Cargando…

Study of the fluorescence and interaction between cyclodextrins and neochlorogenic acid, in comparison with chlorogenic acid

Neochlorogenic acid, a less-studied isomer of chlorogenic acid, has been seen to posses antioxidant, antifungal, anti-inflammatory and anticarcinogenic effects, which makes it an interesting candidate for incorporation in functional foods. However, its poor solubility in water and susceptibility to...

Descripción completa

Detalles Bibliográficos
Autores principales: Navarro-Orcajada, Silvia, Matencio, Adrián, Vicente-Herrero, Cristina, García-Carmona, Francisco, López-Nicolás, José Manuel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7870928/
https://www.ncbi.nlm.nih.gov/pubmed/33558562
http://dx.doi.org/10.1038/s41598-021-82915-9
_version_ 1783648908950372352
author Navarro-Orcajada, Silvia
Matencio, Adrián
Vicente-Herrero, Cristina
García-Carmona, Francisco
López-Nicolás, José Manuel
author_facet Navarro-Orcajada, Silvia
Matencio, Adrián
Vicente-Herrero, Cristina
García-Carmona, Francisco
López-Nicolás, José Manuel
author_sort Navarro-Orcajada, Silvia
collection PubMed
description Neochlorogenic acid, a less-studied isomer of chlorogenic acid, has been seen to posses antioxidant, antifungal, anti-inflammatory and anticarcinogenic effects, which makes it an interesting candidate for incorporation in functional foods. However, its poor solubility in water and susceptibility to oxidation make such a task difficult. To overcome that, its encapsulation in cyclodextrins (CDs) is proposed. The fluorescence of neochlorogenic acid in different pH conditions was analyzed, and caffeic acid was proved to be the fluorescent moiety in the molecule. An encapsulation model whereby the ligand poses two potential complexation sites (caffeic and D-(-)-quinic moieties), showed that α-CD and HP-β-CD formed the best inclusion complexes with neochlorogenic acid, followed by M-β-CD, β-CD and γ-CD. Molecular docking with the two best CDs gave better scores for α-CD, despite HP-β-CD providing stabilization through H-bonds. The encapsulation of chlorogenic acid led to a similar CD order and scores, although constants were higher for α-CD, β-CD and M-β-CD, lower for HP-β-CD, and negligible for γ-CD. The protonation state affected these results leading to a different order of CD preference. The solubility and the susceptibility to oxidation of neochlorogenic acid improved after complexation with α-CD and HP-β-CD, while the antioxidant activity of both isomers was maintained.
format Online
Article
Text
id pubmed-7870928
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher Nature Publishing Group UK
record_format MEDLINE/PubMed
spelling pubmed-78709282021-02-10 Study of the fluorescence and interaction between cyclodextrins and neochlorogenic acid, in comparison with chlorogenic acid Navarro-Orcajada, Silvia Matencio, Adrián Vicente-Herrero, Cristina García-Carmona, Francisco López-Nicolás, José Manuel Sci Rep Article Neochlorogenic acid, a less-studied isomer of chlorogenic acid, has been seen to posses antioxidant, antifungal, anti-inflammatory and anticarcinogenic effects, which makes it an interesting candidate for incorporation in functional foods. However, its poor solubility in water and susceptibility to oxidation make such a task difficult. To overcome that, its encapsulation in cyclodextrins (CDs) is proposed. The fluorescence of neochlorogenic acid in different pH conditions was analyzed, and caffeic acid was proved to be the fluorescent moiety in the molecule. An encapsulation model whereby the ligand poses two potential complexation sites (caffeic and D-(-)-quinic moieties), showed that α-CD and HP-β-CD formed the best inclusion complexes with neochlorogenic acid, followed by M-β-CD, β-CD and γ-CD. Molecular docking with the two best CDs gave better scores for α-CD, despite HP-β-CD providing stabilization through H-bonds. The encapsulation of chlorogenic acid led to a similar CD order and scores, although constants were higher for α-CD, β-CD and M-β-CD, lower for HP-β-CD, and negligible for γ-CD. The protonation state affected these results leading to a different order of CD preference. The solubility and the susceptibility to oxidation of neochlorogenic acid improved after complexation with α-CD and HP-β-CD, while the antioxidant activity of both isomers was maintained. Nature Publishing Group UK 2021-02-08 /pmc/articles/PMC7870928/ /pubmed/33558562 http://dx.doi.org/10.1038/s41598-021-82915-9 Text en © The Author(s) 2021 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Navarro-Orcajada, Silvia
Matencio, Adrián
Vicente-Herrero, Cristina
García-Carmona, Francisco
López-Nicolás, José Manuel
Study of the fluorescence and interaction between cyclodextrins and neochlorogenic acid, in comparison with chlorogenic acid
title Study of the fluorescence and interaction between cyclodextrins and neochlorogenic acid, in comparison with chlorogenic acid
title_full Study of the fluorescence and interaction between cyclodextrins and neochlorogenic acid, in comparison with chlorogenic acid
title_fullStr Study of the fluorescence and interaction between cyclodextrins and neochlorogenic acid, in comparison with chlorogenic acid
title_full_unstemmed Study of the fluorescence and interaction between cyclodextrins and neochlorogenic acid, in comparison with chlorogenic acid
title_short Study of the fluorescence and interaction between cyclodextrins and neochlorogenic acid, in comparison with chlorogenic acid
title_sort study of the fluorescence and interaction between cyclodextrins and neochlorogenic acid, in comparison with chlorogenic acid
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7870928/
https://www.ncbi.nlm.nih.gov/pubmed/33558562
http://dx.doi.org/10.1038/s41598-021-82915-9
work_keys_str_mv AT navarroorcajadasilvia studyofthefluorescenceandinteractionbetweencyclodextrinsandneochlorogenicacidincomparisonwithchlorogenicacid
AT matencioadrian studyofthefluorescenceandinteractionbetweencyclodextrinsandneochlorogenicacidincomparisonwithchlorogenicacid
AT vicenteherrerocristina studyofthefluorescenceandinteractionbetweencyclodextrinsandneochlorogenicacidincomparisonwithchlorogenicacid
AT garciacarmonafrancisco studyofthefluorescenceandinteractionbetweencyclodextrinsandneochlorogenicacidincomparisonwithchlorogenicacid
AT lopeznicolasjosemanuel studyofthefluorescenceandinteractionbetweencyclodextrinsandneochlorogenicacidincomparisonwithchlorogenicacid