Anti-psoriatic and Anti-inflammatory Potentials of Phytochemicals from Curcuma longa against Interleukin-17A and Inducible Nitric Oxide Synthase: An In Silico Study

https://doi.org/10.22146/mot.87528

Misbaudeen Abdul-Hammed(1*), Monsurat Olajide(2), Ibrahim Olaide Adedotun(3), Tolulope Irapada Afolabi(4), Roqeebah Abdul-Razaq(5), Ubaedah Ismail(6), Muhminah Folake Abdullateef(7), Zainab Omowumi Adebayo(8)

(1) *) Ladoke Akintola University of Technology, Ogbomoso, Oyo State *) Computational/Biophysical Chemistry Research Group, Ladoke Akintola University of Technology, Ogbomoso, Oyo State
(2) *) Ladoke Akintola University of Technology, Ogbomoso, Oyo State *) Computational/Biophysical Chemistry Research Group, Ladoke Akintola University of Technology, Ogbomoso, Oyo State *) Crescent University, Abeokuta, Ogun State
(3) *) Ladoke Akintola University of Technology, Ogbomoso, Oyo State *) Computational/Biophysical Chemistry Research Group, Ladoke Akintola University of Technology, Ogbomoso, Oyo State
(4) Ladoke Akintola University of Technology, Ogbomoso, Oyo State
(5) Ladoke Akintola University of Technology, Ogbomoso, Oyo State
(6) *) Ladoke Akintola University of Technology, Ogbomoso, Oyo State *) Computational/Biophysical Chemistry Research Group, Ladoke Akintola University of Technology, Ogbomoso, Oyo State
(7) *) Ladoke Akintola University of Technology, Ogbomoso, Oyo State *) Computational/Biophysical Chemistry Research Group, Ladoke Akintola University of Technology, Ogbomoso, Oyo State
(8) Ladoke Akintola University of Technology, Ogbomoso, Oyo State
(*) Corresponding Author

Abstract


Psoriasis is a chronic autoimmune cell-mediated inflammatory skin disease that affects approximately 125 million people worldwide. Turmeric has been long known for its potent anti-inflammatory activities. In this study, in silico studies were used to evaluate the efficacy of isolated phytochemicals from turmeric in the treatment of psoriasis. One hundred and fifteen phytochemicals from this plant and two standard medications (Flurandrenolide and Triamcinolone), active ingredients used in some topical steroid creams were evaluated for their inhibitory properties against Interleukin-17A (IL-17A) and Inducible NOS (iNOS) receptor using a computer-aided drug design approach. The binding scores and inhibitory efficiencies were obtained via virtual screening. ADMET SAR-2 website was used to conduct the Absorption, Distribution, Metabolism, Excretion, and Toxicity (ADMET) analysis, the Molinspiration and SwissADME tools were used to investigate the drug-likeness characteristics and oral bioavailability of the selected compounds respectively. Other analyses of the selected compounds include bioactivity, activity spectra for substances (PASS) prediction, binding mode, and molecular interaction. The results revealed that Bisabolone (−9.3 kcal/mol), Curcumanolide B (−8.6 kcal/mol), (E)-sesquisabinene hydrate (−8.5 kcal/mol), and procurcumadiol (−8.3 kcal/mol) are potential inhibitors of iNOS receptor, while hop-17(21)-en-3-ol (7.6 kcal/mol) is a potential inhibitor of IL-17A receptor. These compounds have better ADMET properties, binding affinities, drug-likeness, PASS properties, bioactivities, oral bioavailability, good binding mechanism, and interactions with the active site of the target receptor when compared with Flurandrenolide and Triamcinolone. As a result, this preliminary investigation suggests that these phytochemicals should be studied further to design novel psoriasis therapeutics.


