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Current Organocatalysis

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ISSN (Print): 2213-3372
ISSN (Online): 2213-3380

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Research Article

The Molecular Structural Analysis of Biologically Important Catechol Molecule: An Integrative Perspective from Experiments and Futuristic Tools

Author(s): M. Amin Mir*, Kim Andrews, M. Waqar Ashraf, Anuj Kumar, Dharmendra Kumar, Anita Bisht, Reeta Chauhan and Shailendra Prakash

Volume 11, Issue 1, 2024

Published on: 10 October, 2023

Page: [78 - 88] Pages: 11

DOI: 10.2174/2213337210666230901161332

Price: $65

Abstract

Background: Catechol is a phenolic molecule found naturally in plants. It is also known as pyrogallic acid or 1, 2-dihydroxybenzene. Catechol is currently produced commercially by decarboxylating gallic acid at high temperatures and pressures.

Aims and Objectives: This research aimed to understand the biological importance of catechol and perform molecular structural analysis on catechol molecules.

Methods: Catechol (1, 2, dihydroxy benzene) was studied via computational analysis by employing the use of DFT and B3LYP methods. Hirshfeld analysis was carried out to investigate crystal intermolecular interactions, and the NBO study was performed to study chemical donating and accepting interactions. Moreover, the computational study was performed using FTIR, HNMR and other instrumentation like AIM theory for circular dichroism data.

Results: Furthermore, the surface iso-projection study and binding energy results did prove to run in alignment with experimentally obtained values from the computational studies. Fukui functional study and molecular electrostatic potential were utilized in the study to investigate interactions between anionic and cationic sites of catechol. In addition, molecular dynamic simulations revealed that biomolecular stability was also present. Thus, the antibiotic efficacy of catechol displayed chemical oxidative interactions that exhibited close chemical correlations with ascorbic acid, ellagic acid, and gallic acid.

Conclusion: The catechol has been examined experimentally and theoretically. The results were compared with catechol spectra, including IR and UV-visible spectra generated through computer analysis. The experimentally observed spectra were found to be in parallel with theoretical data. According to drug-likeness investigations, the following compounds, gallic acid, ellagic acid, and ascorbic acid, were found to be closely related to catechol as an antibiotic. Hence, it can be concluded that catechol, whether in its entirety or in a portion, is a potent antibacterial, anti-inflammatory, and anti-malarial drug.

Keywords: Catechol, experimental, futuristic tools, Hirshfeld surface analysis, antibacterial, anti-inflammatory.

