Dimethylsulfoniopropionate biosynthesis in Spartina alterniflora1. Evidence that S-methylmethionine and dimethylsulfoniopropylamine are intermediates.

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.

[1]  A. Hanson,et al.  Identification and stereospecificity of the first three enzymes of 3-dimethylsulfoniopropionate biosynthesis in a chlorophyte alga , 1998 .

[2]  A. Hanson,et al.  Salinity promotes accumulation of 3-dimethylsulfoniopropionate and its precursor S-methylmethionine in chloroplasts. , 1998, Plant physiology.

[3]  A. Hanson,et al.  S-Methylmethionine Conversion to Dimethylsulfoniopropionate: Evidence for an Unusual Transamination Reaction , 1997, Plant physiology.

[4]  A. Hanson,et al.  A new route for synthesis of dimethylsulphoniopropionate in marine algae , 1997, Nature.

[5]  M. Taylor,et al.  Recent advances in polyamine research , 1997 .

[6]  A. Hanson,et al.  Transgenically Expressed Betaine Aldehyde Dehydrogenase Efficiently Catalyzes Oxidation of Dimethylsulfoniopropionaldehyde and [omega]-Aminoaldehydes , 1997, Plant physiology.

[7]  A. Hanson,et al.  Betaine-aldehyde dehydrogenase from amaranth leaves efficiently catalyzes the NAD-dependent oxidation of dimethylsulfoniopropionaldehyde to dimethylsulfoniopropionate. , 1997, Archives of biochemistry and biophysics.

[8]  J. Casal.  Phytochrome A Enhances the Promotion of Hypocotyl Growth Caused by Reductions in Levels of Phytochrome B in Its Far-Red-Light-Absorbing Form in Light-Grown Arabidopsis thaliana , 1996, Plant physiology.

[9]  A. Hanson,et al.  Evidence That the Pathway of Dimethylsulfoniopropionate Biosynthesis Begins in the Cytosol and Ends in the Chloroplast , 1996, Plant physiology.

[10]  Yonezo Suzuki.  Purification and characterization of diamine oxidase from Triticum aestivum shoots , 1996 .

[11]  R. Higashi,et al.  Interactive effects of salinity, nitrogen and sulphur on the organic solutes in Spartina alterniflora leaf blades , 1996 .

[12]  G. Malin.  The Role of DMSP and DMS in the Global Sulfur Cycle and Climate Regulation , 1996 .

[13]  U. Karsten,et al.  Dimethylsulfoniopropionate Production in Phototrophic Organisms and its Physiological Functions as a Cryoprotectant , 1996 .

[14]  E. Hirasawa,et al.  3-Aminopropionaldehyde dehydrogenase of millet shoots , 1995 .

[15]  A. Hanson,et al.  Evidence Implicating Dimethylsulfoniopropionaldehyde as an Intermediate in Dimethylsulfoniopropionate Biosynthesis , 1995, Plant physiology.

[16]  E. M. Friis,et al.  The origin and early diversification of angiosperms , 1995, Nature.

[17]  L. Pâquet,et al.  Évidence en faveur de la présence du 3-diméthylsulfoniopropionate chez une large gamme d'Angiospermes , 1995 .

[18]  J. Rivoal,et al.  Biosynthesis of 3-Dimethylsulfoniopropionate in Wollastonia biflora (L.) DC. (Evidence That S-Methylmethionine Is an Intermediate) , 1994, Plant physiology.

[19]  A. Hanson,et al.  Accumulation of the Compatible Solute 3-Dimethylsulfoniopropionate in Sugarcane and Its Relatives, but Not Other Gramineous Crops , 1994 .

[20]  A. Hanson,et al.  Response of Melanthera biflora to Salinity and Water Stress , 1993 .

[21]  G. Somero,et al.  Temperature- and concentration-dependence of compatibility of the organic osmolyte beta-dimethylsulfoniopropionate. , 1992, Cryobiology.

[22]  G. Kirst,et al.  Aspects of Dimethylsulfoniopropionate Effects on Enzymes Isolated from the Marine Phytoplankter Tetraselmis subcordiformis (Stein) , 1991 .

[23]  D. Rhodes,et al.  Effects of heat shock on amino Acid metabolism of cowpea cells. , 1990, Plant physiology.

[24]  D. Stevenson,et al.  L-methionine decarboxylase from Dryopteris filix-mas: purification, characterization, substrate specificity, abortive transamination of the coenzyme, and stereochemical courses of substrate decarboxylation and coenzyme transamination. , 1990, Biochemistry.

[25]  Mudd Sh,et al.  The S-Methylmethionine Cycle in Lemna paucicostata , 1990 .

[26]  Mudd Sh,et al.  The S-Methylmethionine Cycle in Lemna paucicostata. , 1990, Plant physiology.

[27]  W. J. Cooper,et al.  Biogenic sulfur in the environment , 1989 .

[28]  M. D. Keller,et al.  Dimethylsulfide production in marine phytoplankton. , 1989 .

[29]  G. Blunden,et al.  Quaternary Ammonium and Tertiary Sulphonium Compounds of Algal Origin as Alleviators of Osmotic Stress , 1989 .

[30]  B. Peterson,et al.  Contribution of gaseous sulphur from salt marshes to the global sulphur cycle , 1984, Nature.

[31]  A. Datko,et al.  Sulfur Amino Acids in Plants , 1980 .

[32]  W. Bardsley,et al.  Synthesis and oxidation of aminoalkyl-onium compounds by pig kidney diamine oxidase. , 1971, The Biochemical journal.

[33]  V. Zappia,et al.  The specificity of S-adenosylmethionine derivatives in methyl transfer reactions. , 1969, The Journal of biological chemistry.

[34]  T. Lavine,et al.  The formation of sulfonium salts from alcohols and methionine in sulfuric acid. , 1954, The Journal of biological chemistry.