Quaternary ammonium and tertiary sulfonium compounds in higher plants

Annual Review of Plant Physiology and Plant Molecular Biology

Volumn 44, Issue 1, 1993, Pages 357-384

  Rhodes, D ^a   Hanson, A D ^b  

^a PURDUE UNIVERSITY   (United States)

^b UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

Betaines; Choline; Phytochemistry; Quaternary ammonium compounds; Tertiary sulfonium compounds

Indexed keywords

EID: 6244268962     PISSN: 10402519     EISSN: None     Source Type: Journal    
DOI: 10.1146/annurev.pp.44.060193.002041     Document Type: Article

References (195)

1. Ahmad, N., Wyn Jones, R. G. 1979. Glycinebetaine, proline and inorganic ion levels in barley seedlings following transient stress. Plant Sci. Lett. 15:231-37
2. + transport in barley roots. J. Exp. Bot. 38:913-21
3. Al-Amoudi, O. A., Ali, A. Y. 1989. Some practical aspects of measurements of betaines and their sulphur analogues by the use of HPLC. J. Microbiol. Methods 10:289-96
4. Anthoni, U., Christophersen, C., Hougaard, L., Nielsen, P. H. 1991. Quaternary ammonium compounds in the biosphere - an example of a versatile adaptive strategy. Comp. Biochem. Physiol. 99B:1-18
5. Arakawa, K., Katayama, M., Takabe, T. 1990. Levels of betaine and betaine aldehyde dehydrogenase in the green leaves, and etiolated leaves and roots of barley. Plant Cell Physiol. 31:797-803
6. Arakawa, K., Takabe, T., Sugiyama, T., Akazawa, T. 1987. Purification of betaine-aldehyde dehydrogenase from spinach leaves and preparation of its antibody. J. Biochem. 101:1485-88
7. Araya, F., Abarca, O., Zúñiga, G. E., Corcuera, L. J. 1991. Effects of NaCl on glycine-betaine and on aphids in cereal seedlings. Phytochemistry 30:1793-95
8. Benson, A. A., Atkinson, M. R. 1967. Choline sulfate and phosphate in salt excreting plants. Fed. Proc. 26:394
9. Bernard, T., Pocard, J.-A., Perroud, B., Le Rudulier, D. 1986. Variations in the response of salt-stressed Rhizobium strains to betaines. Arch. Microbiol. 143:359-64
10. Bligny, R., Foray, M.-F., Roby, C., Douce, R. 1989. Transport and phosphorylation of choline in higher plant cells: phosphorus-31 nuclear magnetic resonance studies. J. Biol. Chem. 264:4888-95
11. Blunden, G. M., El Barouni, M., Gordon, S. M., McLean, W. F. H., Rogers, D. J. 1981. Extraction, purification and characterisation of Dragendorff-positive compounds from some British marine algae. Bot. Mar. 24:451-56
12. Blunden, G., Gordon, S. M. 1986. Betaines and their sulphonio analogues in marine algae. Prog. Phycol. Res. 4:39-80
13. Blunden, G., Gordon, S. M., Crabb, T. A., Roch, O. G., Rowan, M. G., Wood, B. 1986. NMR spectra of betaines from marine algae. Magn. Resonance Chem. 24:965-71
14. Borowitzka, L. J. 1986. Osmoregulation in blue-green algae. Prog. Phycol. Res. 4:243-56
15. Boyd, L. A., Adam, L., Pelcher, L. E., McHughen, A.,Hirji, R., Selvaraj, G. 1991. Characterization of an Escherichia coli gene encoding betaine aldehyde dehydrogenase (BADH): structural similarity to mammalian ALDHs and a plant BADH. Gene 103:45-52
16. Brady, C. J., Gibson, T. S., Barlow, E. W. R., Speirs, J., Wyn Jones, R. G. 1984. Salt-tolerance in plants. I. Ions, compatible organic solutes and the stability of plant ribosomes. Plant Cell Environ. 7:571-78
17. Brouquisse, R., Weigel, P., Rhodes, D., Yocum, C. F., Hanson, A. D. 1989. Evidence for a ferredoxin-dependent choline monooxygenase from spinach chloroplast stroma. Plant Physiol. 90:322-29
18. Brunk, D. G., Rich, P. J., Rhodes, D. 1989. Genotypic variation for glycinebetaine among public inbreds of maize. Plant Physiol. 91:1122-25
19. Challenger, F. 1959. Aspects of the Organic Chemistry of Sulphur. London: Butterworths
20. Chambers, S. T., Kunin, C. M., Miller, D., Hamada, A. 1987. Dimethylthetin can substitute for glycine betaine as an osmoprotectant molecule for Escherichia coli. J. Bacteriol. 169:4845-47
21. Che, F.-S., Cho, C. Hyeon, S.-B., Isogai, A., Susuki, A. 1990. Metabolism of choline chloride and its analogs in wheat seedlings. Plant Cell Physiol. 31:45-50
22. Chen, F. C. M., Benoiton, N. L. 1976. A new method for quaternizing amines and its use in amino acid and peptide chemistry. Can. J. Chem. 54:3310-11
