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Seed desiccation tolerance and storability: Dependence on flatulence-producing oligosaccharides and cyclitols—review and survey

Published online by Cambridge University Press:  19 September 2008

Marcin Horbowicz  and
Ralph L. Obendorf
Marcin Horbowicz
Affiliation:
Seed Biology, Department of Soil, Crop and Atmospheric Sciences, Cornell University Agricultural Experiment Station, 619 Bradfield Hall, Cornell University, Ithaca, NY 14853-1901, USA
Ralph L. Obendorf*
Affiliation:
Seed Biology, Department of Soil, Crop and Atmospheric Sciences, Cornell University Agricultural Experiment Station, 619 Bradfield Hall, Cornell University, Ithaca, NY 14853-1901, USA
*
*Correspondence. Presented at the International Workshop on Desiccation Tolerance and Sensitivity of Seeds and Vegetative Plant Tissues, Kruger National Park, South Africa, 17–22 January 1994
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Abstract

Stachyose, raffinose and related flatulence-producing oligosaccharides (α-galactosyl derivatives of sucrose) are associated with desiccation tolerance and storability of seed germplasm. Orthodox seeds of species with a sucrose-to-oligosaccharide ratio of <1.0 have storability half-viability periods >10 years while those >1.0 have a storability half-viability period <10 years. Seeds vary in their composition of oligosaccharides and some accumulate α-galactosyl derivatives of cyclitols. Known and proposed pathways for biosynthesis of soluble oligosaccharides, cyclitols and galactosyl derivatives of cyclitols are presented. Axes, cotyledons, embryos or seeds of 19 species in 7 families (all orthodox seeds) were analysed for sucrose, galactosyl derivatives of sucrose, cyclitols and galactosyl derivatives of cyclitols by high resolution gas chromatography. Sucrose and myo-inositol are universally present and galactinol is present in seeds accumulating stachyose series oligosaccharides. Seeds of some species of Leguminosae accumulate mostly stachyose series oligosaccharides, whereas seeds of other species accumulate varying levels of galactosyl derivatives of cyclitols in addition. Castor bean (Euphorbiaceae) seeds accumulate galactinol and buckwheat (Polygonaceae) embryos accumulate galacto-chiro-inositol instead of the stachyose series oligosaccharides. The mass ratio of sucrose:non-sucrose is related to storability and is applicable to seeds accumulating cyclitol derivatives. Galactinol and galacto-chiro-inositol are proposed to function in the same role as raffinose and stachyose in facilitating desiccation tolerance and storability.

Keywords

flatulencegalactosyl cyclitolseed desiccation tolerancestachyose series oligosaccharidesstorability
Type
Review Article
Information
Seed Science Research , Volume 4 , Issue 4 , December 1994 , pp. 385 - 405
Copyright
Copyright © Cambridge University Press 1994

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Footnotes

1

Research Institute of Vegetable Crops, Konstytucji 3 Maja 1/3, 96-100 Skierniewice, Poland

References

Adams, P., Thomas, J.C., Vernon, D.M., Bohnert, H.J. and Jensen, R.G. (1992) Distinct cellular and organismic responses to salt stress. Plant and Cell Physiology 33, 1215–1223.Google Scholar
Amuti, K.S. and Pollard, C.J. (1977) Soluble carbohydrates of dry and developing seeds. Phytochemistry 16, 529–532.Google Scholar
Angyal, S.J., Gallagher, R.T. and Pojer, P.M. (1976) Synthesis of pinpollitol (1,4-di-O-methyl-D-chiro-inositol). Australian Journal of Chemistry 29, 219–222.CrossRefGoogle Scholar
Augustin, R. and Nixon, D.A. (1957) Grass pollen constituents: the meso-inositol content. Nature 179, 530–531.CrossRefGoogle Scholar
