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Biosynthesis of a trypanocide by Chromobacterium violaceum

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Abstract

Radio-isotope studies indicated not only that l-tryptophan can serve as carbon source for synthesis of the trypanocide, violacein by Chromobacterium violaceum (BB-78 strain) but also that isatin and indole 3-acetic acid are both important metabolic intermediates. Using 3-indolyl [2-14C] and [1-14C] acetic acid, it was found that the carboxylic carbon was not eliminated and that indole-3-acetic acid was incorporated intact into the pigment structure. N-Ethyl(5-hydroxy-indol-3-yl)-2-indolylethylamide is also an important metabolic intermediate in the violacein biosynthesis. This is the first report of a metabolic scheme for violacein synthesis which includes an intermediate other than l-tryptophan.

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References

  • Antonio, R.V., Haun, M., Fagundes, L.M., De Conti, R., Pilli, R.A., De Castro, S. & Durán, N. 1992 Activity of an intermediate of violacein biosynthesis against Trypanosoma cruzi. Memorias do Instituto Oswaldo Cruz 87, 198.

    Google Scholar 

  • Antonio, R.V., Pereira, M.D.F., Haun, M. & Durán, N. 1991 Trypanocide activity of violacein. Memorias do Instituto Oswaldo Cruz 86, 233.

    Google Scholar 

  • Ballantine, J.A., Beer, R.J.S., Crutchley, D.J., Dodd, G.M. & Palmer, D.R. 1958 The synthesis of violacein and related compounds. Proceedings of the Chemical Society 232–234.

  • Ballantine, J.A., Beer, R.J.S., Crutchley, D.J., Dodd, G.M. & Palmer, D.R. 1960 The chemistry of bacteria. Part VIII. The synthesis of violacein and related compounds. Journal of the Chemical Society 2292–2299.

  • Caldas, L.R. 1977 Photochemistry and photobiology in Virgin Islands. Photochemistry and Photobiology 26, 1–2.

    Google Scholar 

  • Caldas, L.R., Leitão, A.A.C., Santos, S.M. & Tyrrel, R.M. 1978 Preliminary experiments on photobiological properties of violacein. In Proceedings of International Symposium on Current Topics in Radiology and Photobiology (R.M. Tyrrell, Ed.), pp. 121–126. Rio de Janeiro: Academia Brasileira de Ciências Publ.

    Google Scholar 

  • Davis, P.J., Gustafson, M.E. & Rosazza, J.P. 1976 Formation of indole-3-carboxylic acid by Chromobacterium violaceum. Journal of Bacteriology 126, 544–546.

    Google Scholar 

  • DeMoss, R.D. & Evans, N.R. 1960 Incorporation of 14C-labelled substrate into violacein. Journal of Bacteriology 79, 729–733.

    Google Scholar 

  • Durán, N. 1990. Violaceina: a descoberta de um antibiotico. Ciência Hoje (Brazil) 11, 58–60.

    Google Scholar 

  • Durán, N., Campos, V., Riveros, R., Joyas, A., Pereira, M.F. & Haun, M. 1989 Bacterial chemistry-III: Preliminary studies on trypanosomal activities. Anais da Academia Brasileira de Ciências 61, 31–36.

    Google Scholar 

  • Durán, N., Erazo, S. & Campos, V. 1983 Bacterial chemistry. II. Antimicrobial photoproduct from pigment of Chromobacterium violaceum. Anais da Academia Brasileira de Ciências 55, 231–234.

    Google Scholar 

  • Durán, N. & Faljoni-Alario, A. 1978 Singlet oxygen formation during peroxidase catalyzed degradation of carcinogenic-N-nitrosamine. Biochemical and Biophysical Research Communications 81, 287–294.

    Google Scholar 

  • Durán, N. & Faljoni-Alario, A. 1980 Bacterial chemistry. I. Studies of a potential phototherapeutic substance from Chromobacterium violacein. Anais da Academia Brasileira de Ciências 52, 297–302.

    Google Scholar 

  • Durán, N. & Haun, M. 1991 Trypanocides: state of art. Memorias do Instituto Oswaldo Cruz 86, 29–30.

    Google Scholar 

  • Durán, N., Riveros, R., Campos, V. & Joyas, A. 1986 A new drug with antitrypanosomal activity from 1,3-dihydro-2H-indol-2-one. Memorias do Instituto Oswaldo Cruz 81, 155.

    Google Scholar 

  • Fujioka, M. & Wada, H. 1968 The bacterial oxidation of indole. Biochimica et Biophysica Acta 158, 70–78.

    Google Scholar 

  • Haun, M., Pereira, M.F., Hoffmann, M.E., Joya, A., Campos, V., Filardi, L.S., De Castro, S.L. & Durán, N. 1992 Bacterial chemistry. VI. Biological activities and cytotoxicity of 1,3-dihydro-2H-indol-2-one. Biological Research 25, 21–25.