23. Chillemi, R., Patti, A., Morrone, R., Piattelli, M., Sciuto, S. 1990. The role of methylsulfonium compounds in the biosynthesis of N-methylated metabolites in Chondria coerulescens. J. Nat. Prod. 53:87-93
24. Coughlan, S. J., Heber, U. 1982. The role of glycinebetaine in the protection of thylakoids against freezing stress. Planta 156:62-69
25. Coughlan, S. J., Wyn Jones, R. G. 1982. Glycinebetaine biosynthesis and its control in detached secondary leaves of spinach. Planta 154:6-17
26. Csonka, L. N. 1989. Physiological and genetic responses of bacteria to osmotic stress. Microbiol. Rev. 53:121-47
27. Csonka, L. N., Hanson, A. D. 1991. Prokaryotic osmoregulation: genetics and physiology. Annu. Rev. Microbiol. 45:569-606
28. Dacey, J. W. H., King, G. M., Wakeham, S. G. 1987. Factors controlling emission of dimethylsulfide from salt marshes. Nature 330:643-45
29. Datko, A. H., Mudd, S. H. 1986. Uptake of choline and ethanolamine by Lemna paucicostata Hegelm. 6746. Plant Physiol. 81:285-88
30. Datko, A. H., Mudd, S. H. 1988. Phosphatidylcholine synthesis: differing patterns in soybean and carrot. Plant Physiol. 88:854-61
31. Datko, A. H., Mudd, S. H. 1988. Enzymes of phosphatidylcholine synthesis in Lemna, soybean, and carrot. Plant Physiol. 88:1338-48
32. Dickson, D. M. J., Kirst, G. O. 1986. The role of β-dimethylsulphoniopropionate, glycine betaine and homarine in the osmoacclimation of Platymonas subcordiformis. Planta 167:536-43
33. Dickson, D. M., Wyn Jones, R. G., Davenport, J. 1980. Steady state osmotic adjustment in Ulva lactuca. Planta 150:158-65
34. Essery, J. M., McCaldin, D. J., Marion, L. 1962. The biogenesis of stachydrine. Phytochemistry 1:209-13
35. Fitzgerald, J. W., Luschinski, P. C. 1977. Further studies on the formation of choline sulfate by bacteria. Can. J. Microbiol. 23:483-90
36. Flowers, T. J., Hall, J. L., Ward, M. E. 1978. Salt tolerance in the halophyte, Suaeda maritima (L.) Dum.: properties of malic enzyme and PEP carboxylase. Ann. Bot. 42:1065-74
37. Ford, C. W. 1984. Simultaneous determination of proline and betaines by high performance liquid chromatography. J. Sci. Food Agric. 35:881-86
38. Fougère, F., Le Rudulier, D. 1990. Glycine betaine biosynthesis and catabolism in bacteriods of Rhizobium meliloti: effect of salt stress. J. Gen. Microbiol. 136:2503-10
39. Gabbay-Azaria, R., Tel-Or, E., Schönfeld, M. 1988. Glycinebetaine as an osmoregulant and compatible solute in the marine cyanobacterium Spirulina subsalsa. Arch. Biochem. Biophys. 264:333-39
40. Galinski, E. A., Oren, A. 1991. Isolation and structure determination of a novel compatible solute from the moderately halophilic purple sulfur bacterium Ectothiorhodospira marismortui. Eur. J. Biochem 198:593-98
41. Garami, M., Mincsovics, E. 1989. Separation of some quaternary ammonium compounds from maize by OPLC. J. Planar Chromatog. 2:438-41
42. Garcia-Perez, A., Burg, M. B. 1991. Renal medullary organic osmolytes. Physiol. Rev. 71:1081-115
43. Génard, H., Le Saos, J., Billard, J.-P., Trémolières, A., Boucaud, J. 1991. Effect of salinity on lipid composition, glycine betaine content and photosynthetic activity in chloroplasts of Suaeda maritima. Plant Physiol. Biochem. 29:421-27
44. Gibson, T. S., Speirs, J., Brady, C. J. 1984. Salt-tolerance in plants. II. In vitro translation of m-RNAs from salt-tolerant and salt-sensitive plants on wheat germ ribosomes. Responses to ions and compatible organic solutes. Plant Cell Environ. 7:579-87
45. Giddings, T. H., Hanson, A. D. 1982. Water stress provokes a generalized increase in phosphatidylcholine turnover in barley leaves. Planta 155:493-501
46. Giovanelli, J., Mudd, S. H., Datko, A. H. 1980. Sulfur amino acid in plants. In The Biochemistry of Plants, ed. B. J. Miflin, 5:453-505. New York: Academic
47. Goldberg, Y., Ãbele, E., Bremanis, G., Trapenciers, P., Gaukhman, A., et al. 1990. Betaines derived from amino and hydrazino acids as phase transfer catalysts. Tetrahedron 46-.1911-22
48. Goldmann, A., Boivin, C., Fleury, V., Message, B., Lecoeur, L., et al. 1991. Betaine use by rhizosphere bacteria: genes essential for trigonelline, stachydrine, and carnitine catabolism in Rhizobium meliloti are located on pSym in the symbiotic region. Mol. Plant-Microbe Interact. 4:571-78
