Ricinine and other constituents of aparisthmium cordatum (Euphorbiaceae)

Natural Product Research

Volumn 27, Issue 4-5, 2013, Pages 364-370

  Souza, Karla M R ^a   Guilhon, Giselle Maria Skelding Pinheiro ^a   Santos, Lourivaldo Silva ^a   Cascaes, Marcia M ^a   Secco, Ricardo Souza ^b   Brasil, Davi S B ^a   Andrade, Eloisa H A ^a   Marinho, Patricia S B ^a   Freire, Luciano R ^a   Muller, Adolfo H ^c  

^a FEDERAL UNIVERSITY OF PARÁ   (Brazil)

^b MUSEU PARAENSE EMÍLIO GOELDI   (Brazil)

^c CENTRO UNIVERSITÁRIO DO ESTADO DO PARÁ   (Brazil)

Author keywords

Acetylaleuritolic acid; Aparisthmium cordatum; Ellagic acid; Euphorbiaceae; Isocorilagin; Ricinine

Indexed keywords

ALKALOID DERIVATIVE; APARISTHMIUM CORDATUM EXTRACT; ELLAGIC ACID; GALLIC ACID; PHENOL DERIVATIVE; PLANT EXTRACT; RICININE; SQUALENE; STEROID; TANNIN DERIVATIVE; TRITERPENOID; UNCLASSIFIED DRUG;

ALCHORNEA; ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINOCICEPTION; APARISTHMIUM CORDATUM; ARTICLE; CHEMICAL COMPOSITION; CONCEVEIBA CORDATA; DRUG STRUCTURE; EUPHORBIACEAE; MEMORY CONSOLIDATION; NONHUMAN; PHYTOCHEMISTRY; PLANT LEAF; PLANT STEM; THIN LAYER CHROMATOGRAPHY;

ALKALOIDS; ELLAGIC ACID; EUPHORBIACEAE; PLANT EXTRACTS; PYRIDONES; TANNINS; TRITERPENES;

EID: 84875137825     PISSN: 14786419     EISSN: 14786427     Source Type: Journal    
DOI: 10.1080/14786419.2012.695368     Document Type: Article

References (39)

