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  • Aharoni, A., Giri, A.P., Verstappen, F.W., Bertea, C.M., Sevenier, R., Sun, Z., Jongsma, M.A., Schwab, W. and Bouwmeester, H.J. (2004) Gain and loss of fruit flavor compounds produced by wild and cultivated strawberry species. Plant Cell, 16, 31103131.
  • Ausubel, F.M. (1987) Current Protocols in Molecular Biology. New York: New York Green Publications, Associates and Wiley-Interscience.
  • Bomati, E.K., Austin, M.B., Bowman, M.E., Dixon, R.A. and Noel, J.P. (2005) Structural elucidation of chalcone reductase and implications for deoxychalcone biosynthesis. J. Biol. Chem. 280, 3049630503.
  • Bradford, M.M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248254.
  • Chen, F., Tholl, D., D'Auria, J.C., Farooq, A., Pichersky, E. and Gershenzon, J. (2003) Biosynthesis and emission of terpenoid volatiles from Arabidopsis flowers. Plant Cell, 15, 48194.
  • Choi, K.B., Morishige, T., Shitan, N., Yazaki, K. and Sato, F. (2002) Molecular cloning and characterization of coclaurine N-methyltransferase from cultured cells of Coptis japonica. J. Biol. Chem. 277, 830835.
  • Davis, E.M., Ringer, K.L., McConkey, M.E. and Croteau, R. (2005) Monoterpene metabolism. Cloning, expression, and characterization of menthone reductases from peppermint. Plant Physiol. 137, 873881.
  • De-Eknamkul, W. and Zenk, M.H. (1992) Purification and properties of 1,2-dehydroreticuline reductase from Papaver somniferum seedlings. Phytochemisty, 31, 813821.
  • 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, 99699973.
  • Eisen, M.B., Spellman, P.T., Brown, P.O. and Botstein, D. (1998) Cluster analysis and display of genome-wide expression patterns. Proc. Natl Acad. Sci. USA 95, 1486314868.
  • 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, 2668426690.
  • Facchini, P.J. and Park, S.U. (2003) Developmental and inducible accumulation of gene transcripts involved in alkaloid biosynthesis in opium poppy. Phytochemistry, 64, 177186.
  • Filling, C., Berndt, K.D., Benach, J., Knapp, S., Prozorovski, T., Nordling, E., Ladenstein, R., Jörnvall, H. and Oppermann, U. (2002) Critical residues for structure and catalysis in short-chain dehydrogenases/reductases. J. Biol. Chem. 277, 2567725684.
  • Frick, S. and Kutchan, T.M. (1999) Molecular cloning and functional expression of O-methyltransferases common to isoquinoline alkaloid and phenylpropanoid biosynthesis. Plant J. 17, 329339.
  • Fridman, E. and Pichersky, E. (2005) Metabolomics, genomics, proteomics, and the identification of enzymes and their substrates and products. Curr. Opin. Plant. Biol. 8, 242248.
  • Fridman, E., Wang, J., Iijima, Y., Froehlich, J.E., Gang, D.R., Ohlrogge, J. and Pichersky, E. (2005) Metabolic, genomic, and biochemical analyses of glandular trichomes from the wild tomato species Lycopersicon hirsutum identify a key enzyme in the biosynthesis of methylketones. Plant Cell, 17, 12521267.
  • Gang, D.R., Lavid, N., Zubieta, C., Chen, F., Beuerle, T., Lewinsohn, E., Noel, J.P. and Pichersky, E. (2002) Characterization of phenylpropene O-methyltransferases from sweet basil: facile change of substrate specificity and convergent evolution within a plant O-methyltransferase family. Plant Cell, 14, 505519.
  • Gerardy, R. and Zenk, M.H. (1992) Formation of salutaridine from (R)-reticuline by a membrane-bound cytochrome P-450 enzyme from Papaver somniferum. Phytochemistry, 32, 7986.
  • Gerardy, R. and Zenk, M.H. (1993) Purification and characterization of salutaridine: NADPH 7-oxidoreductase from Papaver somniferum. Phytochemistry, 34, 125132.
  • Ghosh, D., Sawicki, M., Pletnev, V., Erman, M., Ohno, S., Nakajin, S. and Duax, W.L. (2001) Porcine carbonyl reductase. structural basis for a functional monomer in short chain dehydrogenases/reductases. J. Biol. Chem. 276, 1845718463.