Keywords


Anti-inflammatory; Molecular docking; Psoriasis; Skin disorder; Turmeric

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References

Abdul-Ghani, M. A., Tripathy, D., & DeFronzo, R. A. (2006). Contributions of beta-cell dysfunction and insulin resistance to the pathogenesis of impaired glucose tolerance and impaired fasting glucose. Diabetes Care, 29, 1130-1139. https://doi: 10.2337/diacare.2951130

Abe, Y., Hashimoto, S., & Horie, T. (1999). Curcumin inhibition of inflammatory cytokine production by human peripheral blood monocytes and alveolar macrophages. Pharmacological Research, 39, 41-47. https://doi: 10.1006/phrs.1998.0404

Adelusi, T. I., Akinbolaji, G. R., Yin, X., Ayinde, K. S., & Olaoba, O.T. (2021) Neurotrophic, antineuroinflammatory, and redox balance mechanisms of chalcones, European Journal of Pharmacology, 891, 173695. https://doi: 10.1016/j.ejphar.2020.173695

Alici, H., Tahtaci, H., & Demir, K. (2022). Design and various in silico studies of the novel curcumin derivatives as potential candidates against COVID-19 -associated main enzymes. Computational Biology and Chemistry, 98, 107657. http://doi: 10.1016/j.compbiolchem.2022.107657

Al-Mazaideh, G. M., Al-Swailmi, F. K., & Parrey, M. U. R. (2021). Molecular docking study reveals naringenin and hesperetin from desert truffles as promising potential inhibitors for coronavirus (COVID-19). Annals of Clinical and Analytical Medicine, 12(9), 980-985. https://doi: 10.4328/ACAM.20546

Anand, P., Kunnumakkara, A. B., Newman, R. A., & Aggarwal, B. B. (2007). Bioavailability of curcumin: Problems and promises. Molecular Pharmaceuticals, 4(6), 807–818. http://doi: 10.1021/mp700113r

Astinfeshan, M., Rasmi, Y., Kheradmand, F., Karimipour, M., Rahbarghazi, R., Aramwit, P., Nasirzadeh, M., Daeihassani, B., Shirpoor, A., Gholinejad, Z., & Saboory, E. (2019). Curcumin inhibits angiogenesis in endothelial cells using downregulation of the PI3K/Akt signaling pathway. Food Bioscience, 29, 86–93. http://doi:10.1016/j.fbio.2019.04.005

Augustin, M., Glaeske, G., Radtke, M., Christophers, E., Reich, K., & Schäfer, I. (2010). Epidemiology and comorbidity of psoriasis in children. The British Journal of Dermatology, 162, 633–636. http://doi: 10.1111/j.1365-2133.2009.09593.x

Baliwag, J., Barnes, D. H., & Johnston, A. (2015). Cytokines in psoriasis. Cytokine, 73(2), 342–350. http://doi: 10.1016/j.cyto.2014.12.014

Bø, K., Thoresen, M., & Dalgard, F. (2008). Smokers report more psoriasis, but not atopic dermatitis or hand eczema: Results from a Norwegian population survey among adults. Dermatology, 216(1), 40–45. http://doi: 10.1159/000109357

Chen, G. Y., Cheng, Y. W., Wang, C. Y., Hsu, T. J., Hsu, M. M. L., & Yang, P. T. (2008). Prevalence of skin diseases among school children in Magong, Penghu, Taiwan: A community-based clinical survey. Journal of Formosan Medical Association, 107(1), 21–29. http://doi: 10.1016/S0929-6646(08)60004-2

Cheng, F., Li, W., Zhou, Y., Shen, J., Wu, Z., Liu, G., Lee, P. W., & Tang, Y. (2012). admetSAR: A Comprehensive Source and Free Tool for Assessment of Chemical ADMET Properties. Journal of Chemical Information and Modeling. 52(11), 3099-3105. https://doi.org/10.1021/ci300367a

Choi, J. W., Kim, B. R., & Youn, S. W. (2017). Adherence to topical therapies for the treatment of psoriasis: surveys of physicians and patients. Annals of Dermatology, 29(5), 559–564. https://doi: 10.5021/ad.2017.29.5.559

Dai, W., Wang, H., Fang, J., Zhu, Y., Zhou, J., Wang, X., Zhou, Y., & Zhou, M. (2018). Curcumin provides neuroprotection in model of traumatic brain injury via the Nrf2- ARE signaling pathway. Brain Research Bulletin, 140, 65–71. https://doi: 10.1016/j.brainresbull.2018.03.020

