title: Structure-dependent interactions of polyphenols with a biomimetic membrane system.
abstract: Polyphenols are naturally-occurring compounds, reported to be biologically active, and through their interactions with cell membranes. Although association of the polyphenols with the bilayer has been reported, the detailed mechanism of interaction is not yet well elucidated. We report on spatio-temporal real-time membrane dynamics observed in the presence of polyphenols. Two distinct membrane dynamics, corresponding to the two classes of polyphenols used, were observed. Flavonoids (epi-gallocatechin-3-gallate, gallocatechin, theaflavin and theaflavin-3-gallate) caused lipid membrane aggregation and rigidification. As simple structural modification through opening of the aromatic C-ring into an olefin bond, present in trans-stilbenes (resveratrol and picead), completely changed the membrane properties, increasing fluidity and inducing fluctuation. There were differences in the membrane transformations within the same class of polyphenols. Structure-dependent classification of membrane dynamics may contribute to a better understanding of the physicochemical mechanism involved in the bioactivity of polyphenols. In general, an increase in the number of hydrophilic side chains (galloyl, hydroxyl, glucoside, gallate) increased the reactivity of the polyphenols. Most notable was the difference observed through a simple addition of the gallate group. Unraveling the importance of these polyphenols, at a functional group level further opens the key to tailored design of bioactive compounds as potential drug candidates.
authors.affiliation: School of Materials Science, Japan Advanced Institute of Science and Technology, 1-1 Asahidai, Nomi City, Ishikawa 923-1292, Japan.
authors.forename: Huong T T
authors.initials: HT
authors.lastname: Phan
authors.affiliation: School of Materials Science, Japan Advanced Institute of Science and Technology, 1-1 Asahidai, Nomi City, Ishikawa 923-1292, Japan.
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Yoda
authors.affiliation: School of Materials Science, Japan Advanced Institute of Science and Technology, 1-1 Asahidai, Nomi City, Ishikawa 923-1292, Japan; M. Tech. Chemical Synthesis and Process Technologies, Department of Chemistry, University of Delhi, Delhi 110007, India.
authors.forename: Bindu
authors.initials: B
authors.lastname: Chahal
authors.affiliation: School of Materials Science, Japan Advanced Institute of Science and Technology, 1-1 Asahidai, Nomi City, Ishikawa 923-1292, Japan.
authors.forename: Masamune
authors.initials: M
authors.lastname: Morita
authors.affiliation: School of Materials Science, Japan Advanced Institute of Science and Technology, 1-1 Asahidai, Nomi City, Ishikawa 923-1292, Japan.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Takagi
authors.affiliation: School of Materials Science, Japan Advanced Institute of Science and Technology, 1-1 Asahidai, Nomi City, Ishikawa 923-1292, Japan. Electronic address: munde@jaist.ac.jp.
authors.forename: Mun'delanji C
authors.initials: MC
authors.lastname: Vestergaard
mesh_terms: D040761:Biomimetic Materials / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry*; D008567:Membranes, Artificial; D059808:Polyphenols / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D005419:Flavonoids; D008567:Membranes, Artificial; D059808:Polyphenols
keywords: Biomimetic membrane; Flavonoids; Membrane dynamics; Polyphenols; Trans-stilbenes