Abstract
In sections from hypocotyls of dark-grown mung-bean (Vigna radiata L.) seedlings, D-phenylalanine and D-methionine (D-met) inhibited the formation of 1-(malonylamino)cyclopropane-1-carboxylic acid from exogenously administered 1-aminocyclopropane-1-carboxylic acid (ACC), resulting in an increase in free ACC content and stimulation of ethylene production, whereas their L-enantiomers had little or no such effect. When the hypocotyls were administered D-Met, it was mainly metabolized to N-malonylmethionine and N-malonylmethionine sulfoxide, and this malonylation process was inhibited to a greater extent by ACC and D-amino acids (phenylalanine and serine) than by L-amino acids. These results indicate that malonylation of D-amino acids and of ACC are intimately interrelated.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Abbreviations
- ACC:
-
1-aminocyclopropane-1-carboxylic acid
- MACC:
-
1-(malonylamino)cyclopropane-1-carboxylic acid
- Mes:
-
2-(N-morpholino)ethanesulfonic acid
- Met:
-
methionine
- MetSO:
-
methionine sulfoxide
- Phe:
-
phenylalanine
- Ser:
-
serine
References
Adams, D.O., Yang, S.F. (1979) Ethylene biosynthesis: identification of 1-aminocyclopropane-1-carboxylic acid as an intermediate in the conversion of methionine to ethylene. Proc. Natl. Acad. Sci. USA 76, 170–174
Amrhein N., Breuing, F., Eberle, J., Skorupka, H., Tophof, S. (1982) The metabolism of 1-aminocyclopropane-1-carboxylic acid. In: Plant growth substances 1982, pp. 249–258, Wareing, P.F., ed. Academic Press, London New York
Amrhein, N., Schneebeck, D., Skorupka, H., Tophof, S., Stockigt, J. (1981) Identification of a major metabolite of the ethylene precursor 1-aminocyclopronane-1-carboxylic acid in higher plants. Naturwissenschaften 68, 619–620
Fukuda, M., Tokumura, T., Ogawa, T., Sasaoka, K. (1973) D-Alanine in germinating Pisum sativum seedlings. Phytochemistry 12, 2593–2595
Good, N.E., Andreae, W. A. (1957) Malonyltryptophan in higher plants. Plant Physiol. 32, 561–566
Hoffman, N.E., Fu, J., Yang, S.F. (1983a) Identification and metabolism of 1-(malonylamino)cyclopropane-1-carboxylate in germinating peanut seeds. Plant Physiol. 71, 197–199
Hoffman, N.E., Liu, Y., Yang, S.F. (1983b) Changes in 1-(malonylamino)cyclopropane-1-carboxylic acid content in wilted wheat leaves in relation to their ethylene production rates and 1-aminocyclopropane-1-carboxylic acid content. Planta 157, 518–523
Hoffman, N.E., Yang, S.F., McKeon, T. (1982) Identification of 1-(malonylamino)cyclopropane-1-carboxylic acid as a major conjugate of 1-aminocyclopropane-1-carboxylic acid, an ethylene precursor in higher plants. Biochem. Biophys. Res. Commun. 104, 765–770
Hongo, C., Shibazaki, M., Yamada, S., Chibata, I. (1976) Preparation of optically active proline. Optical resolution of N-acyl-DL-proline by preferential crystallization prcedure. J. Agric. Food Chem. 24, 903–906
Kawasaki, Y., Ogawa, T., Sasaoka, K. (1982) Two pathways for formation of D-amino acid conjugates in pea seedlings. Agric. Biol. Chem. 46, 1–5
Keglević, D., Ladešić, B., Pokorny, M. (1968) Biochemical studies in tobacco plants. IV. N-Malonylmethionine, metabolite of D-methionine in Nitotiana rustica. Arch. Biochem. Biophys. 124, 443–449
Ladešić, B., Pokorny, M., Keglević, D. (1971) Metabolic patterns of L- and D-serine in higher and lower plants. Phytochemistry 10, 3085–3091
Lizada, M.C.C., Yang, S.F. (1979) A simple and sensitive assay for 1-aminocyclopropane-1-carboxylic acid. Anal. Biochem. 100, 140–145
Lürssen, K. (1981) Interference of amino acids with the uptake of 1-aminocyclopropane-1-carboxylic acid in soybean leaf discs. Plant Sci. Lett. 20, 365–370
Lürssen, K., Naumann, K., Schröder, R. (1979) 1-Aminocyclopropane-1-carboxylic acid — an intermediate of the ethylene biosynthesis in higher plants. Z. Pflanzenphysiol. 92, 285–294
Lyons, J.M., McGlasson, W.B., Pratt, H.K. (1962) Ethylene production, respiration, and internal gas concentrations in cantaloupe fruits at various stages of maturity. Plant Physiol. 37, 31–36
Pokorny, M., Marčenko, E., Keglević, D. (1970) Comparative studies of L- and D-methionine metabolism in lower and higher plants. Phytochemistry 9, 2175–2188
Rosa, N., Neish, A.C. (1968) Formation and occurrence of N-malonyl-phenylalanine and related compounds in plants. Can. J. Biochem. 46, 797–806
Satoh, S., Esashi, Y. (1981) D-Amino acid stimulated ethylene production: molecular requirements for the stimulation and a possible receptor site. Phytochemistry 20, 947–949
Satoh, S., Esashi, Y. (1982) Effects of α-aminoisobutyric acid and D- and L-amino acids on ethylene production and content of 1-aminocyclopropane-1-carboxylic acid in cotyledonary segments of cocklebur seeds. Physiol. Plant. 54, 147–152
Yang, S.F., Hoffman, N.E., McKeon, T., Riov, J., Kao, C.H., Yung, K.H. (1982) Mechanism and regulation of ethylene biosynthesis. In: Plant growth substances 1982, pp. 239–248, Wareing, P.F., ed. Academic Press, London New York
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Liu, Y., Hoffman, N.E. & Yang, S.F. Relationship between the malonylation of 1-aminocyclopropane-1-carboxylic acid and D-amino acids in mung-bean hypocotyls. Planta 158, 437–441 (1983). https://doi.org/10.1007/BF00397737
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00397737