Skip to main content
Erschienen in: Inflammopharmacology 3/2011

01.06.2011 | Research Article

Anti-inflammatory and analgesic effects of 6α,7β–dihydroxy-vouacapan-17β-oic acid isolated from Pterodon emarginatus Vog. fruits

verfasst von: Camila Benatti Galceran, Jayme Antonio Aboin Sertie, Clarissa Silva Lima, José Carlos Tavares Carvalho

Erschienen in: Inflammopharmacology | Ausgabe 3/2011

Einloggen, um Zugang zu erhalten

Abstract

6α,7β-dihydroxy-vouacapan-17β-oic (tricyclic furanoid diterpene; DHVO) acid was isolated from the hexane extract of Pterodon emarginatus fruits and evaluated for anti-inflammatory and analgesic effects using an assay that induces paw oedema with carrageenan, dextran and prostaglandin E2 (PGE2) in rats and the writhing and formalin tests in mice. Oral administration of 50 mg/kg DHVO significantly inhibited carrageenan-induced oedema formation by 24% (p < 0.05). This treatment did not inhibit dextran-induced oedema but was effective when the inflammatory effect was triggered by PGE2, inhibiting oedema formation by 39% (p < 0.05). In the writhing test, doses of 50, 200 and 400 mg/kg resulted in a dose-dependent effect with a correlation coefficient (r) of 0.983 (F = 29.04, ANOVA). Doses of 50 and 100 mg/kg inhibited both the neurogenic and inflammatory phases (p < 0.05) in the formalin test but were not effective for increasing the lag time in the hot plate test. Together, these results suggest that DHVO has both anti-inflammatory and peripheral analgesic effects.
Literatur
Zurück zum Zitat Brás Filho R, Gottlieb OR, Assumpção RMV (1971) Chemistry of Brazilian Leguminosae. XXXIV isoflavones of Pterodon pubenscens. Phytochemistry 10:2835–2836CrossRef Brás Filho R, Gottlieb OR, Assumpção RMV (1971) Chemistry of Brazilian Leguminosae. XXXIV isoflavones of Pterodon pubenscens. Phytochemistry 10:2835–2836CrossRef
Zurück zum Zitat Campos AM, Craveiro AA, Teixeira TC (1990) Óleo essencial das sementes de Pterodon polygalaeflorus Bent. In: Resumos da Reunião da Sociedade Brasileira de Química PN-004 Campos AM, Craveiro AA, Teixeira TC (1990) Óleo essencial das sementes de Pterodon polygalaeflorus Bent. In: Resumos da Reunião da Sociedade Brasileira de Química PN-004
Zurück zum Zitat Campos AM, Silveira ER, Braz-Filho R, Teixeira TC (1994) Diterpenoids from Pterodon polygalaeflorus. Phytochemistry 36:403–406CrossRef Campos AM, Silveira ER, Braz-Filho R, Teixeira TC (1994) Diterpenoids from Pterodon polygalaeflorus. Phytochemistry 36:403–406CrossRef
Zurück zum Zitat Carvalho JCT, Sertié JAA, Barbosa MVJ, Patrício KCM, Caputo LRG, Sarti SJ, Ferreira LR, Bastos JK (1999) Anti-inflammatory activity of the crude extract from the fruits of Pterodon emarginatus Vog. J Ethnopharmacol 64:127–133PubMedCrossRef Carvalho JCT, Sertié JAA, Barbosa MVJ, Patrício KCM, Caputo LRG, Sarti SJ, Ferreira LR, Bastos JK (1999) Anti-inflammatory activity of the crude extract from the fruits of Pterodon emarginatus Vog. J Ethnopharmacol 64:127–133PubMedCrossRef
Zurück zum Zitat Coderre TJ, Fundytus ME, McKenna JE, Dalal S, Melzack R (1993) The formalin test: a validation of the weighted-scores method of behavioural pain rating. Pain 54:43–50PubMedCrossRef Coderre TJ, Fundytus ME, McKenna JE, Dalal S, Melzack R (1993) The formalin test: a validation of the weighted-scores method of behavioural pain rating. Pain 54:43–50PubMedCrossRef