1. Akiyama, H., Fujii, K., Yamasaki, O., Oono, T., & Iwatsuki, K. (2009). Antibacterial action of several tannins against Staphylococcus aureus. Journal of Antimicrobial Chemotherapy, 48, 487-491.
2. Aoki, T., Matsuo, K., Suga, T., & Ohta, S. (1997). Arachisprenols: polyprenols possessing a geranyl residue from Arachishypogaea. Phytochemistry, 46, 715-720. (Pubitemid 27483834)
3. Asahi Research Center (1985). Handbook of proton-NMR spectra and data. Tokyo: Academic Press Inc.
4. Batista, E.F., Costa, D.R.M., Guilhon, G.M.S.P., Müller, A.H., Santos, L.S., Arruda, M.S.P., .Souza Filho, A.P. (2011). Chemical study, allelopathic and antioxidant activities of Alchorneopsis floribunda Müll. Arg. (Euphorbiaceae). Natural Product Reseach, 25, 1-8.
5. Braca, A., Mendez, J., Menichini, F., & Morelli, I. (2002). Constituents of Alchorneatriplinervia (Euphorbiaceae). Biochemical Systematics and Ecology, 30, 1109-1111.
6. Brasil, D.S.B., Alves, C.N., Guilhon, G.M.S.P., Müller, A.H., Secco, R.S., Peris, G., & Llusar, R. (2008). Crystal structure and theorethical study of IR and 1H and 13C NMR spectra of cordatin, a natural product with antiulcerogenic activity. International Journal of Quantum Chemistry, 108, 2564-2575.
7. Brasil, D.S.B., Moreira, R.Y.O., Müller, A.H., & Alves, C.N. (2006). Theoretical and experimental study of aparisthman: a natural product with anti-ulcer activity. International Journal of Quantum Chemistry, 106, 2706-2713. (Pubitemid 44476065)
8. Breitmaier, E., & Voelter, W. (1990). Carbon-13 NMR spectroscopy: High resolution methods and applications in organic chemistry and biochemistry (3rd ed.). Weinheim: VHC. Bullangpoti, V., Khumrungsee, N., Pluempanupat, W., Kainoh, Y., & Saguanpong, U. (2011). Toxicity of ethyl acetate extract and ricinine from Jatropha gossypifolia senescent leaves against Spodoptera exigua Hubner (Lepidoptera: Noctuidae). Journal of Pestcide Science, 36, 260-263.
9. Calvo, T.R., Lima, Z.P., Silva, J.S., Ballesteros, K.V.R., Pellizon, C.H., Hiruma-Lima, C.A., .Vilegas, W. (2007). Constituents and antiulcer effect of Alchornea glandulosa: activation of cell proliferation in gastric mucosa during the healing process. Biological and Pharmaceutical Bulletin, 30, 451-459. (Pubitemid 46355924)
10. Carvalho, M.G., Alves, C.C.F., Werle, A.A., & Braz-Filho, R. (2006). Metabó litos especiais isolados de Laseguea erecta (Apocynaceae). Revista Brasileira de Famacognosia, 16, 497-500.
11. Chanwitheesuk, A., Teerawutgulrag, A., Kilburn, J.D., & Rakariyatham, N. (2007). Antimicrobial gallic acid from Caesalpinia mimosoides Lamk. Food Chemistry, 100, 1044-1048. (Pubitemid 44062185)
12. Ceruks, M., Romoff, P., Fá vero, A.O., & Lago, J.H.G. (2007). Constituintes fenó licos polares de Schinus terebinthifolius Raddi (Anacardiaceae). Quimica Nova, 30, 597-599.
13. Conegero, L.S., Ide, R.M., Nazari, A.S., Sarragioto, M.H., Dias Filho, B.P., & Nakamura, C.V. (2003). Chemical constituents of Alchornea glandulosa (Euphorbiaceae). Quimica Nova, 26, 825-827. (Pubitemid 38968148)
14. Dadoun, H., Müller, A.H., Cesario, M., Guilhem, J., & Pascard, C. (1987). Cordatin, a new diterpene from Aparisthmium cordatum. Phytochemistry, 26, 2108-2110.
15. Ferraz, A.C., Angelucci, M.E.M., Costa, M.L., Batista, I.R., Oliveira, B.H., & Cunha, C. (1999). Pharmacologycal evaluation of ricinine, a central nervous system stimulant isolated from Ricinuscommunis. Pharmacology Biochemistry and Behaviour, 6, 367-375. (Pubitemid 29287152)
16. Festa, F., Aglitti, T., Duranti, G., Ricordy, R., Perticone, P., & Cozzi, R. (2001). Strong antioxidant activity of ellagic acid in mammalian cells intro reveald by the comet assay. Anticancer Research, 21, 3903-3908. (Pubitemid 34229261)
17. Forgo, P., & Kövé r, K.E. (2004). Gradient enhanced selective experiments in the 1H NMR chemical shift assignment of the skeleton and side-chain resonances of stigmasterol, a phytosterol derivative. Steroids, 69, 43-50. (Pubitemid 38050301)
18. George, V., Muthukrishnan, M., & Chojnacki, T. (2001). The occurrence of polyprenols in Euphorbiaceae. Acta Societatis Botanicorum Poloniae, 70, 39-41. (Pubitemid 33574461)
19. Hart, N.K., Johns, S.R., Lamberton, J.A., & Willing, R.I. (1970). Alkaloids of Alchornea javanensis: the isolation of hexahydroimidazo(1,2-a) pyrimidine and guanidines. Australian Journal of Chemistry, 23, 1679-1693.
20. Hiruma-Lima, C.A., Gracioso, J.S., Toma, W., Almeida, A.B., Paula, A.C.B., Brasil, D.S.B., .Souza Brito, A.R. (2001). Gastroprotective effect of aparisthman, a diterpene isolated from Aparisthmium cordatum, on experimental gastric ulcer models in rats and mice. Phytomedicine, 8, 94-100. (Pubitemid 32267091)
