Arjunolic acid in the ethanolic extract of Combretum leprosum root and its use as a potential multi-functional phytomedicine and drug for neurodegenerative disorders: Anti-inflammatory and anticholinesterasic activities

Journal of the Brazilian Chemical Society

Volumn 16, Issue 6 B, 2005, Pages

  Facundo, Valdir A ^a   Riosa, Katiúscia A ^a   Medeiros, Ciléia M ^b   Militãoa, Júlio S L T ^a   Miranda, Ana Luisa P ^b   Epifanio, Rosângela De A ^c   Carvalho, Meriane P ^c   Andrade, Aline T ^b   Pinto, Angelo C ^b   Rezende, Claudia M ^b  

^a UNIVERSIDADE FEDERAL DE RONDÔNIA   (Brazil)

^b FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^c FLUMINENSE FEDERAL UNIVERSITY   (Brazil)

Author keywords

Anti inflammatory; Arjunolic acid; Cholinesterase inhibitor; Combretaceae; Combretum leprosum; HRGC MS

Indexed keywords

EID: 30844468431     PISSN: 01035053     EISSN: 01035053     Source Type: Journal    
DOI: 10.1590/s0103-50532005000800002     Document Type: Article

References (32)

1. Pio Corrêa, M.; Diccionário de Plantas Úteis do Brasil e das Exóticas Cultivadas, Imprensa Nacional: Rio de Janeiro, 1984, v.2.
2. Matos, F. J. A.; O Formulário Fitoterápico do Professor Dias Rocha, Editora Universidade Federal do Ceará: Ceará, 1997.
3. Lira, S. R. S.; Almeida, R . N.; Almeida, F. R. C.; Oliveira, F. S.; Duarte, J. C.; Pharm. Biol. 2002, 40, 213
4. Militão, J. S. L. T.; Andrade, C. H. S.; Silveira, E. R.; Braz-Filho, R.; Quim. Nova 1993, 16, 35.
5. Facundo, V. A.; Andrade, C. H. S.; Silveira, E. R.; Braz-Filho, R.; Hufford, C. D.; Phytochemistry 1993, 32, 411.
6. King, F. E.; King, T. J.; Ross, J. M.; J. Chem. Soc. 1954, 3995.
7. Ratsimamanga, A. R.; Boiteau, P.; GB pat. 923414 1963 (CA 59: P10239a)
8. Diallo, B.; Vanhaelen, M.; Vanhaelen-Fastre, R.; Konoshima, T.; Kozuka, M.; Tokuda, H.; J. Nat. Prod. 1989, 52, 879;
9. Diallo, B.; Vanhaelen-Fastre, R.; Vanhaelen, M.; Konoshima, T.; Takasaki, M.; Tokuda, H.; Phytother. Res. 1995, 9, 444;
10. Kashiwada, Y.; Wang, H. K.; Nagao, T.; Kitanaka, S.; Yasuda, I.; Fujioka, T.; Yamagishi, T.; Cosentino, L. M.; Kozuka, M.; Okabe, H.; Ikeshiro, Y.; Hu, C. Q.; Yeh, E.; Lee, K. H.; J. Nat. Prod. 1998, 61, 1090;
11. da Silva, T. B. C.; Alves, V. L.; Mendonça, L. V. H.; Conserva, L. M.; da Rocha, E. M. M.; Andrade, E. H. A.; Lemos, R. P. L; Pharm. Biol. 2004, 42, 94;
12. Prasad, M. V. V.; Anbalagan, N.; Patra, A.; Veluchamy, G.; Balakrishna, K; Nat. Prod. Sci. 2004, 10, 240.
13. De Miranda, A. L. P.; Silva, J. R. A.; Rezende, C. M.; Neves, J. S.; Parrini, S. C.; Pinheiro, M. L. B.; Cordeiro, M. C.; Tamborini, E.; Pinto, A. C.; Planta Med. 2000, 66, 284;
14. Andrade, M. T.; Lima, J. A.; Pinto, A. C.; Rezende, C. M.; Carvalho, M. P.; Epifanio, R. de A.; Bioorg. Med. Chem. 2005, 13, 4092;
15. Cardoso, C. L.; Castro-Gamboa, I.; Silva, D. H. S.; Furlan, M.; de Epifanio, R. de A.; Pinto, A. C; Rezende, C. M.; Lima, J. A.; Bolzani, V. S.; J. Nat. Prod. 2004, 67, 1882.
16. Crude extracts of C. leprosum and arjunolic acid (1) purification. C. leprosum leaves and roots were collected in 2001 at Cocalzinho-Viçosa, Ceará, Brazil, and a voucher specimen (no. 12446) is deposited at the Herbarium Prisco Bezerra of the Biology Department, UFC, Ceará, Brazil. Dried and finely powdered leaves and roots of C. leprosum, 3β,6β, 16β-trihydroxylup-20(29)-ene and arjunolic acid were extracted as described in reference 5.
