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Nutrients 2017, 9(12), 1301; doi:10.3390/nu9121301

Study of Structure and Permeability Relationship of Flavonoids in Caco-2 Cells

Key Laboratory of Environment Correlative Dietology, Ministry of Education, Huazhong Agricultural University, Wuhan 430070, China
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Received: 3 November 2017 / Revised: 22 November 2017 / Accepted: 24 November 2017 / Published: 29 November 2017
(This article belongs to the Special Issue Effects of Polyphenol-Rich Foods on Human Health)
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Abstract

Flavonoids exhibit a broad range of biological activities. However, poor absorption of some flavonoids is a major limitation for use of flavonoids as nutraceuticals. To investigate the structure requirements for flavonoids intestinal absorption, transepithelial transport and cellular accumulation (CA) of 30 flavonoids were determined using the Caco-2 cell monolayer. The bilateral permeation of five types of flavonoids followed the order: flavanones ≥ isoflavones > flavones ≥ chalcones > flavonols. The concentration of flavonoids accumulated in cells did not correlate with cell penetration since the correlation coefficient between the apparent permeability coefficient (Papp) and their corresponding CA was poor (R2 < 0.3). Most flavonoids exhibited a ratio of 0.8–1.5 for Papp A to B/Papp B to A, suggesting passive diffusion pathways. However, luteolin, morin and taxifolin may involve the efflux mechanisms. The quantitative structure-permeability relationship (QSPR) study demonstrated that the intestinal absorption of flavonoids can be related to atomic charges on carbon 3′ (QC3′), molecule surface area (SlogP_V3), balance between the center of mass and position of hydrophobic region (vsurf_ID1) and solvation energy of flavonoids (E_sol). These results provide useful information for initially screening of flavonoids with high intestinal absorption. View Full-Text
Keywords: Caco-2; flavonoids; intestinal absorption; permeability; QSPR Caco-2; flavonoids; intestinal absorption; permeability; QSPR
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Fang, Y.; Cao, W.; Xia, M.; Pan, S.; Xu, X. Study of Structure and Permeability Relationship of Flavonoids in Caco-2 Cells. Nutrients 2017, 9, 1301.

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