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Effects of Glyphosate on Metabolism of Phenolic Compounds: VI. Effects of Glyphosine and Glyphosate Metabolites on Phenylalanine Ammonia-Lyase Activity, Growth, and Protein, Chlorophyll, and Anthocyanin Levels in Soybean (Glycine max) Seedlings

Published online by Cambridge University Press:  12 June 2017

Robert E. Hoagland*
Affiliation:
South. Weed Sci. Lab., Sci. Ed. Admin., Agric. Res., U.S. Dep. Agric., Stoneville, MS 38776

Abstract

The growth regulator, glyphosine [N,N-bis(phosphonomethyl)glycine], and other possible metabolites of glyphosine and glyphosate [N-(phosphonomethyl)glycine] [glycine, sarcosine, and aminomethylphosphonic acid (AMPA)] were tested individually (0.5 mM) or as a mixture (each at 0.5 mM) for their effects on growth, extractable phenylalanine ammonia-lyase (PAL) activity, hydroxyphenolic-compound production, chlorophyll and anthocyanin contents, and on soluble-protein levels in soybean [Glycine max (L.) Merr. ‘Hill’] seedlings. Most chemical treatments caused some inhibition of growth either on fresh weight accumulation or on root elongation in the light and dark over 72 h. Glyphosine was generally the most inhibitory and caused the greatest inhibition on axis dry-weight accumulation. Glyphosine significantly increased extractable PAL activity in axes of light- and dark-grown soybeans to a lesser extent than did glyphosate. AMPA had some inhibitory effects on extractable PAL activity whereas other compounds had little influence on the enzyme. These compounds had little effect on total soluble protein in axes or on soluble protein in PAL preparations from 12 to 72 h in light-or dark-grown seedlings. No in vitro effect of the chemicals on PAL activity was found at concentrations up to 0.5 mM. Hydroxyphenolic compound levels increased within 24 to 72 h (per gram fresh weight basis) in light- or dark-grown soybean axes treated with glyphosine, AMPA, or a metabolite mixture (AMPA, sarcosine, and glycine). Anthocyanin content was decreased by glyphosate and to a lesser extent by glyphosine, but was increased by AMPA and the mixture. Glyphosate significantly increased the chlorophyll a/b ratio and decreased total chlorophyll, but glyphosine decreased the chlorophyll content to a lesser degree.

Type
Research Article
Copyright
Copyright © 1980 by the Weed Science Society of America 

