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The Interaction of Abietic Acid with Phospholipid Membranes Francisco J

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The Interaction of Abietic Acid with Phospholipid Membranes Francisco J View metadata, citation and similar papers at core.ac.ukBiochimica et Biophysica Acta 1327Ž. 1997 171±180 brought to you by CORE provided by Elsevier - Publisher Connector The interaction of abietic acid with phospholipid membranes Francisco J. Aranda ), Jose Villalaõn Departamento de Bioquõmica y Biologõa Molecular() A , Edificio de Veterinaria, UniÕersidad de Murcia, Apdo. 4021, E-30080 Murcia, Spain Received 1 November 1996; revised 19 February 1997; accepted 27 February 1997 Abstract Abietic acid is a major component of the oleoresin synthesized by many conifers and constitutes a major class of environmental toxic compounds with potential health hazard to animal, including human, and plant life. Being an amphipathic molecule, the study of the influence of abietic acid on the structure of membranes would be important to get insight into the mechanism of toxic action of the molecule. The interaction of abietic acid with model membranes of dipalmitoylphosphatidylcholineŽ. DPPC and dielaidoylphosphatidylethanolamine Ž. DEPE has been studied by differential scanning calorimetry and 31 P-nuclear magnetic resonance spectroscopy. It has been found that abietic acid greatly affects the phase transition of DPPC, shifting the transition temperature to lower values, giving rise to the appearance of two peaks in the thermogram and to the presence of fluid immiscible phases. In a similar way, the phase transition of DEPE, in the presence of abietic acid, was shifted to lower temperatures, and two peaks appeared in the thermograms. The temperature of the lamellar to hexagonal HII phase transition was also decreased by the presence of abietic acid, but phase immiscibilities were not detected. The possible implications of these effects on the action of abietic acid on biological membranes are discussed. Keywords: Abietic acid; Model membrane; DSC; NMR, 31P-; Lipid polymorphism 1. Introduction hazard to animal and plant life. Abietic acidŽ Scheme 1. is a major component of the rosin fraction of The amount and variety of aromatic hydrocarbons oleoresin synthesized by grand fir Ž.Abies grandis , and their derivatives used in industrial and commer- lodgepole pine Ž.Pinus contorta , and many other cial activities has been increasing over the years. The conifer specieswx 1 . The production of oleoresins by release of these compounds into the environment is conifer species is an important component of the of a great concern because of their potential health defense response against insect attack and fungal pathogen infectionwx 2 . Resin acids are a major class of toxicants discharged in the effluent of pulp and paper mills to aquatic environmentswx 3 and they have Abbreviations: DEPE, dielaidoylphosphatidylethanolamine; been shown to be lethal to fish affecting respiration DPPC, dipalmitoylphosphatidylcholine; DSC, differential scan- 31 31 and energy metabolismwx 4 and causing liver dysfunc- ning calorimetry; P-NMR, P-nuclear magnetic resonance; Tc, main gel to liquid-crystalline phase transition temperature tionwx 5 . It is known that the dehydro derivative of ) Corresponding author. Fax: q34 68 364147. abietic acid is toxic to the rat, impairing co-ordination 0005-2736r97r$17.00 Copyright q 1997 Elsevier Science B.V. All rights reserved. PII S0005-2736Ž. 97 00054-0 172 F.J. Aranda, J. Villalaõn rBiochimica et Biophysica Acta 1327() 1997 171±180 phism'. These non-bilayer structures include the mi- cellar phase, the hexagonal HII phase and lipidic particleswx 16 , which can greatly affect the functional behavior of the membranewx 17 , being intermediates in vesicle fusion and involved in lipid flip-flop. Non- bilayer structures may also modulate the energetics and kinetics of transport across membraneswx 18 . There Scheme 1. Structure of abietic acidŽ 13-isopropylpodocarpa- is also strong evidence that the function of membrane 7,13-dien-15-oic acid. proteins can be affected by the modification of the properties of the lipid matrix in which they are embeddedwx 19 . and producing paralysiswx 6 . It has been suggested Since lipid polymorphism has such potential bio- that abietic acid might be the specific etiologic agent logical importance, in this investigation we have in the development of acute and chronic lung disease checked whether abietic acid might modulate it. We in workers exposed to resin derived from pine wood have studied the interaction between abietic acid and wx7. phosphatidylethanolamine because this phospholipid, The mechanism whereby abietic acid causes the being a major component of eukaryotic membranes, toxic effects is still unknown. Since many amphi- spontaneously adopts hexagonal HII phases in the pathic compounds affect the function and integrity of presence of excess aqueous buffer at physiological cell membranes, it seems possible that resin acids, temperatures. At the same time, we have investigated also amphipathic compounds, might act in a similar the interaction of abietic acid with phosphatidyl- manner. In this