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Research Article

Synthesis, toxicity study and anti-inflammatory effect of MHTP, a new tetrahydroisoquinoline alkaloid

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Pages 400-412 | Received 09 Apr 2015, Accepted 02 Jul 2015, Published online: 27 Jul 2015

References

  • Phanse MA, Patil MJ, Abbulu K, et al. In-vivo and in-vitro screening of medicinal plants for their anti-inflammatory activity: an overview. J Appl Pharmac Sci 2012;2:19–33
  • Sherwood ER, Toliver-Kinsky T. Mechanisms of the inflammatory response. Best Pract Res Clin Anaesthesiol 2004;18:385–405
  • Krishnamoorthy S, Honn KV. Inflammation and disease progression. Can Metast Rev 2006;25:481–491
  • Pober JS, Sessa WC. Evolving functions of endothelial cells in inflammation. Nat Rev Immunol 2007;7:803–815
  • Medzhitov R. Origin and physiological roles of inflammation. Nature 2008;454:428–435
  • Marcinkiewicz E, Chopicki S, Marcinkiewicz J. Nitric oxide- a pro-inflammatory and anti-inflammatory mediator. Centr Eur J Immunol 2003;28:74–78
  • Medzhitov R. Inflammation 2010: new adventures of an old flame. Cell 2010;140:771–776
  • Enos RT, Davis JM, McClellan JL, et al. Indomethacin in combination with exercise leads to muscle and brain inflammation in mice. J Interferon Cytokine Res 2013;33:446–451
  • Kim HA, Park JH, Lee S, et al. Combined delivery of dexamethasone and plasmid DNA in an animal model of LPS-induced acute lung injury. J Control Release 2011;156:60–69
  • Coutinho AE, Chapman KE. The anti-inflammatory and immunosuppressive effects of glucocorticoids, recent developments and mechanistic insights. Mol Cell Endocrinol 2011;35:2–13
  • Dugowson CE, Gnanashanmugam P. Nonsteroidal anti-inflammatory drugs. Phys Med Rehabil Clin N Am 2006;17:347–354
  • Jenkins C, Costello J, Hodge L. Systematic review of prevalence of aspirin induced asthma and its implications for clinical practice. BMJ 2004;328:434–436
  • Russell MW, Jobes D. What should we do with aspirin, NSAIDs, and glycoprotein-receptor inhibitors? Int Anesthesiol Clin 2002;40:63–76
  • Rostom A, Dube C, Wells G, et al. Prevention of NSAID-induced gastroduodenal ulcers. Cochrane Database Syst Rev 2002;4:CD002296
  • Wong VW, Chan FK. Review: misoprostol or COX-2-specific or selective NSAIDs reduce gastrointestinal complications and symptomatic ulcers. ACP J Club 2005;142:75
  • Brater DC, Harris C, Redfern JS, et al. Renal effects of COX-2-selective inhibitors. Am J Nephrol 2001;21:1–15
  • Weir MR. Renal effects of nonselective NSAIDs and coxibs. Cleve Clin J Med 2002;69:SI53–SI58
  • Krotz F, Schiele TM, Klauss V, et al. Selective COX-2 inhibitors and risk of myocardial in-farction. J Vasc Res 2005;42:312–324
  • Poetker DM, Reh DD. A Comprehensive review of the adverse effects of systemic corticosteroids. Otolaryngol Clin North Am 2010;43:753–768
  • Shaikh S, Verma H, Yadav N, et al. Applications of steroid in clinical practice: a review. ISRN Anesthesiol 2012;2012:985495
  • Fardet L, Kassar A, Cabane J, et al. Corticosteroid-induced adverse events in adults: frequency, screening and prevention. Drug Saf 2007;30:861–881
  • Hirsch IB, Paauw DS. Diabetes management in special situations. Endocrinol Metab Clin North Am 1997;26:631–645
  • Chrousos GP. Adrenocorticosteroids & adrenocortical antagonists. In: Katzung BG, ed. Basic & clinical pharmacology. 10th ed. New York (NY): McGraw-Hill; 2007:635–652
  • Atkinson JB, Kosi M, Srikanth MS, et al. Growth hormone reverses impaired wound healing in protein-malnourished rats treated with corticosteroids. J Pediatr Surg 1992;27:1026–1028