Zurück zum Zitat Correa MP (1984) Dicionário das plantas úteis do Brasil e das exóticas cultivadas. Ministério da Agricultura (IBDF), Rio de Janeiro, p 153 Correa MP (1984) Dicionário das plantas úteis do Brasil e das exóticas cultivadas. Ministério da Agricultura (IBDF), Rio de Janeiro, p 153
Zurück zum Zitat Dalles R, Raboisson P, Clavelou P, Saade M, Woda A (1995) Evidence for a peripheral origin of the tonic nociceptive response to subcutaneous formalin. Pain 61:11–16CrossRef Dalles R, Raboisson P, Clavelou P, Saade M, Woda A (1995) Evidence for a peripheral origin of the tonic nociceptive response to subcutaneous formalin. Pain 61:11–16CrossRef
Zurück zum Zitat Deraedt R, Jouquey S, Delevallee F, Flahaut M (1980) Release of prostaglandins E and F in an algogenic reaction and its inhibition. Eur J Pharmacol 61:17–24PubMedCrossRef Deraedt R, Jouquey S, Delevallee F, Flahaut M (1980) Release of prostaglandins E and F in an algogenic reaction and its inhibition. Eur J Pharmacol 61:17–24PubMedCrossRef
Zurück zum Zitat Dos Santos Filho D, Vichnewski W, Baker PM, Gilbert B (1972) Prophylaxis of Schistosomiaris. Diterpenes from pterodon pubenscens. Anais da Acadêmia Brasileira de Ciências 44:45–49 Dos Santos Filho D, Vichnewski W, Baker PM, Gilbert B (1972) Prophylaxis of Schistosomiaris. Diterpenes from pterodon pubenscens. Anais da Acadêmia Brasileira de Ciências 44:45–49
Zurück zum Zitat Duarte IDG, Nakamura M, Ferreira SH (1988) Participation of the sympathetic system in acetic acid induced writhing in mice. Br J Med Biol Res 21:341–343 Duarte IDG, Nakamura M, Ferreira SH (1988) Participation of the sympathetic system in acetic acid induced writhing in mice. Br J Med Biol Res 21:341–343
Zurück zum Zitat Dubuisson D, Dennis SG (1977) The formalin test: a quantitative study of the analgesic effects of morphine, meperidine and brain stem stimulation in rats and cats. Pain 4:161–174PubMedCrossRef Dubuisson D, Dennis SG (1977) The formalin test: a quantitative study of the analgesic effects of morphine, meperidine and brain stem stimulation in rats and cats. Pain 4:161–174PubMedCrossRef
Zurück zum Zitat Esteves I, Souza IR, Rodrigues M, Cardoso LGV, Santos LS, Sertie JAA, Perazzo FF, Lima LM, Schneedorf JM, Bastos JK, Carvalho JCT (2005) Gastric antiulcer and anti-inflammatory activities of the essential oil from Casearia sylvestris Sw. J Ethnopharmacol 101:191–196PubMedCrossRef Esteves I, Souza IR, Rodrigues M, Cardoso LGV, Santos LS, Sertie JAA, Perazzo FF, Lima LM, Schneedorf JM, Bastos JK, Carvalho JCT (2005) Gastric antiulcer and anti-inflammatory activities of the essential oil from Casearia sylvestris Sw. J Ethnopharmacol 101:191–196PubMedCrossRef
Zurück zum Zitat Fascio M, Gilbert B, Mors WB, Nishida T (1970) Two new diterpenes from Pterodon pubenscens. Anais da Academia Brasileira de Ciências 42:97–101 Fascio M, Gilbert B, Mors WB, Nishida T (1970) Two new diterpenes from Pterodon pubenscens. Anais da Academia Brasileira de Ciências 42:97–101
Zurück zum Zitat Fascio M, Mors W, Gilbert B, Mahajan MB, Monteiro MB, dos Santos Filho D, Vichnewski W (1976) Diterpenoid Furans from Pterodon species. Phytochem 15:201–203CrossRef Fascio M, Mors W, Gilbert B, Mahajan MB, Monteiro MB, dos Santos Filho D, Vichnewski W (1976) Diterpenoid Furans from Pterodon species. Phytochem 15:201–203CrossRef
