nach oben

Erschienen in:

01.01.2012 | Note

Triterpenes involved in the anti-inflammatory effect of ethanolic extract of Pterodon emarginatus Vogel stem bark

verfasst von: Weuller F. de Moraes, Pablinny Moreira Galdino, Marcus Vinícius M. Nascimento, Frederico Argollo Vanderlinde, Maria Teresa F. Bara, Elson A. Costa, José Realino de Paula

Erschienen in: Journal of Natural Medicines | Ausgabe 1/2012

Einloggen, um Zugang zu erhalten

Abstract

Bioassay-guided fractionation of the ethanolic extract of Pterodon emarginatus Vogel stem bark (EtEx) resulted in the isolation and characterization of lupeol and betulin. Their structures were elucidated by spectroscopic methods including IR, ¹H-NMR, ¹³C-NMR and comparison with literature values. This study showed the anti-inflammatory activity of EtEx, the hexane (HexL) and dichloromethane (DichL) layers, and lupeol and betulin. The extract, HexL, DichL, lupeol and betulin were able to inhibit acetic acid-induced writhing. In the formalin test, EtEx decreased licking time only in the second phase characterizing anti-inflammatory activity. In the oil-induced ear oedema test, EtEx, lupeol and betulin decrease edema formation. In conclusion, EtEx has antinociceptive effects arising from anti-inflammatory activity; this activity could be due to the presence of lupeol and betulin.

Agra MF, Freitas PF, Barbosa-Filho JM (2007) Synopsis of the plants known as medicinal and poisonous in Northeast of Brazil. Rev Bras Farmacogn 17:114–140CrossRef

Lorenzi H (1998) Árvores Brasileiras. Man Ident Cult Plant Arb Nat Bras 1:227

Pio Correa M (1975) Dicionário das plantas úteis do Brasil e das exóticas cultivadas. Inst Bras Des Flor 1:153

Moraes WF, Matos LG, Nascimento MVM, Paula JR, Bara MTF, Cunha LC, Valadares MC, Costa EA (2009) Anti-inflammatory and antinociceptive effects of Pterodon emarginatus stem bark alcohol extract. Pharm Biol 47:146–150CrossRef

Campos AM, Silveira ER, Braz-Filho R, Teixeira TC (1994) Diterpenoids from Pterodon polygalaeflorus. Phytochemistry 36:403–406CrossRef

Marques DD, Machado MIL, Carvalho MG, Meleira LAC, Braz-Filho R (1998) Isoflavonoids and triterpenoids isolated from Pterodon polygalaeflorus. J Braz Chem Soc 9:295–301

Council for International Organization of Medical Sciences (CIOMS) (1985) International guiding principles for biomedical research involving animals. Available at: http://www.cioms.ch/frame_1985_texts_of_guidelines.htm. Accessed 26 July 2007

Carvalho AAV, Galdino PM, Nascimento MVM, Kato MJ, Valadares MC, Cunha LC, Costa EA (2010) Antinociceptive and antiinflammatory activities of grandisin extracted from Virola surinamensis. Phytother Res 24:113–118PubMedCrossRef

Hunskaar S, Hole K (1987) The formalin test in mice: dissociation between inflammatory and non-inflammatory pain. Pain 30:103–114PubMedCrossRef

10.

Reynolds WF, Mclean S, Poplawski J, Enriquez RG, Escobar LT, Leon I (1986) Total assignment of ¹³C and ¹H spectra of three isomeric triterpenol derivatives by 2D NMR: an investigation of the potential utility of ¹H chemical shifts in structural investigation of complex natural products. Tetrahedron 42:3419–3428CrossRef

11.

Mahato SB, Kundu AP (1994) ¹³C NMR spectra of pentacyclic triterpenoids—a compilation and some salient features. Phytochemistry 37:1517–1575CrossRef

12.

Reyes CP, Núñes MJ, Jiménez IA, Busserolles J, Alcaraz MJ, Bazzocchi IL (2006) Activity of lupane triterpenoids from Maytenus species as inhibitors of nitric oxide and prostaglandin E2. Bioorg Med Chem 14:1573–1579PubMedCrossRef

13.

Berkenkopf JW, Weichman BM (1988) Production of prostacyclin in mice following intraperitoneal injection of acetic acid, phenylbenzoquinone and zymosan: its role in the writhing response. Prostaglandins 36:693–709PubMedCrossRef

14.

Chau TT (1989) Analgesic testing in animals models. In: Chang JY, Lewis AJ (eds) Pharmacological methods in the control of inflammation. Alan R Liss Inc, New York, pp 195–212

15.

Vacher PJ, Duch’ene-Marullaz P, Barbot P (1964) A propos de quelques produits usuels—comparaison de deux methodes d’étude des analgésiques. Med Exp 11:51–58PubMed

16.

Hendershot LC, Forsaith J (1959) Antagonism of the frequency of phenylquinone-induced writhing in the mouse by weak analgesics and nonanalgesics. J Pharmacol Exp Ther 125:237–240PubMed

17.