49. Gorham, J. 1984. Separation of plant betaines and their sulphur analogues by cation-exchange high-performance liquid chromatography. J. Chromatogr. 287:345-51
50. Gorham, J. 1986. Separation and quantitative estimation of betaine esters by high-performance liquid chromatography. J. Chromatogr. 361:301-10
51. Gorham, J., Coughlan, S. J., Storey, R., Wyn Jones, R. G. 1981. Estimation of quaternary ammonium and tertiary sulphonium compounds by thin-layer electrophoresis and scanning reflectance densitometry. J. Chromatogr. 210:550-54
52. Gorham, J., McDonnell, E. 1985. High-performance liquid Chromatographic method for the separation and estimation of choline, glycinebetaine aldehyde and related compounds. J. Chromatogr. 350:245-54
53. Gorham, J., McDonnell, E., Wyn Jones, R. G. 1982. Determination of betaines as ultraviolet-absorbing esters. Anal. Chim. Acta 138:277-83
54. Grattan, S. R., Grieve, C. M. 1985. Betaine status in wheat in relation to nitrogen stress and to transient salinity stress. Plant Soil 85:3-9
55. Greene, R. C. 1962. Biosynthesis of dimethyl-β-propiothetin. J. Biol. Chem. 237:2251-54
56. Grieve, C. M., Grattan, S. R. 1983. Rapid assay for determination of water soluble quaternary ammonium compounds. Plant Soil 70:303-7
57. Grieve, C. M., Maas, E. V. 1984. Betaine accumulation in salt-stressed sorghum. Physiol. Plant. 61:167-71
58. Gröne, T., Kirst, G. O. 1991. Aspects of dimethylsulfoniopropionate effects on enzymes isolated from the marine phytoplankter Tetraselmis subcordiformis (Stein). J. Plant Physiol. 138:85-91
59. Grumet, R., Albrechtsen, R. S., Hanson, A. D. 1987. Growth and yield of barley isopopulations differing in solute potential. Crop Sci. 27:991-95
60. Grumet, R., Hanson, A D. 1986. Genetic evidence for an osmoregulatory function of glycinebetaine accumulation in barley. Aust. J. Plant Physiol. 13:353-64
61. Hall, J. L., Harvey, D. M. R., Flowers, T. J. 1978. Evidence for the cytoplasmic localization of betaine in leaf cells of Suaeda maritima. Planta 140:59-62
62. Hanson, A. D., Gage, D. A. 1991. Identification and determination by fast atom bombardment mass spectrometry of the compatible solute choline-O-sulfate in Limonium species and other halophytes. Aust. J. Plant Physiol. 18:317-27
63. Hanson, A. D., Grumet, R. 1985. Betaine accumulation: metabolic pathways and genetics. In Cellular and Molecular Biology of Plant Stress, ed. J. L. Key, T. Kosuge, pp. 71-92. New York: Alan R. Liss, Inc.
64. Hanson, A. D., May, A. M., Grumet, R., Bode, J., Jamieson, G. C., Rhodes, D. 1985. Betaine synthesis in chenopods: localization in chloroplasts. Proc. Natl. Acad. Sci. USA 82:3678-82
65. 14C]formate metabolism in water-stressed barley leaves. Plant Physiol. 62:305-12
66. Hanson, A. D., Rathinasabapathi, B., Chamberlin, B., Gage, D. A. 1991. Comparative physiological evidence that β-alanine betaine and choline-O-sulfate act as compatible osmolytes in halophytic Limonium species. Plant Physiol. 97: 1199-205
67. 14C Tracer evidence for synthesis of choline and betaine via phosphoryl base intermediates in salinized sugar beet leaves. Plant Physiol. 71:692-700
68. Hanson, A. D., Scott, N. A. 1980. Betaine synthesis from radioactive precursors in attached, water-stressed barley leaves. Plant Physiol. 66:342-48
69. Hanson, A. D., Wyse, R. 1982. Biosynthesis, translocation, and accumulation of betaine in sugar beet and its progenitors in relation to salinity. Plant Physiol. 70:1191-98
70. Hitz, W. D., Hanson, A. D. 1980. Determination of glycine betaine by pyrolysis-gas chromatography in cereals and grasses. Phytochemistry 19:2371-74
71. Hitz, W. D., Ladyman, J. A. R., Hanson, A. D. 1982. Betaine synthesis and accumulation in barley during field water-stress. Crop Sci. 22:47-54
72. Hitz, W. D., Rhodes, D., Hanson, A. D. 1981. Radiotracer evidence implicating phosphoryl and phosphatidyl bases as intermediates in betaine synthesis by water-stressed barley leaves. Plant Physiol. 68:814-22
73. Huang, Z.-H., Gage, D. A., Bieber, L. L., Sweeley, C. C. 1991. Analysis of acylcarnitines as their N-demethylated ester derivatives by gas chromatography-chemical ionization mass spectrometry. Anal. Biochem. 199:98-105