respect, it has been shown that the choline, the most important class of membrane phos- dehydro derivative of abietic acid affects the physical pholipids. We have used differential scanning state of cytoskeletal proteins and the lipid bilayer of calorimetryŽ. DSC and31 P-nuclear magnetic reso- erythrocyte membraneswx 8 . Abietic acid and deriva- nanceŽ 31 P-NMR. to assess the influence of abietic tives have been reported to act as non-specific in- acid on the phase behavior of the phospholipids. The hibitors of platelet aggregationwx 9 , they affect the modulation of DPPC thermotropic properties and permeability of synaptosomal membraneswx 10 and DEPE polymorphic behavior by abietic acid is dis- have a direct lytic activity to alveolar epithelial cells cussed in the light of its possible mechanism of toxic producing profound lung epithelial injurywx 11 . The action. above facts, together with the marked amphipathicity of resin acids, points to biological membranes as one of their target sites of toxic action. From this point of 2. Materials and methods view, the knowledge of the interaction between abi- etic acid and membrane lipids may help to get insight 2.1. Materials into the mechanism of action of the amphipathic toxin. Dipalmitoylphosphatidylcholine and dielaidoyl- The purpose of this study was to investigate in phosphatidylethanolamine were obtained from Avanti detail the interaction of abietic acid with membranes Polar LipidsŽ. Birmingham, AL, USA . Abietic acid using lipid vesicles as model systems. Membrane was obtained from Aldrich ChemieŽ Steinheim, Ger- model systems are widely used to study the mecha- many. Organic solvents were obtained from Merck nism of interaction of membrane active molecules Ž.Darmstadt, Germany . Deionized and twice distilled with lipidswx 12±15 . It is known that dispersion of water was used. individual or mixtures of phospholipids of biological origin or synthetic ones can adopt several non-bilayer 2.2. Differential scanning calorimetry structures, in addition to the familiar bilayer organiza- tion. The ability of certain lipids to adopt these The lipid mixtures for calorimetry measurements different structures is known as `lipid polymor- were prepared by combination of chloroformr F.J. Aranda, J. Villalaõn rBiochimica et Biophysica Acta 1327() 1997 171±180 173 methanolŽ. 1:1 solutions containing 4 mmol of the tion decays were obtained from up to 1600 scans. A phospholipid and the appropriate amount of abietic spectral width of 25 000 Hz, a memory of 32 K data acid as indicated. The organic solvents were evapo- points, a 2 s interpulse time and a 808 radio frequency rated under a stream of dry N22 , free of O , and the pulse were used. Prior to Fourier transformation, an last traces of solvents were removed by a further 3 h exponential multiplication was applied resulting in a evaporation under high vacuum. After the addition of 100 Hz line broadening. 1 ml of 0.1 mM EDTA, 100 mM NaCl, 10 mM HepesŽ. pH 7.4 buffer, multilamellar liposomes were formed by mixing, using a bench-vibrator, always 3. Results keeping the samples at a temperature above the lamellar gel to lamellar liquid-crystalline phase tran- The DSC profiles for pure DPPC and mixtures of sition temperature of the lipid. The suspensions were DPPC with abietic acid are shown in Fig. 1. The pure centrifuged at 13 000 rpm in a bench microfuge and phospholipid showed its main lamellar gel to lamellar the pellets were collected and placed into small alu- liquid-crystalline phase transition temperature Ž.Tc at minum pans. Pans were sealed and scanned in a 40.3"0.28C, in agreement with previous reportswx 21 . Perkin±Elmer DSC-4 calorimeter, using a reference The thermotropic pretransition of DPPC was greatly pan containing buffer. The heating rate was 4 C8rmin affected by the presence of a very low concentration in all the experiments. The DSC instrument was set at of abietic acid, being already abolished at an abietic a sensitivity of 1 mcalrs full scale. For the determi- acid mol fraction of 0.03. Increasing the concentra- nation of the total phospholipid contained in a pan, tion of abietic acid in the membrane produced the this was carefully opened, the lipid was dissolved broadening and shifting of the transition peak to with chloroformrmethanolŽ. 1:1 and the phosphorus lower temperatures. At an abietic acid mol fraction of content were determined using the method of BotcherÈ et al.wx 20 . The instrument was calibrated using in- dium as standard. The points used to construct the boundary lines in the phase diagrams where obtained from the begin- ning and the end of the transition peaks in the heating thermograms. 2.3. 31P-Nuclear magnetic resonance The samples for 31P-NMR were prepared by com- bination of chloroformrmethanolŽ. 1:1 solutions con- taining 50 mg of phospholipid and the appropriate amount of abietic acid. Evaporation of the solvents and multilamellar vesicles were formed as described above. The suspensions were centrifuged at 13 000 rpm in a bench microfuge and pellets were placed into conventional 5 mm NMR tubes and 31P-NMR spectra were obtained in the Fourier Transform mode in a Varian Unity 300 spectrometer.
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