Anti-inflammatory and anti-neuropathic effects of a novel quinic acid derivative from Acanthus syriacus

Document Type : Original Research Article

Author

Department of Pharmaceutical Sciences, Faculty of Pharmacy, Beirut Arab University, 115020 Beirut, Lebanon

Abstract

Objective: Acanthus syriacus (AS) is one of the valuable herbal plants with immunomodulatory potentials. The aim of this study is to assemble a phytochemical investigation of A. syriacus exploring its anti-inflammatory and antinociceptive properties, identification of its most active compound(s) and elucidating their structure and determining their mechanisms of action.
Materials and Methods: Bio-guided fractionation and isolation-schemes were used utilizing RP-HPLC, CC, 1H- and 13C-NMR, and biological-models were used to evaluate their effects against inflammation and neuropathic-pain (NP).
Results: The outcomes showed that the most active fraction (FKCA) of AS was identified. Two of the three components of FKCA were identified by chromatographic-methods, while the third compound was isolated, its structure was elucidated and its was named Kromeic acid (KRA); FKCA contained Ferulic acid (27.5%), kromeic acid (48.1%), and chlorogenic acid (24.4%). AS, FKCA and KRA showed significant (p˂0.05) anti-inflammatory and antinociceptive potentials in the management of allodynia and thermal-hyperalgesia in NP. AS and FCKA showed comparatively equipotent antinociceptive-effects. FKCA showed higher antinociceptive effects than KRA suggesting additive-effects among FKCA components. The anti-inflammatory, insulin secretagogue, oxidative-stress reducing, and protective effects against NO-induced neuronal-toxicity might be amongst the possible mechanisms of tested compounds to alleviate NP.
Conclusion: Here, we report the isolation and structure elucidation of a novel quinic-acid derivative, KRA. A. syriacus, FKCA, and KRA might be used as a novel complementary approach to ameliorate a variety of painful-syndromes.