Bachmann, M. (1993) Metabolism of the raffinose family oligosaccharides in leaves of Ajuga reptans L. Cold induction, sink to source transition and compartmentation. Zurich, Ph.D. Dissertation, University of Zurich.Google Scholar
Bernabé, M., Fenwick, R., Frias, J., Jiménez-Barbero, J., Price, K., Valverde, S. and Vidal-Valverde, C. (1993) Determination by NMR spectroscopy of the structure of ciceritol a pseudotrisaccharide isolated from lentils. Journal of Agricultural and Food Chemistry 41, 870–872.CrossRefGoogle Scholar
Bernal-Lugo, I. and Leopold, A.C. (1992) Changes in soluble carbohydrates during seed storage. Plant Physiology 98, 1207–1210.CrossRefGoogle ScholarPubMed
Bernal-Lugo, I., Diaz de Leon, F., Castillo, A. and Leopold, A.C. (1993) Embryo sugar composition and seed storage performance. pp 789–792 in Côme, D. and Corbineau, F. (Eds) Proceedings of the Fourth International Workshop on Seeds: Basic and Applied Aspects of Seed Biology, Angers, France, 20–24 July 1992. Paris, ASFIS.Google Scholar
Beveridge, R.J., Ford, C.W. and Richards, G.N. (1977) Polysaccharides of tropical pasture herbage. VII. Identification of a new pinitol galactoside from seeds of Trifolium subterraneum (subterranean clover) and analysis of several pasture legume seeds for cyclohexitols and their galactosides. Australian Journal of Chemistry 30, 1583–1590.Google Scholar
Biermann, C.J. (1988) Introduction to analysis of carbohydrates by gas-liquid chromatography (GLC). pp 1–17 in Biermann, C.J. and McGinnis, G.D. (Eds) Analysis of Carbohydrates by GLC and MS. Boca Raton, CRC Press, Inc.Google Scholar
Binder, R.G. and Haddon, W.F. (1984a) Cyclitols of soybean leaves. Journal of Agricultural and Food Chemistry 32, 685–687.Google Scholar
Binder, R.G. and Haddon, W.F. (1984b) Analysis of O-methylinositols by gas-liquid chromatography-mass spectrometry. Carbohydrate Research 129, 21–32.CrossRefGoogle Scholar
Blackman, S.A., Wettlaufer, S.H., Obendorf, R.L. and Leopold, A.C. (1991) Maturation proteins associated with desiccation tolerance in soybean. Plant Physiology 96, 868–874.CrossRefGoogle ScholarPubMed
Blackman, S.A., Obendorf, R.L. and Leopold, A.C. (1992) Maturation proteins and sugars in desiccation tolerance of developing soybean seeds. Plant Physiology 100, 225–230.CrossRefGoogle ScholarPubMed
Blackman, S.A., Obendorf, R.L. and Leopold, A.C. (1993) The role of Lea proteins in desiccation tolerance in soybean. pp 121–126 in Côme, D. and Corbineau, F. (Eds) Proceedings of the Fourth International Workshop on Seeds: Basic and Applied Aspects of Seed Biology, Angers, France, 20–24 July 1992. Paris, ASFIS.Google Scholar
Buckingham, J., Macdonald, F.M. and Bradley, H.M. (Editors) (1994) Dictionary of natural products, Volumes 1–5. London, Chapman & Hall.Google Scholar
Calub, T.M., Waterhouse, A.L. and Chatterton, N.J. (1990) Proton and carbon chemical-shift assignments for 1-kestose from two-dimensional NMR spectral measurements. Carbohydrate Research 119, 11–18.CrossRefGoogle Scholar
Carpenter, J.F., Martin, B., Crowe, L.M. and Crowe, J.H. (1987) Stabilization of phosphofructokinase during air-drying with sugars and sugar-transition metal mixtures. Cryobiology 24, 455–464.Google Scholar
Carpenter, J.F., Martin, B., Loomis, S.H. and Crowe, J.H. (1988) Long-term preservation of dried phosphofructokinase by sugars and sugar-zinc mixtures. Cryobiology 25, 372–376.Google Scholar
CAS (1989) Chemical Abstracts Service Chemical Substance Name Selection Manual, Volume III, Inositols (revised May 1989). Columbus, OH, Chemical Abstracts Service.Google Scholar
CAS (1992) Chemical Abstracts Index Guide 1992. Columbus, OH, Chemical Abstracts Service.Google Scholar
