Abstract
The fibres of the green-lint mutant (Lg) of cotton (Gossypium hirsutum L.) are suberized and contain a large proportion of wax. The unidentified components of the wax were separated into a colourless fluorescent fraction and a yellow pigmented fraction. Using ultraviolet spectroscopy and nuclear-magneticresonance (1H-NMR) spectroscopy, esterified trans-caffeic acid was identified as the only phenolic component in the colourless fraction. This fraction was further purified and was shown to contain caffeic acid esterified to fatty acids (mainly ω-hydroxy fatty acids), and glycerol in molar ratios of 4∶5∶5. When 2-aminoindan-2-phosphonic acid (AIP), an inhibitor of phenylalanine ammonia-lyase (EC 4. 3. 1. 5.) was added to ovules cultured in vitro, at the beginning of secondary wall formation, the fibres remained white and the colourless caffeic-acid derivative and the yellow compounds could no longer be detected by ultraviolet spectroscopy. Fibres grown in the presence of AIP were also examined in the electron microscope. Secondary cell walls were present in the treated fibres, but the electron-opaque suberin layers were replaced by apparently empty spaces. This result indicates that cinnamic-acid derivatives are covalently linked to suberin and have a structural role within the polymer or are involved in anchoring the polymer to the cellulosic secondary wall. Purified cell walls of green cotton fibres contained about 1% (of the dry weight) of bound glycerol, 0.9% of the glycerol being extractable with the wax fraction and 0.1% remaining in the cell-wall residue. The corresponding values for white fibres were 0.03% (total), 0.02% (wax), and 0.01% (cell-wall residue). Fibres synthesizing their secondary walls in the presence of AIP contained about normal amounts of bound glycerol in the wax fraction, but glycerol accumulation in the cell-wall residue was inhibited by about 95%. These observations indicate that glycerol is an important constituent of cotton-fibre suberin. Considerable amounts of bound glycerol could also be determined in exhaustively extracted cell walls of the cork layer of potato periderm (1.2%) and smaller amounts in the outer epidermal cell wall of Agave americana L. leaf (0.1%) indicating that the presence of glycerol in suberins and possibly also in cutins may be more widespread than previously thought.
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Abbreviations
- AIP:
-
2-aminoindan-2-phosphonic acid
- IAA:
-
indole-3-acetic acid
- IBA:
-
indole-3-butyric acid
- NMR:
-
nuclear magnetic resonance
- TLC:
-
thin-layer chromatography
References
Beasley, C.A., Ting, I.P. (1973) The effects of plant growth substances on in vitro fiber development from fertilized cotton ovules. Am. J. Bot. 60, 130–139
Borg-Olivier, O., Monties, B. (1989) Caractérisation des lignines, acides phénoliques et tyramine dans les tissues subérisés du periderme naturel et du periderme de blessure de tubercule de pomme de terre. C R Acad. Sci. Sér. III. Paris 308, 141–147
Brieskorn, C.H., Binnemann, P.H. (1974) Chemische Zusammensetzung des Suberins der Kartoffelschale. Z. Lebensm. Unters. Forsch. 154, 213–222
Daniels, D.G.H., Martin, H.F. (1968) Antioxidants in oats: glyceryl esters of caffeic and ferulic acids. J. Sci. Food Agric. 19, 710–712
Falk, H., El Hadidi, M.N. (1961) Der Feinbau der Suberinschichten verkorkter Zellwände. Z. Naturforsch. 16b, 134–137
Herrmann, K. (1978) Hydroxyzimtsäuren und Hydroxybenzoesäuren enthaltende Naturstoffe in Pflanzen. In: Fortschritte der Chemie organischer Naturstoffe, vol. 35, pp. 73–132. Herz, W., Grisebach, H., Kirby, G.W., eds. Springer, Wien
Holloway, P.J. (1982) Structure and histochemistry of plant cuticular membranes: an overview. In: The plant cuticle (Linnean Society Symposium Series Number 10), pp. 1–32, Cutler, D.F., Alvin, K.L., Price, C.E., eds. Academic press, London
Ibrahim, R., Barron, D. (1989) Phenylpropanoids. In: Methods in plant biochemistry, vol. 1, Plant phenolics, pp. 75–111, Harborne, J.B., ed. Academic Press, London
Kolattukudy, P.E. (1977) Lipid polymers and associated phenols, their chemistry, biosynthesis, and role in pathogenesis. In: Recent advances in phytochemistry, vol. 11: The structure, biosynthesis and degradation of wood, pp. 185–246, Loewus, F.A., Runeckles, V.C., eds. Plenum Press, New York
