The interactions between two flavanols (Catechin and Epicatechin) and (Ala) Alanine (aliphatic amino acid) are evaluated by theoretical chemistry methods. Calculations at the level DFT/B3LYP/6-31+G (d, p) determine their characteristics and those of the monomers. Geometric, energetic, and spectroscopic parameters in addition to QTAIM (Quantum Theory of Atoms In Molecules), NBO (Natural Bond Orbital) and NCI (Non-Covalent Interaction) topological analyses qualify the nature and type of these. The results indicate that the main interactions are O–H⋯O and O–H⋯N between the hydroxyl groups of Cat (Catechin) or Epicat (Epicatechin) and the heteroatoms of Ala. They mention the existence of a secondary one alongside the main. They classify them into proper, improper, moderate, and weak. The spectroscopic parameters prove that O–H⋯O, O–H⋯N and N–H⋯O are proper. They establish that the C–H⋯N and C–H⋯O are improper. QTAIM analysis presents O–H⋯O, O–H⋯N interactions as moderate and C–H⋯O and N–H⋯O as weak. Stabilization energies show that the most reactive sites of Ala Nsp3 and Osp2 interact strongly with the O28–H29, O32–H33 and O34–H35 hydroxyl groups of EpiCat and Cat. These interactions lead to the most stable complexes. This research reveals the existence of the VDW (Van Der Walls) NCI type and repulsive (steric) interactions in these complexes.
| Published in | Science Journal of Chemistry (Volume 11, Issue 3) |
| DOI | 10.11648/j.sjc.20231103.13 |
| Page(s) | 88-107 |
| Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
| Copyright |
Copyright © The Author(s), 2024. Published by Science Publishing Group |
Flavanols, Catechin, Epicatechin, NBO, AIM, NCI, Hydrogen Bond
| [1] | Jian Zhao, Lawrence Davis and Robert Verpoorte. (2005). Elicitor signal transduction leading to production of plant secondary metabolites. Biotechnology advances. (4). doi: 10.1016/j.biotechadv.2005.01.003. |
| [2] | María Lorena Falcone Ferreyra, Sebastián Pablo Rius and Paula Casati. (2012). Flavonoids: Biosynthesis, biological functions, and biotechnological applications. Frontiers in plant science. doi: 10.3389/fpls.2012.00222. |
| [3] | Victor Preedy. (2012). Tea in Health and Disease Prevention, Elsevier Science and Technology Books, San Diego, CA, USA. |
| [4] | Debora Villaño, Maria Soledad Fernández-Pachón, Maria Luisa Moyá, Ana Troncoso and Maria del Carmen Garcia-Parilla. (2007). Radical scavenging ability of polyphenolic compounds towards DPPH free radical. Talanta. (1). doi: 10.1016/j.talanta.2006.03.050. |
| [5] | Marta González-Castejón and Arantxa Rodriguez-Casado. (2011). Dietary phytochemicals and their potential effects on obesity: A review. Pharmacological research. (5). doi: 10.1016/j.phrs.2011.07.004. |
| [6] | Narumi Sugihara, Mikae Ohnishi, Masahiro Imamura et al. (2001). Differences in Antioxidative Efficiency of Cat in Various Metal-Induced Lipid Peroxidations in Cultured Hepatocytes. Journal of HEALTH SCIENCE. (2). doi: 10.1248/jhs.47.99. |
| [7] | Liting Zhao, Jianquan Wu, Yuping Wang, Jijun Yang, Jingyu Wei … and Weina Gao. (2011). Cholesterol metabolism is modulated by quercetin in rats. Journal of agricultural and food chemistry. (4). doi: 10.1021/jf1035367. |
| [8] | Francesca Oliviero, Anna Scanu, Yessica Zamudio-Cuevas, Leonardo Punzi and Paolo Spinella. (2018). Anti-inflammatory effects of polyphenols in arthritis. Journal of the science of food and agriculture. (5). doi: 10.1002/jsfa.8664. |
