Nitric oxide inhibitory potential of Curcuma angustifolia Roxb. essential oil: An in silico and in vitro analysis
DOI:
https://doi.org/10.14719/pst.3410Keywords:
Anti-inflammatory, Curcuma angustifolia, essential oil, in vitro analysis, iNOS, molecular docking, MD simulation, NO, RAW 264.7Abstract
The essential oil (EO) derived from Curcuma angustifolia Roxb. has gained significant interest in traditional medicine, specifically for its potential as a therapeutic agent for inflammatory disorders. Our study aimed to identify the chemical constituents of C. angustifolia EO, investigate its anti-inflammatory effects in lipopolysaccharide (LPS)-treated RAW 264.7 cells and explore potential nitric oxide (NO) inhibitors through in silico based studies. The essential oil obtained through hydro-distillation underwent analysis via gas chromatography-mass spectrometry (GC-MS). The major constituents were identified as velleral (17.82 %), germacrone (12.91 %), cryptomerione (11.52 %), curzerene (5.66 %) and ?-elemene (4.09 %). The EO demonstrated non-toxicity up to a concentration of 50 µg/mL, maintaining over 70 % viability in RAW 264.7 cells. At a concentration of 25 µg/mL, treatment with C. angustifolia EO exhibited significant anti-inflammatory properties, leading to a 66 % decrease in LPS-induced NO production. Inducible nitric oxide synthase (iNOS) crystal structures were sourced from the RCSB database. Compounds identified through GC-MS analysis were retrieved from PubChem, docked by the molecular-docking process and tested for drug-likeness properties. The compounds such as velleral (-5.8 kcal/mol), germacrone (-5.4 kcal/mol), neocurdione (-5.2 kcal/mol) and ?-cadinene (-5.2 kcal/mol) exhibited the highest binding-affinity with iNOS. Molecular dynamics simulation (MDS) showed that the interaction of these 4 phyto-compounds was stable with the active site residues. Important bonds identified in the initial ligand-docked compounds persisted unaltered throughout the MDS. The present work with in vitro and in silico studies revealed that C. angustifolia EO could be a potential anti-inflammatory agent, thus necessitating further in vivo studies to develop promising therapeutic agents in the treatment of inflammation.
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References
Azab A, Nassar A, Azab AN. Anti-inflammatory activity of natural products. Molecules. 2016;21:1321. https://doi.org/10.3390/molecules21101321
Saleem TM, Azeem AK, Dilip C, Sankar C, Prasanth NV, Duraisami R. Anti–inflammatory activity of the leaf extracts of Gendarussa vulgaris Nees. Asian Pac J Trop Biomed. 2011;1:147-49. https://doi.org/10.1016/S2221-1691(11)60014-2
García-Aranda MI, Gonzalez-Padilla JE, Gómez-Castro CZ, Gómez-Gómez YM, Rosales-Hernández MC, et al. Anti-inflammatory effect and inhibition of nitric oxide production by targeting COXs and iNOS enzymes with the 1, 2-diphenylbenzimidazole pharmacophore. Bioorg Med Chem. 2020;28:115427. https://doi.org/10.1016/j.bmc.2020.115427
Venkata M, Sripathy R, Anjana D, Somashekara N, Krishnaraju A, Krishanu S, et al. In silico, in vitro and in vivo assessment of safety and anti-inflammatory activity of curcumin. Am J Infect Dis. 2012;8:26. https://doi.org/10.3844/ajidsp.2012.26.33
Jamali T, Kavoosi G, Jamali Y, Mortezazadeh S, Ardestani SK. In-vitro, in-vivo and in-silico assessment of radical scavenging and cytotoxic activities of Oliveria decumbens essential oil and its main components. Sci Rep. 2021;11:14281. https://doi.org/10.1038/s41598-021-93535-8
Javaid A, Chaudhury FA, Khan IH, Ferdosi MFH. Potential health-related phytoconstituents in leaves of Chenopodium quinoa. Adv Life Sci. 2022;9(4):574-78.