Daina, A., Michielin, O., & Zoete, V. (2017). SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness, and medicinal chemistry friendliness of small molecules. Scientific Reports, 7, Article 42717.https://doi.org/10.1038/srep4271

Ferreira, G., Santos, R. N., Oliva, G., & Andricopulo,

A. D. (2015). Molecular docking and structure-based drug design strategies. Molecules, 20(7), 13384–13421. http://doi: 10.3390/molecules200713384

Filimonov, D. A., Lagunin, A. A., Gloriozova, T. A., Rudik, A. V., Druzhilovskii, D. S., Pogodin, P. V., & Poroikov, V. V. (2014) Prediction of the biological activity spectra of organic compounds using the PASS online web resource. Chemistry of Heterocyclic Compounds, 50, 444–457. https://doi.org/10.1007/s10593-014-1496-1

Garcin, E. D., Arvai, A. S., Rosenfeld, R. J., Kroeger, M. D., Crane, B. R., Andersson, G., Andrews, G., Hamley, P. J., Mallinder, P. R., Nicolls, D. J., St-Gallay, S. A., Tinker, A. C., Gensmantel, N. P., Mete, A., Cheshire, D. R., Conolly, S., Stuehr, D. J., Aberg, A., Wallace, A. V., Tainer, J. A., & Getzoff, E. D. (2008) Anchored plasticity opens doors for selective inhibitor design in nitric oxide synthase Nature Chemical Biology. 4(11), 700-707. https://doi: 10.1038/nchembio.115

Gisondi, P., Del Giglio, M., & Girolomoni, G. (2017). Treatment approaches to moderate to severe psoriasis. International Journal of Molecular Science, 18(11), Article 2427. https://doi: 10.3390/ijms18112427

Golbari, N. M., Porter, M. L., & Kimball, A. B. (2018) Current guidelines for psoriasis treatment: a work in progress. Cutis, 101(3S), 10-12.

Gupta, B., & Ghosh, B. (1999). Curcuma longa inhibits TNF-alpha induced expression of adhesion molecules on human umbilical vein endothelial cells. International Journal of Immunopharmacology. 21(11), 745–757. https://doi: 10.1016/s0192-0561(99)00050-8

Gupta, S., & Ravishankar, S. (2005). A comparison of the antimicrobial activity of garlic, ginger, carrot, and turmeric pastes against Escherichia coli O157:H7 in laboratory buffer and ground beef. Foodborne Pathogens and Disease, 2(4), 330–340. https://doi: 10.1089/fpd.2005.2.330

Hoffman, M. B., Hill, D., & Feldman, S. R. (2016). Current challenges and emerging drug delivery strategies for the treatment of psoriasis. Expert Opinion on Drug Delivery, 13(10), 1461-1473. https://doi: 10.1080/17425247.2016.1188801

Hopkins, A. L., Keseru, G. M., Leeson, P. D., Rees, D. C., & Reynolds C. H. (2014) The role of ligand efficiency metrics in drug discovery. Nature Review Drug Discovery, 13, 105-21. https://doi.org/10.1038/nrd4163

Iweala, E. J., Uche, M. E., Dike, E. D., Etumnu, L. R., Dokunmu, T. M., Oluwapelumi, A. E., Okoro, B. C., Dania, O. E., Adebayo, A. H., & Ugbogu, E. A. (2023). Curcuma longa (Turmeric): Ethnomedicinal uses, phytochemistry, pharmacological activities and toxicity profiles - A review. Pharmacological Research - Modern Chinese Medicine, 6, 100222. https://doi: 10.1016/j.prmcm.2023.100222

Jiang, S., Han, J., Li, T., Xin, Z., Ma, Z., Di, W., Hu, W., Gong, B., Di, S., Wang, D., & Yang, Y. (2017) Curcumin as a potential protective compound against cardiac diseases. Pharmacological Research, 119, 373–383. https://doi: 10.1016/j.phrs.2017.03.001

