| 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+ |
| 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]. |
| 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. [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. [PMID: 20378534] |
|
| [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 |
| Systematic name: |
dihydrobenzophenanthridine:oxygen oxidoreductase |
| Comments: |
A CuII enzyme found in higher plants that produces oxidized forms of the benzophenanthridine alkaloids |
| 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. [PMID: 1444440] |
|
| [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
|
| [EC 1.14.13.56 created 1999, deleted 2018] |
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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 |
| 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. |
| 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] |
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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 |
| 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. |
| 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] |
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