Ursolic acid from Agastache mexicana aerial parts produces antinociceptive activity involving TRPV1 receptors, cGMP and a serotonergic synergism

Pharmacology Biochemistry and Behavior

Volumn 110, Issue , 2013, Pages 255-264

  Verano, Jazmín ^a,b   González Trujano, Ma Eva ^a   Déciga Campos, Myrna ^b   Ventura Martínez, Rosa ^c   Pellicer, Francisco ^a  

^a INSTITUTO NACIONAL DE PSIQUIATRÍA RAMÓN DE LA FUENTE MUÑIZ   (Mexico)

^b INSTITUTO POLITÉCNICO NACIONAL   (Mexico)

^c UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

Agastache mexicana; Antinociception; CGMP; Serotonin; TRPV1; Ursolic acid

Indexed keywords

1H 1,2,4 OXADIAZOLO[4,3 A]QUINOXALIN 1 ONE; AGASTACHE MEXICANA EXTRACT; ARGININE; CAPSAICIN; CYCLIC GMP; DICLOFENAC; FLUMAZENIL; N [2 [4 (2 METHOXYPHENYL) 1 PIPERAZINYL]ETHYL] N (2 PYRIDYL)CYCLOHEXANECARBOXAMIDE; N(G) NITROARGININE METHYL ESTER; NALOXONE; NITRIC OXIDE SYNTHASE; PHOSPHODIESTERASE; PLANT EXTRACT; SEROTONIN 1A AGONIST; THEOPHYLLINE; UNCLASSIFIED DRUG; URSOLIC ACID; VANILLOID RECEPTOR 1;

AGASTACHE; AGASTACHE MEXICANA; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIDEPRESSANT ACTIVITY; ANTINOCICEPTION; ARTICLE; CALCIUM TRANSPORT; CONTROLLED STUDY; DRUG EFFICACY; DRUG STRUCTURE; FEMALE; LD 50; MALE; MOUSE; NEUROGENIC INFLAMMATION; NONHUMAN; OPEN FIELD TEST; PRIORITY JOURNAL; SEROTONINERGIC SYSTEM; TRANQUILIZING ACTIVITY; TREATMENT RESPONSE; WRITHING TEST;

AGASTACHE MEXICANA; MUS; RATTUS;

AGASTACHE MEXICANA; ANTINOCICEPTION; CGMP; SEROTONIN; TRPV1; URSOLIC ACID;

ANALGESICS; ANIMALS; CAPSAICIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLIC GMP; FEMALE; FORMALDEHYDE; MALE; MICE; PLANT COMPONENTS, AERIAL; PLANT EXTRACTS; RATS; RATS, WISTAR; SEROTONIN; TRITERPENES; TRPV CATION CHANNELS;

EID: 84886896145     PISSN: 00913057     EISSN: 18735177     Source Type: Journal    
DOI: 10.1016/j.pbb.2013.07.020     Document Type: Article

References (51)