Kocaadam, B., & Şanlier, N. (2017). Curcumin, an active component of turmeric (Curcuma longa), and its effects on health. Critical Reviews in Food Science and Nutrition, 57(13), 2889–2895. https://doi: 10.1080/10408398.2015.1077195

Kroncke, K. D., Fehsel, K., & Kolb-Bachofen, V. (1998). Inducible nitric oxide synthase in human diseases. Clinical and Experimental Immunology, 113(2), 147–156.https://doi: 10.1046/j.1365-2249.1998.00648.x

Kuroda, M., Mimaki, Y., Nishiyama, T., Mae, T., Kishida, H., & Tsukagawa, K. (2005). Hypoglycemic effects of turmeric (Curcuma longa L. Rhizomes) on genetically diabetic KK-Ay mice. Biological and Pharmaceutical Bulletin, 28(5), 937-939.

Lee, W. H., Loo, C. Y., Bebawy, M., Luk, F., Mason, R. S., & Rohanizadeh, R. (2013). Curcumin and its derivatives: Their application in neuropharmacology and neuroscience in the 21st century. Current Neuropharmacology, 11(4), 338-378.https:// doi: 10.2174/1570159X11311040002

Li, S., Yuan, W., Deng, G., Wang, P., Yang, P., & Aggarwal, B. (2011). Chemical composition and product quality control of turmeric (Curcuma longa L.). Pharmaceutical Crops, 2, 28-54. https//doi: 10.2174/2210290601102010028

Lipinski, C. A. (2004). Lead-and drug-like compounds: The rule-of-five revolution. Drug Discovery Today: Technologies, 1(4), 337-341. https://doi.org/10.1016/j.ddtec.2004.11.007

Liu, S., Dakin, L. A., Xing, L., Withka, J. M., Sahasrabudhe, P. V., Li, W., Banker, M. E., Balbo, P., Shanker, S., Chrunyk, B. A., Guo, Z., Chen, J. M., Young, J. A., Bai, B. A., Vincent, F., Jones, L. H., Xu, H., Hoth, L. R., Geoghegan, K. F., Qui, X., Bunnage, M. E., & Thrarensen, A. (2016). Binding site elucidation and structure guided design of macrocyclic IL-17A antagonist Scientific Reports, 6, 30859-30859. https://doi.org/10.1038/srep30859

MacDonald, A. & Burden, A. (2007). Psoriasis: Advances in pathophysiology and management. Postgraduate Medical Journal, 83(985), 690-697. https://doi: 10.1136/pgmj.2007.061473

MacMicking, J., Xie, Q. W., and Nathan, C. (1997). Nitric oxide and macrophage function. Annual Review of Immunology, 15, 323–350. https://doi: 10.1146/annurev.immunol.15.1.323

Mccarren, P., Springer, C., & Whitehead, L. (2011), ‘An investigation into pharmaceutically relevant mutagenicity data and the influence on Ames predictive potential. Journal of Cheminformatics. 3, Article 51. https://doi.org/10.1186/1758-2946-3-51

Ni, C., & Chiu, M. W. (2014). Psoriasis and comorbidities: Links and risks. Clinical Cosmetology and Investigational Dermatology, 7, 119-132. https://doi: 10.2147/CCID.S44843

Onawole, A. T., Sulaiman, K. O., Adegoke, R. O., & Kolapo, T. U. (2017). Identification of potential inhibitors against the Zika virus using consensus scoring Journal of Molecular Graphics and Modelling, 73, 54-61. https://doi: 10.1016/j.jmgm.2017.01.018

Rahman, A. T., Rafia, Jethro, R. A., Santoso, P., Kharisma, V. D., Murtadlo, A. A. A., Purnamasari, D., Soekamto, N. H., Ansori, ANM., Kuswati, Mandeli, R. S., Aledresi, K. A. M. S., Mohd Yusof, N. F., Jakhmola, V., Rebezov, M., Zainul, R., Dobhal, k., Parashar, T., Ghifari, M. A., & Sari, D. A. P. (2022). In silico study of the potential of endemic Sumatra wildTurmeric rhizomes (Curcuma sumatrana: Zingiberaceae) as anti-cancer. Pharmacognosy Journal,14(6), 806-812. https://doi: 10.5530/pj.2022.14.171