Castillo, E.M., de Lumen, B.O., Reyes, P.S. and de Lumen, H.Z. (1990) Raffinose synthase and galactinol synthase in developing seeds and leaves of legumes. Journal of Agricultural and Food Chemistry 38, 351–355.Google Scholar
Chatterton, N.J., Harrison, P.A., Thornley, W.R. and Bennett, J.H. (1990) Sucrosyloligosaccharides and cool temperature growth in 14 forb species. Plant Physiology and Biochemistry 28, 167–172.Google Scholar
Chen, Y. and Burris, J.S. (1990) Role of carbohydrates in desiccation tolerance and membrane behavior in maturing maize seed. Crop Science 30, 971–975.CrossRefGoogle Scholar
Cosgrove, D.J. (1980) Inositol phosphates: their chemistry, biochemistry and physiology. Amsterdam, Oxford, New York, Elsevier.Google Scholar
Courtois, J.E. and Percheron, F. (1971) Distribution of monosaccharides, oligosaccharides and polyols. pp 207–229 in Harborne, J.B., Boulter, D. and Turner, B.L. (Eds) Chemotaxonomy of the Leguminosae. New York, Academic Press, Inc.Google Scholar
Cristofaro, E., Mottu, F. and Wuhrmann, J.J. (1974) Involvement of the raffinose family of oligosaccharides in flatulence. pp 313–363 in Sepple, H.L. and McNutt, K.W. (Eds) Sugars in nutrition. New York, Academic Press.Google Scholar
Crowe, L.M. and Crowe, J.H. (1992) Stabilization of dry liposomes by carbohydrates. pp 285–294 in May, J.C. and Brown, F. (Eds) Developments in biological standardization, Volume 74. Biological product freezedrying and formulation. Basel, S. Karger AG.Google Scholar
Dey, P.M. (1980) Biosynthesis of planteose in Sesamum indicum. Federation of European Biochemical Societies Letters 114, 153–156.CrossRefGoogle Scholar
Dey, P.M. (1985) D-Galactose-containing oligsaccharides. pp 53–129 in Dey, P.M. (Ed.) Biochemistry of storage carbohydrates in green plants. London, Academic Press.Google Scholar
Dey, P.M. (1990) Oligosaccharides. pp 189–218 in Dey, P.M. (Ed.) Methods in plant biochemistry Volume 2. Carbohydrates. New York, Academic Press.Google Scholar
Dittrich, P. and Brandl, A. (1987) Revision of the pathway of D-pinitol formation in Leguminosae. Phytochemistry 26, 1925–1926.Google Scholar
Dittrich, P. and Korak, A. (1984) Novel biosynthesis of D-pinitol in Simmondsia chinensis. Phytochemistry 23, 65–66.CrossRefGoogle Scholar
Dittrich, P. and Schilling, N. (1988) Formation of liriodendritol in Liriodendron tulipifera. Phytochemistry 27, 773–774.Google Scholar
Dornbos, D.L. and McDonald, M.B., Jr. (1986) Mass and composition of developing soybean seeds at five reproductive growth stages. Crop Science 26, 624–630.CrossRefGoogle Scholar
Farrant, J.M., Pammenter, N.W. and Berjak, P. (1992) Development of the recalcitrant homoiohydrous seeds of Avicennia marina: anatomical, ultrastructural and biochemical events associated with development from histodifferentiation to maturation. Annals of Botany 70, 75–86.CrossRefGoogle Scholar
Farrant, J.M., Pammenter, N.W. and Berjak, P. (1993) Seed development in relation to desiccation tolerance a comparison between desiccation-sensitive (recalcitrant) seeds of Avicennia marina and desiccation-tolerant types. Seed Science Research 3, 1–13.Google Scholar
Fleming, S.E. (1981) A study of relationships between flatus potential and carbohydrate distribution in legume seeds. Journal of Food Science 46, 794–798, 803.Google Scholar
Ford, C.W. (1985) Identification of inositols and their mono-O-methyl ethers by gas-liquid chromatography. Journal of Chromatography 333, 167–170.Google Scholar
Fougère, F., Le Rudulier, D. and Streeter, J.G. (1991) Effects of salt stress on amino acid organic acid and carbohydrate composition of roots, bacteroids and cytosol of alfalfa (Medicago sativa L.). Plant Physiology 96, 1228–1236.CrossRefGoogle ScholarPubMed
