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.
Highlights
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
We discovered that in the molecule of interest, the only moiety that was really fluorescent and, caused neochlorogenic acid to fluoresce, was caffeic acid, since no fluorescence was observed in D-(-)-quinic acid
The fluorescence of this compound in different pH conditions was characterized, as well as the structural background of its fluorescence, which showed that caffeic acid was the main fluorescent moiety in the molecule
Summary
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. Some studies assert that neochlorogenic acid has antioxidant, antifungal, anti-inflammatory and anticarcinogenic bioactivities[8,9,10,11,12,13], and might be an interesting candidate for incorporating in functional foods or nutraceuticals as a bioactive compound. In this respect, the molecule presents problems, including its low solubility in water and susceptibility to oxidation by the enzyme polyphenol oxidase due to its o-diphenol s tructure[14,15], making it necessary to find new strategies. The most common are natural CDs, α, β and γ-CD, which contain six, seven and Scientific Reports | (2021) 11:3275
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