Next Article in Journal
Elucidating the Skin Delivery of Aglycone and Glycoside Flavonoids: How the Structures Affect Cutaneous Absorption
Next Article in Special Issue
Protective Effects of Hesperidin (Citrus Flavonone) on High Glucose Induced Oxidative Stress and Apoptosis in a Cellular Model for Diabetic Retinopathy
Previous Article in Journal
Effect of Gamma-Oryzanol as Therapeutic Agent to Prevent Cardiorenal Metabolic Syndrome in Animals Submitted to High Sugar-Fat Diet
Previous Article in Special Issue
WNT Inhibitory Activity of Malus Pumila miller cv Annurca and Malus domestica cv Limoncella Apple Extracts on Human Colon-Rectal Cells Carrying Familial Adenomatous Polyposis Mutations
Open AccessArticle

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
Author to whom correspondence should be addressed.
Nutrients 2017, 9(12), 1301;
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)
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
Show Figures

Graphical abstract

MDPI and ACS Style

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.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

Back to TopTop