Abstract
The antinociceptive activity of icariside E4, a dihydrobenzofuran-type lignan isolated from Tabebuia roseo-alba (Ridley) Sandwith (Bignoniaceae) bark, was evaluated in mice by using chemical and thermal models of nociception. Intraperitoneal (i.p.) administration of crude T. roseo-alba bark extract and its methanol fraction inhibited acetic acid-induced abdominal constriction in mice. Furthermore, i.p. administration of 0.1, 1, and 10 mg/kg of icariside E4 reduced the number of writhes evoked by acetic acid injection by 46.9, 82.3, and 66.6 %, respectively. Icariside E4 administration had no effect in the first phase of the formalin test, but it reduced nociceptive behavior in the second phase as indicated by a reduction in the licking time. Icariside E4 did not modify thermal nociception in the hot-plate test model, suggesting that it had a peripheral antinociceptive action. The antinociceptive effect of icariside E4 in the writhing test was reversed by pre-administration of glibenclamide, but not of naloxone, atropine, yohimbine, or haloperidol. Together, these results indicated that the antinociceptive activity of icariside E4 from T. roseo-alba in models of chemical pain occurred through ATP-sensitive K+ channel-dependent mechanisms.
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References
Abreul, M.B., A. Temraz, A. Vassalo, A. Braca, and N. Tommasi. 2014. Phenolic glycoside from Tabebuia agentea and Catalpa bignoioides. Phytochemistry Letters 7: 85–88.
Ahmed, F., M.H. Hossain, A.A. Rahman, and I.Z. Shahid. 2006. Antinociceptive and sedative effects of the bark of Cerbera odollam Gaertn. Oriental Pharmacy and Experimental Medicine 6: 344–348.
Alves, D.P., M.A. Tatsuo, R. Leite, and I.D. Duarte. 2004. Diclofenac-induced peripheral antinociception is associated with ATP-sensitive K+ channels activation. Life Sciences 74: 2577–2591.
De Barros, B.S., J.P. Da Silva, J.N. De Souza Ferro, I.K. Agra, F. De Almeida Brito, E.D. Albuquerque, L.C. Caetano, and E. Barreto. 2011. Methanol extract from mycelium of endophytic fungus Rhizoctonia sp. induces antinociceptive and anti-inflammatory activities in mice. Journal of Natural Medicines 65: 526–531.
De Oliveira, A.M., L.M. Conserva, J.N. De Souza, F. De Almeida, R.P. Lyra Lemos, and E. Barreto. 2012. Antinociceptive and anti-inflammatory effects of octacosanol from the leaves of Sabicea grisea var. grisea in mice. International Journal of Molecular Sciences 13: 1598–1611.
Degan, P., I.B. de Aguiar, R. Sader, D. Perecin, and L.R. Pinto. 2001. The influence of drying methods on the conservation of Tabebuia roseo-alba (Ridl.) Sand. seeds. Revista Brasileira de Engenharia Agrícola e Ambiental 5(3): 492–496.
Dirig, D.M., P.C. Isakson, and T.L. Yaksh. 1998. Effect of COX-1 and COX-2 inhibition on induction and maintenance of carrageenan-evoked thermal hyperalgesia in rats. Journal of Pharmacology and Experimental Therapeutics 285: 1031–1038.
Ferro, J.N.D., J.P. Da Silva, L.M. Conserva, and E. Barreto. 2013. Leaf extract from Clusia nemorosa induces an antinociceptive effect in mice via a mechanism that is adrenergic systems dependent. Chinese Journal of Natural Medicines 11: 385–390.
Gaetti-Jardim Jr, E., L.F. Landucci, E.C Geatti-Jardim, J. Sangalli, and F.R.N. Souza. 2009. Inhibitory activity of extracts of the Brazilian Cerrado on anaerobic microorganisms and associated with nosocomial infections. Revista Brasileira de Ciências da Saúde 13: 43–52.
Garcia-Munoz, S., A.M. Corral, L.J. Gonzalez, C.L. Sánchez, A. Rosales, M.M. Dorado, and I.R. Garcia. 2006. Synthesis of dihydrodehydrodiconiferyl alcohol and derivatives through intramolecular C-H insertion. Tetrahedron Letters 62: 12182–12190.
Gomez, R., E.D. Por, K.A. Berg, W.P. Clarke, M.J. Glucksman, and N.A. Jeske. 2011. Metallopeptidase inhibition potentiates bradykinin-induced hyperalgesia. Pain 152: 1548–1554.