74. Incharoensakdi, A., Takabe, T., Akazawa, T. 1986. Effect of betaine on enzyme activity and subunit interaction of ribulose-1,5-bisphosphate carboxylase/oxygenase from Aphanothece halophytica. Plant Physiol. 81:1044-49
75. Itai, C., Paleg, L. G. 1982. Responses of water-stressed Hordeum distichum L. and Cucumis sativus to proline and betaine. Plant Sci. Lett. 25:329-35
76. Jolivet, Y., Larher, F., Hamelin, J. 1982. Osmoregulation in halophytic higher plants: the protective effect of glycine betaine against the heat destabilization of membranes. Plant Sci. Lett. 25:193-201
77. Jones, G. P., Naidu, B. P., Paleg, L. G. 1988. Hygric acid (I) and stachydrine (II) as their hydrochlorides. Acta Crystallogr. C44: 1669-71
78. Jones, G. P., Naidu, B. P., Paleg, L. G., Tiekink, E. R. T., Snow, M. R. 1987. 4-Hydroxy-N-methylproline analogues in Melaleuca spp. Phytochemistry 26:3343-44
79. 1H nuclear magnetic resonance spectroscopy. Aust. J. Plant Physiol. 13:649-58
80. Kahn, V. 1964. Glycine as a methyl donor in dimethyl-β-propiothetin synthesis. J. Exp. Bol. 15:225-31
81. Karsten, U., Wiencke, C., Kirst, G. O. 1990. The β-dimethylsulphoniopropionate (DMSP) content of macroalgae from Antarctica and Southern Chile. Bot. Mar. 33:143-46
82. Kiene, R. P., Visscher, P. T. 1987. Production and fate of methylated sulfur compounds from methionine and dimethylsulfoniopropionate in anoxic salt marsh sediments. Appl. Environ. Microbiol. 53:2426-34
83. Kinney, A. J., Moore, T. S. 1987. Phosphatidylcholine synthesis in castor bean endosperm. I. Metabolism of L-serine. Plant Physiol. 84:78-81
84. Kinney, A. J., Moore, T. S. 1988. Phosphatidylcholine synthesis in castor bean endosperm: characteristics and reversibility of the choline kinase reaction. Arch. Biochem. Biophys. 260:102-8
85. Kjaer, A. 1960. Naturally derived isothiocyanates (mustard oils) and their parent glucosides. Fortschr. Chem. Org. Naturst. 18:122-76
86. Koheil, M. A. H., Hilal, S. H., El-Alfy, T. S., Leistner, E. 1992. Quaternary ammonium compounds in intact plants and cell suspension cultures of Atriplex semibaccata and A. halimus during osmotic stress. Phytochemistry 31:2003-8
87. Ladyman, J. A. R., Ditz, K. M., Grumet, R., Hanson, A. D. 1983. Genotypic variation for glycinebetaine accumulation by cultivated and wild barley in relation to water stress. Crop Sci. 23:465-68
88. Ladyman, J. A. R., Hitz, W. D., Hanson, A. D. 1980. Translocation and metabolism of glycine betaine by barley plants in relation to water stress. Planta 150:191-96
89. Lai, M.-C., Sowers, K. R., Robertson, D. E., Roberts, M. F., Gunsalus, R. P. 1991. Distribution of compatible solutes in the halophilic mathanogenic archaebacteria. J. Bacteriol. 173:5352-58
90. Landfald, B., Strøm, A. R. 1986. Cholineglycine betaine pathway confers a high level of osmotic tolerance in Escherichia coli. J. Bacteriol. 165:849-55
91. Larher, F. 1976. Sur quelques particularités du métabolisme azoté d'une halophyte: Limonium vulgare Mill. D. Sc. Thesis, Université de Rennes
92. Larher, F., Hamelin, J. 1975. L'acide β-triméthylaminopropionïque des rameaux de Limonium vulgare Mill. Phytochemistry 14:205-7
93. Larher, F., Hamelin, J. 1975. Mise en évidence de l'acide 2-triméthylamino 6-cétoheptanoïque dans les rameaux de Limonium vulgare. Phytochemistry 14: 1789-91
94. Larher, F., Hamelin, J. 1979. L'acide diméthylsulfonium-5 pentanoïque de Diplotaxis tenuifolia. Phytochemistry 18:1396-97
95. Larher, F., Hamelin, J., Stewart, G. R. 1977. L'acide diméthylsulfonium-3 pro panoïque de Spartina anglica. Phytochemistry 16:2019-20
96. Laurie, S., Stewart, G. R. 1990. The effects of compatible solutes on the heat stability of glutamine synthetase from chickpeas grown under different nitrogen and temperature regimes. J. Exp. Bot. 41:1415-22
97. Le Rudulier, D., Bernard, T., Goas, G., Hamelin, J. 1984. Osmoregulation in Klebsiella pneumoniae: enhancement of anaerobic growth and nitrogen fixation by proline betaine, γ-butyrobetaine, and other related compounds. Can J. Microbiol. 30:299-305
98. Le Rudulier, D., Strøm, A. R., Dandekar, A. M., Smith, L. T., Valentine, R. C. 1984. Molecular biology of osmoregulation. Science 224:1064-68
99. Le Rudulier, D., Valentine, R. C. 1982. Genetic engineering in agriculture: osmoregulation. Trends Biochem. Sci. 7:431-33
