The Enzyme Database

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EC 1.3.1.107     
Accepted name: sanguinarine reductase
Reaction: (1) dihydrosanguinarine + NAD(P)+ = sanguinarine + NAD(P)H + H+
(2) dihydrochelirubine + NAD(P)+ = chelirubine + NAD(P)H + H+
For diagram of chelirubine, macarpine and sanguinarine biosynthesis, click here
Glossary: sanguinarine = 13-methyl-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4′,5′:4,5]benzo[1,2-c]phenanthridinium
dihydrosanguinarine = 13-methyl-13,14-dihydro-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4′,5′:4,5]benzo[1,2-c]phenanthridine
chelirubine = 5-methoxy-13-methyl-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4′,5′:4,5]benzo[1,2-c]phenanthridinium
dihydrochelirubine = 5-methoxy-13-methyl-13,14-dihydro-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4′,5′:4,5]benzo[1,2-c]phenanthridinium
Systematic name: dihydrosanguinarine:NAD(P)+ oxidoreductase
Comments: The enzyme, purified from the California poppy (Eschscholzia californica), is involved in detoxifying the phytoalexin sanguinarine produced by poppy itself (cf. EC 1.5.3.12, dihydrobenzophenanthridine oxidase), when it binds to the cell wall of the poppy cell. The reaction with NADPH is up to three times faster than that with NADH at low concentrations (<10 uM) of the dinucleotide. At higher concentrations the reaction with NADPH is inhibited but not that with NADH [1].
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Weiss, D., Baumert, A., Vogel, M. and Roos, W. Sanguinarine reductase, a key enzyme of benzophenanthridine detoxification. Plant Cell Environ. 29 (2006) 291–302. [DOI] [PMID: 17080644]
2.  Vogel, M., Lawson, M., Sippl, W., Conrad, U. and Roos, W. Structure and mechanism of sanguinarine reductase, an enzyme of alkaloid detoxification. J. Biol. Chem. 285 (2010) 18397–18406. [DOI] [PMID: 20378534]
[EC 1.3.1.107 created 2014]
 
 
EC 1.5.3.12     
Accepted name: dihydrobenzophenanthridine oxidase
Reaction: (1) dihydrosanguinarine + O2 = sanguinarine + H2O2
(2) dihydrochelirubine + O2 = chelirubine + H2O2
(3) dihydromacarpine + O2 = macarpine + H2O2
For diagram of chelirubine, macarpine and sanguinarine biosynthesis, click here
Systematic name: dihydrobenzophenanthridine:oxygen oxidoreductase
Comments: A CuII enzyme found in higher plants that produces oxidized forms of the benzophenanthridine alkaloids
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 114051-83-1
References:
1.  Schumacher, H.-M. and Zenk, M.H. Partial purification and characterization of dihydrobenzophenanthridine oxidase from Eschscholtzia tenuifolia cell suspension cultures. Plant Cell Reports 7 (1988) 43–46. [PMID: 24241413]
2.  Arakawa, H., Clark, W.G. , Psenak. M. and Coscia, C.J. Purification and characterization of dihydrobenzophenanthridine oxidase from elicited Sanguinaria canadensis cell cultures. Arch. Biochem. Biophys. 299 (1992) 1–7. [DOI] [PMID: 1444440]
[EC 1.5.3.12 created 1999]
 
 
EC 1.14.13.56      
Transferred entry: dihydrosanguinarine 10-monooxygenase. Now EC 1.14.14.100, dihydrosanguinarine 10-monooxygenase
[EC 1.14.13.56 created 1999, deleted 2018]
 
 
EC 1.14.13.57      
Transferred entry: dihydrochelirubine 12-monooxygenase. Now EC 1.14.14.101, dihydrochelirubine 12-monooxygenase
[EC 1.14.13.57 created 1999, deleted 2018]
 