Rajagopal, K., Varakumar, P., Baliwada, A., & Byran, G. (2020). ‘Activity of phytochemical constituents of Curcuma longa (turmeric) and Andrographis paniculata against coronavirus (COVID-19): An In silico approach. Future Journal of Pharmaceutical Sciences, 6(1), 104. https://doi: 10.1186/s43094-020-00126-x

Ramirez-Tortosa, M. C., Mesa, M, D., Aguilera, M. C., Quiles, J. L., Baro, L., Ramirez-Tortosa, C. L., Martinez-Victoria, E., and Gil, A. (1999) Oral administration of a turmeric extract inhibits LDL oxidation and has hypocholesterolemic effects in rabbits with experimental atherosclerosis. Atherosclerosis, 147(2), 371–378. https://doi: 10.1016/s0021-9150(99)00207-5

Ruiz de Morales, J. M. G., Puig, L., Daudén, E., Cañete, J. D., Pablos, J. L., Martín, A. O., Juanate, C. G., Adán, A., Montalbán, X., Borruel, N., Ortí, G., Holgado-Martín, E., García-Vidal, C., Vizcaya-Morales, C., Martín-Vázquez, V., & González-Gay, M. A. (2020). Critical role of interleukin (IL)-17 in inflammatory and immune disorders: An updated review of the evidence focusing in controversies. Autoimmunity Reviews, 19(1), 102429. https://doi: 10.1016/j.autrev.2019.102429

Saeed, M. E. M., Yücer, R., Dawood, M., Hegazy, M-E. F., Drif, A., Ooko, E., Kadioglu, O., Seo, E-J., Kamounah, F. S., Titinchi, S. J. Bachmeier, B., & Efferth, T. (2022). In Silico and In Vitro Screening of 50 Curcumin Compounds as EGFR and NF-κB Inhibitors. International Journal of Molecular Science, 23, 3966. https://doi: 10.3390/ijms23073966

Sanguinetti, M. C., & Tristani-Firouzi, M. (2006) HERG potassium channels and cardiac arrhythmia. Nature, 440(7083), 463-469. https://doi: 10.1038/nature04710

Siviero A., Gallo E., & Maggini V. Curcumin. (2015). A golden spice with a low bioavailability. Journal of Herbal Medicine, 5(2), 57–70. https://doi.org/10.1016/j.hermed.2015.03.001

Takeshita, J., Grewal, S., Langan, S. M., Mehta, N. N., Ogdie, A., Van Voorhees, A. S., & Gelfand, J. M. (2017). Psoriasis and comorbid diseases: Epidemiology. Journal of American Academy of Dermatology, 76(3), 337-390. https://doi: 10.1016/j.jaad.2016.07.064

Tian, W., Chen, C., Lei, X., Zhao J. & Liang, J., (2018). CASTp 3.0: computed atlas of surface topography of proteins. Nucleic Acids Research, 46(W1), W363-W368.https://doi: 10.1093/nar/gky473

Tollefson, M. M., Van Houten, H. K., Asante, D., Yao, X., & Kremers, H. M. (2018). Association of psoriasis with comorbidity development in children with psoriasis. JAMA Dermatology, 154(3), 286-292. https://doi:10.1001/jamadermatol.2017.5417

Tsaioun, K., & Kates, S. A. (2010). ADMET for Medicinal Chemists: A Practical Guide. John Wiley and Sons. https://doi.org/10.1002/9780470915110

Winterfield, L., Menter, A., Gordon, K., & Gottlieb, A. (2005) Psoriasis treatment: Current and emerging directed therapies. Annals of Rheumatic Diseases, 64, ii87–ii90. https://doi: 10.1136/ard.2004.032276



DOI: https://doi.org/10.22146/mot.87528

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