Zurück zum Zitat Jacob JJC, Ramabadran K (1978) Enhancement of a nociceptive reaction by opiate antagonist in mice. Br J Pharmacol 64:91–98PubMed Jacob JJC, Ramabadran K (1978) Enhancement of a nociceptive reaction by opiate antagonist in mice. Br J Pharmacol 64:91–98PubMed
Zurück zum Zitat Koster R, Anderson M, Beer EJ (1959) Acetic acid for analgesic screening. Fed Proc 18:412 Koster R, Anderson M, Beer EJ (1959) Acetic acid for analgesic screening. Fed Proc 18:412
Zurück zum Zitat Le Bars D, Gozariu M, Cadden SW (2001) Animal models of nociception. Pharmacol Rev 53:597–652PubMed Le Bars D, Gozariu M, Cadden SW (2001) Animal models of nociception. Pharmacol Rev 53:597–652PubMed
Zurück zum Zitat Leite de Almeida ME, Gottlieb OR (1975) The chemistry of Brazilian leguminosae. Further isoflavones from Pterodon apparicia. Phytochem 14:2716CrossRef Leite de Almeida ME, Gottlieb OR (1975) The chemistry of Brazilian leguminosae. Further isoflavones from Pterodon apparicia. Phytochem 14:2716CrossRef
Zurück zum Zitat Mahajan JR, Monteiro MB (1973) New diterpenoids from Pterodon emarginatus Vog. J Chem Soc-Perkin Trans 1:520–525CrossRef Mahajan JR, Monteiro MB (1973) New diterpenoids from Pterodon emarginatus Vog. J Chem Soc-Perkin Trans 1:520–525CrossRef
Zurück zum Zitat Mahjan JR, Monteiro MB (1970) New diterpenoids from Pterodon emarginatus. Anais da Academia Brasileira de Ciências 42:103–107 Mahjan JR, Monteiro MB (1970) New diterpenoids from Pterodon emarginatus. Anais da Academia Brasileira de Ciências 42:103–107
Zurück zum Zitat McCall WD, Tanner KD, Levine JD (1996) Formalin induces biphasic activity in C-fibers in the rat. Neurosc Lett 208:45–48CrossRef McCall WD, Tanner KD, Levine JD (1996) Formalin induces biphasic activity in C-fibers in the rat. Neurosc Lett 208:45–48CrossRef
Zurück zum Zitat Mors WB, dos Santos MF, Monteiro HB (1967) Chemoprophyloactic agent in schistosomiasis: 14, 15-epoxygeranylgeraniol. Science 157:950–951PubMedCrossRef Mors WB, dos Santos MF, Monteiro HB (1967) Chemoprophyloactic agent in schistosomiasis: 14, 15-epoxygeranylgeraniol. Science 157:950–951PubMedCrossRef
Zurück zum Zitat Nunan EA (1985) Estudo da atividade antiinflamatória de furano-diterpeno isolados de Pterodon polygalaeflorus Benth e de alguns de seus derivados. Tese de Doutorado. Departamento de Química. UFMG, Belo Horizonte, Minas Gerais, p 129 Nunan EA (1985) Estudo da atividade antiinflamatória de furano-diterpeno isolados de Pterodon polygalaeflorus Benth e de alguns de seus derivados. Tese de Doutorado. Departamento de Química. UFMG, Belo Horizonte, Minas Gerais, p 129
Zurück zum Zitat Okpo SO, Fatokun F, Adeyemi OO (2001) Analgesic and anti-inflammatory activity of Crinum glaucum aqueous extract. J Ethnopharmacol 78:207–211PubMedCrossRef Okpo SO, Fatokun F, Adeyemi OO (2001) Analgesic and anti-inflammatory activity of Crinum glaucum aqueous extract. J Ethnopharmacol 78:207–211PubMedCrossRef
Zurück zum Zitat Perazzo FF, Lima LM, Padilha MM, Rocha LM, Sousa PJC, Carvalho JCT (2008) Anti-inflammatory and analgesic activities of Hypericum brasiliense (Willd) standardized extract. Rev bras farmacogn 18:320–325 Perazzo FF, Lima LM, Padilha MM, Rocha LM, Sousa PJC, Carvalho JCT (2008) Anti-inflammatory and analgesic activities of Hypericum brasiliense (Willd) standardized extract. Rev bras farmacogn 18:320–325