100. Lerma, C., Hanson, A. D., Rhodes, D. 1988. Oxygen-18 and deuterium labeling studies of choline oxidation by spinach and sugar beet. Plant Physiol. 88:695-702
101. Lerma, C., Rich, P. J., Ju, G. C., Yang, W.-J., Hanson, A. D., Rhodes, D. 1991. Betaine deficiency in maize: complementation tests and metabolic basis. Plant Physiol. 95:1113-19
102. Lone, M. I., Kueh, J. S. H., Wyn Jones, R. G., Bright, S. W. J. 1987. Influence of proline and glycinebetaine on salt tolerance of cultured barley embryos. J. Exp. Bot. 38:479-90
103. Low, P. S. 1985. Molecular basis of the biological compatibility of nature's osmolytes. In Transport Processes, Iono- and Osmoregulation, ed. R. Gilles, M. Gilles-Baillien, pp. 469-77. Berlin: Springer-Verlag
104. Manetas, Y. 1990. A re-examination of NaCl effects on phosphoenolpyruvate carboxylase at high (physiological) enzyme concentrations. Physiol. Plant. 78:225-29
105. 4-halophytes. Plant Cell Environ. 9:145-51
106. Martin, B. A., Tolbert, N. E. 1983. Factors which affect the amount of inorganic phosphate, phosphorylcholine, and phosphorylethanolamine in xylem exudate of tomato plants. Plant Physiol. 73:464-70
107. Mason, T. G., Blunden, G. 1989. Quaternary ammonium and tertiary sulphonium compounds of algal origin as alleviators of osmotic stress. Bot. Mar. 32:313-16
108. Matoh, T., Watanabe, J., Takahashi, E. 1987. Sodium, potassium, chloride, and betaine concentrations in isolated vacuoles from salt-grown Atriplex gmelini leaves. Plant Physiol. 84:173-77
109. Matoh, T., Yasuoka, S., Ishikawa, T., Takahashi, E. 1988. Potassium requirement of pyruvate kinase extracted from leaves of halophytes. Physiol. Plant. 74:675-78
110. McCue, K. F., Hanson, A. D. 1990. Drought and salt tolerance: towards understanding and application. Trends Biotech. 8:358-62
111. McCue, K. F., Hanson, A. D. 1992. Salt-inducible betaine aldehyde dehydrogenase from sugar beet: cDNA cloning and expression. Plant Mol. Biol. 18:1-11
112. McCue, K. F., Hanson, A. D. 1992. Effects of soil salinity on the expression of betaine aldehyde dehydrogenase in leaves: investigation of hydraulic, ionic and biochemical signals. Aust. J. Plant Physiol. In press
113. McDonnell, E., Wyn Jones, R. G. 1988. Glycinebetaine biosynthesis and accumulation in unstressed and salt-stressed wheat. J. Exp. Bot. 39:421-30
114. Miller, K. J., Zelt, S. C., Bae, J.-H. 1991. Glycine betaine and proline are the principal compatible solutes of Staphylococcus aureus. Curr. Microbiol. 23:131-37
115. Moore, T. S. 1982. Phospholipid biosynthesis. Annu. Rev. Plant Physiol 33:235-59
116. Mudd, S. H., Datko, A. H. 1986. Phosphoethanolamine bases as intermediates in phosphatidylcholine synthesis by Lemna. Plant Physiol. 82:126-35
117. Mudd, S. H., Datko, A. H. 1989. Synthesis of methylated ethanolamine moieties: regulation by choline in Lemna. Plant Physiol. 90:296-305
118. Mudd, S. H., Datko, A. H. 1989. Synthesis of methylated ethanolamine moieties: regulation by choline in soybean and carrot. Plant Physiol. 90:306-10
119. Mudd, S. H., Datko, A. H. 1989. Synthesis of ethanolamine and its regulation in Lemna paucicostata. Plant Physiol. 91:587-97
120. Mudd, S. H., Datko, A. H. 1990. The S-methylmethionine cycle in Lemna paucicostata. Plant Physiol. 93:623-30
121. Müller, H., Eckert, H. 1989. Simultaneous determination of monoethanolamine and glycine betaine in plants. J. Chromatogr. 479:452-58
122. Murata, N., Mohanty, P. S., Hayashi, H., Papageorgiou, G. C. 1992. Glycine-betaine stabilizes the association of extrinsic proteins with the photosynthetic oxygen-evolving complex. FEBS Lett. 296: 187-89
123. Naidu, B. P., Jones, G. P., Paleg, L. G., Poljakoff-Mayber, A. 1987. Proline analogues in Melaleuca species: response of Melaleuca lanceolata and M. uncinata to water stress and salinity. Aust. J. Plant Physiol. 14:669-77
124. Naidu, B. P., Paleg, L. G., Aspinall, D., Jennings, A. C., Jones, G. P. 1990. Rate of imposition of water stress alters the accumulation of nitrogen-containing solutes by wheat seedlings. Aust. J. Plant Physiol. 17:653-64
125. Naidu, B. P., Paleg, L. G., Aspinall, D., Jennings, A. C., Jones, G. P. 1991. Amino acid and glycine betaine accumulation in cold-stressed wheat seedlings. Phytochemistry 30:407-9
