Anti-urease and cytotoxic activity of 1-Nitro-2-phenylethane and Nerolidol; two major compounds isolated from the seeds
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Medicinal Chemistry Research https://doi.org/10.1007/s00044-020-02607-3
ORIGINAL RESEARCH
Anti-urease and cytotoxic activity of 1-Nitro-2-phenylethane and Nerolidol; two major compounds isolated from the seeds of Dennettia tripetala Samuel E. Ugheighele 1 Kate E. Imafidon1 Muhammad I. Choudhary2,3 Ahmed Shakil2 Majid Khan2 Zaid A. Sherwani3 Zaheer Ul-Haq3 ●
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Received: 4 May 2020 / Accepted: 23 July 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract The study investigated the anti-urease and cytotoxic activities of two major essential oil compounds; 1-Nitro-2-phenylehtane (NPE) and Nerolidol, isolated from the acetone extract of Dennettia tripetala (Pepper Fruit) seeds. Structural characterization of these compounds was performed by NMR, E1MS, and FT-IR spectroscopic techniques. Anti-urease activity of the compounds on Jack bean Urease was accessed by the indophenol method; molecular docking analysis using MOE 2015.010 program was performed to explain the possible mechanism of interaction between the compounds and urease enzyme. Cytotoxic activities of the compounds were also assayed on brine shrimp (Artemia salina L.) nauplii and 3T3 (mouse fibroblast cells). NPE and Nerolidol displayed significant inhibitory activities on Jack Bean urease with percentage inhibition of 82.4% and 78.6% and IC50 ± SD of 27.4 ± 1.80 and 34.9 ± 3.57 µM respectively. Molecular docking analysis of the interactions between these compounds and active site of the PDB of the enzyme displayed favorable conformational binding with docking scores of −5.3716 and −7.3547 and ligand efficiencies of −0.4883 and −0.4597 for NPE and Nerolidol, respectively. Both interactions were characterized by hydrogen bonding; NPE also displayed π-stacking and hydrophobic interactions. Cytotoxic activity evaluation of both compounds on brine shrimp and mouse fibroblasts revealed no toxicity for both compounds. Conclusively, NPE and Nerolidol could be employed in the treatment of infections engendered by ureolytic activity and could serve as templates in the rational design of functional derivatives that possess higher potencies than the isolated compounds with minimal toxicity. Keywords Dennettia tripetala 1-Nitro-2-phenylethane Nerolidol Urease Docking Cytotoxicity ●
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Abbreviations NPE 1-Nitro-2-phenylethane AHA Acetohydroxamic acid
Supplementary information The online version of this article (https:// doi.org/10.1007/s00044-020-02607-3) contains supplementary material, which is available to authorized users.
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Hex DCM EtAOc MeOH SF SG-CC PDB MOE
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Hexane Dichloromethane Ethyl acetate Methanol Sub-fraction Silica gel column chromatography Protein Data Bank Molecular operating environment
* Samuel E. Ugheighele [email protected] 1
Department of Biochemistry, University of Benin, Benin-City 300001, Nigeria
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H.E.J. Research Institute of Chemistry, International Centre for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
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Dr. Pan
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