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Volumn 179, Issue 1, 1996, Pages 73-81

Heterologous expression of alkaloid biosynthetic genes - A review

Author keywords

Baculovirus; Benzophenanthridine alkaloids; Berbamunine synthase; Berberine bridge enzyme; Berberis stolonifera; Bisbenzylisoquinoline alkaloids; Eschscholtzia californica

Indexed keywords

ALKALOID; AROMATIC AMINO ACID; BERBERINE; BISBENZYLISOQUINOLINE ALKALOID; PLANT DNA; RECOMBINANT PROTEIN; SANGUINARINE; TYROSINE; VIRUS VECTOR;

EID: 0030574271     PISSN: 03781119     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-1119(96)00426-X     Document Type: Article
Times cited : (28)

References (43)
  • 1
    • 0001014908 scopus 로고
    • Intracellular compartmentation of two enzymes of berberine biosynthesis in plant cell cultures
    • Amann, M., Wanner, G. and Zenk, M.H. (1986) Intracellular compartmentation of two enzymes of berberine biosynthesis in plant cell cultures. Planta 167, 310-320.
    • (1986) Planta , vol.167 , pp. 310-320
    • Amann, M.1    Wanner, G.2    Zenk, M.H.3
  • 2
    • 0026457612 scopus 로고
    • Purification and characterization of dihydrobenzophenanthridine oxidase from elicited Sanguinaria canadensis cell cultures
    • 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.
    • (1992) Arch. Biochem. Biophys. , vol.299 , pp. 1-7
    • Arakawa, H.1    Clark, W.G.2    Psenak, M.3    Coscia, C.J.4
  • 3
    • 0028321453 scopus 로고
    • Cloning and analysis of a locus (mcr) involved in mitomycin C resistance in Streptomyces lavendulae
    • August, P.R., Flickinger, M.C. and Sherman, D.H. (1994) Cloning and analysis of a locus (mcr) involved in mitomycin C resistance in Streptomyces lavendulae. J. Bacteriol. 176, 4448-4454.
    • (1994) J. Bacteriol. , vol.176 , pp. 4448-4454
    • August, P.R.1    Flickinger, M.C.2    Sherman, D.H.3
  • 6
    • 37049041719 scopus 로고
    • Alkaloid biosynthesis. Part IV. 1-Benzylisoquinolines as precursors of thebaine, codeine and morphine
    • Battersby, A.R., Binks, R., Francis, R.J., McCaldin, D.J. and Ramuz, H. (1964) Alkaloid biosynthesis. Part IV. 1-Benzylisoquinolines as precursors of thebaine, codeine and morphine. J. Chem. Soc. Chem. Commun. 3600-3610.
    • (1964) J. Chem. Soc. Chem. Commun. , pp. 3600-3610
    • Battersby, A.R.1    Binks, R.2    Francis, R.J.3    McCaldin, D.J.4    Ramuz, H.5
  • 7
    • 37049138956 scopus 로고
    • Biosynthesis. Part XXII. The origin of chelidonine and of other alkaloids derived from the tetrahydroprotoberberine skeleton
    • Battersby, A.R., Staunton, J., Wiltshire, H.R., Francis, R.J. and Southgate, R.J. (1975) Biosynthesis. Part XXII. The origin of chelidonine and of other alkaloids derived from the tetrahydroprotoberberine skeleton. J. Chem. Soc. Perkin Trans. I, 1147-1156.
    • (1975) J. Chem. Soc. Perkin Trans. I , pp. 1147-1156
    • Battersby, A.R.1    Staunton, J.2    Wiltshire, H.R.3    Francis, R.J.4    Southgate, R.J.5
  • 10
    • 0023410567 scopus 로고
    • 6-Hydroxy-D-nicotine oxidase of Arthrobacter oxidans. Gene structure of the flavoenzyme and its relationship to 6-hydroxy-L-nicotine oxidase
    • Brandsch, R., Hinkkanen, A.E., Mauch, L., Nagursky, H. and Decker, K. (1987) 6-Hydroxy-D-nicotine oxidase of Arthrobacter oxidans. Gene structure of the flavoenzyme and its relationship to 6-hydroxy-L-nicotine oxidase. Eur. J. Biochem. 167, 315-320.
