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Eugenol derivatives: synthesis, characterization, and evaluation of antibacterial and antioxidant activities

Eugenol is the major component of clove essential oil and has demonstrated relevant biological potential with well-known antimicrobial and antioxidant action. Therefore, this work carried out the synthesis, purification, characterization, and evaluation of the antioxidant and antibacterial potential...

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Autores principales: da Silva, Francisco Felipe Maia, Monte, Francisco José Queiroz, de Lemos, Telma Leda Gomes, do Nascimento, Patrícia Georgina Garcia, de Medeiros Costa, Alana Kelly, de Paiva, Luanda Misley Mota
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer International Publishing 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5880794/
https://www.ncbi.nlm.nih.gov/pubmed/29611004
http://dx.doi.org/10.1186/s13065-018-0407-4
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author da Silva, Francisco Felipe Maia
Monte, Francisco José Queiroz
de Lemos, Telma Leda Gomes
do Nascimento, Patrícia Georgina Garcia
de Medeiros Costa, Alana Kelly
de Paiva, Luanda Misley Mota
author_facet da Silva, Francisco Felipe Maia
Monte, Francisco José Queiroz
de Lemos, Telma Leda Gomes
do Nascimento, Patrícia Georgina Garcia
de Medeiros Costa, Alana Kelly
de Paiva, Luanda Misley Mota
author_sort da Silva, Francisco Felipe Maia
collection PubMed
description Eugenol is the major component of clove essential oil and has demonstrated relevant biological potential with well-known antimicrobial and antioxidant action. Therefore, this work carried out the synthesis, purification, characterization, and evaluation of the antioxidant and antibacterial potential of 19 eugenol derivatives. The derivatives were produced by esterification reactions in the hydroxyl group (−OH) of eugenol with different carboxylic acids and also by addition reactions in the double bond of the allyl group. The derivatives had a promising antibacterial potential, including a lower minimum inhibitory concentration of 500 μg/mL than eugenol (1000 μg/mL). In addition, the derivatives were active against bacterial strains (Escherichia coli, Staphylococcus aureus) that eugenol itself showed no activity, thus increasing the spectrum of antibacterial action. As for the antioxidant activity, it was observed that the derivatives that involved esterification reactions in the hydroxyl group (−OH) of the eugenol molecule’s phenol resulted in a significant reduction of the antioxidant action (IC(50) > 100 μg/mL) when compared with the eugenol precursor molecule (IC(50) = 4.38 μg/mL). On the other hand, the structural changes located in the double bond affected much more smoothly the capacity of capturing radicals than the starting molecule, also being obtained derivatives with proximal antioxidant capacity (IC(50) = 19.30 μg/mL) to commercial standards such as Trolox (IC(50) = 16.00 μg/mL). ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1186/s13065-018-0407-4) contains supplementary material, which is available to authorized users.
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spelling pubmed-58807942018-04-06 Eugenol derivatives: synthesis, characterization, and evaluation of antibacterial and antioxidant activities da Silva, Francisco Felipe Maia Monte, Francisco José Queiroz de Lemos, Telma Leda Gomes do Nascimento, Patrícia Georgina Garcia de Medeiros Costa, Alana Kelly de Paiva, Luanda Misley Mota Chem Cent J Research Article Eugenol is the major component of clove essential oil and has demonstrated relevant biological potential with well-known antimicrobial and antioxidant action. Therefore, this work carried out the synthesis, purification, characterization, and evaluation of the antioxidant and antibacterial potential of 19 eugenol derivatives. The derivatives were produced by esterification reactions in the hydroxyl group (−OH) of eugenol with different carboxylic acids and also by addition reactions in the double bond of the allyl group. The derivatives had a promising antibacterial potential, including a lower minimum inhibitory concentration of 500 μg/mL than eugenol (1000 μg/mL). In addition, the derivatives were active against bacterial strains (Escherichia coli, Staphylococcus aureus) that eugenol itself showed no activity, thus increasing the spectrum of antibacterial action. As for the antioxidant activity, it was observed that the derivatives that involved esterification reactions in the hydroxyl group (−OH) of the eugenol molecule’s phenol resulted in a significant reduction of the antioxidant action (IC(50) > 100 μg/mL) when compared with the eugenol precursor molecule (IC(50) = 4.38 μg/mL). On the other hand, the structural changes located in the double bond affected much more smoothly the capacity of capturing radicals than the starting molecule, also being obtained derivatives with proximal antioxidant capacity (IC(50) = 19.30 μg/mL) to commercial standards such as Trolox (IC(50) = 16.00 μg/mL). ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1186/s13065-018-0407-4) contains supplementary material, which is available to authorized users. Springer International Publishing 2018-04-03 /pmc/articles/PMC5880794/ /pubmed/29611004 http://dx.doi.org/10.1186/s13065-018-0407-4 Text en © The Author(s) 2018 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated.
spellingShingle Research Article
da Silva, Francisco Felipe Maia
Monte, Francisco José Queiroz
de Lemos, Telma Leda Gomes
do Nascimento, Patrícia Georgina Garcia
de Medeiros Costa, Alana Kelly
de Paiva, Luanda Misley Mota
Eugenol derivatives: synthesis, characterization, and evaluation of antibacterial and antioxidant activities
title Eugenol derivatives: synthesis, characterization, and evaluation of antibacterial and antioxidant activities
title_full Eugenol derivatives: synthesis, characterization, and evaluation of antibacterial and antioxidant activities
title_fullStr Eugenol derivatives: synthesis, characterization, and evaluation of antibacterial and antioxidant activities
title_full_unstemmed Eugenol derivatives: synthesis, characterization, and evaluation of antibacterial and antioxidant activities
title_short Eugenol derivatives: synthesis, characterization, and evaluation of antibacterial and antioxidant activities
title_sort eugenol derivatives: synthesis, characterization, and evaluation of antibacterial and antioxidant activities
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5880794/
https://www.ncbi.nlm.nih.gov/pubmed/29611004
http://dx.doi.org/10.1186/s13065-018-0407-4
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