Abstract
Leaf cuticles ofClivia miniata, rubber plant (Ficus elastica), oleander (Nerium oleander), pear (Pyrus communis), and olive (Olea europaea), and fruit cuticles of pepper (Capsicum annuum), eggplant (Solarium melongena), and cucumber (Cucumis sativus) bind 2,4-D and 2,4,5-T covalently. The cutins of these plant species contain epoxy groups which react with the carboxyl groups of the phenoxyacetic acids with the formation of an ester linkage. This reaction is first order, both with respect to the concentration of epoxides and phenoxyacetic acids in the cuticle, and proceeds in isolated cuticles as well asin situ. The biological and ecotoxicological implications are discussed.
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Bathe W, Janecke J, Meerwein H (1953) Analytik von cyclischen Organoxyden. In: Methoden der Organischen Chemie (Houben-Weyl). 4th ed, vol 2, Thieme Verlag, Stuttgart, pp 428–433
Brönsted JN, Kilpatrick M, Kilpatrick M (1929) Kinetic studies on ethylene oxides. J Am Chem Soc 51:428–461
Brown AJ, Kolattukudy PE (1978a) Mammalian utilization of cutin, the cuticular polyester of plants. J Agric Food Chem 26:1263–1266
— (1978b) Evidence that pancreatic lipase is responsible for the mammalian hydrolysis of cutin, a biopolyester present in mammalian diet, and the role of bile salt and colipase in this hydrolysis. Arch Biochem Biophys 190:17–26
Chow C, Montgomery ML, Yu TC (1971) Methodology and analysis for residues of MCP and 2,4,5-T in wheat. Bull Environ Contam Toxicol 6:576–580
Holloway PJ (1982) The chemical constitution of plant cutins. In: Cutler, DF, Alvin, KL, Price, CE (eds) The plant cuticle. Academic Press, London, p 45–85
Holloway PJ, Deas AHB (1973) Epoxyoctadecanoic acids in plant cutins and suberins. Phytochem 12:1721–1735
Holloway PJ, Brown GA, Wattendorff J (1981) Ultrahistochemical detection of epoxides in plant cuticular membranes. J Exp Botany 32:1051–1066
Kipling JJ (1965) Adsorption from solutions of non-electrolytes. Academic Press, New York
Kolattukudy PE, Purdy RE, Maiti IB (1981) Cutinases from fungi and pollen. In: Colowick, SP, Kaplan, NO (eds) Methods in enzymology, vol 71, Academic Press, New York, pp 652–664
Perrin RD, Armarego WLF, Perrin DR (1980) Purification of laboratory chemicals. 2nd ed, Pergamon Press, Oxford, New York
Riederer M (1984) Akkumulation und Transport lipophiler Nichtelektrolyte in der pflanzlichen Kutikula. Doctoral thesis, Technische UniversitÄt München
Riederer M, Schönherr J (1984) Accumulation and transport of 2,4-dichlorophenoxy acetic acid in plant cuticles: I. Sorption in the cuticular membrane and its components. Ecotoxicol Environ Safety 8:236–247
Sachs L (1974) Angewandte Statistik. 4th ed, Springer-Verlag, Berlin
Sandler SR, Karo W (1977) Polymer synthesis. Vol 2, Academic Press, New York
Schmidt HW, Schönherr J (1982) Development of plant cuticles: occurrence and role of non-ester bonds in cutin ofClivia miniata Reg. leaves. Planta 156:380–384
Schönherr J, Bukovac MJ (1972) Dissociation constants of succinic acid 2,2-dimethylhydrazide. J Agric Food Chem 20:1263–1265
Siggia S (1963) Quantitative organic analysis via functional groups. 3rd ed, Wiley, New York
Smith AE (1984) Gas chromatographic method for analysis of 2,4-D in wheat: interlaboratory study. J Assoc Off Anal Chem 67:794–798
Sokal RR, Rohlf FJ (1981) Biometry. 2nd ed, Freeman, San Francisco
Specht W, Tillkes M (1981) Gas-chromatographische Bestimmung von RückstÄnden an Pflanzenbehandlungsmitteln nach Clean-up über Gel-Chromatographie und Mini-Kieselgel-SÄulen-Chromatographie. Fresenius Z Anal Chem 307:257–264
Swinbourne ES (1971) Analysis of kinetic data. Nelson, London.
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Riederer, M., Schönherr, J. Covalent binding of chlorophenoxyacetic acids to plant cuticles. Arch. Environ. Contam. Toxicol. 15, 97–105 (1986). https://doi.org/10.1007/BF01055254
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DOI: https://doi.org/10.1007/BF01055254