126. Naidu, B. P., Paleg, L. G., Jones, G. P. 1992. Nitrogenous compatible solutes in drought-stressed Medicago spp. Phytochemistry 31:1195-97
127. Nash, D., Paleg, L. G., Wiskich, J. T. 1982. Effect of proline, betaine and some other solutes on the heat stability of mitochondrial enzymes. A Aust. J. Plant Physiol. 9:47-57
128. Nikolopoulus, D., Manetas, Y. 1991. Compatible solutes and in vitro stability of Salsola soda enzymes: proline incompatibility. Phytochemistry 30:411-13
129. Nishiguchi, M. K., Somero, G. N. 1992. Temperature- and concentration-dependence of compatibility of the organic osmolyte β-dimethylsulfoniopropionate. Cryobiology 29:118-24
130. Oren, A., Simon, G., Galinski, E. A. 1991. Intracellular salt and solute concentrations in Ectothiorhodospira marismortui: glycine betaine and Nα-carbamoyl glutamine-amide as osmotic solutes. Arch. Microbiol. 156:350-55
131. Paleg, L. G., Douglas, T. J., van Daal, A., Keech, D. B. 1981. Proline, betaine and other organic solutes protect enzymes against heat inactivation. Aust. J. Plant Physiol. 8:107-14
132. Paleg, L. G., Stewart, G. R., Bradbeer, J. W. 1984. Proline and glycine betaine influence protein solvation. Plant Physiol. 75:974-78
133. Pan, S.-M. 1983. The effect of salt stress on the betaine aldehyde dehydrogenase in spinach. Taiwania 28:128-37
134. Pan, S.-M. 1988. Betaine aldehyde dehydrogenase in spinach. Bot. Bull. Acad. Sinica 29:255-63
135. Pan, S.-M., Moreau, R. A., Yu, C., Huang, A. H. C. 1981. Betaine accumulation and betaine-aldehyde dehydrogenase in spinach leaves. Plant Physiol. 67:1105-8
136. Papageorgiou, G. C., Fujimura, Y., Murata, N. 1991. Protection of the oxygen-evolving Photosystem II complex by glycinebetaine. Biochim. Biophys. Acta 1057:361-66
137. Parameshwara, G., Paleg, L. G., Aspinall, D., Jones, G. P. 1990. Solute accumulation in alfalfa in response to environmental stress. In Proceedings of the International Congress of Plant Physiology, New Delhi, India, ed. S. K. Sinha, P. V. Sane, S. C. Bhargava, P. K. Agrawal, 2:1014-21. New Delhi: Soc. Plant Physiol. Biochem.
138. Pearce, R. B., Strange, R. N., Smith, H. 1976. Glycinebetaine and choline in wheat: distribution and relation to infection by Fusarium graminearum. Phytochemistry 15:953-54
139. Pesci, P., Reggiani, R. 1992. The process of abscisic-acid induced proline accumulation and the levels of polyamines and quaternary ammonium compounds in hydrated barley leaves. Physiol. Plant. 84:134-39
140. Pocard, J.-A., Bernard, T., Le Rudulier, D. 1991. Translocation and metabolism of glycine betaine in nodulated alfalfa plants subjected to salt stress. Physiol. Plant. 81:95-102
141. Pokorny, M., Marcenko, E., Keglevic, D. 1970. Comparative studies of L- and D-methionine metabolism in lower and higher plants. Phytochemistry 9:2175-88
142. Poljakoff-Mayber, A., Symon, D. E., Jones, G. P., Naidu, B. P., Paleg, L. G. 1987. Nitrogenous compatible solutes in native South Australian plants. Aust. J. Plant Physiol. 14:341-50
143. Pollard, A., Wyn Jones, R. G. 1979. Enzyme activities in concentrated solutions of glycinebetaine and other solutes. Planta 144:291-98
144. Prud'homme, M.-P., Moore, T. S. 1992. Phosphatidylcholine synthesis in castor bean endosperm: free bases as intermediates. Plant Physiol. 100:1527-35
145. Prud'homme, M.-P., Moore, T. S. 1992. Phosphatidylcholine synthesis in castor bean endosperm: the occurrence of an s-adenosyl - L-methionine:ethanolamine N-methyltransferase. Plant Physiol. 100: 1536-40
146. Rajakylä, E., Paloposki, M. 1983. Determination of sugars (and betaine) in molasses by high-performance liquid chromatography: comparison of the results with those obtained by the classical Lane-Eynon method. J. Chromatogr. 282:595-602
147. Reed, R. H. 1983. Measurement and osmotic significance of β-dimethylsulphoniopropionate in marine macroalgae. Mar. Biol. Lett. 4:173-81
148. Reed, R. H., Chudek, J. A., Foster, R., Stewart, W. D. P. 1984. Osmotic adjustment in cyanobacteria from hypersaline environments. Arch. Microbiol 138:333-37
149. Rhodes, D. 1990. Fast atom bombardment mass spectrometry. In Modern Methods of Plant Analysis, New Ser. Vol. 11: Physical Methods in Plant Science, ed. H. F. Linskens, J. F. Jackson, pp. 95-123. Berlin/Heidelberg: Springer-Verlag
