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Effect of Hydroxyl Groups Esterification with Fatty Acids on the Cytotoxicity and Antioxidant Activity of Flavones

Flavonoids and polyunsaturated fatty acids due to low cytotoxicity in vitro studies are suggested as potential substances in the prevention of diseases associated with oxidative stress. We examined novel 6-hydroxy-flavanone and 7-hydroxy-flavone conjugates with selected fatty acids (FA) of different...

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Autores principales: Kubiak-Tomaszewska, Grażyna, Roszkowski, Piotr, Grosicka-Maciąg, Emilia, Strzyga-Łach, Paulina, Struga, Marta
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8777613/
https://www.ncbi.nlm.nih.gov/pubmed/35056733
http://dx.doi.org/10.3390/molecules27020420
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author Kubiak-Tomaszewska, Grażyna
Roszkowski, Piotr
Grosicka-Maciąg, Emilia
Strzyga-Łach, Paulina
Struga, Marta
author_facet Kubiak-Tomaszewska, Grażyna
Roszkowski, Piotr
Grosicka-Maciąg, Emilia
Strzyga-Łach, Paulina
Struga, Marta
author_sort Kubiak-Tomaszewska, Grażyna
collection PubMed
description Flavonoids and polyunsaturated fatty acids due to low cytotoxicity in vitro studies are suggested as potential substances in the prevention of diseases associated with oxidative stress. We examined novel 6-hydroxy-flavanone and 7-hydroxy-flavone conjugates with selected fatty acids (FA) of different length and saturation and examined their cytotoxic and antioxidant potential. Our findings indicate that the conjugation with FA affects the biological activity of both the original flavonoids. The conjugation of 6-hydroxy-flavanone increased its cytotoxicity towards prostate cancer PC3 cells. The most noticeable effect was found for oleate conjugate. A similar trend was observed for 7-hydroxy-flavone conjugates with the most evident effect for oleate and stearate. The cytotoxic potential of all tested conjugates was not specific towards PC3 because the viability of human keratinocytes HaCaT cells decreased after exposure to all conjugates. Additionally, we showed that esterification of the two flavonoids decreased their antioxidant activity compared to that of the original compounds. Of all the tested compounds, only 6-sorbic flavanone showed a slight increase in antioxidant potential compared to that of the original compound. Our data show that conjugated flavonoids are better absorbed and enhance cytotoxic effects, but the presence of FA lowered the antioxidant potential.
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spelling pubmed-87776132022-01-22 Effect of Hydroxyl Groups Esterification with Fatty Acids on the Cytotoxicity and Antioxidant Activity of Flavones Kubiak-Tomaszewska, Grażyna Roszkowski, Piotr Grosicka-Maciąg, Emilia Strzyga-Łach, Paulina Struga, Marta Molecules Article Flavonoids and polyunsaturated fatty acids due to low cytotoxicity in vitro studies are suggested as potential substances in the prevention of diseases associated with oxidative stress. We examined novel 6-hydroxy-flavanone and 7-hydroxy-flavone conjugates with selected fatty acids (FA) of different length and saturation and examined their cytotoxic and antioxidant potential. Our findings indicate that the conjugation with FA affects the biological activity of both the original flavonoids. The conjugation of 6-hydroxy-flavanone increased its cytotoxicity towards prostate cancer PC3 cells. The most noticeable effect was found for oleate conjugate. A similar trend was observed for 7-hydroxy-flavone conjugates with the most evident effect for oleate and stearate. The cytotoxic potential of all tested conjugates was not specific towards PC3 because the viability of human keratinocytes HaCaT cells decreased after exposure to all conjugates. Additionally, we showed that esterification of the two flavonoids decreased their antioxidant activity compared to that of the original compounds. Of all the tested compounds, only 6-sorbic flavanone showed a slight increase in antioxidant potential compared to that of the original compound. Our data show that conjugated flavonoids are better absorbed and enhance cytotoxic effects, but the presence of FA lowered the antioxidant potential. MDPI 2022-01-10 /pmc/articles/PMC8777613/ /pubmed/35056733 http://dx.doi.org/10.3390/molecules27020420 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
Kubiak-Tomaszewska, Grażyna
Roszkowski, Piotr
Grosicka-Maciąg, Emilia
Strzyga-Łach, Paulina
Struga, Marta
Effect of Hydroxyl Groups Esterification with Fatty Acids on the Cytotoxicity and Antioxidant Activity of Flavones
title Effect of Hydroxyl Groups Esterification with Fatty Acids on the Cytotoxicity and Antioxidant Activity of Flavones
title_full Effect of Hydroxyl Groups Esterification with Fatty Acids on the Cytotoxicity and Antioxidant Activity of Flavones
title_fullStr Effect of Hydroxyl Groups Esterification with Fatty Acids on the Cytotoxicity and Antioxidant Activity of Flavones
title_full_unstemmed Effect of Hydroxyl Groups Esterification with Fatty Acids on the Cytotoxicity and Antioxidant Activity of Flavones
title_short Effect of Hydroxyl Groups Esterification with Fatty Acids on the Cytotoxicity and Antioxidant Activity of Flavones
title_sort effect of hydroxyl groups esterification with fatty acids on the cytotoxicity and antioxidant activity of flavones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8777613/
https://www.ncbi.nlm.nih.gov/pubmed/35056733
http://dx.doi.org/10.3390/molecules27020420
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