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MetaCyc Pathway: dehydroscoulerine biosynthesis
Inferred from experiment

Enzyme View:

Pathway diagram: dehydroscoulerine biosynthesis

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: protoberberine alkaloid biosynthesis, benzophenanthridine alkaloid biosynthesis

Superclasses: BiosynthesisSecondary Metabolites BiosynthesisNitrogen-Containing Secondary Compounds BiosynthesisAlkaloids BiosynthesisIsoquinoline and Benzylisoquinoline Alkaloids Biosynthesis

Some taxa known to possess this pathway include : Berberis, Berberis Wilsoniae, Eschscholzia californica, Papaver somniferum, Thalictrum flavum, Thalictrum flavum glaucum

Expected Taxonomic Range: Viridiplantae

Cytotoxic benzophenanthridine alkaloids are accumulated in certain species of Papaveraceae in response to pathogenic attack and, therefore, function as phytoalexins. Eschscholzia californica California poppy root cultures produce a variety of benzophenanthridine alkaloids, such as sanguinarine, chelirubine and macarpine, with potent biological activity [Park03c]. The accumulation of benzophenanthridine alkaloids and the enzyme activity during diseased states emphasizes the integral role of the berberine bridge enzyme in the plant response to pathogens [Dittrich91]. Several studies involving the introduction of sense and antisense construct of genes of benzophenanthridine alkaloid metabolism have helped in getting a clearer picture and thereby improve approaches to metabolic engineering of benzophenanthridine alkaloid pathways [Park02b].

Created 24-Sep-2009 by Pujar A, Boyce Thompson Institute


Dittrich91: Dittrich H, Kutchan TM (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 U S A 88(22);9969-73. PMID: 1946465

Park02b: Park SU, Yu M, Facchini PJ (2002). "Antisense RNA-mediated suppression of benzophenanthridine alkaloid biosynthesis in transgenic cell cultures of California poppy." Plant Physiol 128(2);696-706. PMID: 11842172

Park03c: Park SU, Yu M, Facchini PJ (2003). "Modulation of berberine bridge enzyme levels in transgenic root cultures of California poppy alters the accumulation of benzophenanthridine alkaloids." Plant Mol Biol 51(2);153-64. PMID: 12602874

Winkler09: Winkler A, Puhl M, Weber H, Kutchan TM, Gruber K, Macheroux P (2009). "Berberine bridge enzyme catalyzes the six electron oxidation of (S)-reticuline to dehydroscoulerine." Phytochemistry 70(9);1092-7. PMID: 19570558

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Hauschild98: Hauschild K, Pauli HH, Kutchan TM (1998). "Isolation and analysis of a gene bbe1 encoding the berberine bridge enzyme from the California poppy Eschscholzia californica." Plant Mol Biol 36(3);473-8. PMID: 9484487

Kutchan95: Kutchan TM, Dittrich H (1995). "Characterization and mechanism of the berberine bridge enzyme, a covalently flavinylated oxidase of benzophenanthridine alkaloid biosynthesis in plants." J Biol Chem 270(41);24475-81. PMID: 7592663

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Samanani05: Samanani N, Park SU, Facchini PJ (2005). "Cell type-specific localization of transcripts encoding nine consecutive enzymes involved in protoberberine alkaloid biosynthesis." Plant Cell 17(3);915-26. PMID: 15722473

Steffens85: Steffens, Paul, Nagakura, Naotaka, Zenk, Meinhart H. "Purification and characterization of the berberine bridge enzyme from Berberis beaniana cell culture." Phytochemistry, 1985, Vol 24 (11):2577-2583).

Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Wed May 4, 2016, biocyc13.