Planta Med 2010; 76(13): 1411-1418
DOI: 10.1055/s-0029-1240891
Pharmacology
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Chemical Composition and Evaluation of the Anti-Hypernociceptive Effect of the Essential Oil Extracted from the Leaves of Ugni myricoides on Inflammatory and Neuropathic Models of Pain in Mice

Nara L. M. Quintão1 , Gislaine F. da Silva1 , Carla S. Antonialli1 , Lilian W. Rocha1 , Valdir Cechinel Filho1 , José F. Cicció2
  • 1Programa de Mestrado em Ciências Farmacêuticas and Núcleo de Investigações Químico-Farmacêuticas (NIQFAR), CCS, Universidade do Vale do Itajaí (UNIVALI), Itajaí-SC, Brazil
  • 2Centro de Investigaciones en Productos Naturales (CIPRONA) and Escuela de Química, Universidad de Costa Rica, Ciudad Universitaria Rodrigo Facio, San José, Costa Rica
Weitere Informationen

Publikationsverlauf

received August 12, 2009 revised January 20, 2010

accepted January 24, 2010

Publikationsdatum:
15. Februar 2010 (online)

Abstract

The study analyzes the chemical composition of the essential oil obtained from the leaves of Ugni myricoides (Kunth) O. Berg (U. myricoides EO). The composition of the essential oil was characterized by GC‐FID and GC‐MS analysis, showing at least six major constituents: α-pinene (52.1 %), 1,8-cineole (11.9 %), α-humulene (4.6 %), caryophyllene oxide + globulol (4.5 %), humulene epoxide II (4.2 %) and β-caryophyllene (2.9 %). It demonstrates for the first time the systemic anti-hypernociceptive properties of this orally administered oil in inflammatory and neuropathic models of hypernociception in mice. The effects of U. myricoides EO and its major constituent, α-pinene, were compared with those of indomethacin or gabapentin, drugs used clinically to treat inflammatory and neuropathic processes. Like indomethacin (5 or 10 mg/kg, p. o.), U. myricoides EO (5–50 mg/kg, p. o.) was able to significantly prevent mechanical hypernociception induced by carrageenan or complete Freund's adjuvant (CFA) in mice. These effects were observed for up to 48 h after i.pl. injection of flogistic agents. Repeated treatment with U. myricoides EO (5–25 mg/kg, p. o.), α-pinene (5–50 mg/kg, p. o.), or gabapentin (70 mg/kg, p. o.) also abolished the mechanical sensitization induced by CFA, or following the partial ligation of the sciatic nerve (PLSN). The present results indicate that U. myricoides EO produces marked anti-hypernociceptive effects in carrageenan and CFA mechanical sensitization models, and also inhibited neuropathic pain-like behavior after PLSN with efficacy similar to that observed for indomethacin or gabapentin. The relevant effects shown by U. myricoides EO are related, at least in part, to the presence of α-pinene and may be of potential interest for the management of inflammatory and neuropathic pain.

