Berberine, bridge enzyme

The berberine bridge enzyme was purified to apparent electrophoretic homogeneity from elicited cell suspension cultures of E. califomica 2 Fifty... 

Fig. 10.2 Reaction catalyzed by the berberine bridge enzyme (BBE) along the biosynthetic pathway leading to protoberberine, berberine and benzo[c]phenanthridine alkaloids.

Fig. 10.8 Selected cDNAs isolated in recent years that encode enzymes involved in the biosynthesis of various classes of isoquinoline alkaloids. 6-OMT, norcoclaurine 6-0-methyltransferase 23 CYP80A1, berbamunine synthase 19 CYP80B1, (S)-A-methylcoclaurine 3 -hydroxylase 20 CPR, cytochrome P-450 reductase 29 4 -OMT, (5)-3 -hydroxy-A-methylcoclaurine 4 -0-methyltransferase 30 BBE, berberine bridge enzyme 12 SalAT, salutaridinol 7-O-acetyltransferase 28 COR, codeinone reductase.25...

STEFFENS, P., NAGAKURA, N., ZENK, M.H., Purification and characterization of the berberine bridge enzyme from Berberis beaniana cell cultures, Phytochemistry, 1985, 24, 2577-2583. 

DITTRICH, H., KUTCHAN, T.M., 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, 1991,88, 9969-9973. 

KUTCHAN, T.M., BOCK, A., DITTRICH, H., Heterologous expression of strictosidine synthase and berberine bridge enzyme in insect cell culture, Phytochemistry, 1994, 35, 353-360. 

KUTCHAN, T.M., DITTRICH, H., Characterization and mechanism of the berberine bridge enzyme, a covalently flavinylated oxidase of benzophenanthridine alkaloid biosynthesis in plants, J. Biol. Chem., 1995,270,24475-24481. 

BENZENE 1,2-DIOXYGENASE PHTHALATE DIOXYGENASE BENZOATE-CoA LIGASE BENZOATE 1,2-DI OXYGENASE BENZOYLFORMATE DECARBOXYLASE BERBERINE BRIDGE ENZYME BETA (j8)... 

Fig. 17 Sequential enzymatic formation of berberine from (S)-reticuline (BBE berberine bridge enzyme SOMT scoulerine O-methyltransferase THCOX tetrahydrocolumbamine oxidase COX columbamine oxidase)...

Fig. 18 Reconstructed isoquinoline alkaloid biosynthetic pathway in microbes (E. coli and S. cerevisiae) [120]. Accession numbers of the genes can be taken from Gene Bank. C3,4-DHPA-A 3,4-dihydroxyphenylacetaldehyde NCS norcoclaurine synthase 60MT 6-0-methyltransferase CNMT coclaurine-/V-mcthyltransferase 4 OMT 4 -0-methyltransferase BBE berberine bridge enzyme NMT /V-methyltransferase)...

Facchini, P.J., Penzes, C., Johnson, A.G., and Bull, D. 1996. Molecular characterization of berberine bridge enzyme genes from opium poppy. Plant Physiol 112 1669-1677. 

S)-Reticuline is a branch-point intermediate in the biosynthesis of most BAs. Most work has focused on branch pathways leading to the benzophenanthridine (e.g., sanguinarine), protoberberine (e.g., berberine), and morphinan (e.g., morphine and codeine) alkaloids.19 Most enzymes involved have been isolated, many have been purified, and four corresponding cDNAs have been cloned.19 The first committed step in benzophenanthridine and protoberberine alkaloid biosynthesis involves the conversion of (S)-reticuline to (5)-scoulerine by the berberine bridge enzyme (BBE) (Fig.7.2). BBE was purified from Berberis beaniana,20 corresponding cDNAs were cloned from E. californica and B. stolonifera,21 22 and BBE genes have been isolated from P. somniferum and E. californica.23,24... 

Figure 7.9 Intercellular and subcellular trafficking in alkaloid biosynthesis. A. Tropane alkaloid biosynthesis in Hyoscyamus muticus. B. Terpenoid indole alkaloid biosynthesis in Catharanthus roseus. C. Trafficking of the berberine bridge enzyme in Papaver somniferum cell cultures.

HAUSCHILD, K., PAULI, H.H., KUTCHAN, T.M., Isolation and analysis of a gene bbel encoding the berberine bridge enzyme from the California poppy Eschscholzia califomica. Plant Mol. Biol., 1998,36,473-478. 

PARK, S.-U., JOHNSON, A.G., PENZES-YOST, C FACCHINI, P.J., Analysis of promoters from tyrosine/dihydroxyphenylalanine decarboxylase and berberine bridge enzyme genes involved in benzylisoquinoline alkaloid biosynthesis in opium poppy. Plant Mol. Biol., 1999,40,121-131. 

BIRD, D.A., FACCHINI, P.J., Berberine bridge enzyme, a key branch-point enzyme in benzylisoquinoline alkaloid biosynthesis, contains a vacuolar-sorting determinant. Planta, 2001,213, 888-897. 

Figure 2.6 Biosynthesis of berberine from (5)-reticuline in Berberis species and Coptis japonica. BBE, berberine bridge enzyme SCMT, (5)-scoulerine-9-0-methyltransferase CAS, (5)-canadine synthase STOX, tetrahydroberberine oxidase COX, enzyme found in Coptis japonica.

Keywords chemotaxonomy patchy distribution biosynthesis genes horizontal gene transfer endophytes evolution tryptophan decarboxylase tyrosine decarboxylase phenylalanine ammonia-lyase chalcone synthase strictosidine synthase berberine bridge enzyme codeine reductase... 

Figure 7.17 Phyiogenetic reiationships in key enzymes of iater steps in SM pathways, based on amino acid sequences, (a) Chaicone synthase (CHS), (b) Strictosidine synthase (STS), (c) Berberine bridge enzyme (BBE). (d) Codeinone reductase (CR).

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