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[1]
Wang, H.; Kang, H.; Zhang, L.; Liu, H.; Liu, H.; Sun, B. Composition of ethyl acetate extracts from three plant materials (shaddock peel, pomegranate peel, pomegranate seed) and their algicidal activities. Pol. J. Environ. Stud., 2015, 24(4), 1803-1807.
[http://dx.doi.org/10.15244/pjoes/36986]
[2]
Upadhyay, G.; Gupta, S.P.; Prakash, O.; Singh, M.P. Pyrogallol-mediated toxicity and natural antioxidants: Triumphs and pitfalls of preclinical findings and their translational limitations. Chem. Biol. Interact., 2010, 183(3), 333-340.
[http://dx.doi.org/10.1016/j.cbi.2009.11.028] [PMID: 19948158]
[3]
Singh, G.; Kumar, P. Extraction, gas chromatography-mass spectrometry analysis and screening of fruits of Terminalia chebula Retz. for its antimicrobial potential. Pharmacognosy Res., 2013, 5(3), 162-168.
[http://dx.doi.org/10.4103/0974-8490.112421] [PMID: 23901211]
[4]
Shahzad, M.; Millhouse, E.; Culshaw, S.; Edwards, C.A.; Ramage, G.; Combet, E. Selected dietary (poly)phenols inhibit periodontal pathogen growth and biofilm formation. Food Funct., 2015, 6(3), 719-729.
[http://dx.doi.org/10.1039/C4FO01087F] [PMID: 25585200]
[5]
Panzella, L.; Napolitano, A. Natural phenol polymers: Recent advances in food and health applications. Antioxidants, 2017, 6(2), 30.
[http://dx.doi.org/10.3390/antiox6020030] [PMID: 28420078]
[6]
Bianco, M.A.; Handaji, A.; Savolainen, H. Quantitative analysis of ellagic acid in hardwood samples. Sci. Total Environ., 1998, 222(1-2), 123-126.
[http://dx.doi.org/10.1016/S0048-9697(98)00294-0]
[7]
Inui, T.; Nakahara, K.; Uchida, M.; Miki, W.; Unoura, K.; Kokeguchi, Y.; Hosokawa, T. Oxidation of ethanol induced by simple polyphenols: Prooxidant property of polyphenols. Bull. Chem. Soc. Jpn., 2004, 77(6), 1201-1207.
[http://dx.doi.org/10.1246/bcsj.77.1201]
[8]
Torii, Y.; Saito, H.; Matsuki, N. Induction of emesis in Suncus murinus by pyrogallol, a generator of free radicals. Br. J. Pharmacol., 1994, 111(2), 431-434.
[http://dx.doi.org/10.1111/j.1476-5381.1994.tb14753.x] [PMID: 8004387]
[9]
Hiramoto, K.; Ojima, N.; Sako, K.; Kikugawa, K. Effect of plant phenolics on the formation of spin-adduct of hydroxyl radical and the DNA strand breaking of hydroxyl radical. Biol. Pharm. Bull., 1996, 19, 558-563.
[http://dx.doi.org/10.1248/bpb.19.558]
[10]
Neese, F. The ORCA program system. Wiley Interdiscip. Rev. Comput. Mol. Sci., 2012, 2(1), 73-78.
[http://dx.doi.org/10.1002/wcms.81]
[11]
Leavay, G.; Ye, Q.; Bodell, W.J. Formation of DNA adducts and oxidative base damage by copper mediated oxidation of dopamine and 6-hydroxydopamine. Exp. Neurol., 1997, 146, 570-574.
[12]
Pryor, W.A.; Stone, K.; Zang, L-Y. Fractionation of aqueous cigarette tar extracts: Fractions that contain the tar radical cause DNA damage. Chem. Res. Toxicol., 1998, 11, 441-448.
[13]
Petersson, G.A.; Bennett, A.; Tensfeldt, T.G.; Al-Laham, M.A.; Shirley, W.A.; Mantzaris, J. A complete basis set model chemistry. I. The total energies of closed-shell atoms and hydrides of the first-row elements. J. Chem. Phys., 1988, 89(4), 2193-2218.
[http://dx.doi.org/10.1063/1.455064]
[14]
Lu, T.; Chen, F. Multiwfn: A multifunctional wavefunction analyzer. J. Comput. Chem., 2012, 33(5), 580-592.
[http://dx.doi.org/10.1002/jcc.22885] [PMID: 22162017]
[15]
Daina, A.; Michielin, O.; Zoete, V. SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci. Rep., 2017, 7(1), 42717.
[http://dx.doi.org/10.1038/srep42717] [PMID: 28256516]
[16]
Origin 8.0;
[17]
Jomroz, M.H. Vibrational Energy Distribution Analysis, VEDA4; Warsaw, 2004.
[18]
Lu, T.C.; Chen, F-W. Calculation of molecular orbital composition. Acta Chimi. Sin., 2011, 69, 2393-2406.
[19]
Rezazadeh, S.; Ebrahimi, A. A computational study on the hydride transfer mechanism between nicotinamide and menadione. Chem. Select, 2018, 342, 11977-11985.
[http://dx.doi.org/10.1002/slct.201802389]
[20]
Murry, J. S.; Sen, K. Molecular Electrostatic Potential Concepts and Applications; Elsevier: Amesterdam, 1996.
[21]
Mir, M.A. DFT, hirshfeld surface, molecular docking and drug likeness studies of medicinally important coumarin molecule. Arab. J. Sci. Eng., 2023, 48(6), 7445-7462.
[http://dx.doi.org/10.1007/s13369-022-07476-z]
[22]
Nowell, H. Attfield X-Ray and neutron powder diffraction studies of the crystal structure of vitamin K3Electronic supplementary information (ESI) available: X-ray powder diffraction data. New J. Chem., 2004, 28, 406.
[http://dx.doi.org/10.1039/b306072a]
[23]
Hirshfeld, F.L. Bonded-atom fragments for describing molecular charge densities. Theor. Chim. Acta, 1977, 44(2), 129-138.
[http://dx.doi.org/10.1007/BF00549096]
[24]
Wang, W.; Ling, Y.; Yang, L-J.; Liu, Q-L.; Luo, Y-H.; Sun, B-W. Crystal structure, topology, DFT and hirshfeld surface analysis of a novel charge transfer complex (L3) of Anthraquinone and 4-{[(anthracen-9-yl) meth-yl] amino}-benzoic Acid (L2) exhibiting photocatalytic properties: An experimental and theoretical approach. Res. Chem. Intermed., 2016, 42(4), 3157-3168.
[http://dx.doi.org/10.1007/s11164-015-2203-2]
[25]
Weinhold, F.; Randis, L.C. Valency and Bonding: A Natural Bond Orbital Donor Acceptor Perspective; Cambridge University Press, 2005.
[26]
Fukui, K. Role of frontier orbitals in chemical reactions. Science, 1982, 218(4574), 747-754.
[http://dx.doi.org/10.1126/science.218.4574.747] [PMID: 17771019]
[27]
Shalini, A.; Tandon, H.; Chakraborty, T. Molecular electrophilicity index - A promising descriptor for predicting toxicological property. J. Bioequival Bioavailab., 2017, 9(6), 518-527.
[28]
Amin Mir, M.; Manzer Manhas, F.; Andrews, K.; Hasnain, S.M.; Iqbal, A.; Sehar, S.; Younis, A. Molecular dynamic, Hirshfeld surface, molecular docking and drug likeness studies of a potent anti-oxidant, anti-malaria and anti-Inflammatory medicine: Pyrogallol. Results Chem., 2023, 5, 100763.
[http://dx.doi.org/10.1016/j.rechem.2023.100763]
[29]
Hermann, J.P.; Ricard, D.; Ducuing, J. Z-scan measurements of the nonlinear refraction in retinal derivatives. Appl. Phys. Lett., 1973, 23(4), 178-180.
[http://dx.doi.org/10.1063/1.1654850]
[30]
Weinhold, F.; Randis, L.C. Valency and Bonding: a Natural Bond Orbital Donor Acceptor Perspective; Cambridge University Press, 2005.

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