| [9] | Peter Hollman, Aedin Cassidy, Blandine Comte, Marina Heinonen, Myriam Richelle … and Stephane Vidry. (2011). The biological relevance of direct antioxidant effects of polyphenols for cardiovascular health in humans is not established. The Journal of nutrition. (5). doi: 10.3945/jn.110.131490. |
| [10] | Claudine Manach, Andrzej Mazur and Augustin Scalbert. (2005). Polyphenols and prevention of cardiovascular diseases. Current opinion in lipidology. (1). doi: 10.1097/00041433-200502000-00013. |
| [11] | Alan Crozier, Indu Jaganath and Michael Clifford. (2009). Dietary phenolics: Chemistry, bioavailability and effects on health. Natural product reports. (8). doi: 10.1039/B802662A. |
| [12] | Elham Assadpour. (2017). Protection of phenolic compounds within nanocarriers. CAB Reviews: Perspectives in Agriculture, Veterinary Science, Nutrition and Natural Resources. (57). doi: 10.1079/PAVSNNR201712057. |
| [13] | Jonathan Hart, Elad Tako, Leon Kochian and Raymond Glan. (2015). Identification of Black Bean (Phaseolus vulgaris L.) Polyphenols That Inhibit and Promote Iron Uptake by Caco-2 Cells. Journal of agricultural and food chemistry. (25). doi: 10.1021/acs.jafc.5b00531. |
| [14] | Satoshi Uchiyama, Yoshimasa Taniguchi, Akiko Saka, Aruto Yoshida and Hiroaki Yajima. (2011). Prevention of diet-induced obesity by dietary black tea polyphenols extracts in vitro and in vivo. Nutrition (Burbank, Los Angeles County, Calif.). (3). doi: 10.1016/j.nut.2010.01.019. |
| [15] | Carine Le Bourvellec, Sylvain Guyot and Catherine Marie Genevieve Claire Renard. (2004). Non-covalent interaction between procyanidins and apple cell wall material: Part I. The effect of some environmental parameters. Biochimica et biophysica acta. (3). doi: 10.1016/j.bbagen.2004.04.001. |
| [16] | Prasun Bandyopadhyay, Amit Kumar Ghosh and Chandrasekhar Ghosh. (2012). Recent developments on polyphenols—protein interactions: Effects on tea and coffee taste, antioxidant properties and the digestive system. Food and function. (6). doi: 10.1039/C2FO00006G. |
| [17] | Elisabeth Jöbstl, John O’Connell, Patrick Fairclough and Mike Williamson. (2004). Molecular model for astringency produced by polyphenol/protein interactions. Biomacromolecules. (3). doi: 10.1021/bm0345110. |
| [18] | Mourad Elhabiri, Charlotte Carrer, Franck Marmolle and Hassan Traboulsi. (2007). Complexation of iron (III) by catecholate-type polyphenols. Inorganica Chimica Acta.(1). doi: 10.1016/j.ica.2006.07.110. |
| [19] | Akpa Eugene Essoh, Boka Robert N’guessan, Ganiyou Adenidji, Kicho Denis Yapo, Ane Adjou and El Hadji Sawaliho Bamba. (2022). Catechin and Epicatechin. What’s the More Reactive? Computational Chemistry. (02). doi: 10.4236/cc.2022.102003. |
| [20] | Karl Siebert, Nataliia Troukhanova and Penelope Lynn. (1996). Nature of Polyphenol−Protein Interactions. Journal of Agricultural and Food Chemistry. (1). doi: 10.1021/jf9502459. |
| [21] | Cecile Simon, Karine Barathieu, Michel Laguerre, Jean-Marie Schmitter, Eric Fouquet … and Eric Dufourc. (2003). Three-dimensional structure and dynamics of wine tannin-saliva protein complexes. A multitechnique approach. Biochemistry. (35). doi: 10.1021/bi034354p. |
| [22] | Zerrin Yuksel, Elif Avci and Yasar Kemal Erdem. (2010). Characterization of binding interactions between green tea flavonoids and milk proteins. Food Chemistry. (2). doi: 10.1016/j.foodchem.2009.12.064. |
| [23] | Jinfeng Liu, Xiao He, John Zhang and Lian-wen Qi. (2018). Hydrogen-bond structure dynamics in bulk water: Insights from ab initio simulations with coupled cluster theory. Chemical science. (8). doi: 10.1039/C7SC04205A. |