  • Grothe, T., Lenz, R. and Kutchan, T.M. (2001) Molecular characterization of the salutaridinol 7-O-acetyltransferase involved in morphine biosynthesis in opium poppy Papaver somniferum. J. Biol. Chem. 276, 3071730723.
  • Guterman, I., Shalit, M., Menda, N. et al. (2002) Rose scent: genomics approach to discovering novel floral fragrance-related genes. Plant Cell, 14, 23252338.
  • Hirata, K., Poeaknapo, C., Schmidt, J. and Zenk, M.H. (2004) 1,2-Dehydroreticuline synthase, the branch point enzyme opening the morphinan biosynthetic pathway. Phytochemistry, 65, 10391046.
  • Huang, F.C. and Kutchan, T.M. (2000) Distribution of morphinan and benzophenanthridine alkaloid gene transcript accumulation in the opium poppy Papaver somniferum. Phytochemistry, 53, 555564.
  • Iijima, Y., Davidovich-Rikanati, R., Fridman, E., Gang, D.R., Bar, E., Lewinsohn, E. and Pichersky, E. (2004) The biochemical and molecular basis for the divergent patterns in the biosynthesis of terpenes and phenylpropenes in the peltate glands of three cultivars of basil. Plant Physiol. 136, 37243736.
  • Ikezawa, N., Tanaka, M., Nagayoshi, M., Shinkyo, R., Sakaki, T., Inouye, K. and Sato, F. (2003) Molecular cloning and characterization of CYP719, a methylenedioxy bridge-forming enzyme that belongs to a novel P450 family, from cultured Coptis japonica cells. J. Biol. Chem. 278, 3855738565.
  • Jörnvall, H., Persson, B., Krook, M., Atrian, S., Gonzàlez-Duarte, R., Jeffery, J. and Ghosh, D. (1995) Short-chain dehydrogenases/reductases (SDR). Biochemistry, 34, 60036013.
  • Jörnvall, H., Höög, J.O. and Persson, B. (1999) SDR and MDR: completed genome sequences show these protein families to be large, of old origin, and of complex nature. FEBS Lett. 445, 261264.
  • Kutchan, T.M. (1998) Molecular genetics of plant alkaloid biosynthesis. In The Alkaloids, Vol. 50 (Cordell, G., ed.). San Diego: Academic Press, pp. 257316.
  • Kutchan, T.M., Frick, S. and Weid, M. (2006) Engineering plant alkaloid biosynthetic pathways – progress and prospects. In Advances in Plant Biochemistry and Molecular Biology, Vol. 1 (Nes, W.D. and Lewis, N.G., eds). Bioengineering and Molecular Biology of Plant Pathways (Bohnert, H.J. and Nguyen, H.T., eds). Oxford: Elsevier Science Ltd. (In press).
  • Laemmli, U.K. (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature, 227, 680685.
  • Lavid, N., Wang, J., Shalit, M. et al. (2002) O-methyltransferases involved in the biosynthesis of volatile phenolic derivatives in rose petals. Plant Physiol. 129, 189918907.
  • Lenz, R. and Zenk, M.H. (1995a) Acetyl coenzyme A:salutaridinol-7-O-acteyltransferase from Papaver somniferum plant cell cultures. J. Biol. Chem. 270, 3109131096.
  • Lenz, R. and Zenk, M.H. (1995b) Purification and properties of codeinone reductase (NADPH) from Papaver somniferum cell cultures and differentiated plants. Eur. J. Biochem. 233, 132139.
  • Millgate, A.G., Pogson, B.J., Wilson, I.W., Kutchan, T.M., Zenk, M.H., Gerlach, W.L., Fist, A.J. and Larkin, P.J. (2004) Morphine-pathway block in top1 poppies. Nature, 431, 413414.
  • Morishige, T., Tsujita, T., Yamada, Y. and Sato, F. (2000) Molecular characterization of the S-adenosyl-l-methionine: 3′-hydroxy-N-methylcoclaurine 4′-O-methyltransferase involved in isoquinoline alkaloid biosynthesis in Coptis japonica. J. Biol. Chem. 275, 2339823405.
  • Morishige, T., Dubouzet, E., Choi, K.B., Yazaki, K. and Sato, F. (2002) Molecular cloning of columbamine-O-methyltransferase from cultured Coptis japonica cells. Eur. J. Biochem. 269, 56595667.
