In vitro gastrointestinal absorption of red wine anthocyanins – Impact of structural complexity and phase II metabolization

•Red wine 3-diglucoside anthocyanins are transported through gastrointestinal cells.•Phase II metabolite malvidin-3-glucuronide was transported through both cell lines.•Free glucoside moieties have an important role in the absorption of anthocyanins. Malvidin-3-O-glucoside, malvidin-3,5-O-diglucosid...

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Bibliographic Details
Published in:Food chemistry 2020-07, Vol.317, p.126398-126398, Article 126398
Main Authors: Han, Fuliang, Oliveira, Hélder, Brás, Natércia F., Fernandes, Iva, Cruz, Luís, De Freitas, Victor, Mateus, Nuno
Format: Article
Language:English
Subjects:
Absorption
Anthocyanins
Bioavailability
Caco-2
Metabolization
MKN-28
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Summary:•Red wine 3-diglucoside anthocyanins are transported through gastrointestinal cells.•Phase II metabolite malvidin-3-glucuronide was transported through both cell lines.•Free glucoside moieties have an important role in the absorption of anthocyanins. Malvidin-3-O-glucoside, malvidin-3,5-O-diglucoside, malvidin-3-O-(6-O-coumaroyl)-glucoside-5-O-glucoside from Chinese Vitis davidii red wine were used to investigate the role of glucoside, diglucoside and coumaroylated glucoside moieties on their transport efficiency through MKN-28 gastric and Caco-2 intestinal cells. Due to the already described conversion of 3-O-glucosylated anthocyanins into 3-O-glucuronidated, the 3-O-glucuronidated metabolite of malvidin-3-O-glucoside was also tested. The antiproliferative activity was higher for the glucuronidated metabolite in both cell lines. All anthocyanins were transported through MKN-28 gastric cells and Caco-2 intestinal cells with transport efficiencies ranging from 4% to 9% in MKN-28 and from 3% to 5% in Caco-2. No significant differences on transport efficiencies were observed at 180 min among the different anthocyanins in MKN-28. The transport efficiency of malvidin-3-O-glucuronide at 180 min was about 3–4% in Caco-2 and MKN-28 cells. Computational studies were performed to evaluate the interaction between anthocyanins and glucose gastric transporters GLUT1 and GLUT3, which supported the experimental findings.
ISSN:0308-8146
1873-7072
DOI:10.1016/j.foodchem.2020.126398