Zurück zum Zitat Puig S, Sorkin LS (1996) Formalin-evoked activity in identified primary afferent fibers: systemic lidocaine suppresses phase-2 activity. Pain 64:345–355PubMedCrossRef Puig S, Sorkin LS (1996) Formalin-evoked activity in identified primary afferent fibers: systemic lidocaine suppresses phase-2 activity. Pain 64:345–355PubMedCrossRef
Zurück zum Zitat Shibata M, Ohkubo T, Takahashi H, Inoki R (1989) Modified formalin test: characteristic biphasic pain response. Pain 38:347–352PubMedCrossRef Shibata M, Ohkubo T, Takahashi H, Inoki R (1989) Modified formalin test: characteristic biphasic pain response. Pain 38:347–352PubMedCrossRef
Zurück zum Zitat Taylor BK, Peterson MA, Basbaum AI (1995) Persistent cardiovascular and behavioral nociceptive responses to subcutaneous formalin require peripheral nerve input. J Neurosc 15:7575–7584 Taylor BK, Peterson MA, Basbaum AI (1995) Persistent cardiovascular and behavioral nociceptive responses to subcutaneous formalin require peripheral nerve input. J Neurosc 15:7575–7584
Zurück zum Zitat Taylor BK, Peterson MA, Basbaum AI (1997) Early nociceptive events influence the temporal profile, but not the magnitude, of the tonic response to subcutaneous formalin: effects with remifentanyl. J Pharmacol Exp Ther 280:876–883PubMed Taylor BK, Peterson MA, Basbaum AI (1997) Early nociceptive events influence the temporal profile, but not the magnitude, of the tonic response to subcutaneous formalin: effects with remifentanyl. J Pharmacol Exp Ther 280:876–883PubMed
Zurück zum Zitat Teixeira TC, Campos AM, Silveira ER (1991). Isolamento do ácido 6α,7β-dihidroxivouocapan-17-β-óico das sementes de Pterodon polygalaeflorus. In: Resumos da Reunião da Sociedade Brasileira de Química PN-048 Teixeira TC, Campos AM, Silveira ER (1991). Isolamento do ácido 6α,7β-dihidroxivouocapan-17-β-óico das sementes de Pterodon polygalaeflorus. In: Resumos da Reunião da Sociedade Brasileira de Química PN-048
Zurück zum Zitat Tjolsen A, Berge OG, Hunskaar S, Rosland JH, Hole K (1992) The formalin test: an evaluation of the method. Pain 51:5–17PubMedCrossRef Tjolsen A, Berge OG, Hunskaar S, Rosland JH, Hole K (1992) The formalin test: an evaluation of the method. Pain 51:5–17PubMedCrossRef
Zurück zum Zitat Vianna GSB, do Vale TG, Rao VSN, Matos FJA (1988) Analgesic and antiinflammatory effects of two chemotypes of Lippia alba: a comparative study. Pharm Biol 36:347–351CrossRef Vianna GSB, do Vale TG, Rao VSN, Matos FJA (1988) Analgesic and antiinflammatory effects of two chemotypes of Lippia alba: a comparative study. Pharm Biol 36:347–351CrossRef
Metadaten
Titel
Anti-inflammatory and analgesic effects of 6α,7β–dihydroxy-vouacapan-17β-oic acid isolated from Pterodon emarginatus Vog. fruits
verfasst von
Camila Benatti Galceran
Jayme Antonio Aboin Sertie
Clarissa Silva Lima
José Carlos Tavares Carvalho
Publikationsdatum
01.06.2011
Verlag
SP Birkhäuser Verlag Basel
Erschienen in
Inflammopharmacology / Ausgabe 3/2011
Print ISSN: 0925-4692
Elektronische ISSN: 1568-5608
DOI
https://doi.org/10.1007/s10787-011-0081-9

Weitere Artikel der Ausgabe 3/2011

Inflammopharmacology 3/2011 Zur Ausgabe