Cargando…

Polyphenols with Anti-Inflammatory Properties: Synthesis and Biological Activity of Novel Curcumin Derivatives

Herein, we describe the synthesis and evaluation of anti-inflammatory activities of new curcumin derivatives. The thirteen curcumin derivatives were synthesized by Steglich esterification on one or both of the phenolic rings of curcumin with the aim of providing improved anti-inflammatory activity....

Descripción completa

Detalles Bibliográficos
Autores principales: González, Yisett, Mojica-Flores, Randy, Moreno-Labrador, Dilan, Cubilla-Rios, Luis, Rao, K. S. Jagannatha, Fernández, Patricia L., Larionov, Oleg V., Lakey-Beitia, Johant
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9966181/
https://www.ncbi.nlm.nih.gov/pubmed/36835104
http://dx.doi.org/10.3390/ijms24043691
_version_ 1784896952040685568
author González, Yisett
Mojica-Flores, Randy
Moreno-Labrador, Dilan
Cubilla-Rios, Luis
Rao, K. S. Jagannatha
Fernández, Patricia L.
Larionov, Oleg V.
Lakey-Beitia, Johant
author_facet González, Yisett
Mojica-Flores, Randy
Moreno-Labrador, Dilan
Cubilla-Rios, Luis
Rao, K. S. Jagannatha
Fernández, Patricia L.
Larionov, Oleg V.
Lakey-Beitia, Johant
author_sort González, Yisett
collection PubMed
description Herein, we describe the synthesis and evaluation of anti-inflammatory activities of new curcumin derivatives. The thirteen curcumin derivatives were synthesized by Steglich esterification on one or both of the phenolic rings of curcumin with the aim of providing improved anti-inflammatory activity. Monofunctionalized compounds showed better bioactivity than the difunctionalized derivatives in terms of inhibiting IL-6 production, and known compound 2 presented the highest activity. Additionally, this compound showed strong activity against PGE(2). Structure–activity relationship studies were carried out for both IL-6 and PGE(2), and it was found that the activity of this series of compounds increases when a free hydroxyl group or aromatic ligands are present on the curcumin ring and a linker moiety is absent. Compound 2 remained the highest activity in modulating IL-6 production and showed strong activity against PGE(2) synthesis.
format Online
Article
Text
id pubmed-9966181
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-99661812023-02-26 Polyphenols with Anti-Inflammatory Properties: Synthesis and Biological Activity of Novel Curcumin Derivatives González, Yisett Mojica-Flores, Randy Moreno-Labrador, Dilan Cubilla-Rios, Luis Rao, K. S. Jagannatha Fernández, Patricia L. Larionov, Oleg V. Lakey-Beitia, Johant Int J Mol Sci Article Herein, we describe the synthesis and evaluation of anti-inflammatory activities of new curcumin derivatives. The thirteen curcumin derivatives were synthesized by Steglich esterification on one or both of the phenolic rings of curcumin with the aim of providing improved anti-inflammatory activity. Monofunctionalized compounds showed better bioactivity than the difunctionalized derivatives in terms of inhibiting IL-6 production, and known compound 2 presented the highest activity. Additionally, this compound showed strong activity against PGE(2). Structure–activity relationship studies were carried out for both IL-6 and PGE(2), and it was found that the activity of this series of compounds increases when a free hydroxyl group or aromatic ligands are present on the curcumin ring and a linker moiety is absent. Compound 2 remained the highest activity in modulating IL-6 production and showed strong activity against PGE(2) synthesis. MDPI 2023-02-12 /pmc/articles/PMC9966181/ /pubmed/36835104 http://dx.doi.org/10.3390/ijms24043691 Text en © 2023 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
González, Yisett
Mojica-Flores, Randy
Moreno-Labrador, Dilan
Cubilla-Rios, Luis
Rao, K. S. Jagannatha
Fernández, Patricia L.
Larionov, Oleg V.
Lakey-Beitia, Johant
Polyphenols with Anti-Inflammatory Properties: Synthesis and Biological Activity of Novel Curcumin Derivatives
title Polyphenols with Anti-Inflammatory Properties: Synthesis and Biological Activity of Novel Curcumin Derivatives
title_full Polyphenols with Anti-Inflammatory Properties: Synthesis and Biological Activity of Novel Curcumin Derivatives
title_fullStr Polyphenols with Anti-Inflammatory Properties: Synthesis and Biological Activity of Novel Curcumin Derivatives
title_full_unstemmed Polyphenols with Anti-Inflammatory Properties: Synthesis and Biological Activity of Novel Curcumin Derivatives
title_short Polyphenols with Anti-Inflammatory Properties: Synthesis and Biological Activity of Novel Curcumin Derivatives
title_sort polyphenols with anti-inflammatory properties: synthesis and biological activity of novel curcumin derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9966181/
https://www.ncbi.nlm.nih.gov/pubmed/36835104
http://dx.doi.org/10.3390/ijms24043691
work_keys_str_mv AT gonzalezyisett polyphenolswithantiinflammatorypropertiessynthesisandbiologicalactivityofnovelcurcuminderivatives
AT mojicafloresrandy polyphenolswithantiinflammatorypropertiessynthesisandbiologicalactivityofnovelcurcuminderivatives
AT morenolabradordilan polyphenolswithantiinflammatorypropertiessynthesisandbiologicalactivityofnovelcurcuminderivatives
AT cubillariosluis polyphenolswithantiinflammatorypropertiessynthesisandbiologicalactivityofnovelcurcuminderivatives
AT raoksjagannatha polyphenolswithantiinflammatorypropertiessynthesisandbiologicalactivityofnovelcurcuminderivatives
AT fernandezpatricial polyphenolswithantiinflammatorypropertiessynthesisandbiologicalactivityofnovelcurcuminderivatives
AT larionovolegv polyphenolswithantiinflammatorypropertiessynthesisandbiologicalactivityofnovelcurcuminderivatives
AT lakeybeitiajohant polyphenolswithantiinflammatorypropertiessynthesisandbiologicalactivityofnovelcurcuminderivatives