Modulation of liposomal membrane fluidity by flavonoids and isoflavonoids.
The polyphenolic structures of flavonoids and isoflavonoids confer them with the ability to scavenge free radicals and to chelate transition metals, a basis for their potent antioxidant abilities. Another possible contributory mechanism toward their antioxidant activities is their ability to stabilize membranes by decreasing membrane fluidity. In this study, the effects of representative flavonoids, isoflavonoids, and their metabolites on membrane fluidity and their preferential localization in the membrane were investigated using large unilamellar vesicles (LUVs) as the membrane models. These results were compared with those of cholesterol and alpha-tocopherol. Changes in fluorescence anisotropy values for a series of n-(9-anthroyloxy) fatty acid probes (n = 6, 12, 16) upon addition of the test compounds were used to monitor alterations in membrane fluidity at graded depths in lipid bilayer. The results of the study suggest that the flavonoids and isoflavonoids, similar to cholesterol and alpha-tocopherol, partition into the hydrophobic core of the membrane and cause a dramatic decrease in lipid fluidity in this region of the membrane. Localization of flavonoids and isoflavonoids into the membrane interiors and their resulting restrictions on fluidity of membrane components could sterically hinder diffusion of free radicals and thereby decrease the kinetics of free radical reactions.
Arora
A
A
Department of Horticulture, Michigan State University, East Lansing, Michigan, 48824, USA.
Byrem
T M
TM
Nair
M G
MG
Strasburg
G M
GM
D002839:Chromans / Q000494:pharmacology; D060754:Equol; D044950:Flavanones; D005419:Flavonoids / Q000494:pharmacology*; D005454:Fluorescence Polarization; D005456:Fluorescent Dyes; D019833:Genistein / Q000494:pharmacology; D066298:In Vitro Techniques; D007529:Isoflavones / Q000494:pharmacology*; D008081:Liposomes / Q000737:chemistry* / Q000187:drug effects*; D008560:Membrane Fluidity / Q000187:drug effects*; D010169:Palmitic Acids; D012431:Rutin / Q000494:pharmacology; D013229:Stearic Acids
C007610:4',7-dihydroxy-3,4-dihydroisoflavone; D002839:Chromans; D044950:Flavanones; D005419:Flavonoids; D005456:Fluorescent Dyes; D007529:Isoflavones; D008081:Liposomes; D010169:Palmitic Acids; D013229:Stearic Acids; C026653:12-(9-anthroyloxy)stearic acid; C040641:genistin; D060754:Equol; D012431:Rutin; C047265:16-(9-anthroyloxy)palmitic acid; D019833:Genistein; C005273:naringenin; C004541:biochanin A