21. Hiruma-Lima, C.A., Gracioso, J.S., Toma, W., Paula, A.C.B., Almeida, A.B.A., Brasil, D.S.B., .Brito, A.R. (2000). Evaluation of the gastroprotective activity of cordatin, a diterpene isolated from Aparisthmium cordatum (Euphorbiaceae). Biological and Pharmaceuthical Bulletin, 23, 1465-1469. (Pubitemid 32016311)
22. Khuong-Huu-Laine, F., Leforestier, J.P., Maillard, G., & Goutarel, R. (1970). Alchorneine, a tetrahydroimidazo (1,2-a)pyrimidine isolated from two African Euphorbiaceae, Alchornea floribunda and Alchornea hirtella. ComptesRendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimis, 270, 2070-2072.
23. Madlener, S., Illmer, C., Horvath, Z., Saiko, P., Losert, A., Herbacek, I., .Szekeres, T. (2007). Gallic acid inhibits ribonucleotidereductase and cyclooxygenases in human HL-60 promyelocytic leukemia cells. Cancer Letters, 245, 156-162. (Pubitemid 44959349)
24. Mahato, S.B., & Kundu, A.P. (1994). 13C NMR spectra of pentacyclic triterpenoids-A compilation and some salient features. Phytochemistry, 37, 1517-1575.
25. Marvar-Manga, H., Haddad, M., Pieters, L., Baccelli, C., Penge, A., & Quetin-Leclercq, J. (2008). Antiinflammatory compounds from leaves and root bark of Alchornea cordifolia (Schumach. & Thonn.) Müll. Arg. Journal of Ethnopharmacology, 115, 25-29. (Pubitemid 350166798)
26. Müller, A.H., Oster, B., Schukmann, W.K., & Bartl, H. (1986). Aparisthman, methy 1-(3-furoylmethyl)-4ahydroxy-1,2-dimethyl-2,3,4,4a,5,8,9,9a- octahydro-1H-benzocycloheptene-6-carboxylate, a seven membered ring diterpenoid from Aparisthmium cordatum. Phytochemistry, 25, 1415-1417.
27. Nes, W.D., Norton, R.A., & Benson, M. (1992). Carbon-13 NMR studies on sitosterol biosynthesized from (13C)mevalonates. Phytochemistry, 31, 805-811.
28. Nyasse, B., Ngantchou, I., Nono, J.J., & Scheidner, B. (2006). Antifilarial activity in vitro of polycarpol and 3-Oacetylaleuritolic acid from Cameroonian medicinal plants against Onchocercagutturosa. Natural Product Research, 20, 391-397. (Pubitemid 43675137)
29. Perazzo, F.F., Carvalho, J.C.T., Rodrigues, M., Morais, E.K.L., & Maciel, M.A.M. (2007). Comparative antiinflammatory and antinociceptive effects of terpenoids and an aqueous extract obtained from Croton cajucara Benth. RevistaBrasileira de Farmacognosia, 17, 521-528.
30. Leite, A.C., Cabral, E.C., Santos, D.A.P., Fernandes, J.B., Vieira, P.C., & Silva, M.F.G.F. (2005). Isolation of the alkaloid ricinine from the leaves of Ricinuscommunis (Euphorbiaceae) through counter-current chromatography. Química Nova, 28, 983-985. (Pubitemid 43104545)
31. Secco, R.S. (2004). Alchorneae (Euphorbiaceae: Alchornea, Aparisthmium e Conceveiba). Flora Neotropica (Monograph no.93, pp. 1-195). Botanical Garden, New York, NY: Organization for Flora Neotropica.
32. Secco, R.S. (2005). Flora da Reserva Ducke, Amazonas, Brasil: Euphorbiaceae-Parte 1. In Rodrigue'sia (Vol. 56, pp. 143-168). Brazil: Instituto Brasileiro de Desenvolvimento Florestal, Instituto de Biologia Vegetal (Brazil), Jardim Botâ nico do Rio de Janeiro, Serviço Florestal.
33. Setzer, W.N., Shen, X., Bates, R.B., Burns, J.R., McClure, K.J., Zhang, P., .Lawton, R.O. (2000). A phytochemical investigation of Alchornea latifolia. Fitoterapia, 71, 195-198. (Pubitemid 30156015)
34. Silva Jr, I.F., Raimondi, M., Zacchino, S., Cechinel Filho, V., Noldin, V.F., Rao, V.S., .Martins, T.O. (2010). Evaluation of the antifungal activity and mode of action of Lafoensia pacari A. St.-Hil., Lythraceae, Stembark extracts, fractions and ellagic acid. Revista Brasileira de Farmacognosia, 20, 422-428.
35. Sule, M.I., & Sani, U.M. (2008). Isolation of ricinine from methanol extracts of three different seed varieties of Ricinuscommunis Linn (Euphorbiaceae). Nigerian Journal of Pharmaceutical Sciences, 7, 114-118.
36. Wood, A., Huang, M.-T., Chang, R.L., Newmark, H.L., Lehr, R.E., Yagi, H., .Conney, A.H. (1982). Inhibition of the mutagenicity of bay-region diol epoxides of polycyclic aromatic hydrocarbons by naturally occurring plant phenols: exceptional activity of ellagic acid. Proceedings of the National Academy of Science USA, 79, 5513-5517. (Pubitemid 13197674)
37. Yuldashev, P.K. (2001). Ricinine and its transformations. Chemistry of Natural Compounds, 37, 274-275.
38. Zhang, Y., DeWitt, D.L., Murugesan, S., & Nair, M.G. (2004). Novel lipid-peroxidation-and cyclooxigenaseinhibitory tannins from Picrorhizakurroa seeds. Chemistry and Biodiversity, 1, 426-441.
39. Zheng, X.-L., Bo, S.-H., Han, C.-X., Qu, N.-N., Wang, Y.-G., & Zhang, H.-L. (2004). Toxicity effect of low dosage of ricinine on mice. Journal of Northwest Forestry University, 19, 97-99, doi: ISSN:1001-7461.0.2004-04-028.