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+ |
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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] |
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[EC 1.3.1.107 created 2014] |
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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 |
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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] |
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[EC 1.5.3.12 created 1999] |
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EC
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1.14.13.56
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Transferred entry: | dihydrosanguinarine 10-monooxygenase. Now EC 1.14.14.100, dihydrosanguinarine 10-monooxygenase
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[EC 1.14.13.56 created 1999, deleted 2018] |
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EC
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1.14.13.57
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Transferred entry: | dihydrochelirubine 12-monooxygenase. Now EC 1.14.14.101, dihydrochelirubine 12-monooxygenase
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[EC 1.14.13.57 created 1999, deleted 2018] |
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EC |
1.14.14.97 |
Accepted name: |
methyltetrahydroprotoberberine 14-monooxygenase |
Reaction: |
(1) (S)-cis-N-methylcanadine + [reduced NADPH—hemoprotein reductase] + O2 = allocryptopine + [oxidized NADPH—hemoprotein reductase] + H2O (2) (S)-cis-N-methylstylopine + [reduced NADPH—hemoprotein reductase] + O2 = protopine + [oxidized NADPH—hemoprotein reductase] + H2O |
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For diagram of canadine biosynthesis, click here and for diagram of stylopine biosynthesis, click here |
Other name(s): |
methyltetrahydroprotoberberine 14-hydroxylase; (S)-cis-N-methyltetrahydroberberine 14-monooxygenase; (S)-cis-N-methyltetrahydroprotoberberine-14-hydroxylase; CYP82N4 (gene name); (S)-N-methylcanadine,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (14-hydroxylating); (S)-cis-N-methylstylopine 14-hydroxylase |
Systematic name: |
(S)-cis-N-methylcanadine,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (14-hydroxylating) |
Comments: |
A cytochrome P-450 (heme-thiolate) protein involved in the biosynthesis of isoquinoline alkaloids in plants. It also hydroxylates (S)-cis-N-methyltetrahydrothalifendine, and (S)-cis-N-methyltetrahydropalmatine. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 113478-42-5 |
References: |
1. |
Rueffer, M. and Zenk, M.H. Enzymatic formation of protopines by a microsomal cytochrome-P-450 system of Corydalis vaginans. Tetrahedron Lett. 28 (1987) 5307–5310. [DOI] |
2. |
Beaudoin, G.A. and Facchini, P.J. Isolation and characterization of a cDNA encoding (S)-cis-N-methylstylopine 14-hydroxylase from opium poppy, a key enzyme in sanguinarine biosynthesis. Biochem. Biophys. Res. Commun. 431 (2013) 597–603. [DOI] [PMID: 23313486] |
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[EC 1.14.14.97 created 1990 as EC 1.14.13.37, transferred 2018 to EC 1.14.14.97, modified 2023] |
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EC |
1.14.14.98 |
Accepted name: |
protopine 6-monooxygenase |
Reaction: |
protopine + [reduced NADPH—hemoprotein reductase] + O2 = 6-hydroxyprotopine + [oxidized NADPH—hemoprotein reductase] + H2O |
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For diagram of stylopine biosynthesis, click here |
Other name(s): |
protopine 6-hydroxylase; CYP82N2 (gene name) |
Systematic name: |
protopine,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (6-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: 128561-60-4 |
References: |
1. |
Tanahashi, T. and Zenk, M.H. Elicitor induction and characterization of microsomal protopine-6-hydroxylase, the central enzyme in benzophenanthridine alkaloid biosynthesis. Phytochemistry 29 (1990) 1113–1122. |
2. |
Takemura, T., Ikezawa, N., Iwasa, K. and Sato, F. Molecular cloning and characterization of a cytochrome P450 in sanguinarine biosynthesis from Eschscholzia californica cells. Phytochemistry 91 (2013) 100–108. [PMID: 22421633] |
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[EC 1.14.14.98 created 1999 as EC 1.14.13.55, transferred 2018 to EC 1.14.14.98] |
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EC |
1.14.14.100 |
Accepted name: |
dihydrosanguinarine 10-monooxygenase |
Reaction: |
dihydrosanguinarine + [reduced NADPH—hemoprotein reductase] + O2 = 10-hydroxydihydrosanguinarine + [oxidized NADPH—hemoprotein reductase] + H2O |
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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. |
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[EC 1.14.14.100 created 1999 as EC 1.14.13.56, transferred 2018 to EC 1.14.14.100] |
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EC |
1.14.14.101 |
Accepted name: |
dihydrochelirubine 12-monooxygenase |
Reaction: |
dihydrochelirubine + [reduced NADPH—hemoprotein reductase] + O2 = 12-hydroxydihydrochelirubine + [oxidized NADPH—hemoprotein reductase] + H2O |
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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. |
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[EC 1.14.14.101 created 1999 as EC 1.14.13.57, transferred 2018 to EC 1.14.14.101] |
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EC |
2.1.1.119 |
Accepted name: |
10-hydroxydihydrosanguinarine 10-O-methyltransferase |
Reaction: |
S-adenosyl-L-methionine + 10-hydroxydihydrosanguinarine = S-adenosyl-L-homocysteine + dihydrochelirubine |
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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. |
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[EC 2.1.1.119 created 1999] |
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EC |
2.1.1.120 |
Accepted name: |
12-hydroxydihydrochelirubine 12-O-methyltransferase |
Reaction: |
S-adenosyl-L-methionine + 12-hydroxydihydrochelirubine = S-adenosyl-L-homocysteine + dihydromacarpine |
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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. |
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[EC 2.1.1.120 created 1999] |
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