26, Number 3, Page 739
[11]
Adam Vagánek, Ján Rimarčík, Vladimír Lukeš, and Erik Klein
Computational and Theoretical Chemistry, 2012, Volume 991, Page 192

Comments (0)

Please log in or register to comment.
Log in