Structural, spectral, biological and antioxidant analyses of baicalin and ıts vanadium complexes: a dft study

Molecular simulation analyses of baicalin and its vanadium complexes were done at B3LYP/6-31+G(d) and B3LYP/ANL2DZ levels, respectively. The conformer analyses were performedfor baicalin and the most stable one is determined at OPLS3e method by using Maestro 11.9program. Structural and spectral analyses of the baicalin – vanadium complex is performed ingas phase and water. Potential energy distribution (PED) analyses were done to evaluate theinfrared (IR) spectra. 1H- and 13C-NMR spectra of V (IV) complex are analyzed. Finally,biological reactivity of related compounds is compared with that of cisplatin by using quantumchemical descriptors (QCD). Antioxidant properties of related structures are compared witheach other by using same QCDs. According to QCD rankings, antioxidant activity of baicalinis increased with the complexing of studied ligand.

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[1] Harborne J. B. and Williams C.A., Advances in flavonoid research since 1992, Phytochemistry 55 (2000) 481-504.
[2] Heim K. E., Tagliaferro A. R. and Bobilya D. J., Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships, Journal of Nutritional Biochemistry 13 (2002) 572-584.
[3] Hollman P. C. H. and Katan M. B., Dietary Flavonoids: Intake, Health Effects and Bioavailability, Food and Chemical Toxicology 37 (9,10) (1999) 937-942.
[4] Mullie P., Clarys P., Deriemaeker P. and Hebbelinck M., Estimation of Daily Human Intake of Food Flavonoids, Plant Foods for Human Nutrition 62(3) (2007) 93-98.
[5] Hertog M. G. L., Feskens E. J. M., Kromhout D., Hertog M. G. L., Hollman P. C. H., Hertog M. G. L. and Katan M. B., Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen Elderly Study, The Lancet 342 (8878) (1993) 1007-1011.
[6] Mullie P., Clarys P., Deriemaeker P. and Hebbelinck M., Estimation of daily human intake of food flavonoids, International Journal of Food Science and Nutrition 59(4) (2008) 291- 298.
[7] Chun O. K., Chung S. J. and Song W. O., Estimated Dietary Flavonoid Intake and Major Food Sources of U.S. Adults, The Journal of Nutrition 137(5) (2007) 1244-1252.
[8] Marchand L. L., Murphy S. P., Hankin J. H., Wilkens L. R. and Kolonel L. N., Intake of Flavonoids and Lung Cancer, JNCI: Journal of the National Cancer Institute 92(2) (2000) 154- 160.
[9] Catoni C., Schaefer H. M. and Peters A., Blackwell Publishing Ltd Fruit for health: the effect of flavonoids on humoral immune response and food selection in a frugivorous bird, Functional Ecology 22 (2008) 649-654.
[10] Wenner C.A., Parker K., Simon M.A., Adams L, Greene K. and Standish L.J, Botanical medicines with gynecological anticancer activity: a literature review., Journal of the American Medical Women's Association (1972), 54-4 (1999) 184-190.
[11] Lai M. Y., Hsiu S. L., Tsai S. Y., Hou Y. C. and Chao P. D. L., Comparison of metabolic pharmacokinetics of baicalin and baicalein in rats, Journal of Pharmacy and Pharmacology 55(2) (2003) 205-209.
[12] Medina J. J. M., Naso L. G., Pérez A. L., Rizzi A., Ferrer E. G. and Williams P. A. M., Antioxidant and anticancer effects and bioavailability studies of the flavonoid baicalin and its oxidovanadium(IV) complex, Journal of Inorganic Biochemistry 166 (2017) 150-161.
[13] R.D. Dennington II, T.A. Keith, J.M. Millam, GaussView 5.0, Wallingford, CT, 2009.
[14] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski and D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.
[15] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2010.
[16] PerkinElmer, 2016. ChemBioDraw Ultra Version (15.1.0.144), CambridgeSoft Waltham, MA, USA.
[17] Michal. H. Jamroz, Vibrational Energy Distribution Analysis VEDA 4, Warsaw, 2004- 2010.