    • (1987) Eur. J. Biochem. , vol.167 , pp. 315-320
    • Brandsch, R.1    Hinkkanen, A.E.2    Mauch, L.3    Nagursky, H.4    Decker, K.5
  • 11
    • 0000927312 scopus 로고
    • Bisbenzylisoquinoline alkaloids in Berberis cell cultures
    • Cassels, B.K., Breitmaier, E. and Zenk, M.H. (1987) Bisbenzylisoquinoline alkaloids in Berberis cell cultures. Phytochemistry 26, 1005-1008.
    • (1987) Phytochemistry , vol.26 , pp. 1005-1008
    • Cassels, B.K.1    Breitmaier, E.2    Zenk, M.H.3
  • 12
    • 84907109577 scopus 로고
    • Therapeutic potential of Eschscholtziae californicae herba
    • Cheney, R.H. (1964) Therapeutic potential of Eschscholtziae californicae herba. Quart. J. Crud. Drugs 3, 413-416.
    • (1964) Quart. J. Crud. Drugs , vol.3 , pp. 413-416
    • Cheney, R.H.1
  • 13
    • 0000867274 scopus 로고
    • Stimulation of sanguinarine production by combined fungal elicitation and hormonal deprivation in cell suspension cultures of Papaver bracteatum
    • Cline, S.D. and Coscia, C.J. (1988) Stimulation of sanguinarine production by combined fungal elicitation and hormonal deprivation in cell suspension cultures of Papaver bracteatum. Plant Physiol. 86, 161-165.
    • (1988) Plant Physiol. , vol.86 , pp. 161-165
    • Cline, S.D.1    Coscia, C.J.2
  • 14
    • 0025751609 scopus 로고
    • 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
    • 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, 9969-9973.
    • (1991) Proc. Natl. Acad. Sci. USA , vol.88 , pp. 9969-9973
    • Dittrich, H.1    Kutchan, T.M.2
  • 15
    • 0021909905 scopus 로고
    • Comparative in vitro activity of sanguinarine against oral microbial isolates
    • Dzink, J.L. and Socransky, S.S. (1985) Comparative in vitro activity of sanguinarine against oral microbial isolates. Antimicrob. Agents Chemother. 27, 663-665.
    • (1985) Antimicrob. Agents Chemother. , vol.27 , pp. 663-665
    • Dzink, J.L.1    Socransky, S.S.2
  • 16
    • 0002555072 scopus 로고
    • Stimulation of sanguinarine accumulation in Papaver somniferum cell cultures by fungal elicitors
    • Eilert, U., Kurz W.G.W. and Constabel, F. (1985) Stimulation of sanguinarine accumulation in Papaver somniferum cell cultures by fungal elicitors. J. Plant Physiol. 119, 65-76.
    • (1985) J. Plant Physiol. , vol.119 , pp. 65-76
    • Eilert, U.1    Kurz, W.G.W.2    Constabel, F.3
  • 17
    • 0028125304 scopus 로고
    • Differential and tissue-specific expression of a gene family for tyrosine/dopa decarboxylase in opium poppy
    • Facchini, P. 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, 26684-26690.
    • (1994) J. Biol. Chem. , vol.269 , pp. 26684-26690
    • Facchini, P.1    De Luca, V.2
  • 18
    • 0001267967 scopus 로고
    • S-Adenosyl-L-methionine: 3′-hydroxy-N-methyl-(S)-coclaurine-4′-O-methyltransferase, a regio-and stereoselective enzyme of the (S)-reticuline pathway
    • Frenzel, T. and Zenk, M.H. (1990) S-Adenosyl-L-methionine: 3′-hydroxy-N-methyl-(S)-coclaurine-4′-O-methyltransferase, a regio-and stereoselective enzyme of the (S)-reticuline pathway. Phytochemistry 29, 3505-3511.
