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

Abstract 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 susceptib...

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Autores principales:	Silvia Navarro-Orcajada, Adrián Matencio, Cristina Vicente-Herrero, Francisco García-Carmona, José Manuel López-Nicolás
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2021
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/8d4cbdbccf74461bb7d6b418b845ae7f
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spelling	oai:doaj.org-article:8d4cbdbccf74461bb7d6b418b845ae7f2021-12-02T14:26:47ZStudy of the fluorescence and interaction between cyclodextrins and neochlorogenic acid, in comparison with chlorogenic acid10.1038/s41598-021-82915-92045-2322https://doaj.org/article/8d4cbdbccf74461bb7d6b418b845ae7f2021-02-01T00:00:00Zhttps://doi.org/10.1038/s41598-021-82915-9https://doaj.org/toc/2045-2322Abstract 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.Silvia Navarro-OrcajadaAdrián MatencioCristina Vicente-HerreroFrancisco García-CarmonaJosé Manuel López-NicolásNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 11, Iss 1, Pp 1-11 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Silvia Navarro-Orcajada Adrián Matencio Cristina Vicente-Herrero Francisco García-Carmona José Manuel López-Nicolás Study of the fluorescence and interaction between cyclodextrins and neochlorogenic acid, in comparison with chlorogenic acid
description	Abstract 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	article
author	Silvia Navarro-Orcajada Adrián Matencio Cristina Vicente-Herrero Francisco García-Carmona José Manuel López-Nicolás
author_facet	Silvia Navarro-Orcajada Adrián Matencio Cristina Vicente-Herrero Francisco García-Carmona José Manuel López-Nicolás
author_sort	Silvia Navarro-Orcajada
title	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_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_sort	study of the fluorescence and interaction between cyclodextrins and neochlorogenic acid, in comparison with chlorogenic acid
publisher	Nature Portfolio
publishDate	2021
url	https://doaj.org/article/8d4cbdbccf74461bb7d6b418b845ae7f
work_keys_str_mv	AT silvianavarroorcajada studyofthefluorescenceandinteractionbetweencyclodextrinsandneochlorogenicacidincomparisonwithchlorogenicacid AT adrianmatencio studyofthefluorescenceandinteractionbetweencyclodextrinsandneochlorogenicacidincomparisonwithchlorogenicacid AT cristinavicenteherrero studyofthefluorescenceandinteractionbetweencyclodextrinsandneochlorogenicacidincomparisonwithchlorogenicacid AT franciscogarciacarmona studyofthefluorescenceandinteractionbetweencyclodextrinsandneochlorogenicacidincomparisonwithchlorogenicacid AT josemanuellopeznicolas studyofthefluorescenceandinteractionbetweencyclodextrinsandneochlorogenicacidincomparisonwithchlorogenicacid
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Study of the fluorescence and interaction between cyclodextrins and neochlorogenic acid, in comparison with chlorogenic acid

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