Formation of the indigo precursor indican in genetically engineered tobacco plants and cell cultures

Plant Biotechnology Journal

Volumn 5, Issue 1, 2007, Pages 185-191

  Warzecha, Heribert ^a   Frank, Andreas ^b   Peer, Markus ^a   Gillam, Elizabeth M J ^c   Guengerich, F Peter ^d   Unger, Matthias ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSITY OF WÜRZBURG   (Germany)

^c UNIVERSITY OF QUEENSLAND   (Australia)

^d VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Cytochrome P450 2A6; Glucosyl transferase; Indican; Indigo; Indole; Indole synthase; Indoxyl; Secondary metabolism

Indexed keywords

BACTERIA (MICROORGANISMS); NICOTIANA OBTUSIFOLIA; NICOTIANA TABACUM; ZEA MAYS;

EID: 33845767428     PISSN: 14677644     EISSN: 14677652     Source Type: Journal    
DOI: 10.1111/j.1467-7652.2006.00231.x     Document Type: Article

References (28)

1. Balfour-Paul, J. (1998) Indigo. London: British Museum Press.
2. Becker, D., Kemper, E., Schell, J. and Masterson, R. (1992) New plant binary vectors with selectable markers located proximal to the left T-DNA border. Plant Mol. Biol. 20, 1195-1197.
3. Bowles, D., Lim, E.K., Poppenberger, B. and Vaistij, F.E. (2006) Glycosyltransferases of lipophilic small molecules. Annu. Rev. Plant Biol. 57, 567-597.
4. Dueckershoff, K., Unger, M., Frank, A., Gillam, E.M., Guengerich, F.P. and Warzecha, H. (2005) Modified nicotine metabolism in transgenic tobacco plants expressing the human cytochrome P450 2A6 cDNA. FEBS Lett. 579, 2480-2484.
5. Ensley, B.D., Ratzkin, B.J., Osslund, T.D., Simon, M.J., Wackett, L.P. and Gibson, D.T. (1983) Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo. Science, 222, 167-169.
6. Frey, M., Chomet, P., Glawischnig, E., Stettner, C., Grun, S., Winklmair, A., Eisenreich, W., Bacher, A., Meeley, R.B., Briggs, S.P., Simcox, K. and Gierl, A. (1997) Analysis of a chemical plant defense mechanism in grasses. Science, 277, 696-699.
7. Gachon, C.M., Langlois-Meurinne, M. and Saindrenan, P. (2005) Plant secondary metabolism glycosyltransferases: the emerging functional analysis. Trends Plant Sci. 10, 542-549.
8. Gierl, A. and Frey, M. (2001) Evolution of benzoxazinone biosynthesis and indole production in maize. Planta, 213, 493-498.
9. Gilbert, K.G. and Cooke, D.T. (2001) Dyes from plants: past usage, present understanding and potential. Plant Growth Regul. 34, 57-69.
10. Gillam, E.M. and Guengerich, F.P. (2001) Exploiting the versatility of human cytochrome P450 enzymes: the promise of blue roses from biotechnology. IUBMB Life, 52, 271-277.
11. Gillam, E.M., Aguinaldo, A.M., Notley, L.M., Kim, D., Mundkowski, R.G., Volkov, A.A., Arnold, F.H., Soucek, P., DeVoss, J.J. and Guengerich, F.P. (1999) Formation of indigo by recombinant mammalian cytochrome P450. Biochem. Biophys. Res. Commun. 265, 469-472.
12. Gillam, E.M., Notley, L.M., Cai, H., De Voss, J.J. and Guengerich, F.P. (2000) Oxidation of indole by cytochrome P450 enzymes. Biochemistry, 39, 13 817-13 824.
13. Hadders, M. (1933) Systematische Verbreitung und Vorkommen der Indoxylglucoside. In Handbuch der Pflanzenanalyse, (Klein, G., ed.), pp. 1062-1063. Wien: Springer.
14. 14C] indole in the rat. Biochem. J. 98, 266-277.
15. Kristensen, C., Morant, M., Olsen, C.E., Ekstrom, C.T., Galbraith, D.W., Moller, B.L. and Bak, S. (2005) Metabolic engineering of dhurrin in transgenic Arabidopsis plants with marginal inadvertent effects on the metabolome and transcriptome. Proc. Natl. Acad. Sci. USA, 102, 1779-1784.
16. Maier, W., Schumann, B. and Groger, D. (1990) Biosynthesis of indoxyl derivatives in Isatis tinctoria and Polygonum tinctorium. Phytochemistry, 29, 817-819.
17. Marcinek, H., Weyler, W., Deus-Neumann, B. and Zenk, M.H. (2000) Indoxyl-UDPG-glucosyltransferase from Baphicacanthus cusia. Phytochemistry, 53, 201-207.
18. Minami, Y., Nishimura, O., Hara-Nishimura, I., Nishimura, M. and Matsubara, H. (2000) Tissue and intracellular localization of indican and the purification and characterization of indican synthase from indigo plants. Plant Cell Physiol. 41, 218-225.
19. Oberthur, C., Graf, H. and Hamburger, M. (2004) The content of indigo precursors in Isatis tinctoria leaves - a comparative study of selected accessions and post-harvest treatments. Phytochemistry, 65, 3261-3268.
20. Paquette, S., Moller, B.L. and Bak, S. (2003) On the origin of family 1 plant glycosyltransferases. Phytochemistry, 62, 399-413.
21. Pflugmacher, S. and Sandermann Jr., H. (1998) Taxonomic distribution of plant glucosyltransferases acting on xenobiotics. Phytochemistry, 49, 507-511.
22. Radwanski, E.R., Zhao, J. and Last, R.L. (1995) Arabidopsis thaliana tryptophan synthase alpha: gene cloning, expression, and subunit interaction. Mol. Gen. Genet. 248, 657-667.
23. Russel, G.A. and Kaupp, G. (1969) Oxidation of carbanions. IV. Oxidation of indoxyl to indigo in basic solution. J. Am. Chem. Soc. 91, 3851-3859.
24. Sapira, J.D., Somani, S., Shapiro, A.P., Scheib, E.T. and Reihl, W. (1971) Some observations concerning mammalian indoxyl metabolism and its relationship to the formation of urinary indigo pigments. Metabolism, 20, 474-486.
25. Taguchi, G., Imura, H., Maeda, Y., Kodaira, R., Hayashida, N., Shimosaka, M. and Okazaki, M. (2000) Purification and characterization of UDP-glucose:hydroxycoumarin 7-O-glucosyltransferase, with broad substrate specificity from tobacco cultured cells. Plant Sci. 157, 105-112.
26. Tanaka, Y., Katsumoto, Y., Brugliera, F. and Mason, J. (2005) Genetic engineering in floriculture. Plant Cell Tiss. Org. Cult. 80, 1-24.
27. Winkel, B.S. (2004) Metabolic channeling in plants. Annu. Rev. Plant Biol. 55, 85-107.
28. Xia, Z.-Q. and Zenk, M.H. (1992) Biosynthesis of indigo precursors in higher plants. Phytochemistry, 31, 2695-2697.