Anti-Bacterial Agents/metabolism; Dimyristoylphosphatidylcholine/chemistry; Indicators and Reagents; Lactones/metabolism; Lipid Bilayers/chemistry; Models, Biological; Spectrometry, Fluorescence; Spectroscopy, Fourier Transform Infrared; Time Factors; Yarrowia/chemistry/metabolism
Abstract :
[en] Some odorant lactones are naturally present in fruits or in fermented products; they can also be used as food additives and can be produced by microorganisms at the industrial scale by biotechnological processes. Gamma-decalactone was previously shown to have antimicrobial properties. We determined by infrared spectroscopy measurements that this compound rapidly diffused into model phospholipid bilayers (within 2 min), modifying the general physical state of a dimyristoyl-L-alpha-phosphatidylcholine (DMPC) film. In vivo, the lactone strongly increased membrane fluidity in the model yeast Yarrowia lipolytica, as evaluated by fluorescence anisotropy measurements. This effect was more important than that of benzyl alcohol, which is known as a fluidizing agent in living cells, and may explain the toxic action of gamma-decalactone in microorganisms.
Disciplines :
Biotechnology
Author, co-author :
Aguedo, Mario ; Université de Liège - ULiège > Chimie et bio-industries > Chimie biologique industrielle
Beney, Laurent
Wache, Yves
Belin, Jean-Marc
Language :
English
Title :
Interaction of an odorant lactone with model phospholipid bilayers and its strong fluidizing action in yeast membrane.
Adams T.B., Greer D.B., Doull J., Munro I.C., Newberne P., Portoghese P.S., Smith R.L., Wagner B.M., Weil C.S., Woods I.A., Ford R.A. The FEMA GRAS assessment of lactones used as flavour ingredients. Food Chem. Toxicol. 36:1998;249-278.
Aguedo M., Waché Y., Belin J.-M. Biotransformation of ricinoleic acid into γ-decalactone by yeast cells: recent progress and current questions. Recent Res. Dev. Biotechnol. Bioeng. 3:2000;167-179.
Akyüz S., Davies J.E.D. Temperature dependent FTIR spectroscopic study of the interaction of α-tocopherol and α-tocopheryl acetate with phospholipid bilayers. J. Mol. Struct. 415:1998;65-70.
Antunes-Madeira M.C., Madeira V.M.C. Membrane fluidity as affected by the insecticide lindane. Biochim. Biophys. Acta. 982:1989;161-166.
Bouchard M., Boudreau N., Auger M. Membrane fluidity response to odorants as seen by 2H-NMR and infrared spectroscopy. Biochim. Biophys. Acta. 1282:1996;233-239.
Coelho de Souza G.P., Elisabetsky E., Nunes D.S., Rabelo S.K.L., Nascimento da Silva M. Anticonvulsant properties of γ-decanolactone in mice. J. Ethnopharmacol. 58:1997;175-181.
Coster H.G., Laver D.R. The effect of benzyl alcohol and cholesterol on the acyl chain order and alkane solubility of bimolecular phosphatidyl membranes. Biochim. Biophys. Acta. 861(3):1986;406-412.
Donato M.M., Jurado A.S., Antunes-Madeira M.C., Madeira V.M.C. Bacillus stearothermophilus as a model to evaluate membrane toxicity of a lipophilic environmental pollutant (DDT). Arch. Environ. Contam. Toxicol. 33:1997;109-116.
Endrizzi-Joran, A., 1994. PhD thesis, Université de Bourgogne, Dijon, France.
Enomoto S., Kashiwayanagi M., Kurihara K. Liposomes having high sensitivity to odorants. Biochim. Biophys. Acta. 1062:1991;7-12.
Enzelberger M.M., Bornscheuer U.T., Gatfield I., Schmid R.D. Lipase-catalysed resolution of γ- and δ-lactones. J. Biotechnol. 56:1997;129-133.
Goormaghtigh E., Raussens V., Ruysschaert J.-M. Attenuated total reflection infrared spectroscopy of proteins and lipids in biological membranes. Biochim. Biophys. Acta. 1422:1999;105-185.
Khalameyzer V., Fischer I., Bornscheuer U.T., Altenbuchner J. Screening, nucleotide sequence, and biochemical characterization of an esterase from Pseudomonas fluorescens with high activity towards lactones. Appl. Environ. Microbiol. 65(2):1999;477-482.
Konopásek I., Strzalka K., Svobodová J. Cold shock in Bacillus subtilis: different effects of benzyl alcohol and ethanol on the membrane organisation and cell adaptation. Biochim. Biophys. Acta. 1464:2000;18-26.
Laroche C., Beney L., Marechal P.A., Gervais P. The effect of osmotic pressure on the membrane fluidity of Saccharomyces cerevisiae at different physiological temperatures. Appl. Microbiol. Biotechnol. 56(1-2):2001;249-254.
Lewis R.N.A.H., McElhaney R.N. The structure and organization of phospholipid bilayers as revealed by infrared spectroscopy. Chem. Phys. Lipids. 96:1998;9-21.
Maga J.A. Lactones in foods. CRC Crit. Rev. Food Sci. Nutr. 8(1):1976;1-56.
Scarselletti R., Faull J.L. In vitro activity of 6-pentyl-α-pyrone, a metabolite of Trichoderma harzianum, in the inhibition of Rhizoctonia solani and Fusarium oxysporum f. sp. lycopersici. Mycol. Res. 98(10):1994;1207-1209.
Shechter E., 1997. In: Masson (Ed.), Biochimie et Biophysique des Membranes. Aspects Structuraux et Fonctionnels, Paris.
Uribe S., Ramirez J., Peña A. Effects of β-pinene on yeast membrane functions. J. Bacteriol. 161(3):1985;1195-1200.
Waché Y., Bergmark K., Courthaudon J.-L., Aguedo M., Nicaud J.-M., Belin J.-M. Medium-size droplets of methyl ricinoleate are reduced by cell-surface activity in the γ-decalactone production by Yarrowia lipolytica. Lett. Appl. Microbiol. 30:2000;183-187.