| [24] | Harshadrai Rawel, Dörte Czajka, Sascha Rohn and Jürgen kroll. (2002). Interactions of different phenolic acids and flavonoids with soy proteins. International Journal of Biological Macromolecules. (3–4). doi: 10.1016/s0141-8130 (02)00016-8. |
| [25] | Jürgen Kroll, Harshadrai Rawel and Sascha Rohn. (2003). Reactions of Plant Phenolic with Food Proteins and Enzymes under Special Consideration of Covalent Bonds. Food Science and Technology Research. (3). doi: 10.3136/fstr.9.205. |
| [26] | Augustin Scalbert, Claudine Manach, Christine Morand, Christian Remesy and Liliana Jimenez. (2005). Dietary polyphenols and the prevention of diseases. Critical reviews in food science and nutrition. (4). doi: 10.1080/1040869059096. |
| [27] | Judith Mak. (2012). Potential role of green tea catechin in various disease therapies: Progress and promise. Clinical and experimental pharmacology and physiology. (3). doi: 10.1111/j.1440-1681.2012.05673.x. |
| [28] | Rahul Lall, Deeba Syed, Vaqar Adhami, Mohammad Imran Khan and Hasan Mukhtar. (2015). Dietary polyphenols in the prevention and treatment of prostate cancer. International journal of molecular sciences. (2). doi: 10.3390/ijms16023350. |
| [29] | Robert Ghormley Parr. (1980). Density Functional Theory of Atoms and Molecules. Horizons of Quantum Chemistry. International Academy of Quantum Molecular Science. (3). doi.org/10.1007/978-94-009-9027-2_2. |
| [30] | Michael Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb … and D. J. Fox. (2009), Gaussian 09 Revision D.01. Gaussian, Inc., Wallingford, CT, |
| [31] | Todd Keith. (2010). AIMAll. 10.05.04. |
| [32] | Eric D. Glendening, A. E. Reed and J. E. Carpenter. (2003). NBO. 3.1. |
| [33] | G. A. Zhurko, D. A. Zhurko. Chemcraft. Version 1.8 (Build 523a). |
| [34] | Tian Lu and Feiwu Chen. (2012). Multiwfn: a multifunctional wavefunction analyzer. Journal of computational chemistry. (5). doi: 10.1002/jcc.22885. |
| [35] | Samuel Francis Boys and Fabriozo. Bernardi. (2006). The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors. Molecular Physics. (4). doi: 10.1080/00268977000101561. |
| [36] | Natarajan Sathiyamoorthy Venkataramanan and Ambigapathy Suvitha. (2017). Structure, electronic, inclusion complex formation behaviour and spectral properties of pillarplex. Journal of Inclusion Phenomena and Macrocyclic Chemistry. (1–2). doi: 10.1007/s10847-017-0711-y. |
| [37] | M. Snehalatha, C. Ravikumar, I. Hubert Joe, N. Sekar and V. S. Jayakumar (2009). Spectroscopic analysis and DFT calculations of a food additive carmoisine. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. (3). doi: 10.1016/j.saa.2008.11.017. |
| [38] | Alan Reed, Larry Curtiss and Frank Weinhold. (1988). Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chemical Reviews. (6). doi: 10.1021/cr00088a005. |
| [39] | Richard Frederick William Bader. (1994). Atoms in molecules: A quantum theory, Clarendon Press; Oxford University press, Oxford, England, New York. |
| [40] | Marcin Ziółkowski, Sławomir Grabowski and Jerzy Leszczynski. (2006). Cooperativeness in hydrogen-bonded interactions: ab initio and “atoms in molecules” analyses. The journal of physical chemistry. A.(20). doi: 10.1021/jp060537k. |
| [41] | Isabel Rozas, Ibon Alkorta and Jose Elguero. (2000). Behaviour of Ylides Containing N, O, and C Atoms as Hydrogen Bond Acceptors. Journal of the American Chemical Society. (45). doi: 10.1021/ja0017864. |
| [42] | Enrique Espinosa, Elies Molins and Claude Lecomte. (1998). Hydrogen bond strengths revealed by topological analyses of experimentally observed electron density. Chemical Physics Letters. (3–4). doi: 10.1016/S0009-2614 (98)00036-0. |