 
EC 1.14.14.100     
Accepted name: dihydrosanguinarine 10-monooxygenase
Reaction: dihydrosanguinarine + [reduced NADPH—hemoprotein reductase] + O2 = 10-hydroxydihydrosanguinarine + [oxidized NADPH—hemoprotein reductase] + H2O
For diagram of chelirubine, macarpine and sanguinarine biosynthesis, click here
Other name(s): dihydrosanguinarine 10-hydroxylase
Systematic name: dihydrosanguinarine,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (10-hydroxylating)
Comments: A cytochrome P-450 (heme-thiolate) protein involved in benzophenanthridine alkaloid synthesis in higher plants.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 144388-41-0
References:
1.  De-Eknamkul, W., Tanahashi, T. and Zenk, M.H. Enzymic 10-hydroxylation and 10-O-methylation of dihydrosanguinarine in dihydrochelirubine formation by Eschscholtzia. Phytochemistry 31 (1992) 2713–2717.
[EC 1.14.14.100 created 1999 as EC 1.14.13.56, transferred 2018 to EC 1.14.14.100]
 
 
EC 1.14.14.101     
Accepted name: dihydrochelirubine 12-monooxygenase
Reaction: dihydrochelirubine + [reduced NADPH—hemoprotein reductase] + O2 = 12-hydroxydihydrochelirubine + [oxidized NADPH—hemoprotein reductase] + H2O
For diagram of chelirubine, macarpine and sanguinarine biosynthesis, click here
Other name(s): dihydrochelirubine 12-hydroxylase
Systematic name: dihydrochelirubine,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (12-hydroxylating)
Comments: A cytochrome P-450 (heme-thiolate) protein from the plant Thalictrum bulgaricum.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 158736-41-5
References:
1.  Kammerer, L., De-Eknamkul, W. and Zenk, M.H. Enzymic 12-hydroxylation and 12-O-methylation of dihydrochelirubine in dihydromacarpine formation by Thalictrum bulgaricum. Phytochemistry 36 (1994) 1409–1416.
[EC 1.14.14.101 created 1999 as EC 1.14.13.57, transferred 2018 to EC 1.14.14.101]
 
 
EC 2.1.1.119     
Accepted name: 10-hydroxydihydrosanguinarine 10-O-methyltransferase
Reaction: S-adenosyl-L-methionine + 10-hydroxydihydrosanguinarine = S-adenosyl-L-homocysteine + dihydrochelirubine
For diagram of chelirubine, macarpine and sanguinarine biosynthesis, click here
Systematic name: S-adenosyl-L-methionine:10-hydroxydihydrosanguinarine 10-O-methyltransferase
Comments: This reaction is part of the pathway for synthesis of benzophenanthridine alkaloids in plants.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 144388-39-6
References:
1.  De-Eknamkul, W., Tanahashi, T. and Zenk, M.H. Enzymic 10-hydroxylation and 10-O-methylation of dihydrosanguinarine in dihydrochelirubine formation by Eschscholtzia. Phytochemistry 31 (1992) 2713–2717.
[EC 2.1.1.119 created 1999]
 
 
EC 2.1.1.120     
Accepted name: 12-hydroxydihydrochelirubine 12-O-methyltransferase
Reaction: S-adenosyl-L-methionine + 12-hydroxydihydrochelirubine = S-adenosyl-L-homocysteine + dihydromacarpine
For diagram of chelirubine, macarpine and sanguinarine biosynthesis, click here
Systematic name: S-adenosyl-L-methionine:12-hydroxydihydrochelirubine 12-O-methyltransferase
Comments: This reaction is part of the pathway for synthesis of benzophenanthridine alkaloid macarpine in plants.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 158736-40-4
References:
1.  Kammerer, L., De-Eknamkul, W. and Zenk, M.H. Enzymic 12-hydroxylation and 12-O-methylation of dihydrochelirubine in dihydromacarpine formation by Thalictrum bulgaricum. Phytochemistry 36 (1994) 1409–1416.
[EC 2.1.1.120 created 1999]
 
 


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