17. -1) to 310°C (15 min). Quantification of the dried roots ethanolic extract was performed by the external standard method and all the TMS derivative samples were run in triplicate. The calibration graph was constructed at concentrations of 0.5 to 5 mg per mL of arjunolic acid and presented a good linearity (r = 0.9930 to 0.9995).
18. Derivatization. TMS ether derivatives of the roots and leaves ethanolic extracts of C. leprosum, arjunolic acid, 3β,6β,16β-trihydroxylup- 20(29)-ene, glucose and fructose were prepared by adding 100 μL of 1% TMCS/BSTFA reagent plus 100 μL of pyridine to 15-100 mg of material following by heat at 60°C for 60 min. Both ethanolic plant extracts were filtered before derivatization.
19. Branco, A.; Pinto, A. C.; Braz-Filho, R.; An. Acad. Bras. Cienc. 2004 76, 505.
20. The anti-inflammatory and analgesic properties of the extracts and arjunolic acid were evaluated in the carrageenan-induced rat paw edema (CIRPE) (a), acetic acid-induced mice abdominal constrictions (b), as previously described in: Ribeiro, I.G.; Silva, K. C. M.; Parrini, S. C.; Miranda, A. L. P.; Fraga, C. A. M.; Barreiro, E. J.; Eur. J. Med. Chem. 1998, 33, 225,
21. -1). Control animals received an equal volume of vehicle. In experiment (a), rats were injected subplantarly with either 0.1 mL of 1% carrageenan solution in saline (1 mg per paw) or sterile saline (NaCl 0.9%) into one of the hind paws, respectively. Paw volumes were measured 3h after carrageenan injection and edema calculated as the volume difference between the carrageenan and saline-treated paw. In experiment (b), mice were injected intraperitoneally with acetic acid 0.6% (0.1 mL per 10 g) and ten minutes after the number of constrictions per animal was recorded for 20 minutes. In experiment (c), 20 μL of TPA (2 μg per ear) or AA (500 μg per ear), dissolved in acetone, were applied to the inner and outer surface of the right ear of the mice. The left ear received acetone. The right and left ears were cute (6h after TPA- and 1h after AA-challenge), weighed and ear edema was measured as the difference in weight between the challenged and the unchallenged ear.
22. In the CIRPE model ulcerogenic effect in rats was investigated as described in: Chan, C. C.; Boice, S.; Brideau, C.; Fordhutchinson, A. W.; Gordon, R.; Guay, D.; Hill, R. G.; Li, C. S.; Mancini, J.; Penneton, M.; Prasit, P.; Rasori, R.; Riendeau, D.; Roy, P.; Tagari, P.; Vickers, P.; Wong, E.; Rodger, I. W.; J. Pharmacol. Exper. Ther. 1995, 274, 1531. Briefly, animals were euthanized and the stomachs excised along its greater curvature for visualization of gastric lesions with a stereomicroscope.
23. Opas, E. E.; Bonney, R. J.; Humes, J. L.; J. Invest. Dermatol. 1985, 84, 253;
24. Lloret, S.; Moreno, J. J.; Biochem. Pharmacol. 1995, 50, 347.
25. TLC assays for AChE and BuChE inhibitory activity (including false positive test) were performed as described in: Rhee, I. K.; van de Meent, M.; Ingkaninan, K.; Verpoorte, R.; J. Chromatogr., A 2001, 915, 217
26. and Rhee, I. K.; van Rijn, R. M.; Verpoorte, R.; Phytochem. Anal. 2003, 14, 127,
27. 4 0.2% (m/v)/2.4% (v/v) solution before heating.
28. Ali, M. S.; Jahangir, M.; ul Hussan, S. S.; Choudhary, M. I.; Phytochemistry 2002, 60, 295.
29. Jew, S. S.; Yoo, C. H.; Lim, D. Y.; Kim, H.; Mook-Jung, I.; Jung, M. W.; Choi, H.; Jung, Y. H.; Kim, H.; Park, H. G.; Bioorg. Med. Chem. Lett. 2000, 10, 119.
30. Sumitra, M.; Manikandan, P.; Kumar, D. A.; Arutselvan, N.; Balakrishna, K.; Manohar, B. M.; Puvanakrishnan, R.; Mol. Cell. Biochem. 2001, 224, 135;
31. Kumar, M. H. V.; Gupta, Y. K.; Clin. Exp. Pharmacol. Physiol. 2003, 30, 336.
32. Youdim, M. B. H.; Buccafusco, J. J.; Trends Pharmacol. Sci. 2005, 26, 27.