References

  • 1 Wilson P G, O'Brien M M, Gadek P A, Quinn C J. Myrtaceae revisited: a reassessment of infrafamilial groups.  Am J Bot. 2001;  88 2013-2025
  • 2 Auricchio M T, Bacchi E. Folha de Eugenia uniflora L. (Pitanga): propriedades farmacobotânicas, químicas e farmacológicas.  Rev Inst Adolfo Lutz. 2003;  62 55-61
  • 3 Santos F A, Rao V S N, Silveira E R. Investigations on the antinociceptive effect of Psidium guajava leaf essential oil and its major constituents.  Phytother Res. 1998;  12 24-27
  • 4 Ojewole J A. Antiinflammatory and analgesic effects of Psidium guajava Linn. (Myrtaceae) leaf aqueous extract in rats and mice.  Methods Find Exp Clin Pharmacol. 2006;  28 441-446
  • 5 Avila-Peña D, Peña N, Quintero L, Suárez-Roca H. Antinociceptive activity of Syzygium jambos leaves extract on rats.  J Ethnopharmacol. 2007;  112 380-385
  • 6 Serafin C, Nart V, Malheiros A, de Souza M M, Fischer L, Delle Monache G, Della Monache F, Cechinel Filho V. Bioactive phenolic compounds from aerial parts of Plinia glomerata.  Z Naturforsch C. 2007;  62 196-200
  • 7 McVaugh R. Flora of Peru: Myrtaceae.  Bot Ser Field Museum Nat History. 1958;  13 569-819
  • 8 Rosário A S, Secco R S, da Silva J B F. Notas sobre Ugni Turcz. (Myrtaceae) na Amazônia Brasileira.  Acta Amazonica. 2004;  34 139-141
  • 9 León J, Poveda L J. Los nombres comunes de las plantas en Costa Rica. San José; Guayacán 2000: 586
  • 10 Aguirre M C, Delporte C, Backhouse N, Erazo S, Letelier M E, Cassels B K, Silva X, Alegría S, Negrete R. Topical anti-inflammatory activity of 2alpha-hydroxy pentacyclic triterpene acids from the leaves of Ugni molinae.  Bioorg Med Chem. 2006;  14 5673-5677
  • 11 Delporte C, Backhouse N, Inostroza V, Aguirre M C, Peredo N, Silva X, Negrete R, Miranda H F. Analgesic activity of Ugni molinae (murtilla) in mice models of acute pain.  J Ethnopharmacol. 2007;  112 162-165
  • 12 van den Dool H, Kratz P D. A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography.  J Chromatogr A. 1963;  11 463-471
  • 13 Adams R P. Identification of essential oil components by gas chromatography/quadrupole mass spectroscopy, 4th edition. Carol Stream, IL; Allured 2007
  • 14 Quintão N L, Medeiros R, Santos A R, Campos M M, Calixto J B. The effects of diacerhein on mechanical allodynia in inflammatory and neuropathic models of nociception in mice.  Anesth Analg. 2005;  101 1763-1769
  • 15 Bortalanza L B, Ferreira J, Hess S C, Delle Monache F, Yunes R A, Calixto J B. Anti-allodynic action of the tormentic acid, a triterpene isolated from plant, against neuropathic and inflammatory persistent pain in mice.  Eur J Pharmacol. 2002;  453 203-208
  • 16 Pichersky E, Noel J P, Dudareva N. Biosynthesis of plant volatiles: nature's diversity and ingenuity.  Science. 2006;  311 808-811
  • 17 Başer K H C, Demirci F. Chemistry of essential oils. Berger RG Flavours and fragrances. Chemistry, bioprocessing and sustainability. Berlin; Springer 2007
  • 18 Wagner K H, Elmadfa I. Biological relevance of terpenoids. Overview focusing on mono-, di- and tetraterpenes.  Ann Nutr Metab. 2003;  47 95-106
  • 19 Spracklen D V, Bonn B, Carslaw K S. Boreal forests, aerosols and the impacts on clouds and climate.  Philos Transact A Math Phys Eng Sci. 2008;  366 4613-4626
  • 20 Cunha T M, Verri Jr W A, Silva J S, Poole S, Cunha F Q, Ferreira S H. A cascade of cytokines mediates mechanical inflammatory hypernociception in mice.  Proc Natl Acad Sci USA. 2005;  102 1755-1760
  • 21 Chan C F, Sun W Z, Lin J K, Lin-Shiau S Y. Activation of transcription factors of nuclear factor kappa B, activator protein-1 and octamer factors in hyperalgesia.  Eur J Pharmacol. 2000;  402 61-68