Javaid A, Khan IH, Ferdosi MFH, Manzoor M, Anwar A. Medically important compounds in Ipomoea carnea flowers. Pak J Weed Sci Res. 2023;29(2):115-21. https://dx.doi.org/10.17582/journal.PJWSR/2023/29.2.115.121
Ibáñez MD, Blázquez MA. Curcuma longa L. rhizome essential oil from extraction to its agri-food applications. A review. Plants. 2020;10:44. https://doi.org/10.3390/plants10010044
Verma RK, Kumari P, Maurya RK, Kumar V, Verma RB, Singh RK. Medicinal properties of turmeric (Curcuma longa L.): A review. Int J Chem Stud. 2018;6:1354-57.
Jena S, Ray A, Sahoo A, Kar B, Panda PC, Nayak S. Chemical constituents of leaf essential oil of Curcuma angustifolia Roxb. growing in eastern India. J Essent Oil-Bear Plants. 2016;19:1527-31. https://doi.org/10.1080/0972060X.2016.1250677
Akinola OS, Irekhore OT, Ademolue RO. Evaluation of growth, reproductive performance and economic benefits of rabbits fed diets supplemented with turmeric (Curcuma longa) powder. Egypt Poult Sci J. 2020;40:701-14. https://doi.org/10.21608/epsj.2020.115968
Umar NM, Parumasivam T, Aminu N, Toh SM. Phytochemical and pharmacological properties of Curcuma aromatica Salisb (wild turmeric). J Appl Pharm Sci. 2020;10:180-94.
Sharma S, Ghataury SK, Sarathe A, Dubey G, Parkhe G. Curcuma angustifolia Roxb. (Zingiberaceae): Ethnobotany, phytochemistry and pharmacology: A review. J Pharmacogn Phytochem. 2019;8:1535-40.
Singh SS. Cultivation practices of Curcuma angustifolia Roxb. ICAR Research Complex for NEH Region, Manipur Centre, Lamphelpat, Imphal, India. Int J Agric Sci. ISSN. 2021:0975-3710.
Bonacina C, da Cruz RM, Nascimento AB, Barbosa LN, Gonçalves JE, Gazim ZC, Magalhaes HM, de Souza SG. Salinity modulates growth, oxidative metabolism and essential oil profile in Curcuma longa L. (Zingiberaceae) rhizomes. S Afr J Bot. 2022;146:1-1. https://doi.org/10.1016/j.sajb.2021.09.023
Dosoky NS, Setzer WN. Chemical composition and biological activities of essential oils of Curcuma species. Nutrients. 2018;10:1196. https://doi.org/10.3390/nu10091196
Chanda S, Ramachandra TV. Phytochemical and pharmacological importance of turmeric (Curcuma longa): A review. Research and Reviews: J Pharmacol. 2019;9:16-23.
Javed S, Mehmood Z, Javaid A, Javaid A. Biocidal activity of citrus peel essential oils against some food spoilage bacteria. J Med Plants Res. 2011;5(16): 2868-72.
Ferdosi MFH, Khan IH, Javaid A. Composition of essential oil isolated from marigold (Tagetes erecta L.) flowers cultivated in Lahore, Pakistan. Bangladesh J Bot. 2022;51(4): 683-88. https://doi.org/10.3329/bjb.v51i4.63486
Setzer WN, Duong L, Poudel A, Mentreddy SR. Variation in the chemical composition of five varieties of Curcuma longa rhizome essential oils cultivated in North Alabama. Foods. 2021;10:212. https://doi.org/10.3390/foods10020212
Nayak S, Jena, AK, Sucharita S. In vitro bioactivity studies of wild Curcuma angustifolia rhizome extract against (HeLa) human cervical carcinoma cells. World Journal of Pharmacy and Pharmaceutical Sciences. 2013;2:4972-86.
Gadnayak A, Dehury B, Nayak A, Jena S, Sahoo A, Panda PC, et al. Mechanistic insights into 5-lipoxygenase inhibition by active principles derived from essential oils of Curcuma species: Molecular docking, ADMET analysis and molecular dynamic simulation study. PloS One. 2022;17:e0271956. https://doi.org/10.1371/journal.pone.0271956
Lipinski CA. Poor aqueous solubility—an industry wide problem in drug discovery. Am Pharm Rev. 2002;5:82-85.