Frydman, R.B. and Neufeld, E.F. (1963) Synthesis of galactosylinositol by extracts from peas. Biochemical and Biophysical Research Communications 12, 121–125.Google Scholar
Gallagher, R.T. (1975) (+)-Pinpollitol, a di-O-methyl-D-(+)-chiro-inositol from Pinus radiata. Phytochemistry 14, 755–757.CrossRefGoogle Scholar
Ganter, J.L.M.S., Correa, J., Reicher, F., Heyraud, A. and Rinaudo, M. (1991) Low molcular weight carbohydrates from Mimosa scabrella seeds. Plant Physiology and Biochemistry 29, 139–146.Google Scholar
Garegg, P.J. and Kvarström, I. (1981) Synthesis of 1D-2-O- and 1D-5-O-(α-D-galactopyranosyl)-4-O-methyl-chiro-inositol: Preference for equitorial hydroxyl groups in the immediate galactosylation procedure. Carbohydrate Research 90, 61–69.CrossRefGoogle Scholar
Gitzelmann, R. and Auricchio, S. (1965) The handling of soya alpha-galactosides by a normal and a galactosemic child. Pediatrics 36, 231–235.Google Scholar
Handley, L.W., Pharr, D.M. and McFeeters, R.F. (1983) Relationship between galactinol synthase activity and sugar composition of leaves and seed of several crop species. Journal of the American Society for Horticultural Science 108, 600–605.Google Scholar
Harborne, J.B. and Baxter, H. (1993) Phytochemical dictionary: a handbook of bioactive compounds from plants. London, Taylor & Francis Ltd.Google Scholar
Hatanaka, S. (1959) Oligosaccharides in seed of Sesamum indicum L. Archives of Biochemistry and Biophysics 82, 188–194.Google Scholar
Hendrix, D.L. (1990) Carbohydrates and carbohydrate enzymes in developing cotton ovules. Physiologia Plantarum 78, 85–92.CrossRefGoogle Scholar
Hendry, G.A.F. (1993) Oxygen, free radical processes and seed longevity. Seed Science Research 3, 141–153.Google Scholar
Henry, R.J. and Saini, H.S. (1989) Characterization of cereal sugars and oligosaccharides. Cereal Chemistry 66, 362–365.Google Scholar
Hipps, P.P., Sehgal, R.K., Holland, W.H. and Sherman, W.R. (1973) Identification and partial characterization of inositol-NAD+ epimerase and inosose: NAD(P)H reductase from the fat body of the American cockroach, Periplaneta americana. Biochemistry 12, 4705–4712.Google ScholarPubMed
Hoekstra, F.A., Crowe, L.M. and Crowe, J.H. (1989) Differential desiccation sensitivity of corn and Pennisetum pollen linked to their sucrose contents. Plant Cell and Environment 12, 83–91.Google Scholar
Hoekstra, F.A., Crowe, J.H., Crowe, L.M., van Roekel, T. and Vermeer, E. (1992) Do phospholipids and sucrose determine membrane phase transitions in dehydrating pollen species? Plant Cell and Environment 15, 601–606.CrossRefGoogle Scholar
Hoffmann-Ostenhof, O. and Pittner, F. (1982) The biosynthesis of myo-inositol and its isomers. Canadian Journal of Chemistry 60, 1863–1871.Google Scholar
Hopf, H., Spanfelner, M. and Kandler, O. (1984) Planteose synthesis in seeds of Sesamum indicum L. (Sesame). Zeitschrift für Pflanzenphysiologie 114, 485–492.Google Scholar
IUPAC-IUB (1976) Nomenclature of cyclitols: recommendations, 1973. Biochemical Journal 153, 23–31.Google Scholar
Karoutis, A.I., Tyler, R.T. and Slater, G.P. (1992) Analysis of legume oligosaccharides by high-resolution gas chromatography. Journal of Chromatography 623, 186–190.Google Scholar
Keller, F. and Ludlow, M.M. (1993) Carbohydrate metabolism in drought-stressed leaves of pigeonpea (Cajanus cajan). Journal of Experimental Botany 44, 1351–1359.Google Scholar
Kerr, P.S. (1993) Soybean products with improved carbohydrate composition and soybean plants. International Patent Publication Number WO 93/07742, 29 April 1993, PCT/US92/08958.Google Scholar
Kerr, P.S., Pearlstein, R.W., Becker-Manley, M.F. and Pierce, J.W. (1993) Nucleotide sequences of galactinol synthase from zucchini and soybean. International Patent Publication Number WO 93/02196, 4 February 1993, PCT/US92/06057.Google Scholar