| [43] | Natarajan Sathiyamoorthy Venkataramanan, Ambigapathy Suvitha and Yoshiyuki Kawazoe. (2017). Intermolecular interaction in nucleobases and dimethyl sulphoxide/water molecules: A DFT, NBO, AIM and NCI analysis. Journal of molecular graphics and modelling. doi: 10.1016/j.jmgm.2017.09.022. |
| [44] | Natarajan Sathiyamoorthy Venkataramanan and Ambigapathy Suvitha. (2018). Nature of bonding and cooperativeness in linear DMSO clusters: A DFT, AIM and NCI analysis. Journal of Molecular Graphics and Modelling. doi: 10.1016/j.jmgm.2018.02.010. |
| [45] | Debdutta Chakraborty and Pratim Kumar Chattaraj. (2018). Confinement induced thermodynamic and kinetic facilitation of some Diels-Alder reactions inside a CB7 cavitand. Journal of computational chemistry. (3). doi: 10.1002/jcc.25094. |
| [46] | Igor Alabugin, Mariappan Manoharan, Scott Peabody and Frank Weinhold. (2003). Electronic basis of improper hydrogen bonding: A subtle balance of hyperconjugation and re-hybridization. Journal of the American Chemical Society. (19). doi: 10.1021/ja034656e. |
| [47] | Ponmalai Kolandaivel and V. Nirmala. (2004). Study of proper and improper hydrogen bonding using Bader’s atoms in molecules (AIM) theory and NBO analysis. Journal of Molecular Structure. (1–3). doi: 10.1016/j.molstruc.2004.01.030. |
| [48] | Pavel Hobza and Zdenek Havlas. (2000). Blue-Shifting Hydrogen Bonds. Chemical reviews. (11). doi: 10.1021/cr990050q. |
| [49] | Elangannan Arunan, Gautam Desiraju, Roger Klein, Joanna Sadlej, Steve Scheiner … and David Nesbitt. (2011). Definition of the hydrogen bond (IUPAC Recommendations 2011). Pure and Applied Chemistry. (8). doi: 10.1351/pac-rec-10-01-02. |
| [50] | Mylsamy Karthika, Ramasamy Kanakaraju and Lakshmipathi Senthilkumar. (2013). Spectroscopic investigations and hydrogen bond interactions of 8-Aza analogues of xanthine, theophylline and caffeine: A theoretical study. Journal of molecular modelling. (4). doi: 10.1007/s00894-012-1742-3. |
| [51] | Gautam Desiraju and Thomas Steiner. (1999). The weak hydrogen bond: In structural chemistry and biology, Oxford University press, Oxford, etc. |
APA Style
Essoh Akpa Eugene, N’Guessan Boka Robert, Adenidji Ganiyou, Adjou Ane, Bamba El Hadji Sawaliho. (2023). Modelling Interactions Between Flavanols and Amine Acids: Case of Catechin and Epicatechin with Alanine; NBO, AIM, NCI Analysis. Science Journal of Chemistry, 11(3), 88-107. https://doi.org/10.11648/j.sjc.20231103.13
ACS Style
Essoh Akpa Eugene; N’Guessan Boka Robert; Adenidji Ganiyou; Adjou Ane; Bamba El Hadji Sawaliho. Modelling Interactions Between Flavanols and Amine Acids: Case of Catechin and Epicatechin with Alanine; NBO, AIM, NCI Analysis. Sci. J. Chem. 2023, 11(3), 88-107. doi: 10.11648/j.sjc.20231103.13
AMA Style
Essoh Akpa Eugene, N’Guessan Boka Robert, Adenidji Ganiyou, Adjou Ane, Bamba El Hadji Sawaliho. Modelling Interactions Between Flavanols and Amine Acids: Case of Catechin and Epicatechin with Alanine; NBO, AIM, NCI Analysis. Sci J Chem. 2023;11(3):88-107. doi: 10.11648/j.sjc.20231103.13
Share This Article
Twitter
Linked In
Facebook
Copy
Download@article{10.11648/j.sjc.20231103.13,
author = {Essoh Akpa Eugene and N’Guessan Boka Robert and Adenidji Ganiyou and Adjou Ane and Bamba El Hadji Sawaliho},
title = {Modelling Interactions Between Flavanols and Amine Acids: Case of Catechin and Epicatechin with Alanine; NBO, AIM, NCI Analysis},
journal = {Science Journal of Chemistry},
volume = {11},