    • (1990) Phytochemistry , vol.29 , pp. 3505-3511
    • Frenzel, T.1    Zenk, M.H.2
  • 19
    • 0001180010 scopus 로고
    • Production of tropane alkaloids in genetically engineered root cultures
    • Hashimoto, T., Yun, D.-J. and Yamada, Y. (1993) Production of tropane alkaloids in genetically engineered root cultures. Phytochemistry 32, 713-718.
    • (1993) Phytochemistry , vol.32 , pp. 713-718
    • Hashimoto, T.1    Yun, D.-J.2    Yamada, Y.3
  • 20
    • 0023945555 scopus 로고
    • Isolation and sequence analysis of a complementary DNA encoding rat liver L-gulono-γ-lactone oxidase, a key enzyme for L-ascorbic acid biosynthesis
    • Koshizaka, T., Nishikimi, M., Ozawa, T. and Yagi, K. (1988) Isolation and sequence analysis of a complementary DNA encoding rat liver L-gulono-γ-lactone oxidase, a key enzyme for L-ascorbic acid biosynthesis. J. Biol. Chem. 263, 1619-1621.
    • (1988) J. Biol. Chem. , vol.263 , pp. 1619-1621
    • Koshizaka, T.1    Nishikimi, M.2    Ozawa, T.3    Yagi, K.4
  • 21
    • 0028928192 scopus 로고
    • Molecular cloning and heterologous expression of a cDNA encoding CYP80, a C-O phenol-coupling cytochrome P-450 from the higher plant Berberis stolonifera
    • Kraus, P.F.X. and Kutchan, T.M. (1995) Molecular cloning and heterologous expression of a cDNA encoding CYP80, a C-O phenol-coupling cytochrome P-450 from the higher plant Berberis stolonifera. Proc. Natl. Acad. Sci. USA 92, 2071-2075.
    • (1995) Proc. Natl. Acad. Sci. USA , vol.92 , pp. 2071-2075
    • Kraus, P.F.X.1    Kutchan, T.M.2
  • 22
    • 0028785275 scopus 로고
    • Characterization and mechanism of BBE, a covalently flavinylated oxidase of benzophenanthridine alkaloid biosynthesis in plants
    • Kutchan, T.M. and Dittrich, H. (1995) Characterization and mechanism of BBE, a covalently flavinylated oxidase of benzophenanthridine alkaloid biosynthesis in plants. J. Biol. Chem. 270, 24475-24481.
    • (1995) J. Biol. Chem. , vol.270 , pp. 24475-24481
    • Kutchan, T.M.1    Dittrich, H.2
  • 23
    • 0028083884 scopus 로고
    • Heterologous expression of the plant proteins strictosidine synthase and berberine bridge enzyme in insect cell culture
    • Kutchan, T.M., Bock, A. and Dittrich, H. (1994) Heterologous expression of the plant proteins strictosidine synthase and berberine bridge enzyme in insect cell culture. Phytochemistry 35, 353-360.
    • (1994) Phytochemistry , vol.35 , pp. 353-360
    • Kutchan, T.M.1    Bock, A.2    Dittrich, H.3
  • 25
    • 0030047722 scopus 로고    scopus 로고
    • Molecular analysis of a new member of the opium poppy tyrosine/3,4-dihydroxyphenylalanine decarboxylase gene family
    • Maldonado-Mendoza, I.E., López-Meyer, M., Galef, J.R., Burnett, R.J. and Nessler, C.L. (1996) Molecular analysis of a new member of the opium poppy tyrosine/3,4-dihydroxyphenylalanine decarboxylase gene family. Plant Physiol. 110, 43-49.
    • (1996) Plant Physiol. , vol.110 , pp. 43-49
    • Maldonado-Mendoza, I.E.1    López-Meyer, M.2    Galef, J.R.3    Burnett, R.J.4    Nessler, C.L.5
  • 26
    • 0025786893 scopus 로고
    • Molecular cloning of hyoscyamine 6β-hydroxylase, a 2-oxoglutarate-dependent dioxygenase, from cultured roots of Hyoscyaus niger
    • 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 Hyoscyaus niger. J. Biol. Chem. 266, 9460-9464.
