The Role of the Various Solvent Polarities on Piperine Reactivity and Stability

Year 2021, Volume: 4 Issue: 2, 10 - 16, 08.12.2021

Lana Ahmed , Rebaz Omer

https://doi.org/10.54565/jphcfum.990410

Cited By: 2

Abstract

Piperine is a natural cytotoxic agent aware of various therapeutic acts. The aim of this study is to look into the effects of solvent polarity on solvent-free energy, dipole moment, polarizability, and hyper-polarizability of the first order, as well as various molecular properties including chemical hardness and softness, chemical potential, electronegativity, and electrophilicity index, in order to gain a better understanding of its reactivity and stability. The Becke, 3-parameter, Lee-Yang-Parr (B3LYP) level of theory with the cc-pVDZ basis set was used to perform all forms of calculations in both the gas phase and in solution. The Solvation Model on Density (SMD) was used to measure the solvation-free energy, dipole moment, and molecular properties of five solvent systems: water, DMSO, ethanol, cyclohexane, and heptane. As the dielectric constant was reduced, the solving energies gradually decreased, i.e. free energy decreased with declining solvent polarity. Piperine's dipole moment has been found to increase when transitioning from non-polar to polar solvents. The dipole moment of piperine was greater than that of the gas phase in various solvents. PPN's dipole moment and first order hyper-polarizability gradually increased as the solvent polarity increased, while its polarizability decreased. In addition, the hardness, chemical potential and electrophilicity index were decreased from non-polar to polar solvent, but with the rise in solvent polarity for the PPN molecule, softness and electronegativity were increased. The determined free energy solvation, dipole moment, polarizability, hyper-polarizability of the first order, and molecular properties identified in this research may contribute to an understanding of the stability and reactivity of piperine in specific solvent systems.

Keywords

PPN, Solvation effects, Dipole moment, Solvation model, Polarizability.