  • Keenan GF. Management of complications of glucocorticoid therapy. Clin Chest Med 1997;18:507–520
  • Allen DB, Bielory L, Derendorf H, et al. Inhaled corticosteroids: past lessons and future issues. J Allergy Clin Immunol 2003;112:S1–S40
  • Ton FN, Gunawardene SC, Lee H, et al. Effects of low-dose prednisone on bone metabolism. J Bone Miner Res 2005;20:464–470
  • Carnahan MC, Goldstein DA. Ocular complications of topical, peri-ocular, and systemic corticosteroids. Curr Opin Ophthalmol 2000;11:478–483
  • Piper J, Ray W, Daugherty J, et al. Corticosteroid use and peptic ulcer disease: role of nonsteroidal anti-inflammatory drugs. Ann Intern Med 1991;114:735–740
  • Wei L, MacDonald TM, Walker BR. Taking glucocorticoids by prescription is associated with subsequent cardiovascular disease. Ann Intern Med 2004;141:764–770
  • Souverein PC, Berard A, Van Staa TP, et al. Use of oral glucocorticoids and risk of cardiovascular and cerebrovascular disease in a population based case-control study. Heart 2004;90:859–865
  • Warrington TP, Bostwick JM. Psychiatric adverse effects of corticosteroids. Mayo Clin Proc 2006;81:1361–1367
  • Kershner P, Wang-Cheng R. Psychiatric side effects of steroid therapy. Psychosomatics 1989;30:135–139
  • Lewis DA, Smith RE. Steroid-induced psychiatric syndromes. J Affect Disord 1983;5:319–332
  • Ojima, I. Mini-perspective: modern natural products chemistry and drug discovery. J Med Chem 2008;51:2587–2588
  • Bhadra K, Kumar GS. Therapeutic potential of nucleic acid-binding isoquinoline alkaloids: binding aspects and implications for drug design. Med Res Rev 2011;31:821–862
  • Clardy J, Walsh C. Lessons from natural molecules. Nature 2004;432:829–837
  • Stöckigt J, Antonchick AP, Wu F, et al. The Pictet–Spengler reaction in nature and in organic chemistry. Angew Chem Int Ed Engl 2011;50:8538–8564
  • Kang YJ, Lee BK, Lee YS, et al. Suppression of tumor necrosis factor-alpha and inducible nitric oxide synthase gene expression by THI 52, a new synthetic naphthylbenzylisoquinoline alkaloid. Biochem Pharmacol 2003;65:457–464
  • Tsoyi K, Kim HJ, Shin JS, et al. HO-1 and JAK2/STAT-1 signals are involved in preferential inhibition of iNOS over COX-2 gene expression by newly synthesized tetrahydroisoquinoline alkaloid, CKD712, in cells activated with lipopolysaccharide. Cell Signal 2008;20:1839–1847
  • Cheng P, Huang N, Jiang ZY, et al. 1-Aryl-tetrahydroisoquinoline analogs as active anti-HIV agents in vitro. Bioorg Med Chem Lett 2008;18:2475–2478
  • Hibbs JB, Taintor RR, Vavrin Z, et al. Nitric oxide: a cytotoxic activated macrophage effector molecule. Bioch Biophys Res Commun 1988;157:87–94
  • Almeida RN, Falcão ACGM, Diniz RST, et al. Metodologia para avaliação de plantas com atividade no Sistema Nervoso Central e alguns dados experimentais. Revista Brasileira de Farmacognosia 1999;80:72–76
  • de Vasconcelos DI, Leite JA, Carneiro LT, et al. Anti-inflammatory and antinociceptive activity of ouabain in mice. Mediators Inflamm 2011;2011:912925
  • Guerra AS, Malta DJ, Laranjeira LP, et al. Anti-inflammatory and antinociceptive activities of indole–imidazolidine derivatives. Int Immunopharmacol 2011;11:1816–1822
  • Pinheiro MM, Fernandes SB, Fingolo CE, et al. Anti-inflammatory activity of ethanol extract and fractions from Couroupita guianensis Aublet leaves. J Ethnopharmacol 2013;146:324–330
  • Sousa LP, Lopes F, Silva DM, et al. PDE4 inhibition drives resolution of neutrophilic inflammation by inducing apoptosis in a PKA-PI3K/Akt-dependent and NF-kappaB-independent manner. J Leukoc Biol 2010;87:895–904
