Stereospecificity in membrane effects of catechins.
Green tea catechins consisting of catechin stereoisomers and their derivatives have been suggested to show biological activities through the interactions with cellular membranes. Their effects on membrane fluidity were comparatively studied by measuring fluorescence polarization of liposomal membranes prepared with phospholipids and cholesterol. All catechin stereoisomers reduced membrane fluidity by acting on the hydrophilic and hydrophobic regions of membrane bilayers at 20-500 microM. Both epicatechins in a cis form were more effective for reducing membrane fluidity than both catechins in a trans form. (-)-Epicatechin, (+)-epicatechin, (-)-catechin and (+)-catechin reduced membrane fluidity in increasing order of intensity. Such difference between optical isomers was increased by chiral cholesterol added to membrane lipids. In reversed-phase chromatographic evaluation, (-)-epicatechin and (+)-epicatechin were more hydrophobic than (-)-catechin and (+)-catechin, although hydrophobicity was not distinguishable between optical isomers. Stereospecificity in the membrane effects of catechin stereoisomers may be induced by the different hydrophobicity of geometrical isomers and the chirality of membrane lipid components. At lower concentrations (5-100 microM), (-)-epigallocatechin gallate and (-)-epicatechin gallate reduced membrane fluidity more significantly than (-)-epicatechin, suggesting that the intensive membrane effect contributes to the potent medicinal utility of (-)-epigallocatechin gallate.
Department of Dental Pharmacology, Asahi University School of Dentistry, 1851 Hozumi, Hozumi-cho, Motosu-gun, 501-0296, Gifu, Japan. hiro@dent.asahi-u.ac.jp
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D015060:1,2-Dipalmitoylphosphatidylcholine / Q000737:chemistry; D015057:1-Naphthylamine / Q000031:analogs & derivatives*; D000817:Anilino Naphthalenesulfonates; D002392:Catechin / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D004161:Diphenylhexatriene / Q000737:chemistry; D005419:Flavonoids / Q000737:chemistry / Q000494:pharmacology; D005454:Fluorescence Polarization; D005456:Fluorescent Dyes; D008081:Liposomes / Q000737:chemistry; D008560:Membrane Fluidity / Q000187:drug effects / Q000502:physiology*; D008567:Membranes, Artificial; D010713:Phosphatidylcholines / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000817:Anilino Naphthalenesulfonates; D005419:Flavonoids; D005456:Fluorescent Dyes; D008081:Liposomes; D008567:Membranes, Artificial; D010713:Phosphatidylcholines; D004161:Diphenylhexatriene; D015060:1,2-Dipalmitoylphosphatidylcholine; C027132:1-anilino-8-naphthalenesulfonate; D002392:Catechin; C005444:N-phenyl-1-naphthylamine; C062669:epicatechin gallate; D015057:1-Naphthylamine; C045651:epigallocatechin gallate; C017251:1,2-oleoylphosphatidylcholine; C057580:gallocatechol; C028694:1-palmitoyl-2-oleoylphosphatidylcholine