Kindl, H. and Hoffmann-Ostenhof, O. (1966) Biosynthesis of cyclitols. XII. Formation of D-ononitol and other cyclitols in Ononis spinosa. Hoppe-Seyler's Zeitschrift für Physiologische Chemie 345, 257–263.Google Scholar
King, R.D. and Puwastien, P. (1987) Respiratory hydrogen following consumption of winged bean seed mild prepared from blanched and soaked seeds and germinated seeds. Journal of Food Science 52, 729–731.Google Scholar
Kosson, R. (1988) Flatulence-causing galactooligosaccharides of Phaseolus coccineus L. and Phaseolus vulgaris L. Acta Societatis Botanicorum Poloniae 57, 493–497.Google Scholar
Koster, K.L. (1991) Glass formation and dessication tolerance in seeds. Plant Physiology 96, 302–304.CrossRefGoogle ScholarPubMed
Koster, K.L. and Leopold, A.C. (1988) Sugars and desiccation tolerance in seeds. Plant Physiology 88, 829–832.CrossRefGoogle ScholarPubMed
Kuo, T.M., VanMiddlesworth, J.F. and Wolf, W.J. (1988) Content of raffinose oligosaccharides and sucrose in various plant seeds. Journal of Agricultural and Food Chemistry 36, 32–36.CrossRefGoogle Scholar
Kuo, T.M. (1992) Isolation and identification of galactinol from castor oilseed meal. Journal of the American Oil Chemists‘ Society 69, 569–574.Google Scholar
L'Annunziata, M.F., Gonzalez-I., J. and Olivares-O., L.A. (1977) Microbial epimerization of myo-inositol to chiro-inositol in soil. Soil Science Society of America Journal 41, 733–736.CrossRefGoogle Scholar
Larher, F., Quemener, B. and Hevochon, P. (1990) Osmotic adjustment during the vegetative growth period of Cicer arietinum as related to sodium chloride. Comptes Rendus de l'Académie des Sciences, Paris (Série III) Sciences de la Vie 312, 55–61.Google Scholar
Larsson, S., Johansson, L.Å. and Svenningsson, M. (1993) Soluble sugars and membrane lipids in winter wheats (Triticum aestivum L.) during cold acclimation. European Journal of Agronomy 1, 85–90.CrossRefGoogle Scholar
Lehle, L. and Tanner, W. (1972) Synthesis of raffinose-type sugars. Methods in Enzymology 28B, 522–530.Google Scholar
Lehle, L. and Tanner, W. (1973) The function of myo-inositol in the biosynthesis of raffinose. Purification and characterization of galactinol: sucrose 6-galactosyltransferase from Vicia faba seeds. European Journal of Biochemistry 38, 103–110.Google Scholar
Leprince, O., Bronchart, R. and Deltour, R. (1990) Changes in starch and soluble sugars in relation to the acquisition of desiccation tolerance during maturation of Brassica campestris seed. Plant Cell and Environment 13, 539–546.Google Scholar
Leprince, O., van der Werf, A., Deltour, R. and Lambers, H. (1992) Assessment of respiratory pathways during germination of Zea mays. Relationship with the soluble sugars and loss of desiccation tolerance. pp 573–577 in Lambers, H. and van derPlas, L.H.W. Plas, L.H.W. (Eds) Molecular, biochemical and physiological aspects of plant respiration. The Hague, SPB Academic Publishing BV.Google Scholar
Leprince, O., Hendry, G.A.F. and McKersie, B.D. (1993) The mechanisms of desiccation tolerance in developing seeds. Seed Science Research 3, 231–246.Google Scholar
Liu, J., Waterhouse, A.L. and Chatterton, N.J. (1991) Proton and carbon chemical-shift assignments for 6-kestose and neokestose from two-dimensional NMR measurements. Carbohydrate Research 217, 43–50.Google Scholar
Loewus, F.A. (1990a) Structure and occurrence of inositols in plants. pp 1–11 in Morré, D.J., Boss, W.F. and Loewus, F.A. (Eds) Inositol metabolism in plants, plant biology, Volume 9. New York, Wiley-Liss.Google Scholar