1. Argueta VA, Cano L, Rodarte M. Atlas of plants from Mexican traditional medicine, vol. III. Mexico City: Indigenous National Institute; 19941355-6.
2. Barberán FAT, GillMI. Chemistry and natural distribution of flavonoids in the Labiatae. In: Harley RM, Reynolds T, editors. Advances in Labiatae Science. London: Rojal Botanic Gardens; 1992. p. 299-305.
3. Berrocoso E, Rojas-Corrales MO, Mico JA. Differential role of 5-HT1A and 5-HT1B receptors on the antinociceptive and antidepressant effect of tramadol inmice. Psychopharmacology 2006;188: 111-8. (Pubitemid 44268247)
4. Bye R, Linares E, Ramamoorthy TP, García F, Collera O, Palomino G, Corona V. Agastache mexicana ssp. xolocotziana (Lamiaceae). A new taxon fromMexicanmedicinal plants. Phytologia 1987;62: 156-63.
5. Caterina MJ, Schumacher MA, Makoto T, Tobias AR, Levine JD, Julius D. The capsaicin receptor: a heat-activated ion channel in the pain pathway. Nature 1997;389: 816-24. (Pubitemid 27462969)
6. Caterina MJ, Leffler A, Malmberg AB, MartinWJ, Trafton J, Petersen-Zeitz KR, Koltzenburg M, BasbaumAI, Julius D. Impaired nociception and pain sensation inmice lacking the capsaicin receptor. Science 2000;288: 306-13. (Pubitemid 30226186)
7. Cervero F, Laird JM. Visceral pain. Lancet 1999;353: 2145-8. (Pubitemid 29278493)
8. Cervero F, Laird JM. Understanding the signaling and transmission of visceral nociceptive events. J Neurobiol 2004;61: 45-54. (Pubitemid 39287769)
9. Coderre TJ, Melzack R. The role of NMDA receptor-operated calcium channels in persistent nociception after formalin-induced tissue injury. J Neurosci 1992;12: 3671-5.
10. Collier HOJ, Dinneen LC, Johnson CA, Schneider C. The abdominal constriction response and suppression by analgesic drugs in the mouse. Br J Pharmacol Chemother 1968;32: 295-310.
11. Dray A. Mechanism of action of capsaicin-like molecules on sensory neurons. Life Sci 1992;51: 1759-65.
12. Estrada-Reyes R, Aguirre-Hernández E,García-Argáez A, Soto-HernándezM, Linares E, Bye R, Heinze G, Martínez- Vázquez M. Comparative chemical composition of Agastache mexicana subsp. mexicana and A. mexicana subsp. xolocotziana. Biochem Syst Ecol 2004;32: 685-94. (Pubitemid 38722388)
13. Estrup AO, Andresen T, Louring CL, Upton RN. Translational pain research: evaluating analgesic effect in experimental visceral pain models. World J Gastroenterol 2009;15: 177-81.
14. Ferrer AEH, Hernández EM, Pérez MCS, Basterrechea RM, Fuentes FVR, Torres FM. Aislamiento de ácido ursólico de las hojas de Cestrum laurifolium L'Herit. Rev Cenic Cienc Quím 2005;38: 243-7.
15. González-Ramírez A, González-Trujano ME, Pellicer F, López-Muñoz FJ. Anti-nociceptive and anti-inflammatory activities of the Agastache mexicana extracts by using several experimental models in rodents. J Ethnopharmacol 2012;142: 700-5.
16. González-Trujano ME, Ventura-Martínez R, ChávezM, Díaz-Reval I, Pellicer F. Spasmolytic and antinociceptive activities of ursolic acid and acacetin identified in Agastache mexicana. Planta Med 2012;78: 793-6.
17. Gudi T, Hong GKP, Vaandrager AB, Lohmann SM, Pilz RB. Nitric oxide and cGMP regulate gene expression in neuronal and glial cells by activating type II cGMP-dependent protein kinase. FASEB J 1999;13: 2143-52.
18. Hernández-Abreu O, Castillo-España P, León-Rivera I, Ibarra-Barajas M, Villalobos-Molina R, González-Christen J, Vergara-Galicia J, Estrada-Soto S. Antihypertensive and vasorelaxant effects of tilianin isolated from Agastache mexicana are mediated by NO/cGMP pathway and potassium channel opening. Biochem Pharmacol 2009;78: 54-61.
