Dimethylsulfoniopropionate Biosynthesis in Spartina alterniflora¹
Evidence That S-Methylmethionine and Dimethylsulfoniopropylamine Are Intermediates

Michael G. Kocsis, Kurt D. Nolte, David Rhodes, Tun-Li Shen, Douglas A. Gage, and Andrew D. Hanson^*

Horticultural Sciences Department, University of Florida, Gainesville, Florida 32611 (M.G.K., K.D.N., A.D.H.); Department of Horticulture, Purdue University, West Lafayette, Indiana 47907 (D.R.); and Department of Biochemistry, Michigan State University, East Lansing, Michigan 48824 (T.-L.S., D.A.G.)

The osmoprotectant 3-dimethylsulfoniopropionate (DMSP) occurs in Gramineae and Compositae, but its synthesis has been studied only in the latter. The DMSP synthesis pathway was therefore investigated in the salt marsh grass Spartina alterniflora Loisel. Leaf tissue metabolized supplied [³⁵S]methionine (Met) to S-methyl-l-Met (SMM), 3-dimethylsulfoniopropylamine (DMSP-amine), and DMSP. The ³⁵S-labeling kinetics of SMM and DMSP-amine indicated that they were intermediates and, consistent with this, the dimethylsulfonium moiety of SMM was shown by stable isotope labeling to be incorporated as a unit into DMSP. The identity of DMSP-amine, a novel natural product, was confirmed by both chemical and mass-spectral methods. S. alterniflora readily converted supplied [³⁵S]SMM to DMSP-amine and DMSP, and also readily converted supplied [³⁵S]DMSP-amine to DMSP; grasses that lack DMSP did neither. A small amount of label was detected in 3-dimethylsulfoniopropionaldehyde (DMSP-ald) when [³⁵S]SMM or [³⁵S]DMSP-amine was given. These results are consistent with the operation of the pathway Met  SMM  DMSP-amine  DMSP-ald  DMSP, which differs from that found in Compositae by the presence of a free DMSP-amine intermediate. This dissimilarity suggests that DMSP synthesis evolved independently in Gramineae and Compositae.

Plant Physiol. (1998) 117: 273-281
Copyright Clearance Center:   0032-0889/98/117/0273/09
© 1998 American Society of Plant Physiologists

This article has been cited by other articles:

				J. Boatright, F. Negre, X. Chen, C. M. Kish, B. Wood, G. Peel, I. Orlova, D. Gang, D. Rhodes, and N. Dudareva Understanding in Vivo Benzenoid Metabolism in Petunia Petal Tissue Plant Physiology, August 1, 2004; 135(4): 1993 - 2011. [Abstract] [Full Text] [PDF]

				M. G. Kocsis, P. Ranocha, D. A. Gage, E. S. Simon, D. Rhodes, G. J. Peel, S. Mellema, K. Saito, M. Awazuhara, C. Li, et al. Insertional Inactivation of the Methionine S-Methyltransferase Gene Eliminates the S-Methylmethionine Cycle and Increases the Methylation Ratio Plant Physiology, April 1, 2003; 131(4): 1808 - 1815. [Abstract] [Full Text] [PDF]

				D. C. Yoch Dimethylsulfoniopropionate: Its Sources, Role in the Marine Food Web, and Biological Degradation to Dimethylsulfide Appl. Envir. Microbiol., December 1, 2002; 68(12): 5804 - 5815. [Full Text] [PDF]

				A. Tagmount, A. Berken, and N. Terry An Essential Role of S-Adenosyl-L-Methionine:L-Methionine S-Methyltransferase in Selenium Volatilization by Plants. Methylation of Selenomethionine to Selenium-Methyl-L-Selenium- Methionine, the Precursor of Volatile Selenium Plant Physiology, October 1, 2002; 130(2): 847 - 856. [Abstract] [Full Text] [PDF]

				M. G. Kocsis and A. D. Hanson Biochemical Evidence for Two Novel Enzymes in the Biosynthesis of 3-Dimethylsulfoniopropionate in Spartina alterniflora Plant Physiology, July 1, 2000; 123(3): 1153 - 1162. [Abstract] [Full Text]

				S. D. McNeil, M. L. Nuccio, D. Rhodes, Y. Shachar-Hill, and A. D. Hanson Radiotracer and Computer Modeling Evidence that Phospho-Base Methylation Is the Main Route of Choline Synthesis in Tobacco Plant Physiology, May 1, 2000; 123(1): 371 - 380. [Abstract] [Full Text]

				M. P. de Souza, C. M. Lytle, M. M. Mulholland, M. L. Otte, and N. Terry Selenium Assimilation and Volatilization from Dimethylselenoniopropionate by Indian Mustard Plant Physiology, April 1, 2000; 122(4): 1281 - 1288. [Abstract] [Full Text]

				A. Rouillon, Y. Surdin-Kerjan, and D. Thomas Transport of Sulfonium Compounds. CHARACTERIZATION OF THE S-ADENOSYLMETHIONINE AND S-METHYLMETHIONINE PERMEASES FROM THE YEAST SACCHAROMYCES CEREVISIAE J. Biol. Chem., October 1, 1999; 274(40): 28096 - 28105. [Abstract] [Full Text] [PDF]

				F. Bourgis, S. Roje, M. L. Nuccio, D. B. Fisher, M. C. Tarczynski, C. Li, C. Herschbach, H. Rennenberg, M. J. Pimenta, T.-L. Shen, et al. S-Methylmethionine Plays a Major Role in Phloem Sulfur Transport and Is Synthesized by a Novel Type of Methyltransferase PLANT CELL, August 1, 1999; 11(8): 1485 - 1498. [Abstract] [Full Text]

				S. D. McNeil, M. L. Nuccio, and A. D. Hanson Betaines and Related Osmoprotectants. Targets for Metabolic Engineering of Stress Resistance Plant Physiology, August 1, 1999; 120(4): 945 - 950. [Full Text]

				P. Ranocha, F. Bourgis, M. J. Ziemak, D. Rhodes, D. A. Gage, and A. D. Hanson Characterization and Functional Expression of cDNAs Encoding Methionine-sensitive and -insensitive Homocysteine S-Methyltransferases from Arabidopsis J. Biol. Chem., May 19, 2000; 275(21): 15962 - 15968. [Abstract] [Full Text] [PDF]