  • Nakajima, K., Hashimoto, T. and Yamada, Y. (1993) Two tropinone reductases with different stereospecificities are short-chain dehydrogenases evolved from a common ancestor. Proc. Natl Acad. Sci. USA, 90, 95919595.
  • Nakajima, K., Oshita, Y., Kaya, M., Yamada, Y. and Hashimoto, T. (1999) Structures and expression patterns of two tropinone reductase genes from Hyoscyamus niger. Biosci. Biotechnol. Biochem. 63, 17561764.
  • Nessler, C.L. and Von Der Haar, R.A. (1990) Cloning and expression analysis of DNA sequences fort he major latex protein of opium poppy. Planta, 180, 487491.
  • Ounaroon, A., Decker, G., Schmidt, J., Lottspeich, F. and Kutchan, T.M. (2003) (R,S)-Reticuline 7-O-methyltransferase and (R,S)-norcoclaurine 6-O-methyltransferase of Papaver somniferum– cDNA cloning and characterization of methyl transfer enzymes of alkaloid biosynthesis in opium poppy. Plant J. 36, 808819.
  • Persson, B., Kallberg, Y., Oppermann, U. and Jörnvall, H. (2003) Coenzyme-based functional assignments of short-chain dehydrogenases/reductases (SDRs). Chem. Biol. Interact. 143–144, 271278.
  • Preininger, V. (1986) Chemotaxonomy of Papaveraceae and Fumariaceae. In The Alkaloids, Vol. 29 (Brossi, A., ed.). San Diego: Academic Press, pp. 198.
  • Raith, K., Neubert, R., Poeaknapo, C., Boettcher, C., Zenk, M.H. and Schmidt, J. (2003) Electrospray tandem mass spectrometric investigations of morphinans. J. Am. Soc. Mass Spectrom. 14, 12621269.
  • Ringer, K.L., McConkey, M.E., Davis, E.M., Rushing, G.W. and Croteau, R. (2003) Monoterpene double-bond reductases of the (−)-menthol biosynthetic pathway: isolation and characterization of cDNAs encoding (−)-isopiperitenone reductase and (+)-pulegone reductase of peppermint. Arch. Biochem. Biophys. 418, 8092.
  • Ringer, K.L., Davis, E.M. and Croteau, R. (2005) Monoterpene metabolism. Cloning, expression, and characterization of (−)-isopiperitenol/(−)-carveol dehydrogenase of peppermint and spearmint. Plant Physiol. 137, 863873.
  • Rönsch, H. (1986) Rhoeadine alkaloids. In The Alkaloids, Vol. 28 (Brossi, A., ed.). San Diego: Academic Press, pp. 193.
  • Samanani, N., Liscombe, D.K. and Facchini, P.J. (2004) Molecular cloning and characterization of norcoclaurine synthase, an enzyme catalyzing the first committed step in benzylisoquinoline alkaloid biosynthesis. Plant J. 40, 302313.
  • Sreenivasulu, N., Altschmied, L., Radchuk, V., Gubatz, S., Wobus, U. and Weschke, W. (2004) Transcript profiles and deduced changes of metabolic pathways in maternal and filial tissues of developing barley grains. Plant J. 37, 539553.
  • Takeshita, N., Fujiwara, H., Mimura, H., Fitchen, J., Yamada, Y. and Sato, F. (1995) Molecular cloning and characterization of S-adenosyl-l-methionine: scoulerine 9-O-methyltransferase from cultured cells of Coptis japonica. Plant Cell Physiol. 36, 2936.
  • Thompson, J.D., Higgins, D.G. and Gibson, T.J. (1994) CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res. 22, 46734680.
  • Unterlinner, B., Lenz, R. and Kutchan, T.M. (1999) Molecular cloning and functional expression of codeinone reductase: the penultimate enzyme in morphine biosynthesis in the opium poppy Papaver somniferum. Plant J. 18, 465475.
  • Xia, Z.Q., Costa, M.A., Pélissier, H.C., Davin, L.B. and Lewis, N.G. (2001) Secoisolariciresinol dehydrogenase purification, cloning, and functional expression. Implications for human health protection. J. Biol. Chem. 276, 1261412623.
  • Ziegler, J., Díaz-Chávez, M.L., Kramell, R., Ammer, C. and Kutchan, T.M. (2005) Comparative macroarray analysis of morphine containing Papaver somniferum and eight morphine free Papaver species identifies an O-methyltransferase involved in benzylisoquinoline biosynthesis. Planta, 222, 458471.