Rates SMK, Barros HMT (1994) Modelos animais para a avaliação da dor: métodos para triagem de novos analgésicos. Rev Bras Farm 75:31–34

18.

Le Bars D, Gozariu M, Cadden SW (2001) Animal models of nociception. Pharmacol Rev 53:597–652PubMed

19.

Shibata M, Ohkubo T, Takahashi H, Inoki R (1989) Modified formalin test: characteristic biphasic pain response. Pain 38:347–352PubMedCrossRef

20.

Dickenson A (1997) Mechanisms of central hypersensitivity: excitatory amino acid mechanisms and their control. In: Dickenson A, Besson JM (eds) The pharmacology of pain. Springer, Berlin, pp 167–210CrossRef

21.

Morrow JD, Roberts LJ (2001) Lipid-derived autacoids: eicosanoids and platelet-activating factor. In: Harman JG, Limbird LE (eds) Goodman & Gilman’s, the pharmacological basis of therapeutics, 10th edn. McGraw Hill, New York, pp 669–683

22.

Recio MC, Giner RM, Manez S, Gueho J, Julien HR, Hostettmann K, Rios JL (1995) Investigations on the steroidal anti-inflammatory activity of triterpenoids from Diospyros leucomelas. Planta Med 61:9–12PubMedCrossRef

23.

Ryu SY, Oak MH, Yoon SK, Chon DI, Yoo GS, Kim TS, Kim KM (2000) Anti-allergic and anti-inflammatory triterpenes from herb of Prunella vulgaris. Planta Med 66:358–360PubMedCrossRef

24.

Geetha T, Varalakshmi P (2001) Anti-inflammatory activity of lupeol and lupeol linoleate in rats. J Ethnopharmacol 76:77–80PubMedCrossRef

25.

Agarwal RB, Rangari VD (2003) Antiinflammatory and antiarthritic activities of lupeol and 19α-H lupeol isolated from Strobilanthus callosus and Strobilanthus ixiocephala roots. Indian J Pharmacol 35:384–387

26.

Ahmad SF, Pandey A, Kour K, Bani S (2010) Downregulation of pro-inflammatory cytokines by lupeol measured using cytometric bead array immunoassay. Phytother Res 24:9–13PubMedCrossRef

27.

Sami A, Taru M, Salme K, Jari YK (2006) Pharmacological properties of the ubiquitous natural product betulin. Eur J Pharm Sci 29:1–13CrossRef

28.

Huguet AI, del Carmen Recio M, Manez S, Giner RM, Rios JL (2000) Effect of triterpenoids on the inflammation induced by protein kinase C activators, neuronally acting irritants and other agents. Eur J Pharmacol 410:69–81PubMedCrossRef

29.

Bernard P, Scior T, Didier B, Hibert M, Berthon J (2001) Ethnopharmacology and bioinformatic combination for leads discovery: application to phospholipase A2 inhibitors. Phytochemistry 58:865–874PubMedCrossRef

30.

Flekhter OB, Medvedeva NI, Karachurina LT, Baltina LA, Zarudii FS, Galin FZ, Tolstikov GA (2002) Synthesis and antiinflammatory activity of new acylated betulin derivatives. Pharm Chem J 36:488–491CrossRef

31.

Karachurina LT, Sapozhnikova TA, Zarudii FS, Flekhter OB, Galin FZ (2002) Antiinflammatory and antiulcer properties of betulin bishemiphthalate. Pharm Chem J 36:432–433CrossRef

Titel: Triterpenes involved in the anti-inflammatory effect of ethanolic extract of Pterodon emarginatus Vogel stem bark
verfasst von: Weuller F. de Moraes
Pablinny Moreira Galdino
Marcus Vinícius M. Nascimento
Frederico Argollo Vanderlinde
Maria Teresa F. Bara
Elson A. Costa
José Realino de Paula
Publikationsdatum: 01.01.2012
Verlag: Springer Japan
Erschienen in: Journal of Natural Medicines / Ausgabe 1/2012
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-011-0547-5

Springer Medizin

Abstract

Bitte loggen Sie sich ein, um Zugang zu diesem Inhalt zu erhalten

Weitere Artikel der Ausgabe 1/2012

Insights into mechanisms underlying the gut and airways modulatory effects of Swertia chirata

Curcumin-like diarylpentanoid analogues as melanogenesis inhibitors

Low-molecular-weight lignin-rich fraction in the extract of cultured Lentinula edodes mycelia attenuates carbon tetrachloride-induced toxicity in primary cultures of rat hepatocytes

Neuroprotective effect of ginkgolide K against acute ischemic stroke on middle cerebral ischemia occlusion in rats

Gambogenic acid-induced time- and dose-dependent growth inhibition and apoptosis involving Akt pathway inactivation in U251 glioblastoma cells

Vascular relaxation induced by aqueous extract of Lespedeza cuneata via the NO-cGMP pathway