150. Rhodes, D., Rich, P. J. 1988. Preliminary genetic studies of the phenotype of betaine deficiency in Zea mays L. Plant Physiol. 88:102-8
151. Rhodes, D., Rich, P. J., Brunk, D. G., Ju, G. C., Rhodes, J. C., Pauly, M. H., Hansen, L. A. 1989. Development of two isogenic sweet corn hybrids differing for glycine-betaine content. Plant Physiol. 91:1112-21
152. Rhodes, D., Rich, P. J., Myers, A. C., Reuter, C. C., Jamieson, G. C. 1987. Determination of betaines by fast atom bombardment mass spectrometry: identification of glycine betaine deficient genotypes of Zea mays. Plant Physiol. 84:781-88
153. Robinson, S. P., Jones, G. P. 1986. Accumulation of glycinebetaine in chloroplasts provides osmotic adjustment during salt stress. Aust. J. Plant Physiol. 13:659-68
154. Rudolph, A. S., Crowe, J. H., Crowe, L. M. 1986. Effects of three stabilizing agents - proline, betaine and trehalose - on membrane phospholipids. Arch. Biochem. Biophys. 245:134-43
155. Sauvage, D., Hamelin, J., Larher, F. 1983. Glycine betaine and other structurally related compounds improve the salt tolerance of Rhizobium meliloti. Plant Sci. Lett. 31:291-302
156. 3 salinity. Plant Physiol. 87:822-27
157. Schwab, K. B., Gaff, D. F. 1990. Influence of compatible solutes on soluble enzymes from desiccation-tolerant Sporobolus stapfianus and desiccation-sensitive Sporobolus pyramidalis. J. Plant Physiol. 137: 208-15
158. Selinioti, E., Nikolopoulus, D., Manetas, Y. 1987. Organic cosolutes as stabilizers of phosphoenolpyruvate carboxylase in storage: an interpretation of their action. Aust. J. Plant Physiol. 14:203-10
159. Shomer-Ilan, A., Jones, G. P., Paleg, L. G. 1991. In vitro thermal and salt stability of pyruvate kinase are increased by proline analogues and trigonelline. Aust. J. Plant Physiol. 18:279-86
160. Shrestha, T., Bisset, N. G. 1991. Quaternary nitrogen compounds from South American Moraceae. Phytochemistry 30:3285-87
161. Sibley, M. H., Yopp, J. H. 1987. Regulation of S-adenosylhomocysteine hydrolase in the halophilic cyanobacterium Aphanothece halophytica: a possible role in glycinebetaine biosynthesis. Arch. Microbiol. 149:43-46
162. Smirnoff, N., Cumbes, Q. J. 1989. Hydroxyl radical scavenging activity of compatible solutes. Phytochemistry 28:1057-60
163. Smirnoff, N., Stewart, G. R. 1985. Stress metabolites and their role in coastal plants. Vegetatio 62:273-78
164. Somero, G. N. 1986. Protons, osmolytes, and fitness of internal milieu for protein function. Am J. Physiol. 251:R197-R213
165. Speed, D., Richardson, M. 1968. Chromatographic methods for the isolation and identification of the products of choline oxidation. J. Chromatogr. 35:497-505
166. Steudler, P. A., Peterson, B. J. 1984. Contribution of gaseous sulphur from salt marshes to the global sulphur cycle. Nature 311:455-57
167. Stewart, G. R., Larher, P., Ahmad, I., Lee, J. A. 1979. Nitrogen metabolism and salt-tolerance in higher plant halophytes. In Ecological Processes in Coastal Environments, ed. R. L. Jefferies, A. J. Davy, pp. 211-27. Oxford: Blackwell
168. Storey, R., Wyn Jones, R. G. 1975. Betaine and choline levels in plants and their relationship to NaCl stress. Plant Sci. Lett. 4:161-68
169. Storey, R., Wyn Jones, R. G. 1979. Responses of Atriplex spongiosa and Suaeda monoica to salinity. Plant Physiol. 63:156-62
170. Strange, R. N., Majer, J. R., Smith, H. 1974. The isolation and identification of choline and betaine as the two major components in anthers and wheat germ that stimulate Fusarium graminearum in vitro. Physiol. Plant Path. 4:277-90
171. Strøm, A. R., Le Rudulier, D., Jakowec, M. W., Bunnell, R. C., Valentine, R. C. 1983. Osmoregulatory (Osm) genes and osmoprotective compounds. In Genetic Engineering of Plants: An Agricultural Perspective, ed. T. Kosuge, C. P. Meredith, A. Hollaender, pp. 39-59. New York: Plenum
172. Stumpf, D. K. 1984. Quantification and purification of quaternary ammonium compounds from halophyte tissue. Plant Physiol. 75:273-74
173. Deleted in proof
174. Takabe, T., Arakawa, K., Ishinti, M. 1989. Betaine accumulation and osmoregulation in higher plants and cyanobacteria. In Plant Water Relations and Growth under Stress, Proceedings of the Yamada Conference XXII, Osaka, Japan, pp. 151-58. Tokyo: Yamada Sci. Found.
