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Summary

Dimethylsulfoniopropionate(DMSP) is the precursor of dimethylsulfide (DMS) which is the most abundant volatile sulfur compound in sea water. Various marine macroalgae and microalgae contain DMSP in high concentration and release DMS. Crypthecodinium cohnii (Dinophyceae) is one of the DMSP producers. In C. cohnii, the sulfur, the methyl carbon and carbons 2 and 3 of the methionine molecule are efficiently incorporated into DMSP. The location of label in the radioactive DMSP is consistent with the conversion of methionine to DMSP by decarboxylation, deamination, and methylation. Methionine incorporation into DMSP was not inhibited in the presence of methionine-related compounds such as S-methylmethionine and S-adenosylmethionine. Methionine incorporation into DMSP was completely inhibited in the presence of methylmercaptopropionic acid but was not inhibited by methylthiooxybutanoic acid. These data are consistent with a biosynthetic pathway in which methionine is first decarboxylated to methylthiopropylamine. This is followed by loss of the amino group and oxidation to give methylmercaptopropionic acid, which is subsequently methylated. Methionine decarboxylase, which may be the key enzyme of biosynthesis of DMSP, was purified from C. cohnii and characterized. This enzyme is pyridoxalphosphate-dependent. The N-terminal amino acid sequence of this enzyme is Ala-Leu-Cys-Trp-Ser-Asp-Ile-Ser-Pro—.

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References

  1. Ackman, R.G., CS. Tocher, and J.McLachlan. 1966. Occurrence of dimethyl-ß-propiothetin in marine phytoplankton. J. Fish. Res. Bd. Can. 23:357–364.

    Article  CAS  Google Scholar 

  2. Akhtar, M., D.E. Stevenson, and D. Gani. 1990. Fern L-methionine dedcarboxylase: kinetics and mechanism of decarboxylation and abortive transamination. Biochemistry. 29: 7648–7660.

    Article  PubMed  CAS  Google Scholar 

  3. Challenger, F. and M.I. Simpson. 1948. Studies on biological methylation. Part 12. A precursor of the dimethyl sulphide evolved by Polysiphonia fasigata. Dimethyl-2-carboxyethyl-sulfonium hydroxide and its salts. J. Chem. Soc. 3: 1591–1597.

    Article  PubMed  CAS  Google Scholar 

  4. Charlson, R.J., J.E. Lovelock, M.O. Andreae, and S.G. Warren. 1987. Oceanic phytoplankton, atmos¬pheric sulphur, cloud albedo and climate. Nature. 326: 655–661.

    Article  CAS  Google Scholar 

  5. Dickson, D.J.J., and G.O. Kirst. 1986. The role of dimethylsulphoniopropionate, glycine betaine and homarine in the osmoacclimation of Platymonas subcordiformis. Planta. 167: 536–543.

    Article  CAS  Google Scholar 

  6. Dickson, D J.J., and G.O. Kirst. 1987. Osmotic adjustment in marine eukaryotic algae:the role of inorganic ions, quaternary ammonium, tertiary sulfonium and cabohydrate solutes: I. Diatoms and a rhodophyte. New Phytol. 106: 645–655.

    Article  CAS  Google Scholar 

  7. Dickson, D.J.J., and G.O. Kirst. 1987. Osmotic adjustment in marine eukryotic algae:the role of inorganic ions, quaternary ammonium, tertiary sulfonium and carbohydrate solutes: II. Prasinophytes and hapto-phytes. New Phytol. 106: 645–655.

    CAS  Google Scholar 

  8. Edwards, D.M., R.H. Reed and W.D.P. Stewart. 1988. Osmoacclimation in Enteromorpha inter stinalis: long-term effects of osmotic stress on organic solute accumulation. Mar. Biol. 98: 467–476.

    Article  Google Scholar 

  9. Gold, K. and CF. Baren. 1966. Growth requirements of Gymnodinium cohnii. J. Protozool. 13: 255–257.

    CAS  Google Scholar 

  10. Green, R.C. 1962. Biosynthesis of dimethyl-ß-propiothetin. J. Biol. Chem. 98: 467–476.

    Google Scholar 

  11. Hanson, A.D., J. Rivoal, L. Paquet, and D.A. Gage. 1994. Biosynthesis of 3-Dimethyl-sulfoniopropionate in Wollastonia biflora (L.) DC. Evidence that S-methylmethionine is an intermediate. 1994. Plant Physiol. 105:103–110.