number = {3},
pages = {88-107},
doi = {10.11648/j.sjc.20231103.13},
url = {https://doi.org/10.11648/j.sjc.20231103.13},
eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20231103.13},
abstract = {The interactions between two flavanols (Catechin and Epicatechin) and (Ala) Alanine (aliphatic amino acid) are evaluated by theoretical chemistry methods. Calculations at the level DFT/B3LYP/6-31+G (d, p) determine their characteristics and those of the monomers. Geometric, energetic, and spectroscopic parameters in addition to QTAIM (Quantum Theory of Atoms In Molecules), NBO (Natural Bond Orbital) and NCI (Non-Covalent Interaction) topological analyses qualify the nature and type of these. The results indicate that the main interactions are O–H⋯O and O–H⋯N between the hydroxyl groups of Cat (Catechin) or Epicat (Epicatechin) and the heteroatoms of Ala. They mention the existence of a secondary one alongside the main. They classify them into proper, improper, moderate, and weak. The spectroscopic parameters prove that O–H⋯O, O–H⋯N and N–H⋯O are proper. They establish that the C–H⋯N and C–H⋯O are improper. QTAIM analysis presents O–H⋯O, O–H⋯N interactions as moderate and C–H⋯O and N–H⋯O as weak. Stabilization energies show that the most reactive sites of Ala Nsp3 and Osp2 interact strongly with the O28–H29, O32–H33 and O34–H35 hydroxyl groups of EpiCat and Cat. These interactions lead to the most stable complexes. This research reveals the existence of the VDW (Van Der Walls) NCI type and repulsive (steric) interactions in these complexes.},
year = {2023}
}
TY - JOUR T1 - Modelling Interactions Between Flavanols and Amine Acids: Case of Catechin and Epicatechin with Alanine; NBO, AIM, NCI Analysis AU - Essoh Akpa Eugene AU - N’Guessan Boka Robert AU - Adenidji Ganiyou AU - Adjou Ane AU - Bamba El Hadji Sawaliho Y1 - 2023/06/09 PY - 2023 N1 - https://doi.org/10.11648/j.sjc.20231103.13 DO - 10.11648/j.sjc.20231103.13 T2 - Science Journal of Chemistry JF - Science Journal of Chemistry JO - Science Journal of Chemistry SP - 88 EP - 107 PB - Science Publishing Group SN - 2330-099X UR - https://doi.org/10.11648/j.sjc.20231103.13 AB - The interactions between two flavanols (Catechin and Epicatechin) and (Ala) Alanine (aliphatic amino acid) are evaluated by theoretical chemistry methods. Calculations at the level DFT/B3LYP/6-31+G (d, p) determine their characteristics and those of the monomers. Geometric, energetic, and spectroscopic parameters in addition to QTAIM (Quantum Theory of Atoms In Molecules), NBO (Natural Bond Orbital) and NCI (Non-Covalent Interaction) topological analyses qualify the nature and type of these. The results indicate that the main interactions are O–H⋯O and O–H⋯N between the hydroxyl groups of Cat (Catechin) or Epicat (Epicatechin) and the heteroatoms of Ala. They mention the existence of a secondary one alongside the main. They classify them into proper, improper, moderate, and weak. The spectroscopic parameters prove that O–H⋯O, O–H⋯N and N–H⋯O are proper. They establish that the C–H⋯N and C–H⋯O are improper. QTAIM analysis presents O–H⋯O, O–H⋯N interactions as moderate and C–H⋯O and N–H⋯O as weak. Stabilization energies show that the most reactive sites of Ala Nsp3 and Osp2 interact strongly with the O28–H29, O32–H33 and O34–H35 hydroxyl groups of EpiCat and Cat. These interactions lead to the most stable complexes. This research reveals the existence of the VDW (Van Der Walls) NCI type and repulsive (steric) interactions in these complexes. VL - 11 IS - 3 ER -
Information
Email: