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Literature summary extracted from

  • Weiss, D.; Baumert, A.; Vogel, M.; Roos, W.
    Sanguinarine reductase, a key enzyme of benzophenanthridine detoxification (2006), Plant Cell Environ., 29, 291-302.
    View publication on PubMed

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.3.1.107 0.0095
-
 sanguinarine pH 7.5, 22°C Eschscholzia californica

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
1.3.1.107 soluble
-
 Eschscholzia californica
-
-

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
1.3.1.107 29430
-
 HPLC–mass spectrometry Eschscholzia californica
1.3.1.107 29432
-
 x * 29432, HPLC-MS Eschscholzia californica

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.3.1.107 dihydrochelirubine + NAD(P)+ Eschscholzia californica key reaction of benzophenanthridine detoxification. Detoxifying the phytoalexin sanguinarine produced by Eschscholzia californica (California poppy) itself, when it binds to the cell wall of the poppy cell chelirubine + NAD(P)H + H+
-
 ir
1.3.1.107 dihydrosanguinarine + NAD(P)+ Eschscholzia californica key reaction of benzophenanthridine detoxification. Detoxifying the phytoalexin sanguinarine produced by Eschscholzia californica (California poppy) itself, when it binds to the cell wall of the poppy cell sanguinarine + NAD(P)H + H+
-
 ir

Organism

EC Number Organism UniProt Comment Textmining
1.3.1.107 Eschscholzia californica D5JWB3
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.3.1.107
-
 Eschscholzia californica

Reaction

EC Number Reaction Comment Organism Reaction ID
1.3.1.107 dihydrochelirubine + NAD(P)+ = chelirubine + NAD(P)H + H+ (2) Eschscholzia californica
a
1.3.1.107 dihydrosanguinarine + NAD(P)+ = sanguinarine + NAD(P)H + H+ (1) Eschscholzia californica
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.3.1.107 chelerythrine + NAD(P)H + H+
-
 Eschscholzia californica dihydrochelerythrine + NAD(P)+
-
 ?
1.3.1.107 dihydrochelirubine + NAD(P)+ key reaction of benzophenanthridine detoxification. Detoxifying the phytoalexin sanguinarine produced by Eschscholzia californica (California poppy) itself, when it binds to the cell wall of the poppy cell Eschscholzia californica chelirubine + NAD(P)H + H+
-
 ir
1.3.1.107 dihydrochelirubine + NADP+ dihydrochelirubine i.e. 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. At alkaloid concentration below 0.1 mM, the reaction velocity is about threefold higher with NADPH than with NADH. Higher alkaloid concentrations cause the NADPH-dependent reduction to slow down, but not the NADH-driven reduction Eschscholzia californica chelirubine + NADPH + H+ chelirubine i.e. 5-methoxy-13-methyl-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridinium ir
1.3.1.107 dihydrosanguinarine + NAD(P)+ key reaction of benzophenanthridine detoxification. Detoxifying the phytoalexin sanguinarine produced by Eschscholzia californica (California poppy) itself, when it binds to the cell wall of the poppy cell Eschscholzia californica sanguinarine + NAD(P)H + H+
-
 ir
1.3.1.107 dihydrosanguinarine + NAD+ dihydrosanguinarine i.e. 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. At alkaloid concentration below 0.1 mM, the reaction velocity is about threefold higher with NADPH than with NADH. Higher alkaloid concentrations cause the NADPH-dependent reduction to slow down, but not the NADH-driven reduction Eschscholzia californica sanguinarine + NADH + H+ sanguinarine i.e. 13-methyl-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridinium ir
1.3.1.107 dihydrosanguinarine + NADP+ dihydrosanguinarine i.e. 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. At alkaloid concentration below 0.1 mM, the reaction velocity is about threefold higher with NADPH than with NADH. Higher alkaloid concentrations cause the NADPH-dependent reduction to slow down, but not the NADH-driven reduction Eschscholzia californica sanguinarine + NADPH + H+ sanguinarine i.e. 13-methyl-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridinium ir
1.3.1.107 sanguinarine + NADH + H+ sanguinarine is converted 1.3times faster than chelerythrine. The reduction cannot be reversed by increasing the product concentrations, i.e. even a hundredfold excess of NAD(P)+ does not cause a detectable oxidation of added dihydrosanguinarine Eschscholzia californica dihydrosanguinarine + NAD+
-
 ir
1.3.1.107 sanguinarine + NADPH + H+
-
 Eschscholzia californica dihydrosanguinarine + NADP+
-
 ?

Subunits

EC Number Subunits Comment Organism
1.3.1.107 ? x * 29432, HPLC-MS Eschscholzia californica

Synonyms

EC Number Synonyms Comment Organism
1.3.1.107 SARED1
-
 Eschscholzia californica

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.3.1.107 22
-
 assay at Eschscholzia californica

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.3.1.107 6.5 7.5
-
 Eschscholzia californica

Cofactor

EC Number Cofactor Comment Organism Structure
1.3.1.107 NADH at alkaloid concentration below 0.1 mM, the reaction velocity is about threefold higher with NADPH than with NADH. Higher alkaloid concentrations cause the NADPH-dependent reduction to slow down, but not the NADH-driven reduction Eschscholzia californica
1.3.1.107 NADH below alkaloid substrate concentrations of 10 microM, the reaction velocity is about threefold higher with NADPH than with NADH and increases with the alkaloid concentration. Higher alkaloid concentrations cause the NADPH-dependent reduction to slow down, but not the NADH-driven reduction Eschscholzia californica
1.3.1.107 NADPH at alkaloid concentration below 0.1 mM, the reaction velocity is about threefold higher with NADPH than with NADH. Higher alkaloid concentrations cause the NADPH-dependent reduction to slow down, but not the NADH-driven reduction Eschscholzia californica
1.3.1.107 NADPH below alkaloid substrate concentrations of 10 microM, the reaction velocity is about threefold higher with NADPH than with NADH and increases with the alkaloid concentration. Higher alkaloid concentrations cause the NADPH-dependent reduction to slow down, but not the NADH-driven reduction Eschscholzia californica