    Article  PubMed  CAS  Google Scholar 

  12. Iida, H., K. Nakamura and T. Tokunaga. 1985. Dimethyl sulfide and dimethyl-ß-propiothetin in sea algae. Nippon Suisan Gakkaishi. 51: 1145–1150.

    CAS  Google Scholar 

  13. Ishida, Y. 1968. Physiological studies on evolution of dimethyl sulfide from unicellular marine algae. Mem. Col. Agric. Kyoto Univ. 94: 47–82.

    Google Scholar 

  14. Karsten, U., C. Wiencke, and G.O. Kirst. 1990. The ß-dimethyl-sulphoniopropionate (DMSP) content of macroalgae from Antarctica and southern Chile. Bot. Mar. 33: 143–146.

    Article  CAS  Google Scholar 

  15. Mazelis, M. 1962.: The pyridoxal phosphate-dependent oxidative decarboxylation of methionine by peroxide. I. Characteristics and properties of the reaction. J. Biol. Chem. 237: 104–108.

    PubMed  CAS  Google Scholar 

  16. Mazelis, M. and L.L. Ingraham. 1962. The pyridoxal phosphate-dependent oxidative decarboxylation of methionine by peroxide. II.Identification of 3-methylthiopropionamide as a product of the reaction. J. Biol. Chem. 237: 109–112.

    PubMed  CAS  Google Scholar 

  17. Misono, H., Y. Kawabata, M. Toyosato, T. Yamamoto and K. Soda. 1980. Purification and properties of L-methionine decarboxylase of Streptomyces sp. Bull. Inst. Chem. Res. Kyoto Univ. 58: 323–333.

    CAS  Google Scholar 

  18. Stevenson, D.E., M. Akhtar, and D. Gani. 1990. Streptomyces L-methionine decarboxylase: purification and properties of the enzyme and stereochemical course of substrate decarboxylation. Biochemistry. 29: 7660–7666.

    Article  PubMed  CAS  Google Scholar 

  19. Stevenson, D.E., M. Akhtar, and D. Gani. 1990. L-methionine decarboxylase from Dryopteris fllix-mas: purification, characterization, substrate specificity, abortive transamination of the coenzyme, and stereochemical courses of substrate decarboxylation and coenzyme transamination. Biochemistry. 29: 7631–7647.

    Article  PubMed  CAS  Google Scholar 

  20. Turner, S.M. and P.S. Liss. 1985. Measurement of various sulphur gases in a coastal marine environment. J. Atoms. Chem. 2: 223–233.

    Article  CAS  Google Scholar 

  21. Turner, S.M., G Malin, and P.S. Liss 1988. The seasonal variation in nearshore waters. Limnol. Oceanogr. 11; 364–375.

    Article  Google Scholar 

  22. Uchida, A., T. Ooguri, and Y. Ishida. 1992. The distribution of dimethylsulphide in the water off Japan and in the subtropical and tropical Pacific Ocean. Nippon Suisan Gakkaishi. 58: 261–265.

    CAS  Google Scholar 

  23. Uchida, A., T. Ooguri, T. Ishida, and Y. Ishida. 1992. Seasonal variation in dimethylsulfidê in the water of Maizuru Bay. Nippon Suisan Gakkaishi. 58: 255–259.

    CAS  Google Scholar 

  24. Uchida, A., T. Ooguri, T. Ishida, and Y. Ishida. 1993. Incorporation of methionine into dimethylthio-propanoic acid in the dinoflagellate Crypthecodinium cohnii. Nippon Suisan Gakkaishi. 59: 851–855.

    CAS  Google Scholar 

  25. Vairavamurthy, A., M.O. Andreae, and R.L. Iverson. 1985. Biosynthesis of dimethylsulfidê and dimethyl-propiothetin by Hymenomonas carterae in relation to sulfur source and salinity variations. Limnol. Oceanogr. 30: 59–70.

    Article  CAS  Google Scholar 

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© 1996 Plenum Press, New York

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Uchida, A., Ooguri, T., Ishida, T., Kitaguchi, H., Ishida, Y. (1996). Biosynthesis of Dimethylsulfoniopropionate in Crypthecodinium Cohnii (Dinophyceae). In: Kiene, R.P., Visscher, P.T., Keller, M.D., Kirst, G.O. (eds) Biological and Environmental Chemistry of DMSP and Related Sulfonium Compounds. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-0377-0_9

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  • DOI: https://doi.org/10.1007/978-1-4613-0377-0_9

  • Publisher Name: Springer, Boston, MA

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