175. Tanaka, K., Tolbert, N. E., Gohlke, A. F. 1966. Choline kinase and phosphorylcholine phosphatase in plants. Plant Physiol. 41:307-12
176. Tretyn, A., Kendrick, R. E. 1991. Acetylcholine in plants: presence, metabolism and mechanism of action. Bot. Rev. 57:33-73
177. Tyihák, E., Sarhan, A. R. T., Cong, N. T., Barna, B., Király, Z. 1988. The level of trigonelline and other quaternary ammonium compounds in tomato leaves in ratio to the changing nitrogen supply. Plant Soil 109:285-87
178. van Diggelen, J., Rozema, J., Dickson, D. M. J., Broekman, R. 1986. β-3-Dimethylsulphoniopropionate, proline and quaternary ammonium compounds in Spartina anglica in relation to sodium chloride, nitrogen and sulphur. New Phytol. 103:573-86
179. Wang, X., Moore, T. S. 1990. Phosphatidylcholine biosynthesis in castor bean endosperm: purification and properties of cytidine 5′-triphosphate:choline-phosphate cytidylyltransferase. Plant Physiol. 93: 250-55
180. Weigel, P., Lerma, C., Hanson, A. D. 1988. Choline oxidation by intact spinach chloroplasts. Plant Physiol. 86:54-60
181. Weigel, P., Weretilnyk, E, A., Hanson, A. D. 1986. Betaine aldehyde oxidation by spinach chloroplasts. Plant Physiol. 82:753-59
182. Weretilnyk, E. A., Bednarek, S., McCue, K. E, Rhodes, D., Hanson, A. D. 1989. Comparative biochemical and immunological studies of the glycine betaine synthesis pathway in diverse families of dicotyledons. Planta 178:342-52
183. Weretilnyk, E. A., Hanson, A. D. 1988. Betaine aldehyde dehydrogenase polymorphism in spinach: genetic and biochemical characterization. Biochem. Genet. 26:143-51
184. Weretilnyk, E. A., Hanson, A. D. 1989. Betaine aldehyde dehydrogenase from spinach leaves: purification, in vitro translation of the mRNA, and regulation by salinity. Arch. Biochem. Biophys. 271:56-63
185. Weretilnyk, E. A., Hanson, A. D. 1990. Molecular cloning of a plant betaine-aldehyde dehydrogenase, an enzyme implicated in adaptation to salinity and drought. Proc. Natl. Acad. Sci. USA 87:2745-49
186. Weretilnyk, E. A., Summers, P.S. 1992. Betaine and choline metabolism in higher plants. In Biosynthesis and Molecular Regulation of Amino Acids in Plants, ed. H. Flores, J. Shannon, B. Singh, pp. 30-39. Rockville: American Society of Plant Physiologists
187. Williams, W. P., Brain, A. P. R., Dominy, P. J. 1992. Induction of non-bilayer lipid phase separations in chloroplast thylakoid membranes by compatible co-solutes and its relation to the thermal stability of Photosystem II. Biochim. Biophys. Acta. 1099:137-44
188. Wood, K. V., Stringham, K. J., Smith, D. L., Volenec, J. J., Hendershot, K. L., et al. 1991. Betaines of alfalfa: characterization by fast atom bombardment and desorption chemical ionization mass spectrometry. Plant Physiol. 96:892-97
189. Wyn Jones, R. G. 1984. Phytochemical aspects of osmotic adaptation. Rec. Adv. Phytochem. 18:55-78
190. Wyn Jones, R. G., Gorham, J. 1983. Aspects of salt and drought tolerance in higher plants. In Genetic Engineering of Plants: An Agricultural Perspective, ed. T. Kosuge, C. P. Meredith, A. Hollaender, pp. 355-70. New York: Plenum
191. Wyn Jones, R. G., Storey, R., Leigh, R. A., Ahmad, N., Pollard, A. 1977. A hypothesis on cytoplasmic osmoregulation. In Regulation of Cell Membrane Activities in Higher Plants, cd. E. Marrè, O. Ciferri, pp. 121-36. Amsterdam: Elsevier/North Holland
192. Wyn Jones, R. G., Storey, R. 1981. Betaines. In The Physiology and Biochemistry of Drought Resistance in Plants, ed. L. G. Paleg, D. Aspinall, pp. 171-204. Sydney: Academic
193. Yancey, P. H., Clark, M. E., Hand, S. C., Bowlus, R. D., Somero, G. N. 1982. Living with water stress: evolution of osmolyte systems. Science 217:1214-22
194. Zhao, Y., Aspinall, D., Paleg, L. G. 1992. Protection of membrane integrity in Medicago sativa L. by glycinebetaine against the effects of freezing. J. Plant Physiol. In press
195. Zúñiga, G. E., Corcuera, L. J. 1987. Glycine-betaine accumulation influences susceptibility of water-stressed barley to the aphid Schizaphis graminum. Phytochemistry 26:367-69