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References

Literature Cited

1. Arnon, D. I. 1949. Copper enzymes in isolated chloroplasts: polyphenol oxidases in Beta vulgaris . Plant Physiol. 24:115.CrossRefGoogle Scholar
2. Baur, J. R. 1979. Reduction of glyphosate-induced tillering in sorghum (Sorghum bicolor) by several chemicals. Weed Sci. 27:6973.Google Scholar
3. Berlin, J. and Widholm, J. M. 1978. Amino acid analog resistant cell lines. A tool for studying secondary metabolism in plant cell cultures. Pages 171176 in Alferman, A. W. and Reinhart, E., eds. Production of Natural Compounds by Cell Culture Methods. Fed. Min. Res. Technol. (FRG) Munich. Google Scholar
4. Betz, B., Schafer, E., and Hahlbrock, K. 1978. Light-induced phenylalanine ammonia-lyase in cell suspension cultures of Petroselinum hortense. Quantitative comparison rates of synthesis and degradation. Arch. Biochem. Biophys. 190:126135.Google Scholar
5. Camm, E. L. and Towers, G. H. N. 1973. Phenylalanine ammonia-lyase. Phytochemistry 12:961973.CrossRefGoogle Scholar
6. Creasy, L. L. and Zucker, M. 1974. Phenylalanine ammonia-lyase and phenolic metabolism. Pages 119 in Runeckles, V. C. and Conn, E. E., eds., Recent Advances in Phytochemistry, Vol. 8, Academic Press, New York.Google Scholar
7. Croft, S. M., Arntzen, C. J., Vanderhoef, L. N., and Zettinger, C. S. 1974. Inhibition of chloroplast ribosome formation by N,N-bis-(phosphonomethyl)glycine. Biochim. Biophys. Acta 335:211217.Google Scholar
8. Duke, S. O. and Hoagland, R. E. 1978. Effects of glyphosate on metabolism of phenolic compounds. I. Induction of phenylalanine ammonia-lyase activity in dark-grown maize roots. Plant Sci. Lett. 11:185190.Google Scholar
9. Duke, S. O., Hoagland, R. E., and Elmore, C. D. 1979. Effects of glyphosate on metabolism of phenolic compounds. IV. Phenylalanine ammonia-lyase activity, free amino acids, and soluble hydroxyphenolic compounds in axes of light-grown soybeans. Physiol. Plant. 46:307317.CrossRefGoogle Scholar
10. Duke, S. O., Hoagland, R. E., and Elmore, C. D. 1980. Effects of glyphosate on metabolism of phenolic compounds. V. Interactions with L-α-aminooxy-β-phenylproprionic acid. Plant Physiol. 65:1721.Google Scholar
11. Duke, S. O. and Naylor, A. W. 1974. Effects of light on phenylalanine ammonia-lyase activity in dark-grown Zea mays (L.) seedlings. Plant Sci. Lett. 2:289293.Google Scholar
12. Duke, S. O. and Naylor, A. W. 1976. Light control of anthocyanin biosynthesis in Zea seedlings. Physiol. Plant. 37:5268.CrossRefGoogle Scholar
13. Ekanayake, A., Wickremasinghe, R. L., and Liyanage, H. D. S. 1979. Studies on the mechanism of herbicidal action of N-(phosphonomethyl)glycine. Weed Res. 19:3943.CrossRefGoogle Scholar
14. Engelsma, G. 1974. On the mechanism of the change in phenylalanine ammonia-lyase activity induced by ultraviolet and blue light in gherkin hypocotyls. Plant Physiol. 54:702705.CrossRefGoogle Scholar
15. Gresshoff, P. M. 1979. Growth inhibition by glyphosate and reversal of its action by phenylalanine and tyrosine. Aust. J. Plant Physiol. 6:177185.Google Scholar
16. Haderlie, L. C., Widholm, J. M., and Slife, F. W. 1977. Effect of glyphosate on carrot and tobacco cells. Plant Physiol. 60:4043.Google Scholar
17. Havir, E. A. and Hanson, K. R. 1970. L-phenylalanine ammonia-lyase (potato tubers). Pages 575581 in Tabor, H. and Tabor, C. W., eds., Methods in Enzymology, Vol. XVIIA, Academic Press, New York.Google Scholar
18. Herbicide Handbook of the Weed Society of America, Fourth Edition. 1979. Champaign, Illinois. 479 pp.Google Scholar
19. Hoagland, R. E. and Duke, S. O. 1979. Effects of herbicides on extractable phenylalanine ammonia-lyase activity in light- and dark-grown Glycine max (L.) Merr. seedlings. Plant Physiol. Suppl. 63:106.Google Scholar
20. Hoagland, R. E. and Duke, S. O. 1979. Effects of herbicides on growth and soluble protein, hydroxyphenolic compound and anthocyanin levels in light- and dark-grown Glycine max (L.) Merr. seedlings. Plant Physiol. Suppl. 63:106.Google Scholar
21. Hoagland, R. E. and Graf, G. 1974. The purification and properties of an amidohydrolase from soybean. Can. J. Biochem. 52:903910.Google Scholar
22. Hoagland, R. E., Duke, S. O., and Elmore, C. D. 1978. Effects of glyphosate on metabolism of phenolic compounds. II. Influence on soluble hydroxyphenolic compound, free amino acid and soluble protein levels in dark-grown maize roots. Plant Sci. Lett. 13:291299.Google Scholar
