Antiproliferative activity and new argininyl bufadienolide esters from the "cururú" toad Rhinella (Bufo) schneideri

Journal of Ethnopharmacology

Volumn 155, Issue 2, 2014, Pages 1076-1085

  Schmeda Hirschmann, Guillermo ^a   Quispe, Cristina ^a   Theoduloz, Cristina ^a   De Sousa, Paulo Teixeira ^b,c   Parizotto, Carlos ^b,c  

^a UNIVERSIDAD DE TALCA   (Chile)

^b FEDERAL UNIVERSITY OF MATO GROSSO   (Brazil)

^c Instituto Nacional de Ciencia e Technologia em Areas Umidas INCT INAU   (Brazil)

Author keywords

Antiproliferative activity; Argininyl bufadienolides; Brazilian pantanal; Bufo; Rhinella schneideri

Indexed keywords

3 ( N AZELAYL ARGININYL)BUFALIN; 3 ( N UNDECADIENOYL ARGININYL)MARINOBUFAGIN; 3 (N ADIPOYL ARGININYL)MARINOBUFAGIN; 3 (N AZELAYL ARGININYL)MARINOBUFAGIN; 3 (N DODECADIENOYL ARGININYL)MARINOBUFAGIN; 3 (N GLUTARYL ARGININYL)MARINOBUFAGIN; 3 (N PIMELOYL ARGININYL)MARINOBUFAGIN; 3 (N PIMELOYL ARGININYL)TELOCINOBUFAGIN; 3 (N SEBACYL ARGININYL)BUFALIN; 3 (N SEBACYL ARGININYL)MARINOBUFAGIN; 3 (N SEBACYL ARGININYL)TELOCINOBUFAGIN; 3 (N SUBEROYL ARGININYL)MARINOBUFAGIN; 3 (N SUBEROYL ARGININYL)TELOCINOBUFAGIN; 3( N SUBEROYL ARGININYL)HELLEBRIGENIN; ADIPYL ARGININE; ANTINEOPLASTIC AGENT; ARGININYL BUFADIENOLIDE ESTER DERIVATIVE; BUFADIENOLIDE DERIVATIVE; BUFALIN; BUFALITOXIN; BUFOTENIDIN; BUFOTENINE; DEHYDROBUFOTENIN; ETOPOSIDE; MARINOBUFAGENIN; PIMELOYL ARGININE; SUBEROYL ARGININE; TELOCINOBUFAGIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; VENOM; AMPHIBIAN VENOM; ESTER;

ANALYTIC METHOD; ANTIPROLIFERATIVE ACTIVITY; ANURA; ARTICLE; BLADDER CARCINOMA; CASE REPORT; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CLINICAL ASSESSMENT; CLINICAL EVALUATION; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG ISOLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IC 50; LUNG CANCER; LUNG FIBROBLAST; PAROTID GLAND; PROMYELOCYTIC LEUKEMIA; SPECTROSCOPY; STOMACH ADENOCARCINOMA; TANDEM MASS SPECTROMETRY; ANIMAL; BRAZIL; BUFONIDAE; CELL LINE; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECTS; DRUG SCREENING; FIBROBLAST; HL 60 CELL LINE; IC50; ISOLATION AND PURIFICATION; METABOLISM; NEOPLASMS; PARAGUAY; PATHOLOGY; TUMOR CELL LINE;

ANURA; BUFO; BUFO AMERICANUS;

AMPHIBIAN VENOMS; ANIMALS; ANTINEOPLASTIC AGENTS; BRAZIL; BUFANOLIDES; BUFONIDAE; CELL LINE; CELL LINE, TUMOR; CELL PROLIFERATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG SCREENING ASSAYS, ANTITUMOR; ESTERS; FIBROBLASTS; HL-60 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; NEOPLASMS; PARAGUAY; TANDEM MASS SPECTROMETRY;

EID: 84906794501     PISSN: 03788741     EISSN: 18727573     Source Type: Journal    
DOI: 10.1016/j.jep.2014.06.025     Document Type: Article

References (39)