Loewus, F.A. (1990b) Cyclitols. pp 219–233 in Dey, P.M. (Ed.) Methods in plant biochemistry Volume 2. Carbohydrates. New York, Academic Press.Google Scholar
Loewus, F.A and Dickinson, D.B. (1982) Cyclitols. pp 193–206 in Loewus, F.A. and Tanner, W. (Eds) Encyclopedia of plant physiology: plant carbohydrates I: intracellular carbohydrates, Volume 13A. Berlin, Springer-Verlag.Google Scholar
Lowell, C.A. and Kuo, T.M. (1989) Oligosaccharide metabolism and accumulation in developing soybean seeds. Crop Science 29, 459–465.Google Scholar
Meredith, F.I., Thomas, C.A., Snook, M.E., Himmelsbach, D.S. and Van Halbeek, H. (1988) Soluble carbohydrates, oligosaccharides and starch in lima bean seeds. Journal of Food Science 53, 786–771.Google Scholar
Murphy, E.L., Horsley, H. and Burr, H.K. (1972) Fractionation of dry bean extracts which increase carbon dioxide egestion in human flatus. Journal of Agricultural and Food Chemistry 20, 813–817.Google Scholar
Naccarato, W.F. and Wells, W.W. (1974) Identification of 6-O-β-D-galactopyranosyl myo-inositol: a new form of myo-inositol in animals. Biochemical and Biophysical Research Communications 57, 1026–1031.CrossRefGoogle Scholar
Naccarato, W.F., Ray, R.E. and Wells, W.W. (1975) Characterization and tissue distribution of 6-O-β-D-galactopyransosyl myo-inositol in the rat. Journal of Biological Chemistry 250, 1872–1876.Google Scholar
Nguyen, A. and Lamant, A. (1988) Pinitol and myo-inositol accumulation in water-stressed seedlings of maritime pine. Phytochemistry 27, 3423–3428.Google Scholar
Nicolas, P., Gertsch, I. and Parisod, C. (1984) Isolation and structure determination of an α-D-galactosyl-α-D-galactosyl-α-D-galactosyl-D-pinitol from the chick pea. Carbohydrate Research 131, 331–334.Google Scholar
Nielsen, N. (1956) The vitamin content of pollen after storing. Acta Chemica Scandinavica 10, 332–333.CrossRefGoogle Scholar
Nielsen, N., Grömmer, J. and Lundén, R. (1955) Investigations on the chemical composition of pollen from some plants. Acta Chemica Scandinavica 9, 1100–1106.Google Scholar
Obendorf, R.L., Horbowicz, M. and Taylor, D.P. (1993) Structure and chemical composition of developing buckwheat seed. pp 244–251 in Janick, J. and Simon, J.E. (Eds) New crops. New York, John Wiley & Sons.Google Scholar
Ooms, J.J.J., Léon-Kloosterziel, K.M., Bartels, D., Koornneef, M. and Karssen, C.M. (1993) Acquisition of desiccation tolerance and longevity in seeds of Arabidopsis thaliana. A comparative study using abscisic acid-insensitive abi3 mutants. Plant Physiology 102, 1185–1191.Google Scholar
Ooms, J.J.J., Wilmer, J.A. and Karssen, C.M. (1994) Carbohydrates are not the sole factor determining desiccation tolerance in seeds of Arabidopsis thaliana. Physiologia Plantarum 90, 431–436.Google Scholar
Ovcharov, K.E. and Koshelev, Y.P. (1974) Sugar content in corn seeds of different viability. Soviet Plant Physiology 21, 805–808.Google Scholar
Pacovsky, R.S. (1989) Carbohydrate protein and amino acid status of Glycine glomus-Bradyrhizobium symbioses. Physiologia Plantarum 75, 346–354.Google Scholar
Pak, Y., Huang, L.C., Lilley, K.J. and Larner, J. (1992) In vivo conversion of [3 H]myo-inositol to [3H]chiro-inositol in rat tissues. Journal of Biological Chemistry 267, 16904–16910.Google Scholar
Pak, Y., Paule, C.R., Bao, Y.D., Huang, L.C. and Larner, J. (1993) Insulin stimulates the biosynthesis of chiro-inositol-containing phospholipids in a rat fibroblast line expressing the human insulin receptor. Proceedings of the National Academy of Sciences, USA 90, 7759–7763.Google Scholar
Paul, M.J. and Cockburn, W. (1989) Pinitol: A compatible solute in Mesembryanthemum crystallinum L. Journal of Experimental Botany 40, 1093–1098.Google Scholar
