Effects of red wine flavonoid components on biomembranes and cell proliferation
Department of Dental Basic Education, Asahi University School of Dentistry, Mizuho, Gifu, Japan
Background: In order to understand the antiproliferative effect of red wine in mechanistic terms, the membrane interactions of flavonoid components and their related structures were compared using liposomal biomimetic membranes prepared with different phospholipids and cholesterol.
Methods and results: A series of fluorescence polarization measurements revealed that anthocyanidins, flavones, flavonols, flavanones, flavanonols, isoflavones, catechins, and chalcones interact with biomimetic membranes in a structure-dependent manner to decrease their fluidity at concentrations of 1–10 µM by preferentially acting in the deeper regions of the lipid bilayers. In the structure and membrane interactivity relationship, greater membrane-interacting potency was associated with a 3-hydroxyl group and a double bond between the 2-carbon and 3-carbon of the C ring, 3’,4’-dihydroxyl groups of the B ring, and 5,7-dihydroxyl groups of the A ring. Cyanidin, quercetin, and (–)-epigallocatechin gallate meet these structural requirements, and were effective in inhibiting the proliferation of tumor cells, showing inhibition rates of 16.4% and 35.4%, 23.3% and 74.3%, and 31.3% and 75.5%, respectively, after culture for 24 and 48 hours. These antiproliferative flavonoids simultaneously decreased the membrane fluidity of tumor cells depending on culture time. The rank order of cell membrane rigidification [(–)-epigallocatechin gallate > quercetin > cyanidin] was consistent with inhibition of cell proliferation.
Conclusion: Membrane interaction is very likely to underlie the antiproliferative effects of wine flavonoids. Membrane-interactive flavonoid components would contribute to the functionality of red wine.
Keywords: red wine, flavonoid, membrane interaction, fluidity change, antiproliferative effect
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