1. R.R.N. Alves, and H.N. Alves The faunal drugstore: animal-based remedies used in traditional medicines in Latin America Journal of Ethnobiology and Ethnomedicine 7 9 2011 43
2. R.R.N. Alves, R.O. Neta, S. de, D.M. Trovao, B. de, J.E. Barbosa, L. de, A.T. Barros, and T.L.P. Dias Traditional uses of medicinal animals in the semi-arid región of Brazil Journal of Ethnobiology and Ethnomedicine 8 41 2012 7
3. F.A.P. Anjolette, J.C. Pereira, A.E.C. Azzolini, S.V. Sampaio, A.I. Assis-Pandochi, E.C. Arantes, and L.S. Pereira-Crott Complement system modulation by components from Rhinella schneideri poison Molecular Immunology 48 14 2011 1694 1695
4. M.A. Baldo, J.L. Liberato, L.D. Godoy, W. Ferreira dos Santos, and E.C. Arantes New perspective for therapy against seizures using molecules from Rhinella schneideri toad poison Toxicon 60 2 2012 103 104
5. E.C.F. Baldo, C.P. da Silva, S.V. Sampaio, and E.C. Arantes Evaluation of the cytotoxic activity of Rhinella schneideri toad poison on tumor cells and on healthy mononuclear cells Toxicon 60 2012 103
6. N.G. Bisset Arrow and dart poisons Journal of Ethnopharmacology 25 1989 1 41
7. G.A. Cunha Filho, C.A. Schwartz, I.S. Resck, M.M. Murta, S.S. Lemos, M.S. Castro, C. Kyaw, O.R. Pires Jr.;J.R.S. Leite, C. Bloch Jr.;and E.F. Schwartz Antimicrobial activity of the bufadienolides marinobufagin and telocinobufagin isolated as major components from skin secretion of the toad Bufo rubescens Toxicon 45 2005 777 782
8. G.A. Cunha-Filho, I.S. Resck, B.C. Cavalcanti, C.Ó. Pessoa, M.O. Moraes, J.R.O. Ferreira, F.A.R. Rodrigues, and M.L. dos Santos Cytotoxic profile of natural and some modified bufadienolides from toad Rhinella schneideri parotoid gland secretion Toxicon 56 2010 339 348
9. J.W. Daly The nature and origin of amphibian alkaloids G.A. Cordell, The Alkaloids: Chemistry and Biology 1998 Academic Press New York 141 169
10. J.W. Daly, H.M. Garraffo, T.F. Spande, H.J.C. Yeh, P.M. Peltzer, P.M. Cacivio, J.D. Baldo, and J. Faivovich Indolizidine 239Q and quinolizidine 275I. Major alkaloids in two Argentinian bufonid toads (Melanophryniscus) Toxicon 52 2008 858 870
11. Dictionary of Natural Products on DVD (2013), CRC Press, Boca Raton, FL, USA.
12. P.M.P. Ferreira, D.J.B. Lima, B.W. Debiasi, B.M. Soares, K. Machado, C. da, J. Noronha, C. da, D. de J. Rodrigues, A.P. Sinhorin, C. Pessoa, and G.M. Vieira Jr. Antiproliferative activity of Rhinella marina and Rhaebo guttatus venom extracts from Southern Amazon Toxicon 72 2013 43 51
13. H. Gao, M. Zehl, A. Leitner, X. Wu, Z. Wang, and B. Kopp. Comparison of toad venoms from different Bufo species by HPLC and LC-DAD-MS/MS Journal of Ethnopharmacology 131 2010 368 376
14. B. Giri, A. Gomes, A. Debnath, A. Saha, A.K. Biswas, S.C. Dasgupta, and A. Gomes Antiproliferative, cytotoxic and apoptogenic activity of Indian toad (Bufo melanostictus, Schneider) skin extract on U937 and K562 cells Toxicon 48 2006 388 400
15. Y. Hu, Z. Yu, Z.J. Yang, G. Zhu, and W. Fond Comprehensive chemical analysis of Venenum Bufonis by using liquid chromatography/electrospray ionization tandem mass spectrometry Journal of Pharmaceutical and Biomedical Analysis 56 2011 210 220
16. 13C NMR chemical shift assignments for thirteen bufadienolides isolated from the traditional Chinese drug Chan Su Collection of Czechoslovak Chemical Communications 66 2001 1841 1848
17. Y. Kamano, H. Yamamoto, K. Hatayama, Y. Tanaka, M. Shinohara, and M. Komatsu The isolation and structure of new bufadienolide, resibufagin and the isolation of marinobufagin Tetrahedron Letters 54 1968 5669 5672
18. C. Lenaerts, M. Demeyer, P. Gerbaux, and B. Blankert Analytical aspects of marinobufagenin Clinica Chimica Acta 421 2013 193 201
19. H.O. Linde-Tempel Konstitution der Bufotoxine. Über Krötengifte, 38. Mitteilung Helvetica Chimica Acta 53 1970 2188 2196
20. H.Y. Ma, J.P. Kou, J.R. Wang, and B.Y. Yu Evaluation of the anti-inflammatory and analgesic activities of Liu-Shen-Wan and its individual fractions Journal of Ethnopharmacology 112 2007 108 114