Petek, F., Villarroya, E. and Courtois, J.E. (1966) Isolation of two galactosides of myo-inositol from vetch seeds. Comptes Rendus de I'Académie des Sciences, Paris (Série D) Sciences Naturelles 263, 195–197.Google Scholar
Petek, F., Villarroya, E. and Courtois, J.E. (1969) Purification and properties of α-galactosidase in germinating Vicia sativa seeds. European Journal of Biochemistry 8, 395–402.Google Scholar
Praefcke, K., Marquardt, P., Kohne, B. and Stephan, W. (1991) Liquid-crystalline inositol ethers: their syntheses and columnar mesophases. Journal of Carbohydrate Chemistry 10, 539–548.CrossRefGoogle Scholar
Priestley, D.A., Cullinan, V.I. and Wolfe, J. (1985) Differences in seed longevity at the species level. Plant Cell and Environment 8, 557–562.Google Scholar
Quemener, B. and Brillouet, J.M. (1983) Ciceritol, a pinitol digalactoside from seeds of chickpea, lentil and white lupin. Phytochemistry 22, 1745–1751.Google Scholar
Rackis, J.J. (1976) Flatulence problems associated with soy products. pp 892–903 in Hill, L.D. (Ed.) World Soybean Research. Proceedings of the World Soybean Research Conference I. Danville, IL, The Interstate Printers and Publishers, Inc.Google Scholar
Richter, A. (1992) Viscumitol: a dimethylether of muco-inositol from Viscum album. Phytochemistry 31, 3925–3927.Google Scholar
Ruis, H. and Hoffmann-Ostenhof, O. (1969) Enzymic epimerization of sequoyitol to D-pinitol in Trifolium incarnatum. European Journal of Biochemistry 7, 442–448.Google Scholar
Ruttloff, H., Täufel, A., Krause, W., Haenel, H. and Täufel, K. (1967) The intestinal enzymatic decomposition of galacto-oligosaccharides in the human and animal intestine, with particular regard to Lactobacillus bifidus. Part II. On the intestinal behaviour of lactulose. Die Nährung 11, 39–46.CrossRefGoogle Scholar
Saini, H.S. and Gladstones, J.S. (1986) Variability in the total and component galactosyl sucrose oligosaccharides of Lupinus species. Australian Journal of Agricultural Research 37, 57–166.Google Scholar
Saravitz, D.M., Pharr, D.M. and Carter, T.E. (1987) Galactinol synthase activity and soluble sugars in developing seeds of four soybean genotypes. Plant Physiology 83, 185–189.Google Scholar
Sasaki, K. and Loewus, F.A. (1980) Metabolism of myo-[2-3H]inositol and scyllo-[R-3H]inositol in ripening wheat kernels. Plant Physiology 66, 740–745.Google Scholar
Schnyder, H., Gillenberg, C. and Hinz, J. (1993) Fructan contents and dry matter deposition in different tissues of the wheat grain during development. Plant Cell and Environment 16, 179–187.Google Scholar
Scholda, R., Bilek, G. and Hoffmann-Ostenhof, O. (1964a) Biosynthesis of cyclitols. V. Further investigations concerning the formation of individual cyclitols in the leaves of Trifolium incarnatum. Hoppe-Seyler's Zeitschrift für Physiologische Chemie 337, 277–281.Google Scholar
Scholda, R., Billek, G. and Hoffmann-Ostenhof, O. (1964b) Biosynthesis of cyclitols. I. Formation of D-pinitol, D-chiro-inositol and sequoyitol from myo-inositol in leaflets of Trifolium incarnatum. Hoppe-Seyler's Zeitschrift für Physiologische Chemie 335, 180–186.Google Scholar
Scholda, R., Billek, G. and Hoffmann-Ostenhof, O. (1964c) Biosynthesis of cyclitols. VIII. Mechanism of conversion of myo-inositol to D-pinitol and D-chiro-inositol in Trifolium incarnatum. Monatshefte für Chemie 95, 1311–1317.CrossRefGoogle Scholar
Schweizer, T.F. and Horman, I. (1981) Purification and structure determination of three α-D-galactopyranosylcyclitols from soya beans. Carbohydrate Research 95, 61–71.CrossRefGoogle Scholar
Schweizer, T.F., Horman, I. and Würsch, P. (1978) Low molecular weight carbohydrates from leguminous seeds; a new disaccharide: galactopinitol. Journal of the Science of Food and Agriculture 29, 148–154.Google Scholar