    • (1991) J. Biol. Chem. , vol.266 , pp. 9460-9464
    • Matsuda, J.1    Okabe, S.2    Hashimoto, T.3    Yamada, Y.4
  • 27
    • 0016441957 scopus 로고
    • Conversion of reticuline into scoulerine by a cell free preparation from Macleaya microcarpa cell suspension cultures
    • Rink, E. and Böhm, H. (1975) Conversion of reticuline into scoulerine by a cell free preparation from Macleaya microcarpa cell suspension cultures. FEBS Lett. 49, 396-399.
    • (1975) FEBS Lett. , vol.49 , pp. 396-399
    • Rink, E.1    Böhm, H.2
  • 28
    • 0000982778 scopus 로고
    • Distant precursors of benzylisoquinoline alkaloids and their enzymatic formation
    • Rueffer, M. and Zenk, M.H. (1987a) Distant precursors of benzylisoquinoline alkaloids and their enzymatic formation. Z. Naturforsch. 42c, 319-332.
    • (1987) Z. Naturforsch. , vol.42 C , pp. 319-332
    • Rueffer, M.1    Zenk, M.H.2
  • 29
    • 0000369164 scopus 로고
    • Enzymatic formation of protopines by a microsomal cytochrome-P-450 system of Corydalis vaginans
    • Rueffer, M. and Zenk, M.H. (1987b) Enzymatic formation of protopines by a microsomal cytochrome-P-450 system of Corydalis vaginans. Tetrahedron Lett. 28, 5307-5310.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 5307-5310
    • Rueffer, M.1    Zenk, M.H.2
  • 30
    • 0001486125 scopus 로고
    • Partial purification of S-adenosyl-L-methionine: (S)-tetrahydroproto-berberine-cis-N-methyltransferase from suspension cultured cells of Eschscholtzia and Corydalis
    • Rueffer, M., Zumstein, G. and Zenk, M.H. (1990) Partial purification of S-adenosyl-L-methionine: (S)-tetrahydroproto-berberine-cis-N-methyltransferase from suspension cultured cells of Eschscholtzia and Corydalis. Photochemistry 29, 3727-3733.
    • (1990) Photochemistry , vol.29 , pp. 3727-3733
    • Rueffer, M.1    Zumstein, G.2    Zenk, M.H.3
  • 31
    • 0001828472 scopus 로고
    • Partial purification and characterization of dihydrobenzophenanthridine oxidase from Eschscholtzia californica cell suspension cultures
    • 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, 43-46.
    • (1988) Plant Cell Rep. , vol.7 , pp. 43-46
    • Schumacher, H.-M.1    Zenk, M.H.2
  • 32
    • 0001598073 scopus 로고
    • Elicitation of benzophenanthridine alkaloid synthesis in Eschscholtzia cell cultures
    • Schumacher, H.-M., Gundlach, H., Fiedler, F. and Zenk, M.H. (1987) Elicitation of benzophenanthridine alkaloid synthesis in Eschscholtzia cell cultures. Plant Cell Rep. 6, 410-413.
    • (1987) Plant Cell Rep. , vol.6 , pp. 410-413
    • Schumacher, H.-M.1    Gundlach, H.2    Fiedler, F.3    Zenk, M.H.4
  • 33
    • 0000848618 scopus 로고
    • Über die Alkaloide von drei Arten der Gattung Eschscholtzia und über die Konstitution des neuen Alkaloids Escholamin
    • Slavikova, L. and Slavik, J. (1966) Über die Alkaloide von drei Arten der Gattung Eschscholtzia und über die Konstitution des neuen Alkaloids Escholamin. Coll. Czech. Chem. Commun. 31, 3362-3372.
    • (1966) Coll. Czech. Chem. Commun. , vol.31 , pp. 3362-3372
    • Slavikova, L.1    Slavik, J.2
  • 34
    • 84986720789 scopus 로고
    • A revision of the generally accepted pathway for the biosynthesis of the benzyltetrahydroisoquinoline alkaloid reticuline
    • Stadler, R. and Zenk, M.H. (1990) A revision of the generally accepted pathway for the biosynthesis of the benzyltetrahydroisoquinoline alkaloid reticuline. Liebigs Ann. Chem. 555-562.
