A new cyclodipeptide from Tetragonisca angustula honey active against Neospora caninum and in silico study

A new cyclic natural compound formed by succinic acid and two alanine amino acid units was isolated from the Tetragonisca angustula honey extract. The chemical structure of 1 was established based on spectroscopic data analysis, including one- ( 1 H and 13 C NMR) and two-dimensional NMR techniques (...

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Bibliographic Details
Published in:Natural product research 2024-08, Vol.38 (16), p.2909-2914
Main Authors: de Oliveira Lima, Ângela Cristina, Nolasco, Matheus, Freitas, Luciana dos Santos, Pinheiro, Alexandre Moraes, de Carvalho, Carlos Alfredo Lopes, de Freitas, Humberto Fonseca, Pita, Samuel Silva da Rocha, Vieira, Ivo José Curcino, Braz Filho, Raimundo, Branco, Alexsandro
Format: Article
Language:English
Subjects:
Alanine
Amino acids
Cell culture
Cell proliferation
cyclodipeptide
Data analysis
DNA biosynthesis
Glial cells
Honey
immune response
Neospora caninum
nitric oxide
NMR
Nuclear magnetic resonance
Parasites
Protein biosynthesis
Succinic acid
Tachyzoites
Tetragonisca angustula
Toxicity
Two dimensional analysis
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Summary:A new cyclic natural compound formed by succinic acid and two alanine amino acid units was isolated from the Tetragonisca angustula honey extract. The chemical structure of 1 was established based on spectroscopic data analysis, including one- ( 1 H and 13 C NMR) and two-dimensional NMR techniques ( 1 H- 1 H-COSY, HSQC and HMBC). A primary culture model previously infected with Neospora caninum was used to evaluate 1 for two time intervals (24 and 72 h), showing a reduction (40-56%) of the number of tachyzoites in the first 24 h and until 72 h, a dose-dependent reduction in parasite proliferation (25-50%). Glial cells treated with 1 did not demonstrate toxicity at concentrations up to 25 ug/mL. Treated and infected cultures showed an increase in NO when compared to control cells in 24 h and 72 h. In silico studies suggest that the new compound may affect DNA synthesis and impair ­protein production.
ISSN:1478-6419
1478-6427
1478-6427
DOI:10.1080/14786419.2023.2245538