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. 2025 May 27;10(22):23397-23408.
doi: 10.1021/acsomega.5c01804. eCollection 2025 Jun 10.

C‑methylated Flavanones with Antitrypanosomal Activity Isolated of Geopropolis from Melipona mondury

Rafael Ferreira Dos Santos  1 , Afonso Santine M M Velez  1 , Gabriel Fulgencio Dos Santos  1 , Paulo Pitasse-Santos  2   3 , Bruno Sena de Oliveira  1 , Marco Edilson Freire de Lima  1 , Carlos Mauricio R Sant'Anna  4 , Raimundo Braz Filho  1 , Debora Decote-Ricardo  5 , Rosane Nora Castro  1
Affiliations

C‑methylated Flavanones with Antitrypanosomal Activity Isolated of Geopropolis from Melipona mondury

Rafael Ferreira Dos Santos et al. ACS Omega. .

Abstract

Geopropolis is a natural antibiotic produced by stingless bees, supplemented with earth and clay. Bee products are a promising source of natural bioactive compounds with potential for the development of new drugs for neglected tropical diseases, such as Chagas disease. This study analyzed extracts of Melipona mondury geopropolis from the Bosque da Barra da Tijuca (RJ, Brazil) and evaluated their activity against Trypanosoma cruzi. The extracts were obtained using commercial grain alcohol 96° GL and fractionated with hexane and dichloromethane. The antichagasic activity was determined, with IC50 values ranging from 4.54 to 53.02 μg/mL. Phytochemical investigation of the dichloromethane fraction resulted in the isolation of two C-methylated flavanones, (2S)-strobopinin and (2S)-cryptostrobin, which were identified for the first time in Brazilian geopropolis. These compounds showed IC50 values of 21.21 μM and 21.55 μM, respectively, with distinct cytotoxities: 33.80 μM for strobopinin and 99.79 μM for cryptostrobin. Molecular modeling studies were conducted to propose a mechanism of action on a candidate enzyme target, glyceraldehyde-3-phosphate dehydrogenase, and possible reasons for the selectivity differences caused by C-methylation. The results highlight M. mondury geopropolis as a promising natural source of antiparasitic agents, supporting its potential for drug development.

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Figures

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1
Proposed structures for substances S1- Strobopinin and S2- Cryptostrobin.
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2D map of interactions in the active site of TcGAPDH for (a) reference GAPDH ligand, S70, after redocking with GoldScore; (b) quercetin best scoring pose (GoldScore); (c) strobopinin best scoring pose (GoldScore); (d) cryptostrobin best scoring pose (GoldScore). Figures generated with Discovery Studio, Dassault Systèmes, 2023.
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Best docking poses (GoldScore) of strobopinin and cryptostrobin, in the active site of HsGAPDH. Figures generated with Discovery Studio, Dassault Systèmes, 2023.
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(a) Best covalent docking pose of strobopinin (sticks, C atoms in pink) into T. cruzi GAPDH (cartoon); (b) best covalent docking pose of cryptostrobin (sticks, C atoms in pink) into T. cruzi GAPDH (cartoon) (catalytic residues Cys166 and His194, sticks, C atoms in green; NAD+, sticks, C atoms in cyan). Figure generated with PyMOL 0.99rc6 (DeLano Scientific LLC).
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5
Predicted pharmacokinetic profile of strobopinin and cryptostrobin. Physicochemical parameters and delineation of the probable scope of inhibition of human metabolic enzymes obtained with Swiss ADME.
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