title: Biophysical study of resin acid effects on phospholipid membrane structure and properties.
abstract: Hydrophobic resin acids (RAs) are synthesized by conifer trees as part of their defense mechanisms. One of the functions of RAs in plant defense is suggested to be the perturbation of the cellular membrane. However, there is a vast diversity of chemical structures within this class of molecules, and there are no clear correlations to the molecular mechanisms behind the RA's toxicity. In this study we unravel the molecular interactions of the three closely related RAs dehydroabietic acid, neoabietic acid, and the synthetic analogue dichlorodehydroabietic acid with dipalmitoylphosphatidylcholine (DPPC) model membranes and the polar lipid extract of soybeans. The complementarity of the biophysical techniques used (NMR, DLS, NR, DSC, Cryo-TEM) allowed correlating changes at the vesicle level with changes at the molecular level and the co-localization of RAs within DPPC monolayer. Effects on DPPC membranes are correlated with the physical chemical properties of the RA and their toxicity.
authors.affiliation: Nano Science Center and Department of Chemistry, University of Copenhagen, Copenhagen, Denmark.
authors.forename: Vivien
authors.initials: V
authors.lastname: Jagalski
authors.affiliation: Institute Laue Langevin, 71 avenue de Matyrs, CS, 20156, 38042 Grenoble Cedex 9, France.
authors.forename: Robert
authors.initials: R
authors.lastname: Barker
authors.affiliation: Division of Physical Chemistry, Department of Chemistry, Lund University, Sweden.
authors.forename: Daniel
authors.initials: D
authors.lastname: Topgaard
authors.affiliation: Department of Plant and Environmental Sciences, University of Copenhagen, Copenhagen, Denmark.
authors.forename: Thomas
authors.initials: T
authors.lastname: Günther-Pomorski
authors.affiliation: Department of Plant and Environmental Sciences, University of Copenhagen, Copenhagen, Denmark.
authors.forename: Björn
authors.initials: B
authors.lastname: Hamberger
authors.affiliation: Nano Science Center and Department of Chemistry, University of Copenhagen, Copenhagen, Denmark; Biofilm - Research Center for Biointerfaces and Department of Biomedical Science, Malmö University, Malmö, Sweden. Electronic address: cardenas@nano.ku.dk.
authors.forename: Marité
authors.initials: M
authors.lastname: Cárdenas
mesh_terms: D015060:1,2-Dipalmitoylphosphatidylcholine / Q000737:chemistry*; D045784:Abietanes / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D000890:Anti-Infective Agents / Q000737:chemistry* / Q000302:isolation & purification; D020285:Cryoelectron Microscopy; D008051:Lipid Bilayers / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010936:Plant Extracts / Q000737:chemistry; D013025:Glycine max / Q000737:chemistry; D064028:Tracheophyta / Q000737:chemistry
chemical_list: C119118:12,14-dichlorodehydroabietic acid; D045784:Abietanes; D000890:Anti-Infective Agents; D008051:Lipid Bilayers; D010936:Plant Extracts; C013913:dehydroabietic acid; D015060:1,2-Dipalmitoylphosphatidylcholine; C023710:abietic acid
keywords: DPPC; Lipid; Neutron reflectometry; Resin acids; Toxicity; ssNMR