[18] Maestro Version 11.9, MMshare Version 4.4.012, Release 2018-4, Platform Windowsx64. Maestro, Schrödinger, LLC, New York, NY, 2019.
[19] Cheng Z., Chen Q., Pontius F.W., Gao X., Tan Y., Ma Y. and Shen Z. Two new predictors combined with quantum chemical parameters for the selection of oxidants and degradation of organic contaminants: A QSAR modeling study, Chemosphere 240 (2020) 124928.
[20] Sayin K., Erkan Kariper S., Alagöz Sayin T. and Karakaş D. Theoretical spectroscopic study of seven zinc(II) complex withmacrocyclic Schiffbase ligand, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 133 (2014) 348-356.
[21] Santiago R. N. S., Freire P. T. C., Ayala A. P., Teixeira A. M. R., Santos H. S., Bandeira P. N., Gonçalves F. G., Oliveria M. T. A., Cruz B. G. and Sena Jr. D. M. Crystal structure, vibrational spectra and quantum chemical parameters of 2- hydroxy-3,4,6-trimethoxyacetophenone isolated from the Croton anisodontus Müll. Arg. (Euphorbiaceae), Journal of Molecular Structure 1171 (2018) 815-826.
[22] Atlam F. M., Awad M. K. and El-Bastawissy E.A., Computational simulation of the effect of quantum chemical parameters on the molecular docking of HMG-CoA reductase drugs, Journal of Molecular Structure 1075 (2014) 311-326.
[23] Sayin K., Karakaş D., Erkan Kariper S. and Alagöz Sayin T., Computational study of some fluoroquinolones: Structural, spectral and docking investigations, Journal of Molecular Structure 1156 (2018) 172-181.
[24] Li L., Niu S. Y., Shi Z. F., Gong L. G., Jin J., Chi Y. X. and Xing Y. H., Structures and lightinduced surface electron behavior of some oxovanadium complexes, Polyhedron 30 (2011) 976-982.
[25] Coletti A., Galloni P., Sartorel A., Conte V. and Floris B., Salophen and salen oxo vanadium complexes as catalysts of sulfides oxidation with H2O2: Mechanistic insights, Catalysis Today 192 (2012) 44-55.
[26] Fernandez T. L., Souza E. T., Visentin L. C., Santos J. V., Mangrich A. S., Faria R. B., Antunes O. A. C. and Scarpellini M. A new oxovanadium complex employing an imidazole-rich tripodal ligand: A bioinspired bromide and hydrocarbon oxidation catalyst, Journal of Inorganic Biochemistry 103 (2009) 474-479.
[27] Günsel A., Kobyaoğlu A., Bilgiçli A.T., Tüzün B., Tosun B., Arabaci G. and Yarasir M.N., Novel biologically active metallophthalocyanines as promising antioxidant-antibacterial agents: Synthesis, characterization and computational properties, Journal of Molecular Structure 1200 (2020) 127127.
[28] Mehri M., Chafai N., Ouksel L., Benbouguerra K., Hellal A. and Chafaa S., Synthesis, electrochemical and classical evaluation of the antioxidant activity of three a-aminophosphonic acids: Experimental and theoretical investigation, Journal of Molecular Structure 1171 (2018) 179-189.
[29] Yamagami C., Akamatsu M., Motohashi N., Hamada S. and Tanahashi T., Quantitative structure–activity relationship studies for antioxidant hydroxybenzalacetones by quantum chemicaland 3-D-QSAR(CoMF) analyses, Bioorganic & Medicinal Chemistry Letters 15 (2005) 2845–2850.
[30] Gaber M., El-Ghamry H.A., Fathalla S.K. and Mansour M.A., Synthesis, spectroscopic, thermal and molecular modeling studies of Zn2+, Cd2+ and UO2 2+ complexes of Schiff bases containing triazole moiety. Antimicrobial, anticancer, antioxidant and DNA binding studies, Materials Science & Engineering C 83 (2018) 78-89.