[1-7-NαC]-Crocaorb A1 and A2, orbitides from the latex of Croton campanulatus.

Autor: Queiroz SAS; Nuclei of Bioassays, Biosynthesis and Ecophysiology of Natural Products, Institute of Chemistry, São Paulo State University - UNESP, 14800-060 Araraquara, SP, Brazil., Dos Santos ALP; Nuclei of Bioassays, Biosynthesis and Ecophysiology of Natural Products, Institute of Chemistry, São Paulo State University - UNESP, 14800-060 Araraquara, SP, Brazil., Bobey AF; Nuclei of Bioassays, Biosynthesis and Ecophysiology of Natural Products, Institute of Chemistry, São Paulo State University - UNESP, 14800-060 Araraquara, SP, Brazil., Cabral VA; Center of Biotechnology, Federal University of Rio Grande do Sul - UFRGS, 91500-970 Porto Alegre, RS, Brazil., Verli H; Center of Biotechnology, Federal University of Rio Grande do Sul - UFRGS, 91500-970 Porto Alegre, RS, Brazil., Dos Santos Magalhães TB; Laboratory of Histotechnics and Cell Culture, Department of Life Sciences, Bahia State University - UNEB, 41150-000 Salvador, BA, Brazil; Laboratory of Tissue Engineering and Immunopharmacology, Gonçalo Moniz Institute, Oswaldo Cruz Foundation -FIOCRUZ, 40296-710 Salvador, BA, Brazil., Guimarães ET; Laboratory of Histotechnics and Cell Culture, Department of Life Sciences, Bahia State University - UNEB, 41150-000 Salvador, BA, Brazil; Laboratory of Tissue Engineering and Immunopharmacology, Gonçalo Moniz Institute, Oswaldo Cruz Foundation -FIOCRUZ, 40296-710 Salvador, BA, Brazil., Soares MBP; Laboratory of Tissue Engineering and Immunopharmacology, Gonçalo Moniz Institute, Oswaldo Cruz Foundation -FIOCRUZ, 40296-710 Salvador, BA, Brazil; Senai Institute for Innovation in Advanced Health Systems, SENAI/CIMATEC, 41650-010 Salvador, BA, Brazil., Aguiar ACC; São Carlos Institute of Physics, University of Sao Paulo - USP, 13568-250 São Carlos, SP, Brazil., Guido RVC; São Carlos Institute of Physics, University of Sao Paulo - USP, 13568-250 São Carlos, SP, Brazil., Trovó M; Federal University of Rio de Janeiro - UFRJ, Botany Department, 21941-853 Rio de Janeiro, RJ, Brazil., Cilli EM; Nuclei of Bioassays, Biosynthesis and Ecophysiology of Natural Products, Institute of Chemistry, São Paulo State University - UNESP, 14800-060 Araraquara, SP, Brazil., Pinto MEF; Nuclei of Bioassays, Biosynthesis and Ecophysiology of Natural Products, Institute of Chemistry, São Paulo State University - UNESP, 14800-060 Araraquara, SP, Brazil. Electronic address: meri.emili@unesp.br., Bolzani VS; Nuclei of Bioassays, Biosynthesis and Ecophysiology of Natural Products, Institute of Chemistry, São Paulo State University - UNESP, 14800-060 Araraquara, SP, Brazil. Electronic address: vanderlan.bolzani@unesp.br.
Jazyk: angličtina
Zdroj: Fitoterapia [Fitoterapia] 2024 Oct; Vol. 178, pp. 106183. Date of Electronic Publication: 2024 Aug 12.
DOI: 10.1016/j.fitote.2024.106183
Abstrakt: Two new heptapeptides, [1-7-NαC]-crocaorbs A1 (1) and A2 (2), were isolated from the latex of Croton campanulatus. Their structures were determined using NMR spectroscopic techniques, ESI-HRMS data, Marfey's method, and further refined using molecular dynamics with simulated annealing (MD/SA). Molecular dynamics calculations of peptides 1 and 2 demonstrated greater stability in simulations using a biological solvent compared to those using DMSO. Compound 1, the most abundant peptide in latex, was assessed for NO production, antiplasmodial and cytotoxicity activities. The peptide significantly increased nitric oxide (NO) production at concentrations of 40, 20 or 10 μM (17.932 ± 1.1, 18.270 ± 0.9, 18.499 ± 0.7, respectively). Its antiplasmodial activity exhibited limited efficacy, with only 5% inhibition of Plasmodium falciparum 3D7 growth at a concentration of 50 μM. Also, it exhibited no cytotoxic effects in the J774A.1 murine macrophages cell line. This study represents the first report of a phytochemical investigation of the species C. campanulatus, which showed orbitides with distinctive sequences in contrast to other peptides described for the genus Croton and contributes to the study of structural diversity within this particular class of compounds.
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2024. Published by Elsevier B.V.)
Databáze: MEDLINE
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