Login Register Cart 0
Generic placeholder image

Current Enzyme Inhibition

Editor-in-Chief

ISSN (Print): 1573-4080
ISSN (Online): 1875-6662

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Metabolite Profiling and in silico Studies to Elucidate the Anti-inflammatory Properties of Pterocarpus milbreadii

Author(s): Patrick Emeka Aba* and Ismaila Onuche Odugbo

Volume 20, Issue 1, 2024

Published on: 12 January, 2024

Page: [71 - 77] Pages: 7

DOI: 10.2174/0115734080277468231129075038

Price: $65

Abstract

Background: Pterocarpus milbreadii (PM), called Rosewood in English, is a leafy vegetable used in preparing soup and has also proven medicinal.

Objective: This study aimed to evaluate the most abundant compounds in the ethylacetate fraction of PM using Gas Chromatography-Mass Spectrometry (GC-MS) and docking it against cyclooxygenase isoenzymes.

Methods: The PM leaves were extracted with ethylacetate using the cold maceration method. The extract was subjected to GC-MS assay. The spectra obtained were matched with NIST 17. AutoDock Vina was used to perform the molecular docking of the most abundant compound of PM and cyclooxygenase. Celecoxib was used as the standard ligand.

Results: The results of the study revealed that the ethyl acetate leaf extract of PM contained different phytochemicals, with hexadecenoic acid being the most abundant, with an intensity count of 9.5 x108 CPS. Docking of hexadecenoic acid and Celecoxib with COX-2 yielded binding energies of -6.7 and -7.7 kcal/mol, respectively, while with COX-1, the binding energies of -6.3 and -9.8 kcal/mol were respectively recorded. Hexadecenoic acid interacted with both COX-1 and COX-2 largely via Van der Waals and pi-Alkyl bonds. Celecoxib made conventional hydrogen, carbon-hydrogen, halogen, pi-sigma, pi-alkyl interactions with the cyclooxygenase isoenzymes.

Conclusion: It was concluded that hexadecenoic acid was the predominant phytochemical in the ethylacetate leaf extract of PM. The hexadecanoic acid ligand produced a better inhibitory effect on COX-2 compared to COX-1.

« Previous Next »
Graphical Abstract

[1]
Nørregaard R, Kwon TH, Frøkiær J. Physiology and pathophysiology of cyclooxygenase-2 and prostaglandin E2 in the kidney. Kidney Res Clin Pract 2015; 34(4): 194-200.
[http://dx.doi.org/10.1016/j.krcp.2015.10.004] [PMID: 26779421]
[2]
Adelizzi RA. COX-1 and COX-2 in health and disease. J Am Osteopath Assoc 1999; 99(11_suppl)(Suppl): S7.
[http://dx.doi.org/10.7556/jaoa.1999.99.11.S7]
[3]
Litalien C, Beaulieu P. Chapter 117 Molecular mechanisms of drug actions: From receptors to effectors. In: Fuhrman BP, Zimmerman JJ, Eds. Pediatric Critical Care. (4th ed.). 2011; pp. 1553-68.

