Biosynthesis of Alkaloids and Betalains

Biochemistry of Plant Secondary Metabolism: Second Edition

Volumn 40, Issue , 2010, Pages 20-91

  Roberts, Margaret F ^c   Strack, Dieter ^a   Wink, Michael ^b  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

^b UNIVERSITY OF HEIDELBERG   (Germany)

^c NONE

Author keywords

Acridone alkaloids; Alkaloid biosynthesis; Alkaloid genes; Benzylisoquinoline alkaloids; Betalains; Ergot alkaloids; Monoterpene in dole alkaloids; Nicotine; Purine alkaloids; Pyrrolizidine alkaloids; Taxol; Tropane alkaloids

Indexed keywords

AMINO ACIDS; BIOCHEMISTRY; BIOSYNTHESIS; GENES; METABOLITES; MONOTERPENES; PLANTS (BOTANY);

ACRIDONES; ALKALOID BIOSYNTHESIS; BENZYLISOQUINOLINE ALKALOIDS; BETALAINS; ERGOT ALKALOIDS; PURINE ALKALOID; PYRROLIZIDINE ALKALOID; TAXOL; TROPANE ALKALOIDS;

NICOTINE;

EID: 84943257591     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781444320503.ch2     Document Type: Chapter

References (290)

1. Adams, J.P., von Elbe, J.H. and Amundson, C.H. (1976) Production of a betacyanine concentrate by fermentation of red beet juice with Candida utilis. J. Food Sci., 41, 78-81.
2. Aerts, R.J. and Baumann, T.W. (1994) Distribution and utilisation of chlorogenic acid in Coffea seedlings. J. Exp. Bot., 45, 457-503.
3. Aerts, R.J. and De Luca, V. (1992) Phytochrome is involved in light-regulation of vindoline biosynthesis in Catharanthus. Plant Physiol., 100, 1029-32.
4. Ansarin, M. andWoolley, J.G. (1993) The obligatory role of phenyllactate in the biosynthesis of tropic acid. Phytochemistry, 32, 1183-7.
5. Ansarin, M. and Woolley, J.G. (1994) The rearrangement of phenyllactic acid in the biosynthesis of tropic acid. Phytochemistry, 35, 935-9.
6. Arakawa, H., Clark, W.G., Psenak, M. and Coscia, C.J. (1992) Purification and characterization of dihydrobenzophenanthridine oxidase from elicited Sanguinaria canadensis cell cultures. Arch. Biochem. Biophys., 299, 1-7.
7. Asano, N., Nash, R.J.,Molyneux, R.J. and Fleet, G.W. (2000) Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic action. Tetrahedron Asymmetry, 11, 1645-80.
8. Ashihara, H. and Crozier, A. (1999) Biosynthesis and catabolism of caffeine in lowcaffeine containing species of Coffea. J. Agric. Food Chem., 47, 3425-31.
9. Ashihara, H. and Suzuki, T. (2004) Distribution and biosynthesis of caffeine in plants. Front. Biosci., 9, 1864-76.
10. Bauer, W. and Zenk, M.H. (1991) Two methylenedioxy bridge forming cytochrome P450-dependent enzymes are involved in (S)-stylopine biosynthesis. Phytochemistry, 30, 2953-61.
11. Baumert, A., Kuzovkina, N. and Gröger, D. (1985) Activation of anthranilic acid and N-methylanthranilic acid by cell-free extracts from Ruta graveolens tissue cultures. Planta Med., 50, 125-7.
12. Baumert, A., Kuzovkina, N.I.,Krauss, G., Hieke,M. and Gröger,D. (1982) Biosynthesis of rutacridone in tissue cultures of Ruta graveolens (L.). Plant Cell Rep., 1, 168-71.
13. Baumert, A., Maier, W., Gröger, D. and Deutzmann, R. (1994) Purification and properties of acridone synthase from cell suspension cultures of Ruta graveolens (L.). Z. Naturforsch., 49c, 26-32.
14. Baumert, A., Porzel, A., Schmidt, J. and Gröger, D. (1992) Formation of 1,3-dihydroxy-N-methylacridone from N-methylanthranoyl-CoA and malonyl-CoA by cell cultures of Ruta graveolens. Z. Naturforsch., 47c, 365-8.
15. Biastoff, S. andDräger, B. (2007) Calystegines. The Alkaloids, 64, 49-102.
16. Bird, D.A., Franceschi, V.R. and Facchini, P.J. (2003) A tale of three cell-types: alkaloid biosynthesis is localised to sieve elements in opium poppy. Plant Cell, 15, 2626-35.
17. Bock, A., Wanner, G. and Zenk, M.H. (2002) Immunocytological localisation of two enzymes involved in berberine biosynthesis. Planta, 216, 57-63.
18. Bokern, M., Heuer, S. and Strack, D. (1992) Hydroxycinnamic acid transferases in the biosynthesis of acylated betacyanins: purification and characterization from cell cultures of Chenopodium rubrum and occurrence in some other members of the Caryophyllales. Bot. Acta, 105, 146-51.
19. Böttcher, F., Adolph, R.-D. and Hartmann, T. (1993) Homospermidine synthase, the first pathway-specific enzyme in pyrrolizidine alkaloid biosynthesis. Phytochemistry, 32, 679-89.
20. Böttcher, F., Ober, D. and Hartmann, T. (1994) Biosynthesis of pyrrolizidine alkaloids: putrescine and spermidine are essential substrates of enzymatic homospermidine formation. Can. J. Chem., 72, 80-5.
21. Brouillard, R. and Dangles, O. (1993) Flavonoids and flower colour, in The Flavonoids: Advances in Research Since 1986 (ed. J.B. Harborne). Chapman & Hall, London, pp. 565-88.
22. Burlat, V., Oudin, A., Courtois, M., Rideau, M. and St. Pierre, B. (2004) Co-expression of three MEP pathway genes and geraniol-10-hydroxylase in internal phloem parenchyma of Catharanthus roseus implicates multicellular location of intermediates during the biosynthesis of monoterpene indole alkaloids and isoprenoidderived primary metabolites. Plant J., 38, 131-41.
23. Callebaut, A., Terahara, N. and Decleire, M. (1996) Anthocyanin acyltransferases in cell cultures of Ajuga reptans. Plant Sci., 118, 109-18.
24. Chesters, N.C.J.E., O'Hagan, D. and Robins, R.J. (1994) The biosynthesis of tropic acid in plants: evidence for the direct rearrangement of phenyllactate to tropate. J. Chem. Soc. Perkin Trans., I, 1159-62.
25. Chesters,N.C.J.E., O'Hagan, D. andRobins, R.J. (1995a) The biosynthesis of tropic acid: the (R)-d-phenyllactyl moiety is processed by the mutase involved in hyoscyamine biosynthesis in Datura stramonium. J. Chem. Soc. Chem. Commun., 127-8.
26. Chesters, N.C.J.E., O'Hagan, D., Robins, R.J., Kastelle, A. and Floss, H.G. (1995b) The biosynthesis of tropic acid: the stereochemical course of the mutase involved in hyoscyamine biosynthesis in Datura stramonium. J. Chem. Soc. Chem. Commun., 129-30.
27. Chesters, N.C.J.E., Walker, K., O'Hagan, D. and Floss, H.G. (1996) The biosynthesis of tropic acid: a re-evaluation of the stereochemical course of the conversion of phenyllactate to tropate in Datura stramonium. J. Am. Chem. Soc., 118, 925-6.
28. Choi, K.-B., Morishige, T., Shitan, N., Yazaki, K. and Sato, F. (2002) Molecular cloning and characterization of coclaurineN-methyltransferase fromcultured cells of Coptis japonica. J. Biol. Chem. 277, 830-35.
29. Clement, J.S. and Mabry, T.J. (1996) Pigment evolution in the Caryophyllales: a systematic overview. Bot. Acta, 109, 360-7.
30. Clement, J.S., Mabry, T.J., Wyler, H. and Dreiding, A.S. (1994) Chemical review and evolutionary significance of the betalains, in Caryophyllales, Evolution and Systematics (eds H.-D. Behnke and T.J. Mabry). Springer-Verlag, Berlin Heidelberg, pp. 247-61.
31. Constabel, F. and Haala, G. (1968) Recherches sur la formation de pigments dans les tissus de betterave fourragère cultivé in vitro. Colloques Nationaux Centre National de la Recherche Scientifique, Paris, pp. 223-9.
32. De Luca, V. (1993) Enzymology of indole alkaloid biosynthesis, in Methods in Plant Biochemistry (ed. P.J. Lea), Vol. 9. Academic Press, London, pp. 345-67.
33. De-Eknamkul, W. and Zenk, M.H. (1990) Enzymic formation of (R)-reticuline from 1,2-dehydroreticuline in the opium poppy plant. Tetrahedron Lett., 34, 4855-8.