23. Hoagland, R. E., Duke, S. O., and Elmore, C. D. 1979. The effects of glyphosate on metabolism of phenolic compounds. III. Phenylalanine ammonia-lyase activity, free amino acids, soluble protein and hydroxyphenolic compounds in axes of dark-grown soybeans. Physiol. Plant. 46:357366.CrossRefGoogle Scholar
24. Hollander, H. and Amrhein, N. 1979. Inhibition by glyphosate of phenylpropanoid synthesis in buckwheat. Plant Physiol. Suppl. 63:41.Google Scholar
25. Huffaker, R. C. and Peterson, J. 1974. Protein turnover in plants and possible means of its regulation. Annu. Rev. Plant Physiol. 18:301324.Google Scholar
26. Jangaard, N. O. 1974. The characterization of phenylalanine ammonia-lyase from several plant species. Phytochemistry 13:17651768.Google Scholar
27. Jangaard, N. O. 1974. The effect of herbicides, plant growth regulators and other compounds on phenylalanine ammonia-lyase activity. Phytochemistry 13:17691775.Google Scholar
28. Jaworski, E. G. 1972. Mode of action of N-(phosphonomethyl)-glycine: inhibition of aromatic amino acid biosynthesis. J. Agric. Food Chem. 20:11951198.Google Scholar
29. Johnson, C. B. and Smith, H. 1978. Phytochrome control of amino acid synthesis in cotyledons of Sinapis alba . Phytochemistry 17:667670.CrossRefGoogle Scholar
30. Kabachnik, M. I., Medved, T. Y., Dyatlova, N. M., and Rudomino, M. V. 1974. Organophosphorus complexones. Russ. Chem. Rev. 43:733744.Google Scholar
31. Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Randall, R. J. 1951. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193:265275.Google Scholar
32. Margna, U. 1977. Control at the level of substrate supply – An alternative in the regulation of phenylpropanoid accumulation in plant cells. Phytochemistry 16:419426.CrossRefGoogle Scholar
33. Moshier, L. J. and Penner, D. 1978. Factors influencing microbial degradation of 14C glyphosate to 14CO2 in soil. Weed Sci. 26: 686691.Google Scholar
34. Murphy, J. B. and Kies, M. W. 1960. Note on a spectrophotometric determination of proteins in dilute solutions. Biochim. Biophys. Acta 45:382384.Google Scholar
35. Nilsson, G. 1977. Effects of glyphosate on the amino acid content in spring wheat plants. Swed. J. Agric. Res. 7:153157.Google Scholar
36. Pecket, R. C. and Hathout-Bassim, T. A. 1974. The effect of kinetin in relation to photocontrol of anthocyanin biosynthesis in Brassica oleracea . Phytochemistry 13:13951399.CrossRefGoogle Scholar
37. Roisch, U. and Lingens, F. 1974. Effect of the herbicide N-phosphonomethyl-glycine on the biosynthesis of aromatic amino acids. Angew. Chem. 86:408.Google Scholar
38. Rueppel, M., Brightwell, B. B., Schaefer, J., and Marvel, J. T. 1977. Metabolism and degradation of glyphosate in soil and water. J. Agric. Food Chem. 25:517528.Google Scholar
39. Seitz, U. and Heinzmann, U. 1975. Influence of gibberellic acid on synthesis of anthocyanin in tissue cultures of Daucus carota . Planta Med. Suppl. 6669.Google Scholar
40. Singleton, Y. L. and Rossi, J. A. Jr. 1965. Colorimetry of total phenolics with phosphomolybdic-phosphotunstic acid reagents. Am. J. Enol. Vitic. 16:144158.CrossRefGoogle Scholar
41. Smith, H., Billett, E. E., and Giles, A. B. 1977. Photocontrol of gene expression in higher plants. Pages 93127 in Smith, H., ed., Regulation of Enzyme Synthesis and Activity in Higher Plants. Academic Press, New York.Google Scholar
42. Sprankle, P., Meggitt, W. F., and Penner, D. 1975. Absorption, action and translocation of glyphosate. Weed Sci. 23:235240.Google Scholar
43. Sprankle, P., Meggitt, W. F., and Penner, D. 1975. Rapid inactivation of glyphosate in the soil. Weed Sci. 23:224228.Google Scholar
44. Sprankle, P., Meggitt, W. F., and Penner, D. 1975. Absorption, mobility, and microbial degradation of glyphosate in the soil. Weed Sci. 23:229234.Google Scholar
45. Sprankle, P., Sandberg, C. L., Meggitt, W. F., and Penner, D. 1978. Separation of glyphosate and possible metabolites by thin-layer chromatography. Weed Sci. 26:673674.Google Scholar
46. Turner, D. J. and Loader, M. P. C. 1978. Complexing agents as herbicide additives. Weed Res. 18:199207.Google Scholar
47. Tymonko, J. M. and Foy, C. L. 1978. Inhibition of protein synthesis by glyphosate. Plant Physiol. Suppl. 61:41.Google Scholar
48. Zaprometov, M. N. and Shipilova, S. V. 1962. Phenylalanine ammonia-lyase and synthesis of phenol compounds in maize seedlings. Sov. Plant Physiol. 19:416420.Google Scholar
49. Zucker, M. 1972. Light and enzymes. Annu. Rev. Plant Physiol. 23:133156.Google Scholar