Kolattukudy, P.E. (1980) Biopolyester membranes of plants: Cutin and suberin. Science 208, 990–1000
Kolattukudy, P.E. (1987) Lipid derived defensive polymers and waxes and their role in plant-microbe interaction. In: The biochemistry of plants. A comprehensive treatise, vol. 9: Lipids: Structure and function, pp. 291–314, Stumpf, P.K. ed. Academic Press, London
Martin, J.T., Juniper, B.E. (1970) The cuticles of plants. Edward Arnold, London
Matzke, K., Riederer, M. (1991) A comparative study into the chemical constitution of cutins and suberins from Picea abies (L.) Karst., Quercus robur L., and Fagus sylvatica L. Planta 185, 233–245
Monties, B. (1989) Lignins. In: Methods in plant biochemistry, vol. 1: Plant phenolics, pp. 113–157, Harborne, J.B., ed. Academic Press London
Nissen, S.J., Sutter, E.G. (1990) Stability of IAA and IBA in nutrient medium to several tissue culture procedures. HortScience 25, 800–802
Pereira, H. (1988) Chemical composition and variability of cork from Quercus suber L. Wood Sci. Technol. 22, 211–218
Ribas, I., Blasco, E. (1940) Investigaciones sobre el corcho. II. Determinacion cuantitativa de la glycerina existente. An. Real Soc. Esp. Fis. Quim. 36, 248–254
Ryser, U. (1985) Cell wall biosynthesis in differentiating cotton fibres. Eur. J. Cell Biol. 39, 236–256
Ryser, U. (1992) Ultrastructure of the epidermis of developing cotton (Gossypium) seeds: suberin, pits, plasmodesmata, and their implication for assimilate transport into cotton fibers. Am. J. Bot. 79, 14–22
Ryser, U., Holloway, P.J. (1985) Ultrastructure and chemistry of soluble and polymeric lipids in cell walls from seed coats and fibres of Gossypium species. Planta 163, 151–163
Ryser, U., Meier, H., Holloway, P.J. (1983) Identification and localization of suberin in the cell walls of green cotton fibres (Gossypium hirsutum L., var. green lint). Protoplasma 117, 196–205
Saeman, J.F., Buhl, J.L., Harris, E.F. (1945) Quantitative saccharification of wood and cellulose. Ind. Eng. Chem. Anal. Ed. 17, 35–37
Schmidt, H.W., Schönherr, J. (1982) Fine structure of isolated and non-isolated potato tuber periderm. Planta 154, 76–80
Sitte, P. (1959) Mischkörperdoppelbrechung der Korkzellwände. Naturwissenschaften 46, 260–261
Sitte, P. (1962) Zum Feinbau der Suberinschichten im Flaschenkork. Protoplasma 54, 555–559
Sitte, P. (1975) Die Bedeutung der molekularen Lamellenbauweise von Korkzellwänden. Biochem. Physiol. Pflanz. 168, 287–297
Spurr, A.R., (1969) A low-viscosity resin embedding medium for electron microscopy. J. Ultrastruct. Res. 26, 31–34
Wattendorff, J., Holloway, P.J. (1984) Periclinal penetration of potassium permanganate into mature cuticular membranes of Agave and Clivia leaves: new implications for plant cuticle development. Planta 161, 1–11
Wieland, O.H. (1984) Glycerol. UV-method. In: Methods of enzymatic analysis, vol. 6, pp. 504–510, Bergmeyer, H.U. ed. Verlag Chemie, Weinheim
Yatsu, L.Y., Espelie, K.E., Kolattukudy, P.E. (1983) Ultrastructural and chemical evidence that the cell wall of green cotton fiber is suberized. Plant Physiol. 73, 521–524
Zimmermann, W., Nimz, H., Seemüller, E. (1985) 1H and 13C NMR spectroscopic study of extracts from corks of Rubus idaeus, Solanum tuberosum, and Quercus suber. Holzforschung 39, 45–49
Zoń, J., Amrhein, N. (1992): Inhibitors of phenylalanine ammonialyase: 2-aminoindan-2-phosphonic acid and related compounds. Liebigs Ann. Chemie, pp. 625–628
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We thank J.P. Métraux and A.J. Buchala (Institut für Botanische Biologie, Freiburg, Switzerland) for critical reading of the manuscript, M. Schorderet for thin-sectioning and electron microscopy, F. Fehr for recording the NMR spectra, and P. Enz and L. Vincent for cultivating the cotton plants. This work was supported by the Swiss National Science Foundation, Grant No. 31-29988.90 to U. Ryser.
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Schmutz, A., Jenny, T., Amrhein, N. et al. Caffeic acid and glycerol are constituents of the suberin layers in green cotton fibres. Planta 189, 453–460 (1993). https://doi.org/10.1007/BF00194445
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DOI: https://doi.org/10.1007/BF00194445