34. De-Eknamkul, W. and Zenk, M.H. (1992) Purification and properties of 1,2-dehydroreticuline reductase from Papaver somniferum seedlings. Phytochemistry, 31, 813-21.
35. Dejong, J.M., Liu, Y.L., Bollon, A.P. (2006) Genetic engineering of Taxol biosynthesis in Saccharomyces cerevisiae. Biotechnol. Bioeng., 93, 212-24.
36. Dethier, M. and De Luca, V. (1993) Partial purification of a N-methyltransferase involved in vindoline biosynthesis in Catharanthus roseus. Phytochemistry, 31, 663-78.
37. Dewick, P.M. (2002) Medicinal Natural Products. A Biosynthetic Approach, 2nd edn. Wiley, New York.
38. Dittrich, H. and Kutchan, T.M. (1991) Molecular cloning, expression and induction of berberine bridge enzyme, an enzyme essential to the formation of benzophenanthridine alkaloids in the response of plants to pathogenic attack. Proc. Natl. Acad. Sci. USA, 88, 9969-73.
39. Dräger, B. (2004) Chemistry and biology of calystegines. Nat. Prod. Rep., 21, 211-23.
40. Dräger, B. (2005) Tropinone reductases, enzymes at the branch points of tropane alkaloid metabolism. Phytochemistry, 67, 327-37.
41. Dräger, B., Funck, C., Höhler, A., Mrachatz, G., Portsteffen, A., Schaal, A. and Schmidt, R. (1994) Calystegines as a new group of tropane alkaloids in Solanaceae. Plant Cell Tiss. Org. Cult., 38, 235-40.
42. Dräger, B., Portsteffen, A., Schaal, A., McCabe, P.H., Peerless, A.C.J. and Robins, R.J. (1992) Levels of tropinone reductase activities influence the spectrum of tropane esters found in transformed root cultures of Datura stramonium. Planta, 188, 581-6.
43. Dräger, B. and Schaal,A. (1994) Tropinone reduction in Atropa belladonna root cultures. Phytochemistry, 35, 1441-7.
44. Dreiding, A.S. (1961) The betacyanins, a class of red pigments in the Centrospermae, in Recent Developments in the Chemistry of Natural Phenolic Compounds (ed. J.B. Harborne). Pergamon, Oxford, pp. 194-211.
45. Ehrendorfer, F. (1976) Closing remarks: systematics and evolution of centrospermous families. Plant Syst. Evol., 126, 99-106.
46. Eilert, U., De Luca, V., Constabel, F. and Kurz,W.G.W. (1987) Elicitor-mediated induction of tryptophan decarboxylase and strictosidine synthase activities in suspension culture of Catharanthus roseus. Arch. Biochem. Biophys., 254, 491-7.
47. Eisnreich,W.,Menhard, B., Hylands, P.J. and Zenk, M.H. (1996) Studies on the biosynthesis of taxol: the taxane carbon skeleton is not of mevalonoid origin. Proc. Natl. Acad. Sci. USA, 93, 6431-6.
48. Elliott, D.C. (1983) The pathway of betalain biosynthesis: effect of cytokinin on enzymic oxidation and hydroxylation of tyrosine in Amaranthus tricolor seedlings. Physiol. Plant, 59, 428-37.
49. Endo, T., Goodbody, A.,Vukovic, J. and Misawa,M. (1986) Enzymes from Catharanthus roseus cell suspension cultures that couple vindoline and catharanthine to form 3′,4′-anhydrovinblastine. Phytochemistry, 27, 2147-9.
50. Endress, R. (1979) Mögliche beteiligung einer phenylalaninhydroxylase and einer tyrosinase bei der Betacyan-Akkumulation in portulaca kallus. Biochem. Physiol. Pflanzen, 174, 17-25.
51. Facchini, P. (2001) Alkaloid biosynthesis in plants: biochemistry, cell biology, molecular regulation, and metabolic engineering applications. Annu. Rev. Plant Physiol. Plant Mol. Biol., 52, 29-66.
52. Facchini, P.J. and De Luca, V. (1994) Differential and tissue specific expression of a gene family for tyrosine/dopa decarboxylase in opium poppy. J. Biol. Chem., 269, 26684-90.
53. Facchini, P.J. and De Luca, V. (1995) Phloem specific expression of tyrosine/dopa decarboxylase genes and the biosynthesis of isoquinoline alkaloids in opium poppy. The Plant Cell, 7, 1811-21.
54. Facchini, P.J. andDe Luca, V. (2008) Opium poppy andMadagascar periwinkle:model non-model systems to investigate alkaloid biosynthesis in plants. The Plant J., 54, 763-84.
55. Facchini, P.J., Johnson, A.G., Poupart, J. and De Luca, V. (1996) Uncoupled defense gene expression and antimicrobial alkaloid accumulation in elicited opium poppy cell cultures. Plant Physiol., 111, 687-97.
56. Facchini, P.J. and St. Pierre, B. (2005) Synthesis and trafficking of alkaloid biosynthesis enzymes. Curr. Opin. Plant Biol., 8, 657-66.
57. Fahn, W. and St öckigt, J. (1990) Purification of acetyl-CoA: 17-O-deacetylvindoline 17-O-acetyltransferase from Catharanthus roseus leaves. Plant Cell Rep., 8, 613-6.
58. Falkenhagen, H. and St öckigt, J. (1995) Enzymic biosynthesis of vomilenine, a key intermediate of the ajmaline pathway, catalysed by a novel cytochrome P450-dependent enzyme from plant cell cultures of Rauwolfa serpentina. Z. Naturforsch., 50c, 45-53.
59. Fecker, L.F., Hillebrandt, S., Rfigenhagen, C., Herminghaus, S., Landsmann, J. and Berlin, J. (1992) Metabolic effects of a bacterial lysine decarboxylase gene expressed in hairy root culture of Nicotiana glauca. Biotech. Lett., 14, 1035-40.
60. Fernandez, J.A., Owen, T.G., Kurz, W.G.W. and De Luca, V. (1989) Immunological detection and quantitation of tryptophan decarboxylase in developing Catharanthus roseus seedlings. Plant Physiol., 91, 79-84.
61. Fischer, N. and Dreiding, A.S. (1972) Biosynthesis of betalaines. On the cleavage of the aromatic ring during the enzymatic transformation of dopa into betalamic acid. Helv. Chim. Acta, 55, 649-58.
62. Fleetwood, D.J., Scott, B., Lane, G.A., Tanaka, A. and Johnson, R.D. (2007) A complex ergovaline gene cluster in Epichloe endophytes of grasses. Appl. Environ. Microbiol., 73, 2571-9.
63. Fleming, P.E., Knaggs, A.R., He, X-G., Mocek, U. and Floss, H.G. (1994) Biosynthesis of taxoids, mode of attachment of the side chain. J. Am. Chem. Soc., 116, 4137-8.
64. Fretz, H. andWoggon,W.-D. (1986) Regioselectivity and deuterium isotope effects in geraniol hydroxylation by the cytochrome P450 monooxygenase from Catharanthus roseus (L.). G. Don. Helv. Chim. Acta, 69, 1959-70.
65. Fretz, H., Woggon, W-D. and Voges, R. (1989) The allylic oxidation of geraniol catalysed by cytochrome P450 proceeding with retention of configuration. Helv. Chim. Acta, 72, 391-400.
66. Friesen, J.B. and Leete, E. (1990) Nicotine synthase: an enzyme from Nicotiana species which catalyses the formation of (S)-nicotine from nicotinic acid and 1-methyl-Δ′-pyrrolinium chloride. Tetrahedron Lett., 31, 6295-8.
67. Fujiwara, H., Takeshita, N., Terano, Y., Fitchen, J.H., Tsujita, T., Katagiri, Y., Sato, F. and Yamada, Y. (1993) Expression of (S)-scoulerine 9-O-methyltransferase in Coptis japonica plants. Phytochemistry, 34, 949-54.
68. Fujiwara, H., Tanakan, Y., Fukui, Y., Nakao, Y., Ashikari, T. and Kusumi, T. (1997) Anthocyanin 5-aromatic acyltransferase from Gentiana triflora: purification, characterization and its role in anthocyanin biosynthesis. Eur. J. Biochem., 249, 45-51.
69. Galneder, E., Rueffer, M., Wanner, G., Tabata, M. and Zenk, M.H. (1988) Alternative final steps in berberine biosynthesis in Coptis japonica cell cultures. Plant Cell Rep., 7, 1-4.
70. Garay, A.S. and Towers, G.H.N. (1966) Studies on the biosynthesis of amaranthin. Can. J. Bot., 44, 231-6.
71. Gebler, J.C. and Poulter, C.D. (1992) Purification and characterisation of dimethylallyltryptophan synthase from Claviceps purpurea. Arch. Biochem. Biophys., 296, 308-13.
72. Gebler, J.C., Woodside, A.B. and Poulter, C.D. (1992) Dimethylallyltryptophan synthase: an enzyme catalysed electrophilic aromatic substitution. J. Am. Chem. Soc., 114, 7354-60.
73. Geerlings, A., Redondo, F.J.,Contin, A. (2001) Biotransformation of tryptamine and secologanin into plant terpenoid indole alkaloids by transgenic yeast. Appl.Microbiol. Biotechnol., 56, 420-4.
74. Gerardy, R. and Zenk, M.H. (1992) Formation of salutaridine from (R)-reticuline by a membrane-bound cytochrome P450 enzyme from Papaver somniferum. Phytochemistry, 32, 79-86.
75. Gerardy, R. and Zenk, M.H. (1993) Purification and characterization of salutaridine: NADPH-7-oxidoreductase. Phytochemistry, 34, 125-32.
76. Girod, P.-A. and Zryd, J.-P. (1991) Biogenesis of betalains: purification and partial characterization of Dopa 4,5-dioxygenase from Amanitamuscaria. Phytochemistry, 30, 169-74.
77. Glägen,W.E. and Seitz,H.U. (1992) Acylation of anthocyanins with hydroxycinnamic acids via 1-O-acylglucosides by protein preparations from cell cultures of Daucus carota (L.). Planta, 186, 582-5.
78. Goddijn, O.J.M. (1992) Regulation of terpenoid indole alkaloid biosynthesis in Catharanthus roseus: the tryptophan decarboxylase gene. Ph.D. Thesis, Leiden University.
79. Goddijn, O.J.M., DeKam, R.J., Zanetti, A., Schilperoot, R.A. and Hoge, J.H.C. (1992) Auxin downregulates transcription of the tryptophan decarboxylase gene from Catharanthus roseus. Plant Mol. Biol., 18, 1113-20.
80. Goldmann, A., Milat, A.-L., Ducrot, P.-H., Lallemand, J.-Y., Maille, M., Lepingle, A., Charpin, I. and Tepfer, D. (1992) Tropane derivatives from Calystegia sepium. Phytochemistry, 29, 2125-7.
81. Goodbody, A.E., Endo, T., Vukovic, J., Kutney, J.P., Choi, L.S.L. and Misawa,M. (1988) Enzymic coupling of catharanthine and vindoline to form 3′,4′-anhydrovinblastine by horseradish peroxidase. Planta Med., 54, 136-40.
82. Goossens, A., Häkkinen, S.T., Laakso, I., Seppänen-Laasko, T., Biondi, S. deSutter, V., Lammertyn, F., Nuutila, A.M., Söderlund, H., Zabeau, M. Inze, D. and Oksman-Caldentey, K.-M. (2003)Afunctional genomics approach toward the understanding of secondary metabolism in plant cells. Proc. Natl. Acad. Sci USA, 100, 8595-600.
83. Graser, G. and Hartmann, T. (1997) Biosynthetic incorporation of the aminobutyl group of spermine into pyrrolizidine alkaloids. Phytochemistry, 45, 1591-2.
84. Graser, G. and Hartmann, T. (2000) Biosynthesis of spermidine, a direct precursor of pyrrolizidine alkaloids in root cultures of Senecio vulgaris L. Planta, 211, 239-45.
85. Groeger, D. and Floss, H.G. (1998) Biochemistry of ergot alkaloids. The Alkaloids, 50, 171-218.
86. Grothe, T., Lenz, R. and Kutchan, T.M. (2001) Molecular characterisation of the salutaridinol-7-O-acetyltransferase involved in morphine biosynthesis in opium poppy Papaver somniferum. J. Biol. Chem., 276, 30717-23.
87. Gueritte-Voegelein, F., Guernard, D. and Potier, P. (1987) Taxol and derivatives: a biogenetic hypothesis. J. Nat. Prod., 50, 9-18.
88. Haarmann, T.,Machada, C., Luebbe, Y., Correia, T., Schardl, C.I., Panaccione, D.G. and Tudzynski, P. (2005) The ergot alkaloid gene cluster in Claviceps purpurea: extension of the cluster sequence and intra specis evolution. Phytochemistry, 66, 1312-20.
89. Häkkinen, S.T., Tilleman, S., Swiatek, A., deSutter, V., Rischer, H., Vanhoutte, I., van Onckelen, H., Hilson, P., Inze, D., Oksman-Caldentey, K.-M., Goossens, A. (2007) Functional characterisation of genes involved in pyridine alkaloid biosynthesis in tobacco. Phytochemistry, 68, 2773-85.
90. Hampp, N. and Zenk, M.H. (1988) Homogeneous strictosidine synthase from cell suspension cultures of Rauvolvia serpentina. Phytochemistry, 27, 3811-5.
91. Hartmann, T. (1991) Alkaloids, in Herbivores: Their Interactions with Secondary Plant Metabolites (eds G.A. Rosenthal and M.R. Berenbaum), 2nd edn. Academic Press, San Diego, CA.
92. Hartmann, T. (1994) Senecio species: biochemistry of the formation of pyrrolizidine alkaloids in root cultures, in Biotechnology inAgriculture and Forestry (ed. Y.P.S. Bajaj), Vol. 26. Springer-Verlag, Berlin Heidelberg, pp. 339-55.
93. Hartmann, T. (2007) From waste products to ecochemicals: fifty years research of plant secondary metabolism. Phytochemistry, 68, 2831-46.
94. Hartmann, T. and Witte, L. (1995) Chemistry, biology and chemoecology of the pyrrolizidine alkaloids, in Alkaloids, Chemical and Biological Perspectives (ed. S.W. Pelletier), Vol. 9. Pergamon, Oxford, pp. 155-233.
95. Hashimoto, T. and Yamada, Y. (1994) Alkaloid biogenesis: molecular aspects. Annu. Rev. Plant Physiol. Plant Mol. Biol., 45, 257-85.
96. Hashimoto, T. and Yamada, Y. (2003)Newgenes in alkaloid metabolism and transport. Curr. Opin. Biotechnol., 14, 163-8.
97. Hawkins, K.M. and Smolke, C.D. (2008) Production of benzylisoquinoline alkaloids in Saccharomyces cerevisiae. Nat. Chem. Biol., 4, 564-73.
98. Heim, W.G., Sykes, K.A., Hildreth, S.B., Sun, J., Lu, R.H. and Jelesko, J.G. (2007) Cloning and characterisation of a Nicotiana tabacum methylputrescine oxidase transcript. Phytochemistry, 68, 454-63.
99. Hempel, J. and Bbhm, H. (1997) Betaxanthin pattern of hairy roots from Beta vulgaris var. lutea and its alteration by feeding of amino acids. Phytochemistry, 44, 847-52.
100. Herbert, R.B. (1989) The Biosynthesis of Secondary Metabolites, 2nd edn. Chapman & Hall, London.
101. Heuer, S., Richter, S., Metzger, J.W., Wray, V., Nimtz, M. and Strack, D. (1994) Betacyanins from bracts of Bougainvillea glabra. Phytochemistry, 37, 761-7.
102. Heuer, S. and Strack, D. (1992) Synthesis of betanin from betanidin and UDP-glucose by a protein preparation from cell suspension cultures of Dorotheanthus bellidiformis (Burin. f.) N.E.Br. Planta, 186, 626-8.
103. Heuer, S., Vogt, T., Böhm, H. and Strack, D. (1996) Partial purification and characterization of UDP-glucose:betanidin 5-O- and 6-O-glucosyltransferases from cell suspension cultures of Dorotheanthus bellidiformis (Burin. f.) N.E.Br. Planta, 199, 244-50.
104. Heuer, S., Wray, V., Metzger, J.W. and Strack, D. (1992) Betacyanins from flowers of Gomphrena globosa. Phytochemistry, 31, 1801-7.
105. Hibi, N., Fujita, T., Hatano, M., Hashimoto, T. and Yamada, Y. (1992) Putrescine N-methyltransferase in cultured roots of Hyoscyamus albus. Plant Physiol., 100, 826-35.
106. Hibi, N., Higashiguchi, S., Hashimoto, T. and Yamada, Y. (1994) Gene expression in tobacco low-nicotine mutants. Plant Cell, 6, 723-35.
107. Hinz, U.G., Fivaz, J., Girod, P.-A. and Zryd, J.-P. (1997) The gene coding for the dioxygenase involved in betalain biosynthesis in Amanita muscaria and its regulation. Mol. Gen. Genet., 256, 1-6.
108. Hörhammer, L., Wagner, H. and Fritsche, W. (1964) Zur biosynthese der betacyane I. Biochemische Zeitschrift, 339, 398-400.
109. Ignatov, A., Clark, W.G., Cline, S.D., Psenak, M., Krueger, R.J. and Coscia, C.J. (1996) Elicitation of dihydrobenzophenanthridine oxidase in Sanguinaria canadensis cell cultures. Phytochemistry, 43, 1141-4.
110. Ikezawa, N., Iwasa, K. and Sato, F. (2007) Molecular cloning and characterisation of methylenedioxy brifge-forming enzymes involved in stylopine biosynthesis in Eschscholzia californica. FEBS J., 274, 1019-1035.
111. Ikezawa, N., Tanaka, M., Nagayoshi, M., Shinkyo, R., Sakaki, T., Inouye, K., Sato, F. (2003) Molecular cloning and characterisation of CYP719, a methylenebridge forming enzyme that belongs to a novel P450 family, from cultured Coptis japonica cells. J. Biol. Chem., 278, 38557-65.
112. Impellizzeri, G. and Piattelli, M. (1972) Biosynthesis of indicaxanthin in Opuntia ficusindica fruits. Phytochemistry, 11, 2499-502.
113. Jennewein, S. and Croteau, R. (2001) Taxol: bioynthesis, molecular genetics, and biotechnological applications. Appl. Microbiol. Biotechnol., 57, 13-19.
114. Jennewein, S., Park,H., Dejong, J.M. (2005) Coexpression in yeast of Taxus cytochrome P450 reductase with cytochrome P450 deoendent oxygenases involved in taxol biosynthesis. Biotechnol. Bioeng., 89, 13595-600.
115. Joy, R.W., Sugiyama, M., Fukuda, H. and Komamine, A. (1995) Cloning and characterization of polyphenol oxidase cDNAs of Phytolacca americana. Plant Physiol., 107, 1083-9.
116. Junghanns, K.T., Kneusel, R.E., Baumert, A., Maier, W., Gröger, D. and Matern, U. (1995) Molecular cloning and heterologous expression of acridone synthase from elicited Ruta graveolens (L.) cell suspension cultures. Plant Mol. Biol., 27, 681-92.
117. Kaiser, H., Richter, U., Keiner, R., Brabant, A., Hause, B. and Dräger, B. (2006) Immunolocalisation of two tropinone reductases in potato (Solanum tuberosum L.) root, stolon, and tuber sprouts. Planta, 225, 127-37.
118. Kammerer, L., De-Eknamkul, W. and Zenk, M.H. (1994) Enzymic 12-hydroxylation and 12-O-methylation of dihydrochelirubine in dihydromacarpine formation by Thalictrum bulgaricum. Phytochemistry, 36, 1409-16.
119. Kamsteeg, J., Van Brederode, J., Hommels, C.H. and Van Nigtevecht, G. (1980) Identification, properties and genetic control of hydroxycinnamoyl-coenzyme A: anthocyanidin 3-rhamnosyl (1→6) glucoside, 4′-hydroxycinnamoyl transferase isolated from petals of Silene dioica. Biochem. Physiol. Pfanzen, 175, 403-11.
120. Kanegae, T., Kajiya, H., Amano, Y., Hashimoto, T. and Yamada, Y. (1994) Speciesdependent expression of the hyoscyamine 6β-hydroxylase gene in the pericycle. Plant Physiol., 105, 483-90.
121. Katoh, A., Shoji, T. andHashimoto, T. (2007) Molecular cloning ofN-methylputrescine oxidase from tobacco. Plant Cell Physiol., 48, 550-4.
122. Keasling, J. (2008) From yeast to alkaloids. Nat. Chem. Biol., 4, 524-5.
123. Kim, I.-S., Kim, S.-U. and Anderson, J.A. (1981) Microsomal agroclavine hydroxylase of Claviceps species. Phytochemistry, 20, 2311-14.
124. Kimler, L., Mears, J., Mabry, T.J. and Rösler, H. (1970) On the question of the mutual exclusiveness of betalains and anthocyanins. Taxon, 19, 875-8.
125. Kobayashi, M. and Floss, H.G. (1987) Biosynthesis of ergot alkaloids: origin of the oxygen atoms in chanoclavine I and elymoclavine. J. Org. Chem., 52, 4350-2.
126. Kozikowski, A.P., Chen, C., Wu, J.-P., Shibuya, M., Kim, C.-G. and Floss, H.G. (1993) Probing alkaloid biosynthesis: intermediates in the formation of ringC. J. Am. Chem. Soc., 115, 2482-8.
127. Kraus, P.F.X. and Kutchan, T.M. (1995) Molecular cloning and heterologous expression of a cDNA encoding berbamunine synthase, a C-O phenol-coupling cytochrome P450 from the higher plant Berberis stolonifera. Proc. Natl. Acad. Sci. USA, 92, 2071-5.
128. Kutchan, T.M. (1989) Expression of enzymatically active cloned strictosidine synthase from the higher plant Rauvolfia serpentina in Escherichia coli. FEBS Lett., 257, 127-30.
129. Kutchan, T.M. (1995) Alkaloid biosynthesis: the basis for metabolic engineering of medicinal plants. The Plant Cell, 7, 1059-70.
130. Kutchan, T.M. (1996) Heterologous expression of alkaloid biosynthetic genes: a review. Gene, 179, 73-81.
131. Kutchan, T.M. and Dittrich, H. (1995) Characterisation and mechanism of berberine bridge enzyme, a covalently flavinylated oxidase of benzophenanthridine alkaloid biosynthesis in plants. J. Biol. Chem., 270, 24475-81.
132. Kutchan, T.M., Dittrich, H., Bracher, D. and Zenk, M.H. (1991) Enzymology and molecular biology of alkaloid biosynthesis. Tetrahedron, 47, 5945-54.
133. Kutchan, T.M. and Zenk, M.H. (1993) Enzymology and molecular biology of benzophenanthridine alkaloid biosynthesis. J. Plant Res. (Special Issue), 3, 165-73.
134. Kutney, J.P. (1987) Studies in plant tissue culture: the synthesis and biosynthesis of indole alkaloids. Heterocycles, 25, 617-40.
135. Leete, E. (1990) Recent developments in the biosynthesis of tropane alkaloids. Planta Med., 56, 339-52.
136. Lenz, R. and Zenk,M.H. (1994) Closure of the oxide bridge inmorphine biosynthesis. Tetrahedron Lett., 35, 3897-900.
137. Lenz, R. and Zenk, M.H. (1995a) Acetyl coenzyme A: salutaridinol-7-Oacetyltransferase from Papaver somniferum cell cultures. J. Biol. Chem., 270, 31091-6.
138. Lenz, R. and Zenk, M.H. (1995b) Purification and properties of codeinone reductase (NADPH) from Papaver somniferum plant cell cultures and differentiated plants. Eur. J. Biochem., 233, 132-9.
139. Liebisch, H.-W., Matschiner, B. and Schdtte, H.R. (1969) Beiträge zur Physiologie and Biosynthese des Betanins. Z. Pfanzenphys., 61, 269-78.
140. Lin, X.,Hezari, M., Koepp, A.E., Floss, H.G. and Croteau, R. (1996) Mechanism of taxadiene synthesis, a diterpene cyclase that catalyzes the first step of taxol biosynthesis in Pacific yew. Biochemistry, 35, 2968-77.
141. Liscombe, D.K. and Facchini, P.J. (2008) Evolutionary and cellular webs in benzylisoquinoline alkaloid biosynthesis. Curr. Opin. Biotechnol., 19, 173-80.
142. Loefer, S. and Zenk, M.H. (1990) The hydroxylation step in the biosynthetic pathway leading from norcoclaurine to reticuline. Phytochemistry, 29, 3499-503.
143. Lotter, H., Gollsitzer, J. and Zenk, M.H. (1992) Revision of the configuration at C-7 of salutaridinol I, the natural intermediate in morphine biosynthesis. Tetrahedron Lett., 33, 2443-6.
144. Mabry, T.J. (1973) Is the order Centrospermae monophyletic? in Chemistry in Botanical Classification (eds G. Bends and J. Santesson). Academic Press, London, pp. 275-85.
145. Maier, W.D., Baumert, A. and Gröger, D. (1995) Partial purification and characterisation of S-adenosyl-L-methinione:anthranilic acid N-methyltransferase. J. Plant Physiol., 145, 1-6.
146. Maier,W., Baumert, A., Schumann, B., Furukawa, H. and Gröger, D. (1993) Synthesis of 1,3-dihydroxy-N-methylacridone and its conversion to rutacridone by cell-free extracts of Ruta graveolens cell cultures. Phytochemistry, 32, 691-8.
147. Maier, W., Schumann, B. and Gröger, D. (1988) Microsomal oxygenases involved in ergoline alkaloid biosynthesis of various Claviceps strains. J. Basic Microbiol., 28, 83-93.
