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Active Compounds in Zingiber officinale as Possible Redox Inhibitors of 5-Lipoxygenase Using an In Silico Approach

5-Lipoxygenase (5-LOX) converts arachidonic acid to lipidic inflammatory mediators such as leukotrienes (LTs). In diseases such as asthma, LTs contribute to a physiopathology that could be reverted by blocking 5-LOX. Natural products with anti-inflammatory potential such as ginger have been used as...

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Autores principales: Ley-Martínez, Jaqueline Stephanie, Ortega-Valencia, Jose Erick, García-Barradas, Oscar, Jiménez-Fernández, Maribel, Uribe-Lam, Esmeralda, Vencedor-Meraz, Carlos Iván, Oliva-Ramírez, Jacqueline
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
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Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9181373/
https://www.ncbi.nlm.nih.gov/pubmed/35682770
http://dx.doi.org/10.3390/ijms23116093
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author Ley-Martínez, Jaqueline Stephanie
Ortega-Valencia, Jose Erick
García-Barradas, Oscar
Jiménez-Fernández, Maribel
Uribe-Lam, Esmeralda
Vencedor-Meraz, Carlos Iván
Oliva-Ramírez, Jacqueline
author_facet Ley-Martínez, Jaqueline Stephanie
Ortega-Valencia, Jose Erick
García-Barradas, Oscar
Jiménez-Fernández, Maribel
Uribe-Lam, Esmeralda
Vencedor-Meraz, Carlos Iván
Oliva-Ramírez, Jacqueline
author_sort Ley-Martínez, Jaqueline Stephanie
collection PubMed
description 5-Lipoxygenase (5-LOX) converts arachidonic acid to lipidic inflammatory mediators such as leukotrienes (LTs). In diseases such as asthma, LTs contribute to a physiopathology that could be reverted by blocking 5-LOX. Natural products with anti-inflammatory potential such as ginger have been used as nutraceuticals since ancient times. 6-Gingerol and 6-shogaol are the most abundant compounds in the ginger rhizome; they possess anti-inflammatory, antioxidant, and chemopreventive properties. In the present study, 6-gingerol and 6-shogaol structures were analyzed and compared with two commercial 5-LOX inhibitors (zileuton and atreleuton) and with other inhibitor candidates (3f, NDGA, CP 209, caffeic acid, and caffeic acid phenethyl ester (CAPE)). The pharmacokinetics and toxicological properties of 6-gingerol, 6-shogaol, and the other compounds were evaluated. Targeted molecular coupling was performed to identify the optimal catalytic pocket for 5-LOX inhibition. The results showed that 6-gingerol and 6-shogaol follow all of the recommended pharmacokinetic parameters. These compounds could be inhibitors of 5-LOX because they present specific interactions with the residues involved in molecular inhibition. The current study demonstrated the potential of 6-gingerol and 6-shogaol as anti-inflammatory agents that inhibit 5-LOX, as they present a high level of performance in the toxicological analysis and could be catabolized by the cytochrome p450 enzymatic complex; however, 6-gingerol was superior in safety compared to 6-shogaol.
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spelling pubmed-91813732022-06-10 Active Compounds in Zingiber officinale as Possible Redox Inhibitors of 5-Lipoxygenase Using an In Silico Approach Ley-Martínez, Jaqueline Stephanie Ortega-Valencia, Jose Erick García-Barradas, Oscar Jiménez-Fernández, Maribel Uribe-Lam, Esmeralda Vencedor-Meraz, Carlos Iván Oliva-Ramírez, Jacqueline Int J Mol Sci Article 5-Lipoxygenase (5-LOX) converts arachidonic acid to lipidic inflammatory mediators such as leukotrienes (LTs). In diseases such as asthma, LTs contribute to a physiopathology that could be reverted by blocking 5-LOX. Natural products with anti-inflammatory potential such as ginger have been used as nutraceuticals since ancient times. 6-Gingerol and 6-shogaol are the most abundant compounds in the ginger rhizome; they possess anti-inflammatory, antioxidant, and chemopreventive properties. In the present study, 6-gingerol and 6-shogaol structures were analyzed and compared with two commercial 5-LOX inhibitors (zileuton and atreleuton) and with other inhibitor candidates (3f, NDGA, CP 209, caffeic acid, and caffeic acid phenethyl ester (CAPE)). The pharmacokinetics and toxicological properties of 6-gingerol, 6-shogaol, and the other compounds were evaluated. Targeted molecular coupling was performed to identify the optimal catalytic pocket for 5-LOX inhibition. The results showed that 6-gingerol and 6-shogaol follow all of the recommended pharmacokinetic parameters. These compounds could be inhibitors of 5-LOX because they present specific interactions with the residues involved in molecular inhibition. The current study demonstrated the potential of 6-gingerol and 6-shogaol as anti-inflammatory agents that inhibit 5-LOX, as they present a high level of performance in the toxicological analysis and could be catabolized by the cytochrome p450 enzymatic complex; however, 6-gingerol was superior in safety compared to 6-shogaol. MDPI 2022-05-29 /pmc/articles/PMC9181373/ /pubmed/35682770 http://dx.doi.org/10.3390/ijms23116093 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Ley-Martínez, Jaqueline Stephanie
Ortega-Valencia, Jose Erick
García-Barradas, Oscar
Jiménez-Fernández, Maribel
Uribe-Lam, Esmeralda
Vencedor-Meraz, Carlos Iván
Oliva-Ramírez, Jacqueline
Active Compounds in Zingiber officinale as Possible Redox Inhibitors of 5-Lipoxygenase Using an In Silico Approach
title Active Compounds in Zingiber officinale as Possible Redox Inhibitors of 5-Lipoxygenase Using an In Silico Approach
title_full Active Compounds in Zingiber officinale as Possible Redox Inhibitors of 5-Lipoxygenase Using an In Silico Approach
title_fullStr Active Compounds in Zingiber officinale as Possible Redox Inhibitors of 5-Lipoxygenase Using an In Silico Approach
title_full_unstemmed Active Compounds in Zingiber officinale as Possible Redox Inhibitors of 5-Lipoxygenase Using an In Silico Approach
title_short Active Compounds in Zingiber officinale as Possible Redox Inhibitors of 5-Lipoxygenase Using an In Silico Approach
title_sort active compounds in zingiber officinale as possible redox inhibitors of 5-lipoxygenase using an in silico approach
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9181373/
https://www.ncbi.nlm.nih.gov/pubmed/35682770
http://dx.doi.org/10.3390/ijms23116093
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