Sheriff, D.W., Fisher, M.J., Rusitzka, G. and Ford, C.W. (1986) Physiological reactions to an imposed drought by two twining pasture legumes: Macroptilium atropurpureum desiccation sensitive and Galactia striata desiccation insensitive. Australian Journal of Plant Physiology 13, 431–445.Google Scholar
Shiomi, N., Takeda, T. and Kiriyama, S. (1988) A new digalactosyl cyclitol from seed balls of sugar beet. Agricultural and Biological Chemistry 52, 1587–1588.Google Scholar
Sköt, L. and Egsgaard, H. (1984) Identification of ononitol and O-methyl-scyllo-inositol in pea root nodules. Planta 161, 32–36.Google Scholar
Smith, P.T., Kuo, T.M. and Crawford, C.G. (1991) Purification and characterization of galactinol synthase from mature zucchini squash leaves. Plant Physiology 96, 693–698.Google Scholar
Sommer, C., Thonke, B. and Popp, M. (1990) The compatibility of D-pinitol and 1D-1-O-methyl-muco-inositol with malate dehydrogenase activity. Botanica Acta 103, 270–273.Google Scholar
Streeter, J.G. (1985) Identification and distribution of ononitol in nodules of Pisum sativum and Glycine max. Phytochemistry 24, 174–176.Google Scholar
Sun, W.Q. and Leopold, A.C. (1993) The glassy state and accelerated aging of soybeans. Physiologia Plantarum 89, 767–774.Google Scholar
Sun, W.Q., Irving, T.C. and Leopold, A.C. (1994) The role of sugar, vitrification and membrane phase transition in seed desiccation tolerance. Physiologia Plantarum 90, 621–628.Google Scholar
Traitler, H., Del Vedovo, S. and Schweizer, T.F. (1984) Gas chromatographic separation of sugars by on-column injection on glass capillary column. Journal of High Resolution Chromatography and Chromatography Communications 7, 558–562.Google Scholar
Vernon, D.M. and Bohnert, H.J. (1992a) Increased expression of a myo-inositol methyl transferase in Mesembryanthemum crystallinum is part of a stress response distinct from Crassulacean Acid Metabolism induction. Plant Physiology 99, 1695–1698.Google Scholar
Vernon, D.M. and Bohnert, H.J. (1992b) A novel methyl transferase induced by osmotic stress in the facultative halophyte Mesembryanthemum crystallinum. European Molecular Biology Organization Journal 11, 2077–2085.Google Scholar
Vernon, D.M., Tarczynski, M.C., Jensen, R.G. and Bohnert, H.J. (1993) Cyclitol production in transgenic tobacco. Plant Journal 4, 199–205.Google Scholar
Woeber, G. and Hoffmann-Ostenhof, O. (1969) Biosynthesis of cyclitols. XXII. Cyclitols in Chlorella fusca. Monatshefte für Chemie 100, 369–375.Google Scholar
Woeber, G., Ruis, H. and Hoffmann-Ostenhof, O. (1971) Biosynthesis of cyclitols. XXVII. A dehydrogenase system that can catalyze the epimerization of myo-inositol to D-chiro-inositol in Chlorella fusca. Monatshefte für Chemie 102, 459–464.Google Scholar
Yasui, T. (1980) Identification of a new galactosyl cyclitol from seeds of Vigna angularis Ohwi et Ohashi (adzuki bean). Agricultural and Biological Chemistry 44, 2253–2255.Google Scholar
Yashi, T. (1985) Dissimilarity in low molecular weight carbohydrate composition of the seeds of cultivated soybean [Glycine max (L.) Merrill subsp. max] and wild soybean [G. max subsp. soja (Sieb. et Zucc.) Ohashi]. Agricultural and Biological Chemistry 49, 933–937.Google Scholar
Yasui, T., Endo, Y. and Ohashi, H. (1987) Infrageneric variation of the low molecular weight carbohydrate composition of the seeds of the genus Vicia (Leguminosae). Botanical Magazine, Tokyo 100, 255–272.CrossRefGoogle Scholar
Yazdi-Samadi, G., Rinne, R.W. and Seif, R.D. (1977) Components of developing soybean seeds: Oil, protein, sugars, starch, organic acids, and amino acids. Agronomy Journal 69, 481–486.CrossRefGoogle Scholar