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  • Abdulrazzak, N., Pollet, B., Ehlting, J. et al. (2006) A coumaroyl-ester-3-hydroxylase insertion mutant reveals the existence of nonredundant meta-hydroxylation pathways and essential roles for phenolic precursors in cell expansion and plant growth. Plant Physiol. 140, 3048.
  • Anterola, A.M. and Lewis, N.G. (2002) Trends in lignin modification: a comprehensive analysis of the effects of genetic manipulations/mutations on lignification and vascular integrity. Phytochemistry, 61, 221294.
  • Beuerle, T. and Pichersky, E. (2002) Enzymatic synthesis and purification of aromatic coenzyme A esters. Anal. Biochem. 302, 305312.
  • Bourgaud, F., Hehn, A., Larbat, R., Doerper, S., Gontier, E., Kellner, S. and Matern, U. (2006) Biosynthesis of coumarins in plants: a major pathway still to be unravelled for cytochrome P450 enzymes. Phytochem. Rev. 5, 293308.
  • Britsch, L., Ruhnau-Brich, B. and Forkmann, G. (1992) Molecular cloning, sequence analysis, and in vitro expression of flavanone 3-β-hydroxylase from Petunia hybrida. J. Biol. Chem. 267, 53805387.
  • Brown, S.A. (1962) Biosynthesis of coumarin and herniarin in lavender. Science, 137, 977978.
  • Bugg, T.D.H. (2003) Dioxygenase enzymes: catalytic mechanisms and chemical models. Tetrahedron, 59, 70757101.
  • Carpinella, M.C., Ferrayoli, C.G. and Palacios, S.M. (2005) Antifungal synergistic effect of scopoletin, a hydroxycoumarin isolated from Melia azedarach L. fruits. J. Agric. Food. Chem. 53, 29222927.
  • Chong, J., Baltz, R., Schmitt, C., Beffa, R., Fritig, B. and Saindrenan, P. (2002) Downregulation of a pathogen-responsive tobacco UDP-Glc:phenylpropanoid glucosyltransferase reduces scopoletin glucoside accumulation, enhances oxidative stress, and weakens virus resistance. Plant Cell, 14, 10931107.
  • Clayden, J., Greeves, N., Warren, S. and Wothers, P. (2001) Organic Chemistry. New York: Oxford University Press.
  • Dmitriev, A., Tena, M. and Jorrin, J. (2003) Systemic acquired resistance in sunflower (Helianthus annuus L.). Tsitol. Genet. 37, 915 (in Russian).
  • Fritig, B., Hirth, L. and Ourisson, G. (1970) Biosynthesis of the coumarins: scopoletin formation in tobacco tissue cultures. Phytochemistry, 9, 19631975.
  • Gachon, C., Baltz, R. and Saindrenan, P. (2004) Over-expression of a scopoletin glucosyltransferase in Nicotiana tabacum leads to precocious lesion formation during the hypersensitive response to tobacco mosaic virus but does not affect virus resistance. Plant Mol. Biol. 54, 137146.
  • Gebhardt, Y., Witte, S., Forkmann, G., Lukačin, R., Matern, U. and Martens, S. (2005) Molecular evolution of flavonoid dioxygenases in the family Apiaceae. Phytochemistry, 66, 12731284.
  • Gee, K.R., Sun, W.-C., Bhalgat, M.K., Upson, R.H., Klaubert, D.H., Latham, K.A. and Hauglant, R.P. (1999) Fluorogenic substrates based on fluorinated umbelliferones for continuous assays of phosphatases and β-galactosidases. Anal. Biochem. 273, 4148.
  • Gestetner, B. and Conn, E.E. (1974) The 2-hydroxylation of trans-cinnamic acid by chloroplasts from Melilotus alba Desr. Arch. Biochem. Biophys. 163, 617624.
  • Goujon, T., Ferret, V., Mila, I., Pollet, B., Ruel, K., Burlat, V., Joseleau, J.-P., Barrière, Y., Lapierre, C. and Jouanin, L. (2003) Down-regulation of the AtCCR1 gene in Arabidopsis thaliana: effects on phenotype, lignins and cell wall degradability. Planta, 217, 218228.
  • Hamberger, B. and Hahlbrock, K. (2004) The 4-coumarate:CoA ligase gene family in Arabidopsis thaliana comprises one rare, sinapate-activating and three commonly occurring isoenzymes. Proc. Natl Acad. Sci. USA, 101, 22092214.
  • Hamerski, D. and Matern, U. (1988a) Biosynthesis of psoralens. Psoralen 5-monooxygenase activity from elicitor-treated Ammi majus cells. Eur. J. Biochem. 239, 263265.
  • Hamerski, D. and Matern, U. (1988b) Elicitor-induced biosynthesis of psoralens in Ammi majus L. suspension cultures. Microsomal conversion of demethylsuberosin into (+)-marmesin and psoralen. Eur. J. Biochem. 171, 369375.
  • Hashidoko, Y., Tanaka, T. and Tahara, S. (2001) Induction of 4-hydroxycinnamate decarboxylase in Klebsiella oxytoca cells exposed to substrates and non-substrate 4-hydroxycinnamate analogs. Biosci. Biotechnol. Biochem. 65, 26042612.