Keywords

Main Subjects


Asongalem EA, Foyet HS, Ekobo S, Dimo T, Kamtchouing P. 2004. Antiinflammatory, lack of central analgesia and antipyretic properties of Acanthus montanus (Ness) T. Anderson. J Ethnopharmacol, 95:63-68.
Babu BH, Shylesh BS, Padikkala J. 2001. Antioxidant and hepatoprotective effect of Acanthus ilicifolius. Fitoterapia, 72:272-277.
Babu BH, Shylesh BS, Padikkala J. 2002. Tumour reducing and anticarcinogenic activity of Acanthus ilicifolius in mice. J Ethnopharmacol, 79:27-33.
Baydoun S, Chalak L, Dalleh H, Arnold N. 2015. Ethnopharmacological survey of medicinal plants used in traditional medicine by the communities of Mount Hermon, Lebanon. J Ethnopharmacol 173:139-156.
Bravo HR, Copaja SV, Argandona VH. 2004. Chemical basis for the antifeedant activity of natural hydroxamic acids and related compounds. J Agric Food Chem, 52:2598-2601.
Cameron NE, Cotter MA. 2008. Pro-inflammatory mechanisms in diabetic neuropathy: focus on the nuclear factor kappa B pathway. Curr Drug Targets, 9:60-67.
Capanlar S, Boke N, Yasa I, Kirmizigul S, 2010. A novel glycoside from Acanthus hirsutus (Acanthaceae). Nat Prod Commun, 5:563-566.
Comelli F, Bettoni I, Colleoni M, Giagnoni G, Costa B. 2009. Beneficial effects of a Cannabis sativa extract treatment on diabetes-induced neuropathy and oxidative stress. Phytother Res, 23:1678-1684.
Ellman GL. 1959. Tissue sulfhydryl groups. Arch BiochemBiophys, 82:70-77.
Gardmark M, Hoglund AU, Hammarlund-Udenaes M. 1998. Aspects on tail-flick, hot-plate and electrical stimulation tests for morphine antinociception, Pharmacol Toxicol. 83:252-258.
Green LC, Wagner DA, Glogowski J, Skipper PL, Wishnok JS, Tannenbaum SR. 1982. Analysis of nitrate, nitrite, and [15N] nitrate in biological fluids. Anal Biochem.126:131-138.
HibatallahJ, Carduner C, Poelman MC. 1999. In-vivo and in-vitro assessment of the free-radical-scavenger activity of Ginkgo flavone glycosides at high concentration. J Pharm Pharmacol, 51:1435-1440.
Jamalan M, Rezazadeh M, Zeinali M, Ghaffari MA. 2015. Effect of ascorbic acid and alpha-tocopherol supplementations on serum leptin, tumor necrosis factor alpha, and serum amyloid A levels in individuals with type 2 diabetes mellitus. Avicenna J Phytomed, 5:531-539.
Joharchi K, Jorjani M. 2007. The role of nitric oxide in diabetes-induced changes of morphine tolerance in rats. Eur J Pharmacol, 570:66-71.
Khaneshi F, Nasrolahi O, Azizi S, Nejati V. 2013. Sesame effects on testicular damage in streptozotocin-induced diabetes rats. Avicenna J Phytomed, 3:347-355.
Micov A, Tomić M, Pecikoza U, Ugrešić N, Stepanović-Petrović R. 2015. Levetiracetam synergises with common analgesics in producing antinociception in a mouse model of painful diabetic neuropathy. Pharmacol Res. 97:131-142.
Muthuraman A, Diwan V, Jaggi AS, Singh N, Singh D. 2008. Ameliorative effects of Ocimum sanctum in sciatic nerve transection-induced neuropathy in rats. J Ethnopharmacol, 120:56-62.
Nishiyama T, Ogawa M. 2005. Intrathecal edaravone, a free radical scavenger, is effective on inflammatory-induced pain in rats. Acta Anaesthesiol Scand, 49:147-151.
Ohkawa H, Ohishi N, Yagi K. 1979. Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction. Anal Biochem, 95:351-358.
Ohsawa M, Aasato M, Hayashi SS, Kamei J. 2011. RhoA/Rho kinase pathway contributes to the pathogenesis of thermal hyperalgesia in diabetic mice. Pain, 152:114-122.
Ozkul A, Ayhan M, Yenisey C, Akyol A, Guney E, Ergin FA. 2010. The role of oxidative stress and endothelial injury in diabetic neuropathy and neuropathic pain. Neuro Endocrinol Lett, 31:261-264.
Pabbidi RM, Cao DS, Parihar A, Pauza ME, Premkumar LS. 2008. Direct role of streptozotocin in inducing thermal hyperalgesia by enhanced expression of transient receptor potential vanilloid 1 in sensory neurons. Mol Pharmacol, 73:995-1004.
Raafat K, El-Darra N, Saleh FA, Rajha HN, Maroun RG, Louka N. 2017a. Infrared-assisted extraction and HPLC-analysis of Prunusarmeniaca L. pomace and detoxified-kernel and their antidiabetic effects. Phytochem Anal, 1:1-12.
Raafat K, El-Haj R, Shoumar D, Alaaeddine R, Fakhro Y, Tawil N, Shaer F, Daher A, Awada N, Sabra A, Atwi K, Khaled M, Messi R, Abouzaher N, Houri M, Al Jallad S. 2017b. Neuropathic pain: literature review and recommendations of potential phytotherapies. Pharmacog J 9:1-10.
Raafat K, El-Lakany A. 2018. Phytochemical and antinociceptive investigations of anemone coronaria active part ameliorating diabetic neuropathy pain. Planta Med Int Open, 5: e5-e13.
Raafat K, Hdaib F. 2017. Neuroprotective effects of Moringa oleifera: bio-guided GC-MS identification of active compounds in diabetic neuropathic pain model. Chin J IntegrMed. 1:e1-e10.
Raafat K, Wael S. 2018. Phytochemical and biological evaluation of ultrasound-assisted spray dried Lonicera etrusca for potential management of diabetes records of natural products, 12:367-379.
Raafat KM, Omar AG. 2016. Phytotherapeutic activity of curcumol: Isolation, GC-MS identification, and assessing potentials against acute and subchronic hyperglycemia, tactile allodynia, and hyperalgesia. Pharm Biol, 54:1334-1344.
Salama RAM, El Gayar NH, Georgy SS, Hamza M. 2016. Equivalent intraperitoneal doses of ibuprofen supplemented in drinking water or in diet: a behavioral and biochemical assay using antinociceptive and thromboxane inhibitory dose–response curves in mice. Peer J, 4: e2239.
Saleh FA, El-Darra N, Raafat K. 2017. Hypoglycemic effects of Prunus cerasus L. pulp and seed extracts on alloxan-induced diabetic mice with histopathological evaluation. Biomed Pharmacother, 88:870-877.
Shi C, Liu J, Wu F, Yew DT. 2010. Ginkgo biloba extract in Alzheimer's disease: from action mechanisms to medical practice. Int J Mol Sci, 11:107-123.
Sullivan KA, Hayes JM, Wiggin TD, Backus C, Su Oh S, Lentz SI, Brosius F. 3rd, Feldman, EL. 2007. Mouse models of diabetic neuropathy. Neurobiol Dis, 28:276-285.
Taliyan R, Sharma PL. 2012. Protective effect and potential mechanism of Ginkgo biloba extract EGb 761 on STZ-induced neuropathic pain in rats. Phytother Res, 26:1823-1829.
Willoughby DA, DiRosa M. 1972. Studies on the mode of action of non-steroid anti-inflammatory drugs. Ann Rheum Dis, 31:540-551.
Yasmineh WG, Kaur TP, Blazar BR, Theologides A. 1995. Serum catalase as marker of graft-vs-host disease in allogeneic bone marrow transplant recipients: pilot study. Clin Chem, 41: 1574-1580.
Ziegler D. 2008. Treatment of diabetic neuropathy and neuropathic pain: how far have we come? Diabetes Care. 31 Suppl 2: S255-261.
Ziegler D. 2010. [Can diabetic polyneuropathy be successfully treated?]. MMW Fortschr Med, 152:64-68.