Quantum Mechanical Predictions of the Antioxidant Capability of Moracin C Isomers

Overview

Journal Front Chem

Specialty Chemistry

Date 2021 May 10

PMID 33968905

Citations 7

Authors

Angela Parise

Bruna Clara De Simone

Tiziana Marino

Marirosa Toscano

Nino Russo

Affiliations

Soon will be listed here.

Abstract

The antioxidant capability of moracin C and -moracin C isomers against the OOH free radical was studied by applying density functional theory (DFT) and choosing the M05-2X exchange-correlation functional coupled with the all electron basis set, 6-311++G(d,p), for computations. Different reaction mechanisms [hydrogen atom transfer (HAT), single electron transfer (SET), and radical adduct formation (RAF)] were taken into account when considering water- and lipid-like environments. Rate constants were obtained by applying the conventional transition state theory (TST). The results show that, in water, scavenging activity mainly occurs through a radical addition mechanism for both isomers, while, in the lipid-like environment, the radical addition process is favored for -moracin C, while, redox- and non-redox-type reactions can equally occur for moracin C. The values of pKa relative to the deprotonation paths at physiological pH were predicted in aqueous solution.

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References

Naik R, Harmalkar D, Xu X, Jang K, Lee K . Bioactive benzofuran derivatives: moracins A-Z in medicinal chemistry. Eur J Med Chem. 2014; 90:379-93. DOI: 10.1016/j.ejmech.2014.11.047. View

Ceron-Carrasco J, Bastida A, Requena A, Zuniga J, Miguel B . A theoretical study of the reaction of beta-carotene with the nitrogen dioxide radical in solution. J Phys Chem B. 2010; 114(12):4366-72. DOI: 10.1021/jp911846h. View

Cerezo J, Zuniga J, Bastida A, Requena A, Ceron-Carrasco J, Eriksson L . Antioxidant properties of β-carotene isomers and their role in photosystems: insights from Ab initio simulations. J Phys Chem A. 2012; 116(13):3498-506. DOI: 10.1021/jp301485k. View

Lee S, Choi S, Kim H, Hwang J, Lee B, Gao J . Mulberroside F isolated from the leaves of Morus alba inhibits melanin biosynthesis. Biol Pharm Bull. 2002; 25(8):1045-8. DOI: 10.1248/bpb.25.1045. View

Hakim E, Fahriyati A, Kau M, Achmad S, Makmur L, Ghisalberti E . Artoindonesianins A and B, two new prenylated flavones from the root of Artocarpus champeden. J Nat Prod. 1999; 62(4):613-5. DOI: 10.1021/np980279l. View

Marenich A, Cramer C, Truhlar D . 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. J Phys Chem B. 2009; 113(18):6378-96. DOI: 10.1021/jp810292n. View

Zhao Y, Truhlar D . Assessment of Model Chemistries for Noncovalent Interactions. J Chem Theory Comput. 2015; 2(4):1009-18. DOI: 10.1021/ct060044j. View

Na M, Hoang D, Njamen D, Mbafor J, Fomum Z, Thuong P . Inhibitory effect of 2-arylbenzofurans from Erythrina addisoniae on protein tyrosine phosphatase-1B. Bioorg Med Chem Lett. 2007; 17(14):3868-71. DOI: 10.1016/j.bmcl.2007.05.005. View

Delogu G, Matos M, Fanti M, Era B, Medda R, Pieroni E . 2-Phenylbenzofuran derivatives as butyrylcholinesterase inhibitors: Synthesis, biological activity and molecular modeling. Bioorg Med Chem Lett. 2016; 26(9):2308-13. DOI: 10.1016/j.bmcl.2016.03.039. View

10.

Gazquez J, Cedillo A, Vela A . Electrodonating and electroaccepting powers. J Phys Chem A. 2007; 111(10):1966-70. DOI: 10.1021/jp065459f. View

11.

Seong S, Ha M, Min B, Jung H, Choi J . Moracin derivatives from Morus Radix as dual BACE1 and cholinesterase inhibitors with antioxidant and anti-glycation capacities. Life Sci. 2018; 210:20-28. DOI: 10.1016/j.lfs.2018.08.060. View

12.

Perez-Gonzalez A, Garcia-Hernandez E, Chigo-Anota E . The antioxidant capacity of an imidazole alkaloids family through single-electron transfer reactions. J Mol Model. 2020; 26(11):321. DOI: 10.1007/s00894-020-04583-2. View

13.

Kapche G, Fozing C, Donfack J, Fotso G, Amadou D, Tchana A . Prenylated arylbenzofuran derivatives from Morus mesozygia with antioxidant activity. Phytochemistry. 2009; 70(2):216-21. DOI: 10.1016/j.phytochem.2008.12.014. View

14.

Lee J, Ko H, Woo E, Lee S, Moon B, Lee C . Moracin M inhibits airway inflammation by interrupting the JNK/c-Jun and NF-κB pathways in vitro and in vivo. Eur J Pharmacol. 2016; 783:64-72. DOI: 10.1016/j.ejphar.2016.04.055. View

15.

Kapche D, Lekane N, Kulabas S, Ipek H, Tok T, Ngadjui B . Aryl benzofuran derivatives from the stem bark of Calpocalyx dinklagei attenuate inflammation. Phytochemistry. 2017; 141:70-79. DOI: 10.1016/j.phytochem.2017.05.007. View

16.

Li X, Xie H, Zhan R, Chen D . Effect of Double Bond Position on 2-Phenyl-benzofuran Antioxidants: A Comparative Study of Moracin C and Iso-Moracin C. Molecules. 2018; 23(4). PMC: 6017532. DOI: 10.3390/molecules23040754. View

17.

Galano A, Alvarez-Idaboy J . A computational methodology for accurate predictions of rate constants in solution: application to the assessment of primary antioxidant activity. J Comput Chem. 2013; 34(28):2430-45. DOI: 10.1002/jcc.23409. View

18.

Ahmadi S, Marino T, Prejano M, Russo N, Toscano M . Antioxidant Properties of the Vam3 Derivative of Resveratrol. Molecules. 2018; 23(10). PMC: 6222371. DOI: 10.3390/molecules23102446. View

19.

Galano A, Mazzone G, Alvarez-Diduk R, Marino T, Alvarez-Idaboy J, Russo N . Food Antioxidants: Chemical Insights at the Molecular Level. Annu Rev Food Sci Technol. 2016; 7:335-52. DOI: 10.1146/annurev-food-041715-033206. View

20.

Pel P, Chae H, Nhoek P, Kim Y, Chin Y . Chemical Constituents with Proprotein Convertase Subtilisin/Kexin Type 9 mRNA Expression Inhibitory Activity from Dried Immature Morus alba Fruits. J Agric Food Chem. 2017; 65(26):5316-5321. DOI: 10.1021/acs.jafc.7b02088. View