  • 22 Mendell J R, Sahenk Z. Painful sensory neuropathy.  N Engl J Med. 2003;  348 1243-1255
  • 23 Sommer C, Kress M. Recent findings on how proinflammatory cytokines cause pain: peripheral mechanisms in inflammatory and neuropathic hyperalgesia.  Neurosci Lett. 2004;  361 184-187
  • 24 Orhan I, Küpeli E, Aslan M, Kartal M, Yesilada E. Bioassay-guided evaluation of anti-inflammatory and antinociceptive activities of pistachio, Pistacia vera L.  J Ethnopharmacol. 2006;  105 235-240
  • 25 Manuele M G, Ferraro G, Anesini C. Effect of Tilia x viridis flower extract on the proliferation of a lymphoma cell line and on normal murine lymphocytes: contribution of monoterpenes, especially limonene.  Phytother Res. 2008;  22 1520-1526
  • 26 Santos F A, Rao V S. Antiinflammatory and antinociceptive effects of 1,8-cineole a terpenoid oxide present in many plant essential oils.  Phytother Res. 2000;  14 240-244
  • 27 Santos F A, Silva R M, Tomé A R, Rao V S, Pompeu M M, Teixeira M J, De Freitas L A, De Souza V L. 1,8-Cineole protects against liver failure in an in-vivo murine model of endotoxemic shock.  J Pharm Pharmacol. 2001;  53 505-511
  • 28 Liapi C, Anifandis G, Chinou I, Kourounakis A P, Theodosopoulos S, Galanopoulou P. Antinociceptive properties of 1,8-Cineole and beta-pinene, from the essential oil of Eucalyptus camaldulensis leaves, in rodents.  Planta Med. 2007;  73 1247-1254
  • 29 Chao L K, Hua K F, Hsu H Y, Cheng S S, Liu J Y, Chang S T. Study on the antiinflammatory activity of essential oil from leaves of Cinnamomum osmophloeum.  J Agric Food Chem. 2005;  53 7274-7278
  • 30 da Silva S L, Figueiredo P M, Yano T. Chemotherapeutic potential of the volatile oils from Zanthoxylum rhoifolium Lam leaves.  Eur J Pharmacol. 2007;  576 180-188
  • 31 Fernandes E S, Passos G F, Medeiros R, da Cunha F M, Ferreira J, Campos M M, Pianowski L F, Calixto J B. Anti-inflammatory effects of compounds alpha-humulene and (−)-trans-caryophyllene isolated from the essential oil of Cordia verbenacea.  Eur J Pharmacol. 2007;  569 228-236
  • 32 Medeiros R, Passos G F, Vitor C E, Koepp J, Mazzuco T L, Pianowski L F, Campos M M, Calixto J B. Effect of two active compounds obtained from the essential oil of Cordia verbenacea on the acute inflammatory responses elicited by LPS in the rat paw.  Br J Pharmacol. 2007;  151 618-627
  • 33 Menezes I A, Marques M S, Santos T C, Dias K S, Silva A B, Mello I C, Lisboa A C, Alves P B, Cavalcanti S C, Marçal R M, Antoniolli A R. Antinociceptive effect and acute toxicity of the essential oil of Hyptis fruticosa in mice.  Fitoterapia. 2007;  78 192-195
  • 34 Passos G F, Fernandes E S, da Cunha F M, Ferreira J, Pianowski L F, Campos M M, Calixto J B. Anti-inflammatory and anti-allergic properties of the essential oil and active compounds from Cordia verbenacea.  J Ethnopharmacol. 2007;  110 323-333
  • 35 Lin C T, Chen C J, Lin T Y, Tung J C, Wang S Y. Anti-inflammation activity of fruit essential oil from Cinnamomum insularimontanum Hayata.  Bioresour Technol. 2008;  99 8783-8787
  • 36 Sousa O V, Silvério M S, Del-Vechio-Vieira G, Matheus F C, Yamamoto C H, Alves M S. Antinociceptive and anti-inflammatory effects of the essential oil from Eremanthus erythropappus leaves.  J Pharm Pharmacol. 2008;  60 771-777
  • 37 Takaki I, Bersani-Amado L E, Vendruscolo A, Sartoretto S M, Diniz S P, Bersani-Amado C A, Cuman R K. Anti-inflammatory and antinociceptive effects of Rosmarinus officinalis L. essential oil in experimental animal models.  J Med Food. 2008;  11 741-746

Prof. N. L. M. Quintão

Programa de Mestrado em Ciências Farmacêuticas
Universidade do Vale do Itajaí

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