19. Ibarra-Alvarado C, Rojas A, Mendoza S, Bah M, Gutiérrez DM, Hernández-Sandoval L, Martínez M. Vasoactive and antioxidant activities of plants used in Mexican traditional medicine for the treatment of cardiovascular diseases. Pharm Biol 2010;48: 732-9.
20. Itokawa H, Suto K, Takeya K. Structures of isoagastochoside and agastachin, new glucosylflavones isolated from Agastache rugosa. Chem Pharm Bull 1981;29: 1777-9. (Pubitemid 11053884)
21. Jin Y, Kim J, Kwak J. Activation of the cGMP/protein kinase G pathway by nitric oxide can decrease TRPV1 activity in cultured rat dorsal root ganglion neurons. Korean J Physiol Pharmacol 2012;16: 211-7.
22. Kang SY, Yoon SY, Roh DH, JeonMJ, Seo HS, Uh DK, Kwon YB, KimHW, Han HJ, Lee HJ, Lee JH. The anti-arthritic effect of ursolic acid on zymosan-induced acute inflammation and adjuvant-induced chronic arthritismodels. J PharmPharmacol 2008;60: 1347-54.
23. Kim WM, Yoon MH, Cui JH. Role of PKG-L-type calcium channels in the antinociceptive effect of intrathecal sildenafil. J Vet Sci 2010;11: 103-6.
24. Lagarto A, Bueno V, Martínez A, García R, Lara M, Fernández A, Gabilondo T, Valdés O, Carrillo C. Gastric irritation caused by sodium diclofenac: comparative study of controlled release tablets in rabbits. Rev Toxicol 2008;25: 32-7.
25. Laird JMA, Martinez-Caro L, Garcia-Nicas E, Cervero F. A new model of visceral pain and referred hyperalgesia in the mouse. Pain 2001;92: 335-42. (Pubitemid 32480163)
26. Linares E, Flores B, Bye R. Selection of medicinal plants of Mexico. Mexico City: Limusa; 19881-125.
27. Linares E, Flores B, Bye R. Medicinal plants of Mexico: uses and traditional remedies. 2nd ed.Mexico, City: Electronic and Computer Technology Center and Biology Institute at the National Autonomous University of Mexico; 19951-155.
28. Lorke D. A new approach to practical acute toxicity testing. Arch Toxicol 1983;54: 275-87. (Pubitemid 14205493)
29. Marcon R, Luiz AP, Werner MF, Freitas CS, Baggio CH, Nascimento FP, Soldi C, Pizzolatti MG, Santos AR. Evidence of TRPV1 receptor and PKC signaling pathway in the antinociceptive effect of amyrin octanoate. Brain Res 2009;1295: 76-88.
30. Martínez-Ruíz A, Cadenas S, Lamas S. Nitric oxide signaling: classical, less classical, and nonclassical mechanisms. Free Radic Biol Med 2011;51: 17-29.
31. Millan MJ, Seguin l, Honore P, Girardon S, Bervoets K. Pro- and antinociceptive actions of serotonin 5-HT1A agonists and antagonists in rodents: relationship to algesiometric paradigm. Behav Brain Res 1996;73: 69-77.
32. Miyamoto T, Dubin AE, Petrus MJ, Patapoutian A. TRPV1 and TRPA1 mediate peripheral nitric oxide-induced nociception in mice. PLoS One 2009;410:e7596-7.
33. Molina-Hernández M, Téllez-Alcántara P, Martínez E. Agastache mexicana may produce anxiogenic-like actions in the male rat. Phytomedicine 2000;7: 199-203. (Pubitemid 30415077)
34. Najid A, Simon A, Cook J, Chable-Rabinovitch H, Delage C, Chulia A, Riguad M. Characterization of ursolic acid as a lipoxygenase and cyclooxygenase inhibitor using macrophages, platelets and differentiated HL60 leukemic cells. FEBS Lett 1992;299: 213-7.