  • Haskins, F.A., Williams, L.G. and Gorz, H.J. (1964) Light-induced trans to cis conversion of β-d-glucosyl-O-hydroxycinnamic acid in Melilotus alba leaves. Plant Physiol. 39, 777781.
  • Kai, K., Shimizu, B., Mizutani, M., Watanabe, K. and Sakata, K. (2006) Accumulation of coumarins in Arabidopsis thaliana. Phytochemistry, 67, 379386.
  • Keating, G.J. and O’Kennedy, R. (1997) The chemistry and occurrence of coumarins. In Coumarins: Biology, Applications and Mode of Action (O’Kennedy, R. and Thornes, R.D., eds). Chichester: John Wiley & Sons, pp. 2366.
  • Kitamura, Y., Ikenaga, T., Ooe, Y., Hiraoka, N. and Mizukami, H. (1998) Induction of furanocoumarin biosynthesis in Glehnia littoralis cell suspension cultures by elicitor treatment. Phytochemistry, 48, 113117.
  • Kosuge, T. (1961) Studies on the identity of bound coumarin in sweet clover. Arch. Biochem. Biophys. 95, 211218.
  • Kühnl, T., Koch, U., Heller, W. and Wellmann, E. (1989) Elicitor induced S-adenosyl-l-methionine:caffeoyl-CoA 3-O-methyltransferase from carrot cell suspension cultures. Plant Sci. 60, 2125.
  • Lange, T., Kegler, C., Hedden, P., Phillips, A.L. and Graebe, J.E. (1997) Molecular characterisation of gibberellin 20-oxidases. Structure–function studies on recombinant enzymes and chimaeric proteins. Physiol. Plant. 100, 543549.
  • Larbat, R., Kellner, S., Specker, S., Hehn, A., Gontier, E., Hans, J., Bourgaud, F. and Matern, U. (2007) Molecular cloning and functional characterization of psoralen synthase, the first committed monooxygenase of furanocoumarin biosynthesis. J. Biol. Chem. 282, 542554.
  • Lester, D.R., Ross, J.J., Davies, P.J. and Reid, J.B. (1997) Mendel’s stem length gene (Le) encodes a gibberellin 3β-hydroxylase. Plant Cell, 9, 14351443.
  • Liu, Y.G., Mitsukawa, N., Oosumi, T. and Whittier, R.F. (1995) Efficient isolation and mapping of Arabidopsis thaliana T-DNA insert junctions by thermal asymmetric interlaced PCR. Plant J. 8, 457463.
  • Lukačin, R. and Britsch, L. (1997) Identification of strictly conserved histidine and arginine residues as part of the active site in Petunia hybrida flavanone 3β-hydroxylase. Eur. J. Biochem. 249, 748757.
  • Lukačin, R., Gröning, I., Pieper, U. and Matern, U. (2000) Site-directed mutagenesis of the active serine290 in flavanone 3β-hydroxylase from Petunia hybrida. Eur. J. Biochem. 267, 853860.
  • Matern, U. (1991) Coumarins and other phenylpropanoid compounds in the defense response of plant cells. Planta Med. 57, S15S20.
  • Matsuda, J., Okabe, S., Hashimoto, T. and Yamada, Y. (1991) Molecular cloning of hyoscyamine 6β-hydroxylase, a 2-oxoglutarate-dependent dioxygenase, from cultured roots of Hyoscyamus niger. J. Biol. Chem. 266, 94609464.
  • Maury, S., Geoffroy, P. and Legrand, M. (1999) Tobacco O-methyltransferases involved in phenylpropanoid metabolism. The different caffeoyl-coenzyme A/5-hydroxyferuloyl-coenzyme A 3/5-O-methyltransferase and caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase classes have distinct substrate specificities and expression patterns. Plant Physiol. 121, 215224.
  • Minamikawa, T., Akazawa, T. and Uritani, I. (1963) Analytical study of umbelliferone and scopoletin synthesis in sweet potato roots infected by Ceratocystis fimbriata. Plant Physiol. 38, 493497.
  • Murray, R.D.H. (1989) Coumarins. Nat. Prod. Rep. 6, 591624.
  • Nair, R.B., Bastress, K.L., Ruegger, M.O., Denault, J.W. and Chapple, C. (2004) The Arabidopsis thaliana REDUCED EPIDERMAL FLUORESCENCE1 gene encodes an aldehyde dehydrogenase involved in ferulic acid and sinapic acid biosynthesis. Plant Cell, 16, 544554.
  • Oba, K., Conn, E.E., Canut, H. and Boudet, A.M. (1981) Subcellular localization of 2-(β-d-glucosyloxy)-cinnamic acids and the related β-glucosidase in leaves of Melilotus alba Desr. Plant Physiol. 68, 13591363.
  • Pakusch, A.E., Kneusel, R.E. and Matern, U. (1989) S-Adenosyl-l-methionine:trans-caffeoyl-coenzyme A 3-O-methyltransferase from elicitor-treated parsley cell suspension cultures. Arch. Biochem. Biophys. 271, 488494.