21. N.M. Maciel, C.A. Schwartz, O.R. Pires Júnior, A. Sebben, M.S. Castro, M.V. Sousa, W. Fontes, and E.N.F. Schwartz Composition of indolealkylamines of Bufo rubescens cutaneous secretions compared to six other Brazilian bufonids with phylogenetic implications Comparative Biochemistry and Physiology Part B: Biochemistry and Molecular Biology 134 2003 641 649
22. N.M. Maciel, R.G. Collevatti, G.R. Colli, and E.F. Schwartz Late Miocene diversification and phylogenetic relationships of the huge toads in the Rhinella marina (Linnaeus, 1758) species group (Anura: Bufonidae) Molecular Phylogenetics and Evolution 57 2010 787 797
23. Z. Meng, P. Yang, Y. Shen, W. Bei, Y. Zhang, Y. Ge, R.A. Newman, L. Cohen, L. Liu, B. Thornton, D.Z. Chang, Z. Liao, and R. Kurzrock Pilot study of Huachansu in patients with hepatocellular carcinoma, nonsmall-cell lung cancer, or pancreatic cancer Cancer 115 2009 5309 5318
24. G.R. Pettit, and Y. Kamano Bufadienolides. 28. Marinobufotoxin Journal of Organic Chemistry 39 1974 3003 3006
25. F. Qi, A. Li, L. Zhao, H. Xu, Y. Inagaki, D. Wang, X. Cui, B. Gao, N. Kokudo, M. Nakata, and W. Tang Cinobufacini, an aqueous extract from Bufo bufo gargarizans Cantor, induces apoptosis through a mitochondria-mediated pathway in human hepatocellular carcinoma cells Journal of Ethnopharmacology 128 2010 654 661
26. F. Qi, A. Li, Y. Inagaki, N. Kokudo, S. Tamura, M. Nakata, and W. Tang Antitumor activity of extracts and compounds from the skin of the toad Bufo bufo gargarizans Cantor International Immunopharmacology 11 2011 342 349
27. J.A. Rodriguez, and M. Haun Cytotoxicity of trans-dehydrocrotonin from Croton cajucara on V79 cells and rat hepatocytes Planta Medica 65 1999 522 526
28. J.M. Sciani, P.L. de-Sá-Júnior, A.K. Ferreira, A. Pereira, M.M. Antoniazzi, C. Jared, and D.C. Pimenta Cytotoxic and antiproliferative effects of crude amphibian skin secretions on breast tumor cells Biomedicine & Preventive Nutrition 3 2013 10 18
29. K. Shimada, J.S. Ro, K. Ohishi, and T. Nambara Isolation and characterization of cinobufagin 3-glutaroyl-L-arginine ester from Bufo bufo gargarizans Cantor Chemical and Pharmaceutical Bulletin 33 1985 2767 2771
30. K. Shimada, Y. Fujii, Y. Niizaki, and T. Nambara Isolation of gamabufotalin 3-pimeloylarginine ester from the skin of Japanese toad Tetrahedron Letters 9 1975 653 654
31. K. Shimada, Y. Sato, Y. Fujii, and T. Nambara Occurrence of bufalitoxin, cinobufotoxin and their homologs in Japanese toad Chemical and Pharmaceutical Bulletin 24 1976 1118 1120
32. K. Shimada, Y. Fujii, E. Yamashita, Y. Niizaki, Y. Sato, and T. Nambara Studies on cardiotonic steroids from the skin of Japanese toad Chemical and Pharmaceutical Bulletin 25 1977 714 730
33. A.G. Tempone, D.C. Pimenta, I. Lebrun, P. Sartorelli, N.N. Taniwaki, H.F. de Andrade Jr.;M.M. Antoniazzi, and C. Jared Antileishmanial and antitrypanosomal activity of bufadienolides isolated from the toad Rhinella jimi parotoid macrogland secretion Toxicon 52 2008 13 21
34. The State Pharmacopoeia Commission of Peoplés Republic of China Pharmacopoeia of the Peoplés Republic of China, Beijing China Chemical Industry Press 2005 265 266
35. H. Wassen The frog motive among the South American Indians Anthropos 29 1934 319 370
36. H. Wassen The frog in Indian mythology and imaginative world Anthropos 29 1934 613 658
37. A.T. Weil, and W. Davis Bufo alvarius: a potent hallucinogen of animal origin Journal of Ethnopharmacology 41 1994 1 8
38. M. Ye, J. Han, D. An, G. Tu, and D. Guo New cytotoxic bufadienolides from the biotransformation of resibufogenin by Mucor polymorphosporus Tetrahedron 61 2005 8947 8955
39. M. Ye, G. Qu, H. Guo, and D. Guo Novel cytotoxic bufadienolides derived from bufalin by microbial hydroxylation and their structure-activity relationships Journal of Steroid Biochemistry & Molecular Biology 91 2004 87 98