148. Marasco, E.K. and Schmidt-Dannert, C. (2007) Biosynthesis of plant natural products and characterization of plant biosynthetic pathways in recombinant microorganisms, in Applications of Plant Metabolic Engineering (eds R. Verpoorte, A.W. Alfermann and T.S. Johnson). Springer, Heidelberg, pp. 1-43.
149. Markert, A., Steffan, N., Ploss, K.,Hellwig, S., Steiner, U. Drewke, C., Li, S.-M., Boland, W. and Leistner, E. (2008) Biosynthesis and accumulation of ergoline alkaloids in a mutualistic association between Ipomoea asarifolia (Convolvulaceae) and a Clavicipitalean fungus. Plant Physiol., 147, 296-305.
150. McCarthy, A. and McCarthy, J.G. (2007) The structure of two N-methyltransferases from the caffeine biosynthetic pathway. Plant Physiol., 144, 879-89.
151. McCoy, E. and O'Connor, S.E. (2006) Directed biosynthesis of alkaloid analogues in the medicinal plant Catharanthus roseus. J. Am. Chem. Soc., 128, 14276-7.
152. McKnight, T.D., Bergey, D.R., Burnett, R.J. and Nessler, C.L. (1991) Expression of enzymatically active and correctly targeted strictosidine synthase in transgenic tobacco plants. Planta, 185, 148-52.
153. McLauchlan, W.R., McKee, R.A. and Evans, D.M. (1993) The purification and immunocharacterisation of N-methylputrescine oxidase from transformed root cultures of Nicotiana tabacum (L.) cv SC58. Planta, 191, 440-5.
154. Meijer, A.H., DeWall, A. and Verpoorte, R. (1993a) Purification of the cytochrome P450 enzyme, geraniol 10-hydroxylase, from cell cultures of Catharanthus. J. Chromatogr., 635, 237-49.
155. Meijer, A.H., Verpoorte, R. and Hoge, J.H.C. (1993b) Regulation of enzymes and genes involved in terpenoid indole alkaloid biosynthesis in Catharanthus roseus. J. Plant Res. (Special Issue), 3, 145-64.
156. Minale, L., Piattelli, M. and Nicolaus, R.A. (1965) Pigments of Centrospermae-IV. On the biogenesis of indicaxanthin and betanin in Opuntia ficus-indica Mill. Phytochemistry, 4, 593-7.
157. Minami, H., Dubouzet, E., Iwasa, K. and Sato, F. (2007) Functional analysis of norcoclaurine synthase in Coptis japonica. J. Biol. Chem., 282, 6274-82.
158. Minami, H., Kim, J.-S., Ikezawa, N., Takemura, T., Katayama, T., Kumagai, H. and Sato, F. (2008) Microbial production of plant benzoquinoline alkaloids. Proc. Natl. Acad. Sci. USA, 105, 7393-8.
159. Miura, Y., Hirata, K., Kurano, N., Miyamoto, K. and Uchida, K. (1988) Formation of vinblastine in shoot cultures of Catharanthus roseus. Planta Med., pp. 18-20.
160. Moll, S.,Anke, S., Kahmann, U.,Hänsch, R., Hartmann, T.,Ober, D. (2002) Cell specific expresssion of homospermidine synthase, the entry enzyme of the pyrrolizidine alkaloids in Senecio vernalis in comparison to its ancestor deoxyhypusine synthase. Plant Physiol., 130, 47-57.
161. Morishige, T., Tsujita, T. Yamada, Y. (2000) Molecular characterization of S-adenosyl-L-methionine: 3′hydroxyl-N-methylcoclaurine 4′-O-methyltransferase involved in isoquinoline alkaloid biosynthesis in Coptis japonica. J. Biol. Chem., 275, 23398-405.
162. Mothes, K., Schütte, H.R. and Luckner, M. (1985) Biochemistry of Alkaloids. Verlag Chemie, Weinheim.
163. Mueller, L.A., Hinz, U., Uzé, M., Sautter, C. and Zryd, J.-P. (1997b) Biochemical complementation of the betalain biosynthetic pathway in Portulaca grandiora by a fungal 3,4-dihydroxyphenylalanine dioxygenase. Planta, 203, 260-63.
164. Mueller, L.A., Hinz, U. and Zryd, J.-P. (1996) Characterization of a tyrosinase from Amanita muscaria involved in betalain biosynthesis. Phytochemistry, 42, 1511-5.
165. Mueller, L.A., Hinz, U. and Zryd, J.-P. (1997a) The formation of betalamic acid and muscafiavin by recombinant Dopa-dioxygenase from Amanita. Phytochemistry, 44, 567-69.
166. Murata, J., Roepke, J., Gordon, H. and De Luca, V. (2008) The leaf epidermone of Catharanthus roseus reveals its biochemical specialization. The Plant Cell, 20, 524-42.
167. Nakajima, K. and Hashimoto, T. (1999) Two tropinone reductases that catalyse opposite stereospecific reductions in tropane alkaloid biosynthesis are localized in plant root with different cell-specific patterns. Plant Cell Physiol., 40, 1099-107.
168. Nakajima, K., Hashimoto, T. and Yamada, Y. (1993) cDNA encoding tropinone reductase-II from Hyoscyamus niger. Plant Physiol., 103, 1465-6.
169. Nakajima, K., Hashimoto, T. and Yamada, Y. (1994) Opposite stereospecificity of two tropinone reductases is conferred by the substrate-binding sites. J. Biol. Chem., 269, 11695-8.
170. Nakajima, K., Yamashita, A., Akama, H., Nakatsu, T., Kato, H., Hashimoto, T., Oda, J. and Yamada, Y. (1998) Crystal structures of two tropinone reductases: different reaction stereospecificities in the same protein fold. Proc. Natl. Acad. Sci. USA, 95, 4876-81.
171. Ober,D. (2005) Seeing double- gene duplication and diversification in plant secondary metabolism. Trends Plant Sci., 10, 444-9.
172. Ober, D. and Hartmann, T. (1999) Homospermidine synthase, the first pathwayspecific enzyme of pyrrolizidine alkaloid biosynthesis, evolved from deyoxyhypusine synthase. Proc. Natl. Acad. Sci. USA, 96, 14777-82.
173. Ogita, S.,Uefuji, H. Morimoto,M. (2004) Application of RNAi to confirm theobromine as a new intermeiate for caffeine biosynthesis in coffee plants with potential for construction of decaffeinated varieties. Plant Mol. Biol., 54, 931-41.
174. Okada, N., Shinmyo, A., Okada, H. and Yamada, Y. (1988) Purification and characterisation of (S)-tetrahydroberberine oxidase from cultured Coptis japonica cells. Phytochemistry, 27, 979-82.
175. Oksman-Caldentey, K.-M., Häkkinen, S.T. and Rischer, H. (2007) Metabolic engineering of the alkaloid biosynthesis in plants: functional genomic approaches, in Applications of Plant Metabolic Engineering (eds R. Verpoorte, A.W. Alfermann and T.S. Johnson). Springer, Heidelberg, pp. 109-43.
176. Pasquali, G., Goddijn, O.J.M., DeWaal, A., Verpoorte, R., Schilperoot, R.A., Hoge, J.H.C. and Memelink, J. (1992) Coordinated regulation of two indole alkaloid biosynthetic genes from Catharanthus roseus by auxin and elicitors. Plant Mol. Biol., 18, 1121-31.
177. Pauli, H.H. and Kutchan, T.M. (1998) Molecular cloning and functional heterologous expression of two alleles encoding (S)-N-methylcoclaurine 3′-hydroxylase (CYP80B1), a new methyl jasmonate-inducible cytochrome p-450 dependent monooxygenase of benzylisoquinoline biosynthesis. Plant J., 13, 793-801.
178. Pelletier, S.W. (1983-1996) Alkaloids: Chemical and Biological Perspectives, Vols 1-11. Pergamon, Oxford.
179. Pennings, E.J.M., Groen, B.W., Duine, J.A. and Verpoorte, R. (1989) Tryptophan decarboxylase from Catharanthus roseus is a pyridoxo-quinoprotein. FEBS Lett., 255, 97-100.
180. Pfitzner, U.M. and Zenk, M.H. (1989) Homogeneous strictosidine synthase isoenzymes from cell suspension cultures of Catharanthus roseus. Planta Med., 55, 525-30.
181. Piattelli, M. and Imperato, F. (1970a) Betacyanins from Bougainvillea. Phytochemistry, 9, 455-8.
182. Piattelli, M. and Imperato, F. (1970b) Pigments of Bougainvillea glabra. Phytochemistry, 9, 2557-60.
183. Piattelli, M., Minale, L. and Prota, G. (1964) Isolation, structure and absolute configuration of indicaxanthin. Tetrahedron, 20, 2325-9.
184. Polz, L., Schiibel, H. and St öckigt, J. (1986) Characterisation of 2′(R)-17-Oacetylajmalan: acetylesterase a specific enzyme involved in the biosynthesis of the Rauwolfa alkaloid ajmalicine. Z. Naturforsch., 42c, 333-42.
185. Portsteffen, A., Dräger, B. and Nahrstedt, A. (1992) Two tropinone reducing enzymes from Datura stramonium transformed root cultures. Phytochemistry, 31, 1135-8.
186. Portsteffen, A., Dräger, B. and Nahrstedt, A. (1994) The reduction of tropinone in Datura stramonium root cultures by two specific reductases. Phytochemistry, 37, 391-400.
187. Pourrat, H., Lejeune, B., Regerat, F. and Pourrat, A. (1983) Purification of red beetroot dye by fermentation. Biotech. Lett., 5, 381-4.
188. Rabot, S., Peerless, A.C.J. and Robins, R.J. (1995) Tigloyl-CoA:pseudotropine acyl transferase: a novel enzyme of tropane alkaloid biosynthesis. Phytochemistry, 39, 315-22.
189. Rhodes, M.J.C., Robins, R.J., Aird, E.L.H., Payne, J., Parr, A.J. and Walton, N.J. (1989) Regulation of secondary metabolism in transformed root cultures, in Primary and Secondary Metabolism of Plant Cell Cultures. II (ed. W.G.W. Kurz). Springer-Verlag, Berlin Heidelberg, pp. 58-72.
190. Rhodes, M.J.C., Robins, R.J., Parr, A.J. andWalton, N.J. (1990) Secondary metabolism in transformed root cultures, in Secondary Products from Plant Tissue Culture (eds B.V. Charlwood and M.J.C. Rhodes). Oxford University Press, Oxford, pp. 201-25.
191. Richter, U., Rother, G., Fabian, A.-K., Rahfeld, B. and Dräger, B. (2005) Overexpression of tropinone reductases alters alkaloid composition in Atropa belladonna root cultures. J. Exp. Bot., 56, 645-52.
192. Rischer, H., Oresic, M., Seppänen-Laakso, T., Katajamaa, M., Lammertyn, F., Ardiles-Diaz, W., von Montagu, M.C.E., Inze, D., Oksman-Caldentey, K.-M. and Goosens, A. (2006) Gene-to-metabolite networks for terpenoid indole alkaloid biosynthesis in Catharanthus roseus cells. Proc. Natl. Acad. Sci. USA, 103, 5614-9.
193. Roberts, M.F. and Wink, M. (1998) Alkaloids: Biochemistry, Ecological Functions and Medical Applications. Plenum, New York.
194. Robins, R.J.,Abraham, T., Parr, A.J., Eagles, J. andWalton, N.J. (1997) The biosynthesis of tropane alkaloids Datura stramonium: the identity of the intermediate between N-methylpyrrolinium salt and tropinone. J. Am. Chem. Soc., 119, 10929-34.
195. Robins, R.J., Bachmann, P. and Woolley, J.G. (1994b) Biosynthesis of hyoscyamine involves an intramolecular rearrangement of littorine. J. Chem. Soc. Perkin Trans. I., 615-9.
196. Robins, R.J., Chesters, N.C.J.E., O'Hagan, D., Parr, A.J.,Walton, N.J. andWoolley, J.G. (1995) The biosynthesis of hyoscyamine: the process by which littorine rearranges to hyoscyamine. J. Chem. Soc. Perkin Trans., 1, 481-5.
197. Robins, R.J., Hamill, J.D., Parr, A.J., Smith, K., Walton, N.J. and Rhodes, M.J.C. (1987) Potential use of nicotinic acid as a selective agent for isolation of high-nicotineproducing lines of Nicotiana rustica hairy root cultures. Plant Cell Rep., 6, 122-6.
198. Robins, R.J. and Walton, N.J. (1993) The biosynthesis of tropane alkaloids, in The Alkaloids (ed. G.A. Cordell), Vol. 44. Academic Press, Orlando, pp. 115-87.
199. Robins, R.J.,Woolley, J.G., Ansarin,M., Eagles, J. and Goodfellow, B.J. (1994a) Phenyllactic acid but not tropic acid is an intermediate in the biosynthesis of tropane alkaloids in Datura and Brugmansia transformed root cultures. Planta, 194, 86-94.
200. Roewer, I.A., Cloutier, N., Nessler, C.L. and De Luca, V. (1992) Transient induction of tryptophan decarboxylase (TDC) and strictosidine synthase (SS) genes in cell suspension cultures of Catharanthus roseus. Plant Cell Rep., 11, 86-9.
201. Rohmer,M., Knani, M., Simonin, P., Sutter, B. and Sahmn, H. (1993) Isopreniod biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate. Biochem. J., 295, 517-24.
202. Rueffer, M. and Zenk, M.H. (1985) Berberine synthase, the methylenedioxy groupforming enzyme in berberine synthase. Tetrahedron Lett., 26, 201-2.
203. Rueffer, M. and Zenk, M.H. (1987a) Distant precursors of benzylisoquinoline alkaloids and their enzymatic formation. Z. Naturforsch., 42c, 319-22.
204. Rueffer, M. and Zenk, M.H. (1987b) Enzymatic formation of protopines by a microsomal cytochrome P450 system of Corydalis vaginans. Tetrahedron Lett., 28, 5307-310.
205. Rueffer, M. and Zenk, M.H. (1994) Canadine synthase from Thalictrum tuberosum cell cultures catalyses the formation of the methylenedioxy bridge in berberine synthesis. Phytochemistry, 36, 1219-23.
206. Rueffer, M., Zumstein, G. and Zenk, M.H. (1990) Partial purification and properties of S-adenosyl-L-methionine:(S)-tetrahydroprotoberberine-cis-N-methyltransferase from suspension-cultured cells of Eschscholtzia and Corydalis. Phytochemistry, 29, 3727-33.
207. Ruppert, M., Xueyan, M. and St öckigt, J. (2005) Alkaloid biosynthesis in RauvolfiacDNA cloning of the major enzymes of the ajmaline pathway. Curr. Org. Chem., 9, 1431-44.
208. Samanani, N., Liscombe, D.K., Facchini, P.J. (2004) Molecular cloning and characterisation of norcoclaurine synthase, an enzyme catalysing the first committed step in benzylisoquinoline biosynthesis. Plant J., 40, 302-13.
209. Samanani, N., Park, S.-U., Facchini, P.J. (2005) Cell type-specific localisation of transcripts encoding nine consecutive enzymes involved in protoberberine alkaloid biosynthesis. Plant Cell, 17, 915-26.
210. Sato, F., Inai, K. and Hashimoto, T. (2007) Metabolic engineering in alkaloid biosynthesis: case studies in tyrosine and putrescine derived alkaloids, in Applications of Plant Metabolic Engineering (eds R. Verpoorte, A.W. Alfermann and T.S. Johnson). Springer, Heidelberg, pp. 145-73.
211. Schäfer, H. and Wink, M. (2009) Medicinally important secondary metabolites in recombinant microorganisms or plants: Progress in alkaloid biosynthesis. Biotechnological Journal 4, 1684-703.
212. Schiel, O., Witte, L. and Berlin, J. (1987) Geraniol-10-hydroxylase activity and its relation to monoterpene indole alkaloid accumulation in cell suspension cultures of Catharanthus roseus. Z. Naturforsch., 42c, 1075-81.
213. Schliemann,W., Steiner, U. and Strack, D. (1998) Betanidin formation from dihydroxyphenylalanine in a model assay system. Phytochemistry, 49, 1593-8.
214. Schliemann, W. and Strack, D. (1998) Intramolecular stabilization of acylated betacyanins. Phytochemistry, 49, 585-8.
215. Schmidt, D. and St öckigt, J. (1995) Enzymic formation of the sarpagan-bridge: a key step in the biosynthesis of sarpagine-ajmalicine-type alkaloids. Planta Med., 61, 254-8.
216. Schübel, H., Stöckigt, J., Feicht, R. and Simon, H. (1986) Partial purification and characterisation of raucaffricine β-D-glucosidase from plant cell suspension cultures of Rauwolfia serpentina Benth. Helv. Chim. Acta, 69, 538-47.
217. Schulthess, B.H. and Baumann, T.W. (1995) Stimulation of caffeine biosynthesis in suspensioncultured coffee cells and the in situ existence of 7-methylxanthosine. Phytochemistry, 38, 1381-6.
218. Schumacher, H.-M. and Zenk,M.H. (1988) Partial purification and characterization of dihydrobenzophenanthridine oxidase from Eschscholtzia californica cell suspension cultures. Plant Cell Rep., 7, 43-6.
