Seed α-D-Galactosides of Selected Vicia Species and Enzymes Involved in Their Biosynthesis
We compared the soluble carbohydrate composition of seeds of ten wild and cultivated species of the genus Vicia. In some Vicia species (V. angustifolia, V. grandiflora, V. sativa, V. sepium) they contained only raffinose family oligosaccharides (RFOs) and in others also D-pinitol and its α-D-galactosides. In terms of galactosyl pinitol composition they were divided into three groups: those accumulating small amounts of mono-, di-, tri-galactosyl pinitol A (GPA, ciceritol and TGPA, respectively) and unknown compound (V. sylvatica and V. hirsuta); those accumulating more ciceritol than TGPA (V. tetrasperma and V. villosa); and those accumulating more TGPA than ciceritol (V. cracca and V. tenuifolia). The differences in the activity of galactosyltransferases engaged in RFOs and galactosyl pinitol synthesis confirmed this classification. Seeds of V. angustifolia, naturally accumulating only RFOs, showed an ability to accumulate exogenously applied D-pinitol or D-chiro-inositol and to form the respective α-D-galactosyl cyclitols. Levels of synthesized galactosides depended on the type and concentration of cyclitol in the feeding solution, and seed maturation stage. However, even a high level of D-pinitol or D-chiro-inositol in the feeding solution caused accumulation of only small amounts of mono- and di-galactosyl pinitols, or tri-galactosyl D-chiro-inositol in seeds of V. angustifolia. Enhanced synthesis of galactosyl cyclitols, mainly mono- and di-galactosides of D-chiro-inositol (fagopyritols), clearly reduced production of verbascose. We suggest that exogenously applied free cyclitols inhibit biosynthesis of tri- and di-galactosides and/or cause substrate competition in enzymes of Vicia species.
Blöchl A, Peterbauer T, and Richter A. 2007. Inhibition of raffinose oligosaccharide breakdown delays germination of pea seeds. Journal of Plant Physiology 164: 1093-1096.
Bock C, Ray H, and Georges F. 2009. Down-regulation of galactinol synthesis in oilseed Brassica napus leads to significant reduction of antinutritional oligosaccharides. Botany/Botanique 87: 597-603.
Chiera JM, Streeter JG, and Finer JJ. 2006. Ononitol and pinitol production in transgenic soybean containing the inositol methyl transferase gene from Mesembryanthemum crystallinum. Plant Science 171: 647-654.
Coon CN, Leske KL, Akavanichan O, and Cheng TK. 1990. Effect of oligosaccharide-free soybean meal on true metabolizable energy and fiber digestion in adult roosters. Poultry Science 69: 787-793.
Dierking EC, and Bilyeu KD. 2008. Association of a soybean raffinose synthase gene with low raffinose and stachyose seed phenotype. The Plant Genome 1: 135-145.
Dierking EC, and Bilyeu KD. 2009. Raffinose and stachyose are not required for efficient soybean seed germination. Journal of Plant Physiology 166: 1329-1335.
Fleming SE. 1981. A study of relationship between flatus potential and carbohydrate distribution in legume seeds. Journal of Food Science 46: 794-797.
Frias J, Bakhsh A, Jones DA, Arthur AE, Vidal-Valverde C, Rhodes MJC, and Hedley CL. 1999. Genetic analysis of the raffinose oligosaccharide pathway in lentil seeds. Journal of Experimental Botany 50: 469-476.
Gomes CI, Obendorf RL, and Horbowicz M. 2005. myo-Inositol, D-chiro-inositol, and D-pinitol synthesis, transport, and galactoside formation in soybean explants. Crop Science 45(2): 1312-1319.
Hitz WD, Carlson TJ, Kerr PS, and Sebastian SA. 2002. Biochemical and molecular characterization of a mutation that confers a decreased raffinosaccharide and phytic acid phenotype on soybean seeds. Plant Physiology 128: 650-660.
Hoch G, Peterbauer T, and Richter A. 1999. Purification and characterization of stachyose synthase from lentil (Lens culinaris) seeds: galactopinitol and stachyose synthesis. Archives of Biochemistry and Biophysics 366(1): 75-81.
Horbowicz M, and Obendorf RL. 1994. Seed desiccation tolerance and storability: Dependence on flatulence-producing oligosaccharides and cyclitols. Seed Science Research 4: 385-405.
Horbowicz M, Brenac P, and Obendorf RL. 1998. Fagopyritol B1, O-α-D-galactopyranosyl-(1-2)-D-chiro-inositol, a galactosyl cyclitol in maturing buckwheat seeds associated with desiccation tolerance. Planta 205: 1-11.
Jaaska V. 2005. Isozyme variation and phylogenetic relationships in Vicia subgenus Cracca (Fabaceae). Annals of Botany 96: 1085-1096.
Kerr PS, AND Sebastian S.A. 2000. Soybean products with improved carbohydrate composition and soybean plants. U.S. patent 6147193. Date issued: 14 November.
Lahuta LB, Górecki RJ, Gojło E, and Horbowicz M. 2005a. Differences in accumulation of soluble α-galactosides during seed maturation of several Vicia species. Acta Physiologiae Plantarum 27: 163-171.
