Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Anti-trypanosomal Bufadienolides From the Oocytes of the Toad Rhinella alata (Anura, Bufonidae)

Candelario Rodriguez
,
Roberto Ibáñez
ORCID logo ,
Dionisio A. Olmedo
ORCID logo ,
Michelle Ng
,
Carmenza Spadafora
,
Armando A. Durant-Archibold
,
Marcelino Gutiérrez
* ORCID logo
Version 1 : Received: 5 December 2023 / Approved: 6 December 2023 / Online: 6 December 2023 (08:44:31 CET)

A peer-reviewed article of this Preprint also exists.

Rodriguez, C.; Ibáñez, R.; Olmedo, D.A.; Ng, M.; Spadafora, C.; Durant-Archibold, A.A.; Gutiérrez, M. Anti-Trypanosomal Bufadienolides from the Oocytes of the Toad Rhinella alata (Anura, Bufonidae). Molecules 2024, 29, 196. Rodriguez, C.; Ibáñez, R.; Olmedo, D.A.; Ng, M.; Spadafora, C.; Durant-Archibold, A.A.; Gutiérrez, M. Anti-Trypanosomal Bufadienolides from the Oocytes of the Toad Rhinella alata (Anura, Bufonidae). Molecules 2024, 29, 196.

Abstract

Amphibians are widely known as a prolific source of bioactive metabolites. In this work we isolated and characterized compounds with antiparasitic activity from the oocytes of the toad Rhinella alata collected in Panama. Bio-guided isolation and structural elucidation was carried out using chromatographic and spectroscopic techniques. The organic crude extract was subjected to solid phase extraction followed by HPLC purification of the fraction with in vitro activity against Trypanosoma cruzi trypomastigotes. Seven steroids (1-7) of the bufadienolide family were isolated and their structures determined using NMR and MS analyses; of these 19-formyl-dyscinobufotalin (3) is reported as a new natural product. Compounds 1, 3-7, resulted with a good anti-trypanosomal activity profile, among these 16β-hydroxyl-hellebrigenin (1) and bufalin (7) showed significant selectivity for T. cruzi. Furthermore, molecular docking analysis showed compounds 1, 3 and 7 interact through H-bonds with the amino acid residues GLN-19, ASP-158, HIS-159 and TRP-177 from cruzipain, at the catalytic site. Given the lack of therapeutic options to currently treat the American trypanosomiasis, this work can serve as the basis for further studies that aim the development of bufadienolides or their derivatives as drugs against Chagas disease.

Keywords

Rhinella alata; toads; Bufonidae; oocytes; bufadienolides; anti-trypanosomal activity; Trypanosoma cruzi

Subject

Chemistry and Materials Science, Other

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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