Egan WJ. Predicting ADME properties in drug discovery. Drug design: structure-and ligand-based approaches. Cambridge University Press. 2010:165-77. https://doi.org/10.1017/CBO9780511730412.013
Pollastri MP. Overview on the rule of five. Current Protocols in Pharmacology. 2010;49:9-12. https://doi.org/10.1002/0471141755.ph0912s49
Jena S, Ray A, Banerjee A, Sahoo A, Nasim N, Sahoo S, et al. Chemical composition and antioxidant activity of essential oil from leaves and rhizomes of Curcuma angustifolia Roxb. Nat Prod Res. 2017;31:2188-91. https://doi.org/10.1080/14786419.2017.1278600
Srivastava AK, Srivastava SK, Syamsundar KV. Volatile composition of Curcuma angustifolia Roxb. rhizome from central and southern India. Flavour Fragr J. 2006;21:423-26. https://doi.org/10.1002/ffj.1680
Gouthamchandra K, Sudeep HV, Chandrappa S, Raj A, Naveen P, Shyamaprasad K. Efficacy of a standardized turmeric extract comprised of 70 % bisdemothoxy-curcumin (REVERC3) against LPS-induced inflammation in RAW264. 7 cells and carrageenan-Induced paw edema. J Inflamm Res. 2021;14:859. https://doi.org/10.2147/JIR.S291293
Ricciardolo FL, Sterk PJ, Gaston B, Folkerts G. Nitric oxide in health and disease of the respiratory system. Physiol Rev. 2004;84:731-65. https://doi.org/10.1152/physrev.00034.2003
Ray A, Jena S, Sahoo A, Kamila PK, Das PK, Mohanty S, et al. Chemical composition, antioxidant, anti-inflammatory and anticancer activities of bark essential oil of Cryptocarya amygdalina from India. J Essent Oil-Bear Plants. 2021;24:617-31. https://doi.org/10.1080/0972060X.2021.1950051
Schmitt CA, Dirsch VM. Modulation of endothelial nitric oxide by plant-derived products. Nitric Oxide. 2009;21:77-91. https://doi.org/10.1016/j.niox.2009.05.006
de Cássia da Silveira e Sá R, Andrade LN, de Sousa DP. A review on anti-inflammatory activity of monoterpenes. Molecules. 2013;18:1227-54. https://doi.org/10.3390/molecules18011227
Garcin ED, Arvai AS, Rosenfeld RJ, Kroeger MD, Crane BR, Andersson G, et al. Anchored plasticity opens doors for selective inhibitor design in nitric oxide synthase. Nat Chem Biol. 2008;4:700-07. https://doi.org/10.1038/nchembio.115
Xu J, Peng M, Sun X, Liu X, Tong L, Su G, et al. Bioactive diterpenoids from Trigonostemon chinensis: structures, NO inhibitory activities and interactions with iNOS. Bioorg Med Chem Lett. 2016;26:4785-89. https://doi.org/10.1016/j.bmcl.2016.08.026
Chayah M, Carrión MD, Gallo MA, Jiménez R, Duarte J, Camacho ME. Development of urea and thiourea kynurenamine derivatives: synthesis, molecular modeling and biological evaluation as nitric oxide synthase inhibitors. Chem Med Chem. 2015;10:874-82. https://doi.org/10.1002/cmdc.201500007
Eftekhari SA, Toghraie D, Hekmatifar M, Sabetvand R. Mechanical and thermal stability of armchair and zig-zag carbon sheets using classical MD simulation with Tersoff potential. Phys. E: Low-Dimens. Syst Nanostructures. 2021;133:114789. https://doi.org/10.1016/j.physe.2021.114789
Nayak A, Gadnayak A, Dash KT, Jena S, Ray A, Nayak S, Sahoo A. Exploring molecular docking with MM-GBSA and molecular dynamics simulation to predict potent inhibitors of cyclooxygenase (COX-2) enzyme from terpenoid-based active principles of Zingiber species. J Biomol Struct Dyn. 2023;41:10840-50. https://doi.org/10.1080/07391102.2022.2161011
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Copyright (c) 2024 Ayushman Gadnayak, Ananya Nayak, Sudipta Jena, Ambika Sahoo, Pratap Chandra Panda, Asit Ray, Sanghamitra Nayak
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