This review is a presentation of data gathered on the interactions of several polyphenolics (i.e., phenolic acids, stilbenes, flavonoids) with lipid bilayers of different lipid compositions. These polyphenolics have been investigated through a combination of fluorescence spectroscopy, electron paramagnetic resonance spectroscopy, and differential scanning calorimetry, to detect changes in membrane fluidity. Among the investigated phenolic acids, the least polar phenolic acid, p-coumaric acid, has the greatest effect on lipid membrane structure. It appears to have a greater ability to cross membranes by passive transport than more polar phenolic acids. On the other hand, among the flavonoids that have been studied, the anthocyanins cyanidin-3-glucoside and its aglycone are inactive. All of the flavonols tested, except for epigallocatechin-3-gallate, promote small decreases in membrane fluidity. Computer simulation of electron paramagnetic resonance spectra for flavonoids indicated two or three regions in the phosphatidylcholine/ phosphatidylserine (2.4:1) membrane with different fluidity characteristics. The effects of the different flavonoids are correlated to their structural characteristics, whereby even the difference in one -OH group can be important, as can the number of H-bonds they form. The role of membrane composition and flavonoid structure in these interactions with lipid membranes are of great importance for bioavailability of these compounds and for their biological effects in an organism.
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