References

• 1. R. Omar, P. Koparir, and M. Koparir, SYNTHESIS OF 1, 3-THIAZOLE DERIVATIVES. 2021.
• 2. K. Vasavirama and M. Upender, Piperine: a valuable alkaloid from piper species. Int J Pharm Pharm Sci, 2014. 6(4): p. 34-8.
• 3. L. Gorgani, et al., Piperine—the bioactive compound of black pepper: from isolation to medicinal formulations. Comprehensive Reviews in Food Science and Food Safety, 2017. 16(1): p. 124-140.
• 4. C. Pradeep and G. Kuttan, Effect of piperine on the inhibition of lung metastasis induced B16F-10 melanoma cells in mice. Clinical & experimental metastasis, 2002. 19(8): p. 703-708.
• 5. G. Shoba₁, et al., Influence of piperine on the pharmacokinetics of curcumin in animals and human volunteers. Planta medica, 1998. 64: p. 353-356.
• 6. J.J. Johnson, et al., Enhancing the bioavailability of resveratrol by combining it with piperine. Molecular nutrition & food research, 2011. 55(8): p. 1169-1176.
• 7. F. Gökalp, A study on piperine, active compound of black pepper. Akademik Platform Mühendislik ve Fen Bilimleri Dergisi, 2016. 4(3).
• 8. P. Koparir, K. Sarac, and R.A. Omar, Synthesis, Molecular Characterization, Biological and Computational Studies of New Molecule Contain 1, 2, 4-Triazole, and Coumarin Bearing 6, 8-Dimethyl. 2021.
• 9. G. Zazeri, et al., Experimental approaches and computational modeling of rat serum albumin and its interaction with piperine. International journal of molecular sciences, 2019. 20(12): p. 2856.
• 10. P. Choudhary, et al., Computational studies reveal piperine, the predominant oleoresin of black pepper (Piper nigrum) as a potential inhibitor of SARS-CoV-2 (COVID-19). Current Science (00113891), 2020. 119(8).
• 11. F.S. Alves, et al., Spectroscopic methods and in silico analyses using density functional theory to characterize and identify piperine alkaloid crystals isolated from pepper (Piper Nigrum L.). Journal of Biomolecular Structure and Dynamics, 2020. 38(9): p. 2792-2799.
• 12. P. Anbarasan, et al., Geometries, electronic structures and electronic absorption spectra of silicon dichloride substituted phthalocyanine for dye sensitized solar cells. Recent Research in Science and Technology, 2010.
• 13. P. Lakshmi Praveen and D. Ojha, Substituent and solvent effects on UV‐visible absorption spectra of liquid crystalline disubstituted biphenylcyclohexane derivatives–a computational approach. Crystal Research and Technology, 2012. 47(1): p. 91-100.
• 14. M.F. Khan, et al., Computational study of geometry, solvation free energy, dipole moment, polarizability, hyperpolarizability and molecular properties of 2-methylimidazole. Sultan Qaboos University Journal for Science [SQUJS], 2016. 21(2): p. 89-101.
• 15. M. Targema, N.O. Obi-Egbedi, and M.D. Adeoye, Molecular structure and solvent effects on the dipole moments and polarizabilities of some aniline derivatives. Computational and theoretical Chemistry, 2013. 1012: p. 47-53.
• 16. A. Jayaprakash, et al., Vibrational and electronic investigations, thermodynamic parameters, HOMO and LUMO analysis on crotonaldehyde by ab initio and DFT methods. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2011. 83(1): p. 411-419.
• 17. R.A. Omer, et al., Theoretical analysis of the reactivity of chloroquine and hydroxychloroquine. Indian Journal of Chemistry-Section A (IJCA), 2020. 59(12): p. 1828-1834.
• 18. L.A. OMER and R.O. ANWER, Population Analysis and UV-Vis spectra of Dopamine Molecule Using Gaussian 09. Journal of Physical Chemistry and Functional Materials. 3(2): p. 48-58.
• 19. O. Rebaz, et al., Computational determination the reactivity of salbutamol and propranolol drugs. Turkish Computational and Theoretical Chemistry, 2020. 4(2): p. 67-75.
• 20. K.F. Al-Azawi, et al., Experimental and quantum chemical simulations on the corrosion inhibition of mild steel by 3-((5-(3, 5-dinitrophenyl)-1, 3, 4-thiadiazol-2-yl) imino) indolin-2-one. Results in Physics, 2018. 9: p. 278-283.
• 21. L.A. OMER and O. Rebaz, Computational Study on Paracetamol Drug. Journal of Physical Chemistry and Functional Materials, 2020. 3(1): p. 9-13.
• 22. L. AHMED and O. Rebaz, Spectroscopic properties of Vitamin C: A theoretical work. Cumhuriyet Science Journal, 2020. 41(4): p. 916-928.
• 23. A. Hssain and H. Kebiroglu, Serotonin: Structural characterization and determination of the Band Gap Energy. Journal of Physical Chemistry and Functional Materials. 2(2): p. 54-58.
• 24. M.F. Khan, R.B. Rashid, and M.A. Rashid, Computational study of geometry, molecular properties and docking study of aspirin. World J Pharm Res, 2015. 4: p. 2702-2714.
• 25. M.F. Khan, et al., In silico molecular docking studies of lichen metabolites against cyclooxygenase-2 enzyme. Bangladesh Pharmaceutical Journal, 2015. 18(2): p. 90-96.
• 26. M.F. Khan, et al., Effects of solvent polarity on solvation free energy, dipole moment, polarizability, hyperpolarizability and molecular reactivity of aspirin. Int. J. Pharm. Pharm. Sci, 2017. 9(2): p. 217-221.
• 27. M.F. Khan, et al., Effects of Solvent Polarity on Solvation Free Energy, Dipole Moment, Polarizability, Hyperpolarizability and Molecular Properties of Metronidazole. Bangladesh Pharmaceutical Journal, 2016. 19(1): p. 9-14.
• 28. A. Tomberg, GAUSSIAN 09W TUTORIAL AN INTRODUCTION TO COMPUTATIONAL CHEMISTRY USING G09W AND AVOGADRO SOFTWARE.
• 29. R.A. OMER, et al., Computational and spectroscopy study of melatonin. Indian Journal of Chemistry-Section B (IJC-B), 2021. 60(5): p. 732-741.
• 30. 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. The Journal of Physical Chemistry B, 2009. 113(18): p. 6378-6396.
• 31. L. AHMED and O. Rebaz, A theoretical study on Dopamine molecule. Journal of Physical Chemistry and Functional Materials, 2019. 2(2): p. 66-72.
• 32. D. Kleinman, Nonlinear dielectric polarization in optical media. Physical Review, 1962. 126(6): p. 1977.
• 33. R.G. Parr, et al., Electronegativity: the density functional viewpoint. The Journal of Chemical Physics, 1978. 68(8): p. 3801-3807.
• 34. R.G. Parr and R.G. Pearson, Absolute hardness: companion parameter to absolute electronegativity. Journal of the American chemical society, 1983. 105(26): p. 7512-7516.
• 35. R.G. Parr and P.K. Chattaraj, Principle of maximum hardness. Journal of the American Chemical Society, 1991. 113(5): p. 1854-1855.
• 36. R.G. Parr, L.v. Szentpály, and S. Liu, Electrophilicity index. Journal of the American Chemical Society, 1999. 121(9): p. 1922-1924.
• 37. P.K. Chattaraj, B. Maiti, and U. Sarkar, Philicity: a unified treatment of chemical reactivity and selectivity. The Journal of Physical Chemistry A, 2003. 107(25): p. 4973-4975.
• 38. R. Parthasarathi, et al., Toxicity analysis of benzidine through chemical reactivity and selectivity profiles: a DFT approach. Internet Electronic Journal of Molecular Design, 2003. 2(12): p. 798-813.
• 39. R. Parthasarathi, et al., Intermolecular reactivity through the generalized philicity concept. Chemical physics letters, 2004. 394(4-6): p. 225-230.
• 40. R. Parthasarathi, et al., Toxicity analysis of 33'44'5-pentachloro biphenyl through chemical reactivity and selectivity profiles. Current Science, 2004. 86(4): p. 535.