In, S.J., K.H. Seo, N.Y. Song, D.S. Lee, Y.C. Kim, and N.I. Beak. 2014. Lignans and neolignans from the stems of Vibrunum erosum and their neuroprotective and anti-inflammatory activity. Archives of pharmacal research. doi:10.1007/s12272-014-0358-9.
Iorizzi, M., V. Lanzotti, S. De Marino, F. Zollo, M. Blanco-Molina, A. Macho, and E. Munoz. 2001. New glycosides from Capsicum annuum L. var. acuminatum. Isolation, structure determination, and biological activity. Journal of Agriculture and Food Chemistry 49: 2022–2029.
Kim, C.S., O.W. Kwon, S.Y. Kim, and K.R. Lee. 2013. Bioactive lignans from the trunk of Abies holophylla. Journal of Natural Products 76: 2131–2135.
Miyase, T., A. Ueno, N. Takizawa, H. Kobayashi, and H. Oguchi. 1989. Ionone and lignan glycosides from Epimedium diphyllum. Phytochemistry 28: 3483–3485.
Mukherjee, T., S. Chowdhury, A. Kumar, H.K. Majumder, P. Jaisankar, and S. Mukhopadhyay. 2012. Saracoside: a new lignan glycoside from Saraca indica, a potential inhibitor of DNA topoisomerase IB. Natural Products Communications 7: 767–769.
Ocana, M., C.M. Cendan, E.J. Cobos, J.M. Entrena, and J.M. Baeyens. 2004. Potassium channels and pain: present realities and future opportunities. European Journal of Pharmacology 500: 203–219.
Ortiz, M.I., J.E. Torres-Lopez, G. Castaneda-Hernandez, R. Rosas, G.C. Vidal-Cantu, and V. Granados-Soto. 2002. Pharmacological evidence for the activation of K(+) channels by diclofenac. European Journal of Pharmacology 438: 85–91.
Park, S.H., Y.B. Sim, Y.J. Kang, S.S. Kim, C.H. Kim, S.J. Kim, and H.W. Suh. 2013. Mechanisms involved in the antinociceptive effects of orally administered oleanolic acid in the mouse. Archives of Pharmacal Research 36: 905–911.
Rodrigues, A.R., and I.D. Duarte. 2000. The peripheral antinociceptive effect induced by morphine is associated with ATP-sensitive K(+) channels. British Journal of Pharmacology 129: 110–114.
Sichaem, J., S. Kaennakam, P. Siripong, and S. Tip-Pyang. 2012. Tabebuialdehydes A-C, cyclopentene dialdehyde derivatives from the roots of Tabebuia rosea. Fitoterapia 83: 1456–1459.
Tjolsen, A., O.G. Berge, S. Hunskaar, J.H. Rosland, and K. Hole. 1992. The formalin test: an evaluation of the method. Pain 51: 5–17.
Warashina, T., Y. Nagatani, and T. Noro. 2004. Constituents from the bark of Tabebuia impetiginosa. Phytochemistry 65: 2003–2011.
Warashina, T., Y. Nagatani, and T. Noro. 2005. Further constituents from the bark of Tabebuia impetiginosa. Phytochemistry 66: 589–597.
Woo, K.W., S.U. Choi, J.C. Park, and K.R. Lee. 2011. A new lignan glycoside from Juniperus rigida. Archives of Pharmacal Research 34: 2043–2049.
Woolf, C.J. 2004. Pain: Moving from symptom control toward mechanism-specific pharmacologic management. Annals of Internal Medicine 140(6): 441–451.
Ye, Y., M. Li, and X. Chen. 2013. Purification and characterization of a novel antinociceptive peptide from venom of Agkistrodon halys Pallas. Archives of Pharmacal Research 36: 448–456.
Acknowledgments
This project was supported by the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), the Programa de Cooperação Acadêmica/Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (PROCAD/CAPES) and the Fundação de Amparo à Pesquisa do Estado de Alagoas (FAPEAL) (Brazil).
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Ferreira-Júnior, J.C., Conserva, L.M., Lyra Lemos, R.P. et al. Isolation of a dihydrobenzofuran lignan, icariside E4, with an antinociceptive effect from Tabebuia roseo-alba (Ridley) Sandwith (Bignoniaceae) bark. Arch. Pharm. Res. 38, 950–956 (2015). https://doi.org/10.1007/s12272-014-0468-4
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DOI: https://doi.org/10.1007/s12272-014-0468-4