    • (1990) Liebigs Ann. Chem. , pp. 555-562
    • Stadler, R.1    Zenk, M.H.2
  • 35
    • 0027497440 scopus 로고
    • The purification and characterization of a unique cytochrome P-450 enzyme from Berberis stolonifera plant cell cultures
    • Stadler, R. and Zenk, M.H. (1993) The purification and characterization of a unique cytochrome P-450 enzyme from Berberis stolonifera plant cell cultures. J. Biol. Chem. 268, 823-831.
    • (1993) J. Biol. Chem. , vol.268 , pp. 823-831
    • Stadler, R.1    Zenk, M.H.2
  • 37
    • 0001322468 scopus 로고
    • (S)-Norcoclaurine is the central intermediate in benzylisoquinoline alkaloid biosynthesis
    • Stadler, R., Kutchan, T.M. and Zenk, M.H. (1989) (S)-Norcoclaurine is the central intermediate in benzylisoquinoline alkaloid biosynthesis. Phytochemistry 28, 1083-1086.
    • (1989) Phytochemistry , vol.28 , pp. 1083-1086
    • Stadler, R.1    Kutchan, T.M.2    Zenk, M.H.3
  • 38
    • 0000760039 scopus 로고
    • Purification and characterization of BBE from Berberis beaniana cell cultures
    • Steffens, P., Nagakura, N. and Zenk, M.H. (1985) Purification and characterization of BBE from Berberis beaniana cell cultures. Phytochemistry 24, 2577-2583.
    • (1985) Phytochemistry , vol.24 , pp. 2577-2583
    • Steffens, P.1    Nagakura, N.2    Zenk, M.H.3
  • 39
    • 0020581579 scopus 로고
    • Biosynthesis of benzophenanthridine alkaloids sanguinarine, chelirubine and macarpine
    • Takao, N., Kamigauchi, M. and Okada, M. (1983) Biosynthesis of benzophenanthridine alkaloids sanguinarine, chelirubine and macarpine. Helv. Chim. Acta 66, 473-484.
    • (1983) Helv. Chim. Acta , vol.66 , pp. 473-484
    • Takao, N.1    Kamigauchi, M.2    Okada, M.3
  • 40
    • 0000860639 scopus 로고
    • Elicitor induction and characterization of microsomal protopine-6-hydroxylase, the central enzyme in benzophenanthridine alkaloid biosynthesis
    • Tanahashi, T. and Zenk, M.H. (1990) Elicitor induction and characterization of microsomal protopine-6-hydroxylase, the central enzyme in benzophenanthridine alkaloid biosynthesis. Phytochemistry 29, 1113-1122.
    • (1990) Phytochemistry , vol.29 , pp. 1113-1122
    • Tanahashi, T.1    Zenk, M.H.2
  • 42
    • 0027078552 scopus 로고
    • Metabolic engineering of medicinal plants: Transgenic Atropa bellandonna with an improved alkaloid composition
    • Yun, D.-J., Hashimoto, T. and Yamada, Y. (1992) Metabolic engineering of medicinal plants: transgenic Atropa bellandonna with an improved alkaloid composition. Proc. Natl. Acad. Sci. USA 89, 11799-11803.
    • (1992) Proc. Natl. Acad. Sci. USA , vol.89 , pp. 11799-11803
    • Yun, D.-J.1    Hashimoto, T.2    Yamada, Y.3
  • 43
    • 0024845487 scopus 로고
    • Phenol oxidative coupling of benzylisoquinoline alkaloids is catalysed by regio-and stereo-selective cytochrome P-450 linked plant enzymes: Salutaridine and berbamunine
    • Zenk, M.H., Gerardy, R. and Stadler, R. (1989) Phenol oxidative coupling of benzylisoquinoline alkaloids is catalysed by regio-and stereo-selective cytochrome P-450 linked plant enzymes: salutaridine and berbamunine. J. Chem. Soc. Chem. Commun. 1725-1727.
    • (1989) J. Chem. Soc. Chem. Commun. , pp. 1725-1727
    • Zenk, M.H.1    Gerardy, R.2    Stadler, R.3


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