Aglycone structures and glycosylations affect anthocyanin transport and uptake in human gastric epithelial (NCI-N87) cells

Sigurdson, Gregory T.; Atnip, Allison; Bomser, Joshua A.; Giusti, M. Mónica

doi:10.1016/j.jfca.2017.09.007

Cited by 17 publications

(5 citation statements)

References 17 publications

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“…Notably, even though a certain anthocyanin exhibits the highest amount of transport, its transport rate may be the lowest, which may signal that the additional mechanisms of anthocyanins uptake and transport [ 31 ].…”

Section: Resultsmentioning

confidence: 99%

“…In NCI-N87 cell monolayers, Cy-3-glc and Pn-3-glc are preferentially transported and absorbed. When the aglycone structure is the same, the type of glycosyl may also affect the absorption of anthocyanins, and the transport rate of pentose glycosylated anthocyanins is higher than that of hexosylated anthocyanins [ 31 ]. Human trials indicate that acylation reduces the absorption efficiency of anthocyanins, and the absorption efficiency of anthocyanin-3-(xylose-spiroyl-glucose)-galactoside is lower than that of non-acylated anthocyanins with the same structure [ 32 ].…”

Section: Introductionmentioning

confidence: 99%

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Methylation, Hydroxylation, Glycosylation and Acylation Affect the Transport of Wine Anthocyanins in Caco-2 Cells

Liu

Lin

Tien

et al. 2022

Foods

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Anthocyanins are substances with multiple physiological activities widely present in red wine, but the influence of structure (methylation, hydroxylation, acylation, glycosylation) on the transport remains ill-defined. In the present study, Caco-2 monolayers were used as an in vitro model of the absorptive intestinal epithelium to transport different types of anthocyanin samples. Results showed that both methylation and acetylation promote the level of transport. Monoglycoside standard exhibited higher transport amount and rate compared to diglycoside standard while the transport level of the monoglycoside mixture was unexpectedly lower than that of the diglycoside mixture. Caco-2 monolayers appeared to be more capable of transporting the single standard than the mixed standard. Meanwhile, the transport of anthocyanins in Caco-2 cell model showed time- and concentration-dependent trends. Anthocyanin treatment had a greater effect on sodium-dependent glucose transporter 1 (SGLT1) mRNA expression than glucose transporter 2 (GLUT2), and significantly down-regulated the protein expression of SGLT1. Although the low bioavailability of anthocyanins requires much more research, further evidence of the role of structure is provided.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Methylation, Hydroxylation, Glycosylation and Acylation Affect the Transport of Wine Anthocyanins in Caco-2 Cells

Liu

Lin

Tien

et al. 2022

Foods

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“…Meanwhile, it suggests that the interaction between FA-g-CS and ANC was substantial, thus warranting more attention [ 41 ]. This may be due to the variation of the ANC chemical structure caused by FA-g-CS [ 42 ]. Previous work has also suggested that polyphenols in sour cherries extracted by solid-phase extraction can decrease the transmembrane absorption efficiency of ANCs by fivefold–tenfold, which may be related to the interaction between ANCs and polyphenols [ 39 ].…”

Section: Discussionmentioning

confidence: 99%

The Effect of Ferulic Acid-Grafted Chitosan (FA-g-CS) on the Transmembrane Transport of Anthocyanins by sGLT1 and GLUT2

Chen

Diao

et al. 2022

Foods

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This work aims to evaluate the effect of ferulic acid-grafted chitosan (FA-g-CS) on the interaction between anthocyanin (ANC) and sGLT1/GLUT2 and their functions in ANC transmembrane transport using Caco-2 cells. The transmembrane transport experiments of ANC showed its low transport efficiency (Papp < 10−6 cm/s), whereas the phenomenon of a significantly rise in anthocyanins transport efficiency was observed with the incubation of FA-g-CS (p < 0.05). In order to investigate the mechanism of FA-g-CS improving ANC transmembrane transport, Caco-2 cells were transfected with small interfering RNA (siRNA) specific for transporters sGLT1 and GLUT2, and incubated with ANC, FA-g-CS, or their combination. Subsequently, Western blot analyses and immunofluorescence staining were carried out to monitor the intracellular sGLT1 and GLUT2 levels. These siRNA-transfected cells, incubated with compounds, indicate that sGLT1 and GLUT2 participated in the ANC transmembrane transport and that FA-g-CS, ANC, or their combination enhance sGLT1/GLUT2 expression. In particular, Caco-2 cells incubated with both FA-g-CS and ANC show significantly increased sGLT1 or GLUT2 expression (>80%) compared with exclusively using FA-g-CS or ANC (<60%). Molecular docking results demonstrate that there is a good binding between FA-g-CS/ANC and sGLT1 or GLUT2. These results highlight that FA-g-CS promotes the transmembrane transport of ANC by influencing the interaction between ANC and sGLT1/GLUT2; the interaction between FA-g-CS and ANC could be another key factor that improves the bioavailability of ANC.

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“…Another crucial aspect is the acidification of the extracting solvent, in order to obtain superior recovery yield and ensure a better preservation of ANs [92]. Hydrochloric, formic, acetic, and trifluoroacetic acids are amongst the most utilized acids [85,93].…”

Section: Effects Of Extraction Methods On Ansmentioning

confidence: 99%

Anthocyanins as Key Phytochemicals Acting for the Prevention of Metabolic Diseases: An Overview

et al. 2022

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Anthocyanins are water-soluble pigments present in fruits and vegetables, which render them an extensive range of colors. They have a wide distribution in the human diet, are innocuous, and, based on numerous studies, have supposed preventive and therapeutical benefits against chronic affections such as inflammatory, neurological, cardiovascular, digestive disorders, diabetes, and cancer, mostly due to their antioxidant action. Despite their great potential as pharmaceutical applications, they have a rather limited use because of their rather low stability to environmental variations. Their absorption was noticed to occur best in the stomach and small intestine, but the pH fluctuation of the digestive system impacts their rapid degradation. Urine excretion and tissue distribution also occur at low rates. The aim of this review is to highlight the chemical characteristics of anthocyanins and emphasize their weaknesses regarding bioavailability. It also targets to deliver an update on the recent advances in the involvement of anthocyanins in different pathologies with a focus on in vivo, in vitro, animal, and human clinical trials.

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Aglycone structures and glycosylations affect anthocyanin transport and uptake in human gastric epithelial (NCI-N87) cells

Cited by 17 publications

References 17 publications

Methylation, Hydroxylation, Glycosylation and Acylation Affect the Transport of Wine Anthocyanins in Caco-2 Cells

Methylation, Hydroxylation, Glycosylation and Acylation Affect the Transport of Wine Anthocyanins in Caco-2 Cells

The Effect of Ferulic Acid-Grafted Chitosan (FA-g-CS) on the Transmembrane Transport of Anthocyanins by sGLT1 and GLUT2

Anthocyanins as Key Phytochemicals Acting for the Prevention of Metabolic Diseases: An Overview

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