title: Interaction of Artepillin C with model membranes.
abstract: Green propolis, a mixture of beeswax and resinous compounds processed by Apis mellifera, displays several pharmacological properties. Artepillin C, the major compound in green propolis, consists of two prenylated groups bound to a phenyl group. Several studies have focused on the therapeutic effects of Artepillin C, but there is no evidence that it interacts with amphiphilic aggregates to mimic cell membranes. We have experimentally and computationally examined the interaction between Artepillin C and model membranes composed of dimyristoylphosphatidylcholine (DMPC) because phosphatidylcholine (PC) is one of the most abundant phospholipids in eukaryotic cell membranes. PC is located in both outer and inner leaflets and has been used as a simplified membrane model and a non-specific target to study the action of amphiphilic molecules with therapeutic effects. Experimental results indicated that Artepillin C adsorbed onto the DMPC monolayers. Its presence in the lipid suspension pointed to an increased tendency toward unilamellar vesicles and to decreased bilayer thickness. Artepillin C caused point defects in the lipid structure, which eliminated the ripple phase and the pre-transition in thermotropic chain melting. According to molecular dynamics (MD) simulations, (1) Artepillin C aggregated in the aqueous phase before it entered the bilayer; (2) Artepillin C was oriented along the direction normal to the surface; (3) the negatively charged group on Artepillin C was accommodated in the polar region of the membrane; and (4) thinner regions emerged around the Artepillin C molecules. These results help an understanding of the molecular mechanisms underlying the biological action of propolis.
authors: Department of Physics, Faculty of Philosophy, Sciences and Letters of Ribeirão Preto, University of São Paulo, Av. Bandeirantes, 3900, Ribeirão Preto, São Paulo, 14040-901, Brazil.|Dutch Polymer Institute (DPI), PO Box 902, 5600 AX, Eindhoven, The Netherlands.
authors: Wallance Moreira
authors: WM
authors: Pazin
authors: Department of Physics, Faculty of Philosophy, Sciences and Letters of Ribeirão Preto, University of São Paulo, Av. Bandeirantes, 3900, Ribeirão Preto, São Paulo, 14040-901, Brazil.|Dutch Polymer Institute (DPI), PO Box 902, 5600 AX, Eindhoven, The Netherlands.
authors: Danilo da Silva
authors: DD
authors: Olivier
authors: Macromolecular and Organic Chemistry, Physical Chemistry & Institute for Complex Molecular Systems, Eindhoven University of Technology, 5600 MB, Eindhoven, The Netherlands.
authors: Neus
authors: N
authors: Vilanova
authors: Department of Chemistry, Faculty of Philosophy, Sciences and Letters of Ribeirão Preto, University of São Paulo, Av. Bandeirantes, 3900, Ribeirão Preto, São Paulo, 14040-901, Brazil.
authors: Ana Paula
authors: AP
authors: Ramos
authors: Macromolecular and Organic Chemistry, Physical Chemistry & Institute for Complex Molecular Systems, Eindhoven University of Technology, 5600 MB, Eindhoven, The Netherlands.|Dutch Polymer Institute (DPI), PO Box 902, 5600 AX, Eindhoven, The Netherlands.
authors: Ilja Karina
authors: IK
authors: Voets
authors: Department of Genetics, Ribeirão Preto Medical School, University of São Paulo, Av. Bandeirantes, 3900, Ribeirão Preto, São Paulo, 14049-900, Brazil.
authors: Ademilson Espencer Egea
authors: AE
authors: Soares
authors: Department of Physics, Faculty of Philosophy, Sciences and Letters of Ribeirão Preto, University of São Paulo, Av. Bandeirantes, 3900, Ribeirão Preto, São Paulo, 14040-901, Brazil. amandosi@ffclrp.usp.br.
authors: Amando Siuiti
authors: AS
authors: Ito
mesh_terms: D004134:Dimyristoylphosphatidylcholine / Q000737:chemistry / Q000378:metabolism; D008051:Lipid Bilayers / Q000737:chemistry / Q000378:metabolism; D008968:Molecular Conformation; D056004:Molecular Dynamics Simulation; D010666:Phenylpropionates / Q000737:chemistry / Q000378:metabolism*; D011485:Protein Binding; D053835:Unilamellar Liposomes / Q000737:chemistry / Q000378:metabolism*
chemical_list: D008051:Lipid Bilayers; D010666:Phenylpropionates; D053835:Unilamellar Liposomes; C102259:artepillin C; D004134:Dimyristoylphosphatidylcholine
keywords: Artepillin C; DMPC; Green propolis; Langmuir monolayer; Model membranes