[4]
Blobaum AL, Marnett LJ. Structural and functional basis of cyclooxygenase inhibition. J Med Chem 2007; 50(7): 1425-41.
[http://dx.doi.org/10.1021/jm0613166] [PMID: 17341061]
[5]
Chen QW, Zhang XM, Zhou JN, et al. Analysis of small fragment deletions of the APC gene in chinese patients with familial adenomatous polyposis, a precancerous condition. Asian Pac J Cancer Prev 2015; 16(12): 4915-20.
[http://dx.doi.org/10.7314/APJCP.2015.16.12.4915] [PMID: 26163615]
[6]
Shin S. Safety of celecoxib versus traditional nonsteroidal anti-inflammatory drugs in older patients with arthritis. J Pain Res 2018; 11(11): 3211-9.
[http://dx.doi.org/10.2147/JPR.S186000] [PMID: 30588073]
[7]
Aba PE, Udechukwu IR. Comparative hypoglycemic potentials and phytochemical profiles of 12 common leafy culinary vegetables con-sumed in Nsukka, Southeastern Nigeria. J Basic Clin Physiol Pharmacol 2018; 29(4): 313-20.
[http://dx.doi.org/10.1515/jbcpp-2017-0134] [PMID: 29641414]
[8]
Ujowundu CO, Okafor OE, Agha NC, Nwaogu LA, Igwe KO, Igwe CU. Phytochemical and chemical composition of combretum zenkeri leaves. J Med Plants Res 2010; 4(10): 965-8.
[9]
Usunomena U, Chinwe IV. Phytochemical screening, mineral composition and in vitro antioxidant activities of Pterocarpus mildbraedii leaves. Int J Sci World 2016; 4(1): 23-30.
[http://dx.doi.org/10.14419/ijsw.v4i1.6066]
[10]
Sousa SF, Fernandes PA, Ramos MJ. Protein–ligand docking: Current status and future challenges. Proteins 2006; 65(1): 15-26.
[http://dx.doi.org/10.1002/prot.21082] [PMID: 16862531]
[11]
Muegge I, Rarey M. Small molecule docking and scoring. Rev Comput Chem 2001; 17: 1-60.
[12]
Sparkman DO, Penton Z, Kitson FG. Gas Chromatography and Mass Spectrometry: A Practical Guide. 2011. ISBN 978-0-08- 092015-3
[13]
Jones M. Gas Chromatography-Mass Spectrometry American Chemical Society Retrieved 19 Nov 2019.
[14]
Idu M, Aihiokhai MO, Imoni CA, Akokigho CE, Olali NC. Gas chromatography-mass spectrometry (GC-MS) analysis and phytochemical screening of polyherbal aqueous leaves extract (PALE). Journal of Complementary and Alternative Medical Research 2021; 14(2): 10-8.
[http://dx.doi.org/10.9734/jocamr/2021/v14i230240]
[15]
Trott O, Olson AJ. AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 2010; 31(2): 455-61.
[http://dx.doi.org/10.1002/jcc.21334] [PMID: 19499576]
[16]
Ganesan T, Subban M, Leslee DBC, Kuppannan SB, Seedevi P. Structural characterization of n-hexadecanoic acid from the leaves of Ipo-moea eriocarpa and its antioxidant and antibacterial activities. Biom Conv Bioref 2022.
[http://dx.doi.org/10.1007/s13399-022-03576-w]
[17]
Kalpana D, Shanmugasundaram R, Mohan V. GC–MS analysis of ethanol extract of Entada pursaetha DC seed. Biosci Disc 2012; 3: 30-3.
[18]
Islam MT, Ayatollahi SA, Zihad SMNK, et al. Phytol anti-inflammatory activity: Pre-clinical assessment and possible mechanism of ac-tion elucidation. Cell Mol Biol 2020; 66(4): 264-9.
[http://dx.doi.org/10.14715/cmb/2020.66.4.31] [PMID: 32583784]
[19]
Sathish S, Rajesh P, Kala A, Gopathy R, Kandan P, Rajesh P. Spectroscopic and theoretical studies on1,1′-bicyclopropyl]-2-octanoic acid, 2′-hexyl-. Methyl Ester Int J Sci Tech Res 2020; 9(4): 3577-84.
[20]
Rohlf JW. Modern Physics from α to Z. ISBN 0471572705. 1994; p. 20.
[21]
Ralte L, Khiangte L, Thangjam NM, Kumar A, Singh YT. GC–MS and molecular docking analyses of phytochemicals from the underuti-lized plant, Parkia timoriana revealed candidate anti-cancerous and anti-inflammatory agents. Sci Rep 2022; 12(1): 3395.
[http://dx.doi.org/10.1038/s41598-022-07320-2] [PMID: 35233058]
[22]
Terefe EM, Ghosh A. molecular docking, validation, dynamics simulations, and pharmacokinetic prediction of phytochemicals isolated from croton dichogamus against the hiv-1 reverse transcriptase. Bioinform Biol Insights 2022; 16.
[http://dx.doi.org/10.1177/11779322221125605] [PMID: 36185760]
[23]
Choi SH, Aid S, Bosetti F. The distinct roles of cyclooxygenase-1 and -2 in neuroinflammation: Implications for translational research. Trends Pharmacol Sci 2009; 30(4): 174-81.
[http://dx.doi.org/10.1016/j.tips.2009.01.002] [PMID: 19269697]
[24]
Aïd S, Bosetti F. Gene expression of cyclooxygenase-1 and Ca2+-independent phospholipase A2 is altered in rat hippocampus during normal aging. Brain Res Bull 2007; 73(1-3): 108-13.
[http://dx.doi.org/10.1016/j.brainresbull.2007.02.015] [PMID: 17499644]
[25]
Bitencourt-Ferreira G, Veit-Acosta M, de Azevedo WF Jr. Hydrogen bonds in protein-ligand complexes. Methods Mol Biol 2019; 2053: 93-107.
[http://dx.doi.org/10.1007/978-1-4939-9752-7_7] [PMID: 31452101]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy