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Medicines 2017, 4(2), 39; doi:10.3390/medicines4020039

Synthesis, Antimicrobial, and Antioxidant Activities of Chalcogen-Containing Nitrone Derivatives from (R)-citronellal

1
Laboratório de Síntese Orgânica Limpa, LASOL, Universidade Federal de Pelotas, UFPel, Pelotas, RS 96010-900, Brazil
2
Faculdade de Agronomia Eliseu Maciel, DCTA, Universidade Federal de Pelotas, UFPel, Pelotas, RS 96010-900, Brazil
3
Centro de Desenvolvimento Tecnológico, Unidade Biotecnologia, Universidade Federal de Pelotas, UFPel, Pelotas, RS 96010-900, Brazil
*
Authors to whom correspondence should be addressed.
Academic Editor: Eleni Skaltsa
Received: 27 April 2017 / Revised: 1 June 2017 / Accepted: 5 June 2017 / Published: 10 June 2017
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Abstract

Background: The main constituents of Cymbopogonnardus (L) Rendle and C. citratus (DC) Stapfessential oils are (R)-citronellal and citral, respectively. Organochalcogen compounds can boost the biological activities of natural products. Methods: Several chalcogen-containing nitrones derived from (R)-citronellal and citral were prepared and evaluated for their antimicrobial and antioxidant activities. The antimicrobial activity was evaluated by the disc diffusion test and the antioxidant properties were evaluated in vitro by DPPH (1,1-diphenyl-2-picryl-hydrazyl), ABTS (2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid), and FRAP (ferric ion reducing antioxidant power) assays. Results: In the antimicrobial assay, (E)-N,3,7-trimethyl-3-(phenylthio)oct-6-en-1-imine oxide 5c exhibited halos between 21.5 mm (Escherichia coli O157:H7) and 26.0 mm (Listeria monocytogenes), while (E)-N,3,7-trimethyloct-6-en-1-imine oxide 5d presented halos between 22.5 mm (E. coli O157:H7) and 31.0 mm (L. monocytogenes). (E)-N,3,7-Trimethyl-2-(phenylthio)oct-6-en-1-imine oxide 5a showed the lowest minimal inhibitory concentration (MIC) value against Bacillus cereus (0.48 mM), and 5c was the most potent bactericide, with a minimal bactericidal concentration (MBC) of 0.52 mM for E. coli O157:H7. In the antioxidant assays, 5c, 5d, and 10 ((E)-3,7-dimethyl-2-(phenylselanyl)oct-6-enal oxime) were the most actives in the DPPH, ABTS, and FRAP assays, respectively. Conclusions: The presence of a phenylthio group in the nitrone increases its antimicrobial activity against Gram-positive and Gram-negative foodborne pathogens in the disk diffusion test and the antioxidant activity in vitro. View Full-Text
Keywords: citronellal; organochalcogen; foodborne bacteria; antioxidant; antibacterial citronellal; organochalcogen; foodborne bacteria; antioxidant; antibacterial
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MDPI and ACS Style

Ferraz, M.C.; Mano, R.A.; Oliveira, D.H.; Maia, D.S.V.; Silva, W.P.; Savegnago, L.; Lenardão, E.J.; Jacob, R.G. Synthesis, Antimicrobial, and Antioxidant Activities of Chalcogen-Containing Nitrone Derivatives from (R)-citronellal. Medicines 2017, 4, 39.

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