219. Sciuto, S., Oriente,G. and Piattelli, M. (1972) Betanidin glucosylation in Opuntia dillenii. Phytochemistry, 11, 2259-62.
220. Sciuto, S., Oriente, G., Piattelli, M., Impellizzeri, G. and Amico, V. (1974) Biosynthesis of amaranthin in Celosia plumosa. Phytochemistry, 13, 947-51.
221. Seigler, D.S. (1998) Plant Secondary Metabolism. Kluwer, Norwell.
222. Shibuya, M., Chou, H.-M., Fountoulakis, M., Hassam, S., Kim, S.-U., Kobayashi, K., Otsuka, H., Rogalska, E., Cassady, J.M. and Floss, H.G. (1990) Stereochemistry of the isoprenylation of tryptophan catalysed by 4-(γ,γ-dimethylallyl)tryptophan synthase from Claviceps, the first pathway-specific enzyme in ergot alkaloid biosynthesis. J. Am. Chem. Soc., 112, 297-304.
223. Shoji, T., Winz, R., Iwase, T., Nakajima, K., Yamada, Y. and Hashimoto, T. (2002) Expression patterns of two tobacco isoflavone reductase-like genes and their possible roles in secondary metabolism of tobacco. Plant Mol. Biol., 50, 427-40.
224. Siminszky, B., Gavilano, L., Brown, S.W., Dewey, R.E. (2005) Conversion of nicotine to nornicotine in Nicotiana tabacum is mediated by CYP82E4, a cytochrome P450 mono-oxygenase. Proc. Natl. Acad. Sci. USA, 102, 14919-24.
225. Songstad, D.D., De Luca, V., Brisson, N., Kurz, W.G.W. and Nessler, C.L. (1990) High levels of tryptamine accumulation in transgenic tobacco expressing tryptophan decarboxylase. Plant Physiol., 94, 1410-3.
226. Stadler, R. and Zenk, M.H. (1990) A revision of the generally accepted pathway for the biosynthesis of tetrahydroisoquinoline alkaloid reticuline. Liebigs Ann. Chem., 555-62.
227. Stadler, R. and Zenk, M.H. (1993) The purification and characterization of a unique cytochrome P450 enzyme from Berberis stolonifera plant cell cultures. J. Biol. Chem., 268, 823-31.
228. Stafford,H.A. (1994) Anthocyanins and betalains: evolution of the mutually exclusive pathways. Plant Sci., 101, 91-8.
229. Steglich,W. and Strack, D. (1990) Betalains, in TheAlkaloids,Chemistry and Pharmacology (ed. A. Brossi). Academic Press, London, pp. 1-62.
230. Steiner, U., Schliemann, W. and Strack, D. (1996) Assay for tyrosine hydroxylation activity of tyrosinase frombetalain-forming plants and cell cultures. Anal. Biochem., 238, 72-5.
231. Steiner, U., Ahimsa-Muller, M. A., Markert, A., Kucht, S., Gross, J., Kauf, N., Kuzma, M., Zych, M., Lamshoft, M., Furmanowa, M., Knoop, V., Drewke, C. and Leistner, E. (2006) Molecular characterization of a seed transmitted clavicipitaceous fungus occurring on dicotyledoneous plants (Convolvulaceae). Planta, 224, 533-44.
232. Steiner, U., Schliemann, W., Böhm, H. and Strack, D. (1999) Tyrosinase involved in betalain biosynthesis of higher plants. Planta, 208, 114-24.
233. Stevens, L.H., Blom, T.J.M. and Verpoorte, R. (1993) Subcellular localisation of tryptophan decarboxylase, strictosidine synthase and strictosidine glucosidase in cell suspension cultures of Catharanthus roseus and Tabermaemontana divaricata. Plant Cell Rep., 12, 572-6.
234. Stierle, A., Strobel, G., Stierle, D. (1993) Taxol and taxane production by Taxomyces andreanae, an endophytic fungus of Pacific yew. Science, 260, 214-16.
235. Stobart, A.K. and Kinsman, L.T. (1977) The hormonal control of betacyanin synthesis in Amaranthus caudatus. Phytochemistry, 16, 1137-42.
236. St öckigt, J., Lansing, A., Falkenhagen, H., Endreb, S. and Ruyter, C.M. (1992) Plant cell cultures: a source of novel phytochemicals and enzymes, in Plant Tissue Culture and Gene Manipulation for Breeding and Formation of Phytochemicals (eds K. Oono, T. Hirabayashi, S. Kikuchi, H. Handa and K. Kajiwara). Niar, Japan, pp. 277-92.
237. St öckigt, J., Panjikar, S., Ruppert, M., Barleben, L., Ma, X., Loris, E. and Hill, M. (2007) Themolecular architecture of the major enzymes from ajmaline biosynthetic pathway. Phytochem. Rev., 6, 15-34.
238. St-Pierre, B. and De Luca, V. (1995) A cytochrome, P450 monooxygenase, catalyses the first step in the conversion of tabersonine to vindoline in Catharanthus roseus. Plant Physiol., 109, 131-9.
239. Strack, D., Marxen, N., Reznik, H. and Ihlenfeld, H.-D. (1990) Distribution of betacyanins and hydroxycinnamic acid-glucose esters in flowers of the Ruschieae. Phytochemistry, 29, 2175-8.
240. Strack, D., Steglich, W. and Wray, V. (1993) Betalains, in Methods in Plant Biochemistry (eds P.M. Dey and J.B. Harborne), Vol. 8, Alkaloids and Sulphur Compounds (ed. P.G. Waterman). Academic Press, London, pp. 421-50.
241. Strack, D. andWray, V. (1994a) Recent advances in betalain analysis, in Caryophyllales, Evolution and Systematics (eds H.-D. Behnke and T.J. Mabry). Springer-Verlag, Berlin Heidelberg, pp. 263-77.
242. Strack, D. and Wray, V. (1994b) The anthocyanins, in The Flavonoids, Advances in Research Since 1986 (ed. J.B. Harborne). Chapman & Hall, London, pp. 1-22.
243. Suzuki, K., Yamada, Y. and Hashimoto, T. (1999) Expression of Atropa belladonna putrescineN-methyltransferase gene in root pericycle. Plant Cell Physiol., 40, 289-97.
244. Takamura, Y., Matsushita, Y., Nagareya,N., Abe, M., Takaya, J., Juichi, M.,Hashimoto, T., Kan, Y., Takoaka, S., Asakawa, Y., Omura, M., Ito, C. and Furukawa, H. (1995) Citbismine-A, citbismine-B and citbismine-C, new binary acridone alkaloids from Citrus plants. Chem. Pharm. Bull., 43, 1340-5.
245. Teramoto, S. and Komamine, A. (1988) l-Dopa production in plant cell cultures, in Biotechnology in Agriculture and Forestry (ed. Y.P.S. Bajaj), Vol. 4, Medicinal and Aromatic Plants. Springer-Verlag, Berlin, pp. 209-24.
246. Terradas, F. and Wyler, H. (1991a) 2,3- and 4,5-Secodopa, the biosynthetic intermediates generated from L-Dopa by an enzyme system extracted from the fly agaric, Amanita muscaria L., and their spontaneous conversion to muscaflavin and betalamic acid, respectively, and betalains. Helv. Chim. Acta, 74, 124-40.
247. Terradas, F. and Wyler, H. (1991b) The seco-Dopas, natural pigments in Hygrocybe conica and Amanita muscaria. Phytochemistry, 30, 3251-3.
248. Teuber, M., Azemi, M.E., Namjoyan, F., Meier, A.-C., Wodak, A., Brandt, W. and Dräger, B. (2007) Putrescine N-methyltransferases - a structure-function analysis. Plant Mol. Biol., 63, 787-801.
249. Teusch, M., Forkmann, G. and Seyffert, W. (1987) Genetic control of hydroxycinnamoylcoenzyme A: anthocyanidin 3-glycoside-hydroxycinnamoyltransferases from petals of Matthiola incana. Phytochemistry, 26, 991-4.
250. Trezzini, G.F. (1990) Génétique des bétalaïnes chez Portulaca grandiora Hook. Doctoral Thesis, Lausanne.
251. Trezzini, G.F. and Zryd, J.-P. (1990) Portulaca grandiflora: a model system for the study of the biochemistry and genetics of betalain synthesis. Acta Hortic., 280, 581-5.
252. Tydzynski, P., Correia, T. and Keller, U. (2001) Biotechnology and genetics of ergot alkaloids. Appl. Microbiol. Biotechnol., 57, 593-605.
253. Uefuji, H., Ogita, S. Yamaguchi, Y. (2003) Molecular cloning and functional characterisation of three distinct N-methyltransferases involved in caffeine biosynthetic pathway in coffee plants. Plant Physiol., 132, 372-80.