    Google Scholar 

  • Haun, M., Pereira, M.F., Riveros, R., Durán, N. & Hoffmann, M.E. 1988. Toxicidade e genotoxicidade da violaceina e derivados. In Proceedings of the 8th Workshop on Biorganic Chemistry (E. Silva & E. Lissi, Eds), Vol. 6, pp. 78–80. Santiago, Chile: Pontificia Universidad Catolica de Chile Publ.

    Google Scholar 

  • Hoshino, T., Kondo, T., Uchiyama, T. & Ogasawara, N. 1987a Biosynthesis of violacein: a novel rearrangement in tryptophan metabolism with a 1,2-shift of the indole ring. Agricultural and Biological Chemistry 51, 965–968.

    Google Scholar 

  • Hoshino, T. & Ogasawara, N. 1990 Biosynthesis of violacein: evidence for the intermediacy of 5-hydroxy-l-tryptophan and the structure of a new pigment, oxyviolacein produced by the metabolism of 5-hydroxytryptophan. Agricultural and Biological Chemistry 54, 2339–2346.

    Google Scholar 

  • Hoshino, T., Takano, T., Hori, S. & Ogasawara, N. 1987b Biosynthesis of violacein: origins of hydrogen, nitrogen and oxygen atoms in the 2-pyrrolidone nucleus. Agricultural and Biological Chemistry 51, 2733–2741.

    Google Scholar 

  • Huang, H., Iwasawa, N. & Mukaiyama, T. 1984 A convenient method for the construction of beta-lactam compounds from beta-acids using 2-chloro-1-methylpyridinium iodide as condensing reagent. Chemistry Letters 1465–1466.

  • Laatsch, H., Thomsom, R.H. & Cox, P.J. 1984 Spectroscopic properties of violacein and related compounds: crystal structure of tetramethylviolacein. Journal of the Chemical Society, Perkin Transactions II, 1331–1339.

    Google Scholar 

  • Lichstein, H.C. & Van De Sand, V.F. 1945 Violacein, and antibiotic pigment produced by Chromobacterium violaceum. Journal of Infectious Diseases 76, 47–51.

    Google Scholar 

  • Mitoma, C., Weissbach, R.H. & Udenfriend, S. 1956 5-Hydroxytryptophan formation and tryptophan metabolism in C. violaceum. Archives of Biochemistry and Biophysics 63, 122–130.

    Google Scholar 

  • Pemberton, J.M., Vincent, K.M. & Penfold, R.J. 1991 Cloning and heterologous expression of the violacein biosynthesis gene cluster from Chromobacterium violaceum. Current Microbiology 22, 355–358.

    Google Scholar 

  • Riveros, R. 1986 Chemistry and biological activity of 1,3-dihydro-2H-indol-2-one derivatives. M.Sc Thesis. Universidade Estadual de Campinas, Campinas, Brazil.

  • Riveros, R., Campos, V., Joyas, A. & Durán, N. 1985 A new antitrypanosomal drug. In Proceedings of 12th Annual Meeting on Basic Research of Chagas' Disease, p. 134. Caxambu, Brazil: Instituto Oswaldo Cruz Publ.

    Google Scholar 

  • Riveros, R., Haun, M. & Durán, N. 1988 Bacterial chemistry-IV: complete characterization of violacein: an antibiotic and trypanocide from Chromobacterium violaceum. Arquivos de Biologia e Tecnologia (Brazil) 31, 475–487.

    Google Scholar 

  • Riveros, R., Haun, M. & Durán, N. 1989 Effect of growth conditions on production of violacein by Chromobacterium violaceum (BB-78 strain). Brazilian Journal of Medical and Biological Research 22, 569–577.

    Google Scholar 

  • Sakamoto, Y., Uchida, M. & Ichihara, K. 1953 The bacterial decomposition of indole. I. Studies on its metabolic pathway by successive adaptation. Medical Journal of Osaka University 3, 477–480.

    Google Scholar 

  • Sebek, O.K. & Jagger, H. 1962 Divergent pathways of indole metabolism in Chromobacterium violaceum. Nature (London) 196, 793–795.

    Google Scholar 

  • Yonaha, K. & Soda, K. 1986 Applications of stereoselectivity of enzymes: synthesis of optically active, and stereospecific isotope-labelling of amino acids, amines and coenzymes. Advances in Biochemical Engineering and Biotechnology 33, 95–130.

    Google Scholar 

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Durán, N., Antonio, R.V., Haun, M. et al. Biosynthesis of a trypanocide by Chromobacterium violaceum . World J Microbiol Biotechnol 10, 686–690 (1994). https://doi.org/10.1007/BF00327960

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