Lahuta LB, Horbowicz M, Gojło E, Goszczyńska J, and Górecki RJ. 2005b. Exogenously applied D-pinitol and D-chiro-inositol modifies the accumulation of α-d-D-galactosides in developing tiny vetch (Vicia hirsuta [L.] S.F. Gray) seeds. Acta Societatis Botanicorum Poloniae 74(4): 287-296.
Lahuta LB., Górecki RJ, and Horbowicz M. 2005c. High concentrations of D-pinitol or D-chiro-inositol inhibit the biosynthesis of raffinose family oligosaccharides in maturing smooth tare (Vicia tetrasperma [L.] Schreb.) seeds. Acta Physiologiae Plantarum 27(4A): 505-513.
Lahuta LB. 2006. Biosynthesis of raffinose family oligosaccharides and galactosyl pinitols in developing and maturing seeds of winter vetch (Vicia villosa Roth.). Acta Societatis Botanicorum Poloniae 75(3): 219-227.
Lahuta LB, and Goszczyńska J. 2009. Inhibition of raffinose family oligosaccharides and galactosyl pinitols breakdown delays germination of winter vetch (Vicia villosa Roth.) seeds. Acta Societatis Botanicorum Poloniae 78: 203-208.
Liu JJ, Odegard W, and de Lumen BO. 1995. Galactinol synthase from kidney bean cotyledon and zucchini leaf. Purification and N-terminal sequences. Plant Physiology 109: 505-511.
Ma JM, Horbowicz M, and Obendorf RL. 2005. Cyclitols galactosides in embryos of buckwheat stem-leaf-seed explants fed D-chiro-inositol, myo-inositol or D-pinitol. Seed Science Research 15: 329-338.
Obendorf RL. 1997. Oligosaccharides and galactosyl cyclitols in seed desiccation tolerance. Seed Science Research 7: 63-74.
Obendorf RL, Odorcic S, Ueda T, Coseo MP, and Vasallo E. 2004. Soybean galactinol synthase forms fagopyritol B1 but not galactosyl pinitols: substrate feeding of isolated embryos and heterologous expression. Seed Science Research 14: 321-333.
Obendorf RL, Mcinnis CE, Horbowicz M, Keresztes I, and Lahuta LB. 2005. Molecular structure of lathyritol, a galactosyl bornesitol from Lathyrus odoratus seeds by NMR. Carbohydrates Research 340: 1441-1446.
Obendorf RL, Zimmerman AD, Zhang Q, Castillo A, Kosina SM, Bryant EG, Sensenig EM, Wu J, and Schnelby SR. 2009. Accumulation of soluble carbohydrates during seed development and maturation of low-raffinose, low-stachyose soybean. Crop Science 49: 329-341.
Peterbauer T, and Richter A. 2001. Biochemistry and physiology of raffinose family oligosaccharides and galactosyl cyclitols in seeds. Seed Science Research 11: 185-197.
Peterbauer T, Lahuta LB, Blöchl A, Mucha J, Jones DA, Hedley CL, Górecki RJ, and Richter A. 2001. Analysis of the raffinose family oligosaccharide pathway in pea seeds with contrasting carbohydrate composition. Plant Physiology 127: 1764-1772.
Peterbauer T, Mucha J, Mach L, and Richter A. 2002a. Chain elongation of raffinose in pea seeds. Isolation, characterization, and molecular cloning of a multifunctional enzyme catalyzing the synthesis of stachyose and verbascose. Journal of Biological Chemistry 277: 194-200.
Peterbauer T, Mach L, Mucha J, and Richter A. 2002b. Functional expression of a cDNA encoding pea (Pisum sativum L.) raffinose synthase, partial purification of the enzyme from maturing seeds, and steady-state kinetic analysis of raffinose synthesis. Planta 215: 839-846.
Peterbauer T, Karner U, Mucha J, Mach L, Jones DA, Hedley CL, and Richter A. 2003. Enzymatic control of the accumulation of verbascose in pea seeds. Plant Cell & Environment 26: 1385-1391.
Polowick PL, Baliski DS, Bock C, Heather R, and Fawzy G. 2009. Over-expression of a-galactosidase in pea seeds to reduce raffinose oligosaccharide content. Botany/Botanoque 87: 526-532.
Szczeciński P, Gryff-Keller A, Horbowicz M, and Lahuta LB. 2000. Galactosylpinitols isolated from vetch (Vicia villosa Roth.) seeds. Journal of Agricultural and Food Chemistry 48: 2717-2720.
Turner LB, and Pollock CJ. 1998. Changes in stolon carbohydrates during the winter in four varieties of white clover (Trifolium repens L.) with contrasting hardiness. Annals of Botany 81: 97-107.
Ueda T, Coseo MP, Harrell TJ, and Obendorf RL. 2005. A multifunctional galactinol synthase catalyzes the synthesis of fagopyritol A1 and fagopyritol B1 in buckwheat seed. Plant Science 168: 681-690.
Yasui T, Endo Y, and Ohashi H. 1987. Infrageneric variation of the low molecular weight carbohydrate composition of the seeds of genus Vicia (Leguminosae). The Botanical Magazine Tokyo 100: 255-272.
Yasui T, and Ohashi H. 1990. The low molecular weight carbohydrate composition of seeds in the Leguminosae - a new taxonomic character in the family. Science Reports of the Tohoku University Fourth Series, Biology 39: 257-393.