  • Poulton, J.E., McRee, D.E. and Conn, E.E. (1980) Intercellular localization of two enzymes involved in coumarin biosynthesis in Melilotus alba. Plant Physiol. 65, 171175.
  • Que, L., Jr (2000) One motif – many different reactions. Nat. Struct. Biol. 7, 182184.
  • Ranjeva, R., Alibert, G. and Boudet, A.M. (1977) Metabolisme des composes phenoliques chez le Petunia. V. Utilisation de la phenylalanine par des chloroplastes isoles. Plant Sci. Lett. 10, 225234.
  • Saito, K., Kobayashi, M., Gong, Z., Tanaka, Y. and Yamazaki, M. (1999) Direct evidence for anthocyanidin synthase as a 2-oxoglutarate-dependent oxygenase: molecular cloning and functional expression of cDNA from a red form of Perilla frutescens. Plant J. 17, 181189.
  • Schoch, G., Goepfert, S., Morant, M., Hehn, A., Meyer, D., Ullmann, P. and Werck-Reichhart, D. (2001) CYP98A3 from Arabidopsis thaliana is a 3′-hydroxylase of phenolic esters, a missing link in the phenylpropanoid pathway. J. Biol. Chem. 276, 3656636574.
  • Sefkow, M. (2001) First efficient synthesis of chlorogenic acid. Eur. J. Org. Chem. 6, 11371141.
  • Shimizu, B., Miyagawa, H., Ueno, T., Sakata, K., Watanabe, K. and Ogawa, K. (2005) Morning glory systemically accumulates scopoletin and scopolin after interaction with Fusarium oxysporum. Z. Naturforsch. 60c, 8390.
  • Stanfill, S.B., Brown, C.R., Yan, X.J., Watson, C.H. and Ashley, D.L. (2007) Quantification of flavor-related compounds in the unburned contents of bidi and clove cigarettes. J. Agric. Food. Chem. 54, 85808588.
  • Stanjek, V. and Boland, W. (1998) Biosynthesis of angular furanocoumarins: mechanism and stereochemistry of the oxydative dealkylation of columbianetine to angelicin in Heracleum mantegazzianum (Apiaceae). Helv. Chim. Acta, 81, 15961607.
  • Stanjek, V., Miksch, M., Lueer, P., Matern, U. and Boland, W. (1999) Biosynthesis of psoralen: machanism of a cytochrome P450 catalyzed oxidative bond cleavage. Angew. Chem. 38, 400402.
  • Stanley, W.L. and Vannier, S.H. (1967) Psoralens and substituted coumarins from expressed oil of lime. Phytochemistry, 6, 585596.
  • Takaishi, K. (1968) Studies of the coumarin components in the leaves of cherry-tree. Yakugaku Zasshi, 88, 14671471 (in Japanese).
  • Tal, B. and Robeson, D.J. (1986) The metabolism of sunflower phytoalexins ayapin and scopoletin: plant–fungus interactions. Plant Physiol. 82, 167172.
  • Tietjen, K.G. and Matern, U. (1983) Differential response of cultured parsley cells to elicitors from two non-pathogenic strains of fungi. 2. Effects on enzyme activities. Eur. J. Biochem. 131, 409413.
  • Valle, T., López, J.L., Hernández, J.M. and Corchete, P. (1997) Antifungal activity of scopoletin and its differential accumulation in Ulmus pumila and Ulmus campestris cell suspension cultures infected with Ophiostoma ulmi spores. Plant Sci. 125, 97101.
  • Vazquez-Flota, F., Carolis, E.D., Alarco, A.-M. and Luca, V.D. (1997) Molecular cloning and characterization of desacetoxyvindoline-4-hydroxylase, a 2-oxoglutarate dependent-dioxygenase involved in the biosynthesis of vindoline in Catharanthus roseus (L.) G. Don. Plant Mol. Biol. 34, 935948.
  • Wakelyn, P.J., Stipanovic, R.D. and Bell, A.A. (1974) Identification of scopoletin in dried bract of the cotton plant. J. Agric. Food. Chem. 22, 567568.
  • Wilmouth, R.C., Turnbull, J.J., Welford, R.W.D., Clifton, I.J., Prescott, A.G. and Schofield, C.J. (2002) Structure and mechanism of anthocyanidin synthase from Arabidopsis thaliana. Structure, 10, 93103.
  • Zhong, R., Morrison, W.H., III, Negrel, J. and Ye, Z.H. (1998) Dual methylation pathways in lignin biosynthesis. Plant Cell, 10, 20332045.
  • Zhou, Q., Wintersteen, C.L. and Cadwallader, K.R. (2002) Identification and quantification of aroma-active components that contribute to the distinct malty flavor of buckwheat honey. J. Agric. Food. Chem. 50, 20162021.
  • Zobel, A.M. (1997) Coumarins in fruits and vegetables. In Phytochemistry of Fruits and Vegetables (Tomas-Barberan, F.A.A. and Robins, R.J., eds). Oxford: Clarendon Press, pp. 173203.