254. Unterlinner, B., Lenz, R. and Kutchan, T.M. (1999) Molecular cloning and functional expression of codeinone reductase: the penultimate enzyme in morphine biosynthesis in opium poppy Papaver somniferum. Plant J., 18, 465-75.
255. Van Der Heijden, R., Jacobs, D.I., Snoeijer,W. (2004) The Catharanthus alkaloids. Pharmacognosy and biotechnoloy. Curr. Med. Chem., 11, 607-28.
256. van Wyk B.E. and Wink, M. (2004) Medicinal Plants of the World. BRIZA, Pretoria.
257. Vazquez-Flota, F. and De Luca, V. (1998) Jasmonatemodulates development and lightdependent alkaloid biosynthesis in Catharanthus roseus. Phytochemistry, 49, 395-402.
258. Vazquez-Flota, F., De Carolis, E., Alarco, A.-M. and De Luca, V. (1997) Molecular cloning and characterization of desacetoxyvindoline-4-hydroxylase, a 2-oxyglutarate-dependent dioxygenase involved in the biosynthesis of vindoline in Catharanthus roseus (L.) G. Don. Plant Mol. Biol., 34, 935-48.
259. Verpoorte, R., Alfermann, A.W. and Johnson, T.S. (2007) Applications of PlantMetabolic Engineering. Springer, Heidelberg.
260. Vogt, T., Zimmermann, E., Grimm, R., Meyer, M. and Strack, D. (1997) Are the characteristics of betanidin glucosyltransferases from cell-suspension cultures of Dorotheanthus bellidiformis indicative of their phylogenetic relationship with flavonoid glucosyltransferases? Planta, 203, 349-61.
261. Waldhauser, S.S.M. and Baumann, T.W. (1996) Compartmentation of caffeine and related purine alkaloid depends exclusively on the physical chemistry of their vacuolar complex formation with chlorogenic acids. Phytochemistry, 42, 985-96.
262. Waldhauser, S.S.M., Gillies, F.M., Crozier, A. and Baumann, T.W. (1997b) Separation of N-7-methyltransferase, the key enzyme of caffeine biosynthesis. Phytochemistry, 45, 1407-14.
263. Waldhauser, S.S.M., Kretschmar, J.A. and Baumann, T.W. (1997a)N-methyltransferase activities in caffeine biosynthesis: biochemical characterisation and time course during leaf development of Coffea arabica. Phytochemistry, 44, 853-9.
264. Walker, K. and Croteau, R. (2001) Taxol biosynthetic genes. Phytochemistry, 58, 1-7.
265. Walton, N.J. and Belshaw, N.J. (1988) The effect of cadaverine on the formation of anabasine from lysine in hairy root cultures of Nicotiana hesperis. Plant Cell Rep., 7, 115-8.
266. Walton, N.J., Robins, R.J. and Rhodes, M.J.C. (1988) Perturbation of alkaloid production by cadaverine in hairy root cultures of Nicotiana rustica. Plant Sci., 54, 125-31.
267. Walton, N.J., Peerless, A.C.J., Robins, R.J., Rhodes, M.J.C., Boswell, H.D. and Robins, D.J. (1994) Purification and properties of putrescine N-methyltransferase from transformed roots of Datura stramonium (L.). Planta, 193, 9-15.
268. Weid,M., Ziegler, J. andKutchan, T.M. (2004) The role of latex and the vascular bundle in morphine biosynthesis in the opium poppy, Papaver somniferum. Proc. Natl. Acad. Sci. USA, 101, 13957-4962.
269. Wildi, E. and Wink, M. (2002) Biotechnology potential of hairy root culture, in Recent Progress in Medicinal plants, Vol. 4, Biotechnology and Genetic Engineering (eds J.N. Govil, P. Ananda Kumar and V.K. Singh). Sci Tech Pub. Raleigh, USA, pp. 441-54.
270. Wilhelm, R. and Zenk, M.H. (1997) Biotransformation of thebaine by cell cultures of Papaver somniferum and Mahonia nervosa. Phytochemistry, 46, 701-8.
271. Wink,M. (1989) Genes of secondarymetabolism: differential expression in plants and in vitro cultures and functional expression in genetically transformed microorganisms, in Primary and Secondary Metabolism of Plant Cell Cultures (ed. W.G.W. Kurz). Springer-Verlag, Berlin, pp. 239-51.
272. Wink, M. (1993) Allelochemical properties and the raison d'etre of alkaloids, in The Alkaloids (ed. G. Cordell), Vol. 43. Academic Press, Orlando pp. 1-118.
273. Wink, M. (2000) Interference of alkaloids with neuroreceptors and ion channels, in Bioactive Natural Products (ed. Atta-Ur-Rahman), Vol. 11. Elsevier, Amsterdam, pp. 3-129.
274. Wink,M. (2007) Molecularmodes of action of cytotoxic alkaloids - from DNA intercalation, spindle poisoning, topoisomerase inhibition to apoptosis and multiple drug resistance, in The Alkaloids (ed. G. Cordell), Vol. 64. Elsevier, Amsterdam, pp. 1-48.
275. Wink, M. (2008) Ecological roles of alkaloids, in Modern Alkaloids (eds E. Fattorusso and O. Taglialatela-Scafati).Wiley-VCH, Weinheim, pp. 3-24.
276. Wink, M. (2010) Annual Plant Reviews, Vol. 39: Functions and Biotechnology of Plant Secondary Metabolites, 2nd ed.Wiley-Blackwell, Oxford.
277. Wink,M. and Roberts, M.F. (1998) Compartmentation of alkaloid synthesis, transport and storage, in Alkaloids: Biochemistry, Ecology and Medical Applications (eds M.F. Roberts and M. Wink). Plenum, New York, pp. 239-62.
278. Wu, S. and Chappell, J. (2008) Metabolic engineering of natural products in plants; tools of the trade and challenges for the future. Curr. Opin. Biotechnol., 19, 145-52.
279. Wyler, H., Mabry, T.J. and Dreiding, A.S. (1963) Über die konstitution des randenfarbstoffes betanin: zur struktur des betanidins. Helv. Chim. Acta, 46, 1745-8.
280. Wyler, H., Meuer, U., Bauer, J. and Stravs-Mombelli, L. (1984) Cyclodopa glucoside ( = (2S)-5-(β-D-glucopyranosyloxy)-6-hydroxyindoline-2-carboxylic acid) and its occurrence in red beet (Beta vulgaris var. rubra L.). Helv. Chim. Acta, 67, 1348-55.
281. Yun, D.-J., Hashimoto, T. and Yamada, Y. (1993) Expression of hyoscyamine 6′-hydroxylase gene in transgenic tobacco. Biosci. Biotech. Biochem., 57, 502-3.
282. Zenk, M.H. (1989) Biosynthesis of alkaloids using plant cell cultures. Rec. Adv. Phytochem., 23, 429-57.
283. Zenk,M.H. (1990) Plant cell culture: a potential in food biotechnology. Food Biotechnol., 4, 461-70.
284. Zenk,M.H. (1995) Chasing the enzymes of biosynthesis, in Organic Reactivity: Physical and Biological Aspects. (eds B.T. Golding, R.J. Griffin and H. Maskill) The Royal Society of Chemistry, London, UK, pp. 89-109.
285. Zenk, M.H., Gerardy, R. and Stadler, R. (1995) Phenol oxidative coupling of benzylisoquinoline alkaloids is catalyzed by regio- and stereo-selective cytochrome P450 linked plant enzymes: salutaridine and berbamunine. J. Chem. Soc. Chem. Commun., pp. 1725-27.
286. Zenk,M.H. and Juenger,M. (2007) Evolution and current status of the phytochemistry of nitrogenous compounds. Phytochemistry, 68, 2757-72.
287. Zhang, L., Ding, R., Chai, Y., Bonfill, M., Oksman-Caldentey, K.-M., Xu, T., Pi, Y., Wang, Z., Zhang, H., Kai, G., Liao, Z., Sun, X. and Tang, K. (2004) Engineering tropane biosynthetic pathway in Hyoscyamus niger hairy root cultures. Proc. Natl. Acad. Sci. USA, 101, 6786-91.
288. Ziegler, J. and Facchini, P.J. (2008) Alkaloid biosynthesis: metabolism and trafficking. Annu. Rev. Plant Biol., 59, 735-69.
289. Ziegler, J. Voegtländer, S., Schmidt, J., Kramell, R.,Miersch, O., Ammer, C., Gesell, A. and Kutchan, T.M. (2006) Comparative transcript and alkaloid profiling in Papaver species identifies a short chain dehydrogenase/reductase involved in morphine biosynthesis. Plant. J., 48, 177-92.
290. Zont, J. and Amrhein, N. (1992) Inhibitors of phenylalanine ammonia-lyase: 2-aminoindan-2-phosphonic acid and related compounds. Liebigs Ann. Chem., 625-8.