  • Loh TP, Leong SM, Sethi SK. High concentration of IgM-κ paraprotein causes over-estimation of serum total protein by certain biuret method. Clin Chem Lab Med 2013;51:e205–e207
  • Yingkun N, Zhenyu W, Jing L, et al. Stevioside protects LPS-induced acute lung injury in mice. Inflammation 2013;36:242–250
  • Bozza PT, Castro-Faria-Neto HC, Silva AR, et al. Lipopolysaccharide-induced pleural neutrophil accumulation depends on marrow neutrophils and platelet-activating factor. Eur J Pharmacol 1994;270:143–149
  • Green LC, Wagner DA, Glogowski J, et al. Analysis of nitrate, nitrite, and [15N]nitrate in biological fluids. Anal Biochem 1982;126:131–138
  • Bhadra K, Kumar GS. Therapeutic potential of nucleic acid-binding isoquinoline alkaloids: binding aspects and implications for drug design. Med Res Rev 2011;31:821–862
  • Evans WC., ed Trease and Evans pharmacognosy. 16th ed. Edinburgh: WB Saunders; 2009
  • Roberts MF, Wink M. Alkaloids: biochemistry, ecology, and medicinal applications. Nova York: Plenum Press; 1998
  • Gorinsky C, Luscombe DK, Nicholls PJ. Neuromuscular blocking and local anesthetic activities of warifteine hydrochloride, an alkaloid isolated from Cissampelos ovalifolia. J Pharm Pharmacol 1972;24:147–188
  • Côrtes SF, Alencar JL, Thomas G, et al. Spasmolytic actions of warifteine, a bisbenzylquinoline alcaloid isolated from the root bark of Cissampelos sympodialis Eichl. Phytother Res 1995;9:579–583
  • Bezerra-Santos CR, Vieira-de-Abreu A, Barbosa-Filho JM, et al. Anti-allergic properties of Cissampelos sympodialis and its isolated alkaloid warifteine. Int Immunopharmacol 2006;6:1152–1160
  • Ferreira Costa H, Bezerra-Santos CR, Barbosa Filho JM, et al. Warifteine, a bisbenzylisoquinoline alkaloid, decreases immediate allergic and thermal hyperalgesic reactions in sensitized animals. Int Immunopharmacol 2008;8:519–525
  • Baumann H, Gauldie J. The acute phase response. Immunol Today 1994;15:74–80
  • Downton SR, Colten HR. Acute phase reactants in inflammation and infection. Sem Hematol 1988;35:84
  • Ross R. The pathogenesis of atherosclerosis: a perspective for the 1990. Nature 1993;362:801–809
  • Anderson GD. Gender differences in pharmacological response. Int Rev Neurobiol 2008;83:1–10
  • Di Rosa M, Giroud JP, Willoughby DA. Studies on the mediators of the acute inflammatory response induced in rats in different sites by carrageenan and turpentine. J Pathol 1971;104:15–29
  • Di Rosa M, Papadimitriou JM, Willoughby DA. A histopathological and pharmacological analysis of the mode of action of nonsteroidal anti-inflammatory drugs. J Pathol 1971;105:239–256
  • Di Rosa M. Biological properties of carrageenan. J Pharm Pharmacol 1972;24:89–102
  • Garcia Leme J, Hamamura L, Leite MP, et al. Pharmacological analysis of the acute inflammatory process induced in the rat’s paw by local injection of carrageenan and by heating. Br J Pharmacol 1973;48:88–96
  • Posadas I, Bucci M, Roviezzo F, et al. Carrageenan-induced mouse paw oedema is biphasic, age-weight dependent and displays differential nitric oxide cyclooxygenase-2 expression. Br J Pharmacol 2004;142:331–338
  • Guay J, Bateman K, Gordon R, et al. Carrageenan-induced paw edema in rat elicits a predominant prostaglandin E2 (PGE2) response in the central nervous system associated with the induction of microsomal PGE2 synthase-1. J Biol Chem 2004;279:24866–24872
  • Necas J, Bartosikova L. Carrageenan: a review. Vet Med 2013;58:187–205
  • Bhattacharyya S, Dudeja PK, Tobacman JK. Carrageenan-induced NFκB activation depends on distinct pathways mediated by reactive oxygen species and Hsp27 or by Bcl10. Biochim Biophys Acta 2008;1780:973–982