35. RigoniM, Trevisani M, Gazzieri D, Nadaletto R, Tognetto M, Creminon Ch, Davis JB, Campi B, Amadesi S, Geppetti P, Harrison S. Neurogenic responses mediated by vanilloid receptor-1 (TRPV1) are blocked by the high affinity antagonist, iodo-resiniferatoxin. Br J Pharmacol 2003;138: 977-85. (Pubitemid 36390655)
36. Romero L, Artigas F. Preferential potentiation of the effects of serotonin uptake inhibitors by 5-HT1A receptor antagonists in the dorsal raphe pathway: role of somatodendritic autoreceptors. J Neurochem 1997;68: 2593-603. (Pubitemid 27218184)
37. Safayhi H, Rall B, Sailer E, Ammon H. Inhibition of boswellic acids of human leucocyte elastase. J Pharmacol Exp Ther 1997;281: 460-3. (Pubitemid 27203102)
38. Sanders RW. Taxonomy of Agastache section Brittonastrum (Lamiaceae-Nepeteae). Syst Bot Monogr 1987;15: 1-92.
39. Santillán RM, López VE, Aguilar RS, Aguilar CA. Etnobotany, leaf architecture, and vegetative anatomy of Agastache mexicana ssp. mexicana and A. mexicana ssp. xolocotziana. Rev Mex Biodivers 2008;79: 513-24.
40. Schmidtko A, Gao W, Sausbier M, Rauhmeier I, Sausbier U, Niederberger E, Scholich K, Huber A, Neuhuber W, Allescher J, Hofmann F, Tegeder I, Ruth P, Geisslinger G. Cysteine-rich protein 2, a novel downstream effector of cGMP/cGMP-dependent protein kinase I-mediated persistent inflammatory pain. J Neurosci 2008;28: 1320-30. (Pubitemid 351231528)
41. Schmidtko A, Tegeder I, Geisslinger G. No NO, no pain? The role of nitric oxide and cGMP in spinal pain processing. Trends Neurosci 2009;32: 339-46.
42. Simpson PJ, Nighorn A,Morton DB. Identification of a novel guanylyl cyclase that is related to receptor guanylyl cyclases, but lacks extracellular and transmembrane domains. J Biol Chem 1999;274: 4440-6.
43. Souter AJ. Nonsteroidal anti-inflammatory drugs. In: White P, editor. Intravenous anesthesia. Baltimore: Williams & Wilkins; 1997. p. 247-58.
44. Suh N, Honda T, Finlay HJ, Barchowsky A, Williams C, Benoit NE, Xie QW, Nathan C, Gribble GW, Sporn MB. Novel triterpenoids suppress inducible nitric oxide synthase (iNOS) and inducible cyclooxygenase (COX-2) in mouse macrophages. Cancer Res 1998;58: 717-23. (Pubitemid 28099483)
45. Tallarida RJ. Dose-response analysis. In: Tallarida RJ, editor. Drug synergism and dose effect data-analysis. New York: Chapman & Hall/CRC; 2000. p. 21-39.
46. TavianoMF, Miceli N,MonforteMT, Tzakou O, Galati EM. Ursolic acid plays a role in Nepeta sibthorpii Bentham CNS depressing effects. Phytother Res 2007;21: 382-5. (Pubitemid 46595986)
47. Ugalde M, Reza V, González-Trujano ME, Avula B, Khan IA, Navarrete A. Isobolographic analysis of the sedative interaction between six central nervous system depressant drugs and Valeriana edulis hydroalcoholic extract in mice. J Pharm Pharmacol 2005;57: 631-9. (Pubitemid 40562402)
48. Wheeler-Aceto H, Cowan A. Standardization of the rat paw formalin test for the evaluation of analgesics. Psychopharmacology 1990;104: 35-44.
49. Yoshida T, Inoue R, Morii T, Takahashi N, Yamamoto S, Hara Y, Tominaga M, Shimizu S, Sato Y, Mori Y. Nitric oxide activates TRP channels by cysteine S-nitrosylation. Nat Chem Biol 2006;2: 596-607. (Pubitemid 44610344)
50. Zhang Y, Sreekrishna K, Lin Y, Huang L, Eickhoff D, Degenhardt C, Xu T. Modulation of transient receptor potential (TRP) channels by Chinese herbal extracts. Phytother Res 2011;25: 1666-70.
51. Zimmermann M. The guidelines on ethical standards for investigation of experimental pain in animals. Pain 1983;16: 109-10. (Pubitemid 13058546)