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Article

Bufadienolides from the Skin Secretions of the Neotropical Toad Rhinella alata (Anura: Bufonidae): Antiprotozoal Activity against Trypanosoma cruzi

by
Candelario Rodriguez
1,2,3,
Roberto Ibáñez
4,
Luis Mojica
5,
Michelle Ng
6,
Carmenza Spadafora
6,
Armando A. Durant-Archibold
1,3,* and
Marcelino Gutiérrez
1,*
1
Centro de Biodiversidad y Descubrimiento de Drogas, Instituto de Investigaciones Científicas y Servicios de Alta Tecnología (INDICASAT AIP), Apartado 0843-01103, Panama
2
Department of Biotechnology, Acharya Nagarjuna University, Nagarjuna Nagar, Guntur 522510, India
3
Departamento de Bioquímica, Facultad de Ciencias Naturales, Exactas y Tecnología, Universidad de Panamá, Apartado 0824-03366, Panama
4
Smithsonian Tropical Research Institute (STRI), Balboa, Ancon P.O. Box 0843-03092, Panama
5
Centro Nacional de Metrología de Panamá (CENAMEP AIP), Apartado 0843-01353, Panama
6
Centro de Biología Celular y Molecular de Enfermedades, INDICASAT AIP, Apartado 0843-01103, Panama
*
Authors to whom correspondence should be addressed.
Molecules 2021, 26(14), 4217; https://doi.org/10.3390/molecules26144217
Submission received: 25 May 2021 / Revised: 28 June 2021 / Accepted: 1 July 2021 / Published: 12 July 2021
(This article belongs to the Section Natural Products Chemistry)
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Abstract

Toads in the family Bufonidae contain bufadienolides in their venom, which are characterized by their chemical diversity and high pharmacological potential. American trypanosomiasis is a neglected disease that affects an estimated 8 million people in tropical and subtropical countries. In this research, we investigated the chemical composition and antitrypanosomal activity of toad venom from Rhinella alata collected in Panama. Structural determination using mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy led to the identification of 10 bufadienolides. Compounds identified include the following: 16β-hydroxy-desacetyl-bufotalin-3-adipoyl-arginine ester (1), bufotalin (2), 16β-hydroxy-desacetyl-bufotalin-3-pimeloyl-arginine ester (3), bufotalin-3-pimeloyl-arginine ester (4), 16β-hydroxy-desacetyl-bufotalin-3-suberoyl-arginine ester (5), bufotalin-3-suberoyl-arginine ester (6), cinobufagin-3-adipoyl-arginine ester (7), cinobufagin-3-pimeloyl-arginine ester (8), cinobufagin-3-suberoyl-arginine ester (9), and cinobufagin (10). Among these, three new natural products, 1, 3, and 5, are described, and compounds 1–10 are reported for the first time in R. alata. The antitrypanosomal activity assessed in this study revealed that the presence of an arginyl-diacid attached to C-3, and a hydroxyl group at C-14 in the structure of bufadienolides that is important for their biological activity. Bufadienolides showed cytotoxic activity against epithelial kidney Vero cells; however, bufagins (2 and 10) displayed low mammalian cytotoxicity. Compounds 2 and 10 showed activity against the cancer cell lines MCF-7, NCI-H460, and SF-268.
Keywords: Rhinella alata; toad; bufadienolides; Trypanosoma cruzi Rhinella alata; toad; bufadienolides; Trypanosoma cruzi

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MDPI and ACS Style

Rodriguez, C.; Ibáñez, R.; Mojica, L.; Ng, M.; Spadafora, C.; Durant-Archibold, A.A.; Gutiérrez, M. Bufadienolides from the Skin Secretions of the Neotropical Toad Rhinella alata (Anura: Bufonidae): Antiprotozoal Activity against Trypanosoma cruzi. Molecules 2021, 26, 4217. https://doi.org/10.3390/molecules26144217

AMA Style

Rodriguez C, Ibáñez R, Mojica L, Ng M, Spadafora C, Durant-Archibold AA, Gutiérrez M. Bufadienolides from the Skin Secretions of the Neotropical Toad Rhinella alata (Anura: Bufonidae): Antiprotozoal Activity against Trypanosoma cruzi. Molecules. 2021; 26(14):4217. https://doi.org/10.3390/molecules26144217

Chicago/Turabian Style

Rodriguez, Candelario, Roberto Ibáñez, Luis Mojica, Michelle Ng, Carmenza Spadafora, Armando A. Durant-Archibold, and Marcelino Gutiérrez. 2021. "Bufadienolides from the Skin Secretions of the Neotropical Toad Rhinella alata (Anura: Bufonidae): Antiprotozoal Activity against Trypanosoma cruzi" Molecules 26, no. 14: 4217. https://doi.org/10.3390/molecules26144217

APA Style

Rodriguez, C., Ibáñez, R., Mojica, L., Ng, M., Spadafora, C., Durant-Archibold, A. A., & Gutiérrez, M. (2021). Bufadienolides from the Skin Secretions of the Neotropical Toad Rhinella alata (Anura: Bufonidae): Antiprotozoal Activity against Trypanosoma cruzi. Molecules, 26(14), 4217. https://doi.org/10.3390/molecules26144217

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