  • Bhattacharyya S, Ravinder G, Chen ML, et al. Toll-like receptor 4 mediates induction of Bcl10-NFκB-IL-8 inflammatory pathway by carrageenan in human intestinal epithelial cells. J Biol Chem 2008;283:10550–10558
  • Damas J, Remacle-Volon G. Influence of a long-acting bradykinin antagonist, Hoe 140, on some acute inflammatory reactions in the rat. Eur J Pharmacol 1992;211:81–86
  • Handy RL, Moore PK. A comparison of the effects of L-NAME, 7-NI and LNIL on carrageenan-induced hindpaw oedema and NOS activity. Br J Pharmacol 1998;123:1119–1126
  • Medeiros MV, Binhara IM, Moreno H, Jr, et al. Effect of chronic nitric oxide synthesis inhibition on the inflammatory responses induced by carrageenan in rats. Eur J Pharmacol 1995;285:109–114
  • Vaz ZR, Filho VC, Yunes RA, et al. Antinociceptive action of 2-(4- bromobenzoyl)-3-methyl-4,6-dimethoxy benzofuran, a novel xanthoxyline derivative on chemical and thermal models of nociception in mice. J Pharmacol Exp Ther 1996;278:304–312
  • Dey I, Lejeune M, Chadee K. Prostaglandin E2 receptor distribution and function in the gastrointestinal tract. Br J Pharmacol 2006;149:611–623
  • Dewitt DL. Prostaglandin endoperoxide synthase: regulation of enzyme expression. Biochim Biophys Acta 1991;1083:121–134
  • Jutel M, Akdis M, Akdis CA. Histamine, histamine receptors and their role in immune pathology. Clin Exp Allergy 2009;39:1786–1800
  • Skidgel RA, Erdös EG. Histamine, bradykinin, and their antagonists. In: Brunton LL, Lazo JS, Parker KL, eds. Goodman & Gilman’s the pharmacological basis of therapeutics. 12th ed. New York: McGraw-Hill; 2010:937–958
  • Tatemoto K, Nozaki Y, Tsuda R, et al. Immunoglobulin E-independent activation of mast cell is mediated by Mrg receptors. Biochem Biophys Res Commun 2006;349:1322–1328
  • Silva VG, Silva RO, Damasceno SR, et al. Anti-inflammatory and antinociceptive activity of epiisopiloturine, an imidazole alkaloid isolated from Pilocarpus microphyllus Valdela. J Nat Prod 2013;276:1071–1077
  • Malech HL, Gallin JI. Current concepts: immunology. Neutrophils in human diseases. N Engl J Med 1987;317:687–694
  • Wheeler AP, Bernard GR. Acute lung injury and the acute respiratory distress syndrome: a clinical review. Lancet 2007;369:1553–1564
  • Raghavendran K, Pryhuber GS, Chess PR, et al. Pharmacotherapy of acute lung injury and acute respiratory distress syndrome. Curr Med Chem 2008;15:1911–1912
  • Leikauf GD, McDowell SA, Wesselkamper SC, et al. Acute lung injury: functional genomics and genetic susceptibility. Chest 2002;121:70S–75S
  • Groeneveld ABJ. Vascular pharmacology of acute lung injury and acute respiratory distress syndrome. Vascul Pharmacol 2003;39:247–256
  • Silliman CC, Voelkel NF, Allard JD, et al. Plasma and lipids from stored packed red blood cells cause acute lung injury in an animal model. J Clin Invest 1998;101:1458–1467
  • Fujihara M, Muroi M, Tanamoto K. Molecular mechanisms of macrophage activation and deactivation by lipopolysaccharide: roles of the receptor complex. Pharmacol Ther 2003;100:171–194
  • Bradley JR. TNF-mediated inflammatory disease. J Pathol 2008;214:149–160
  • Remppis A, Bea F, Greten HJ, et al. Rhizoma coptidis inhibits LPS-induced MCP-1/CCL2 production in murine macrophages via an AP-1 and NF B-dependent pathway. Mediators Inflamm 2010;2010:194896
  • Iyer SS, Ghaffari AA, Cheng G. Lipopolysaccharide-mediated IL-10 transcriptional regulation requires sequential induction of type I IFNs and IL-27 in macrophages. J Immunol 2010;185:6599–6607

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