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Literature summary extracted from
- Molecular cloning and characterization of methylenedioxy bridge-forming enzymes involved in stylopine biosynthesis in Eschscholzia californica (2007), FEBS J., 274, 1019-1035.
Cloned(Commentary)
| EC Number | Cloned (Comment) | Organism |
|---|---|---|
| 1.14.19.64 | CYP719A2 and CYP719A3, DNA and amino acid sequence determination and analysis, expression patterns, expression in Saccharomyces cerevisiae microsomes | Eschscholzia californica |
| 1.14.19.64 | two full-length P450 cDNAs, CYP719A2 and CYP7193A, expression in Saccharomyces cerevisiae | Eschscholzia californica |
| 1.14.19.73 | expression in Saccharomyces cerevisiae | Eschscholzia californica |
KM Value [mM]
| EC Number | KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 1.14.19.64 | 0.00054 | - |
(S)-scoulerine | CYP719A3 variant, determined with HPLC | Eschscholzia californica |  |
| 1.14.19.64 | 0.032 | - |
(R,S)-scoulerine | CYP719A2 variant, determined with HPLC | Eschscholzia californica | |
| 1.14.19.73 | 0.00054 | - |
(S)-scoulerine | microsomal protein, pH 7.6, 30°C | Eschscholzia californica | |
Localization
| EC Number | Localization | Comment | Organism | GeneOntology No. | Textmining |
|---|---|---|---|---|---|
| 1.14.19.73 | endoplasmic reticulum | sequence contains a putative endoplasmic reticulum-localizing signal | Eschscholzia californica | 5783 | - |
| 1.14.19.73 | microsome | - |
Eschscholzia californica | - |
- |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.19.64 | (R,S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2 | Eschscholzia californica | - |
(R,S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.19.64 | (S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2 | Eschscholzia californica | stylopine biosynthesis involves the sequential formation of two methylenedioxy bridges, (S)-stylopine is an important intermediate in the biosynthesis of benzophenanthridine alkaloids, such as sanguinarine | (S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.19.64 | additional information | Eschscholzia californica | the methylenedioxy bridge-forming enzyme is involved in stylopine biosynthesis in Eschscholzia californica, biosynthetic pathway for a variety of isoquinoline alkaloids, overview | ? | - |
? | |
| 1.14.19.73 | (R,S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2 | Eschscholzia californica | - |
(R,S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.19.73 | (S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2 | Eschscholzia californica | - |
(S)-nandinine + [oxidized NADPH-hemoprotein reductase] + H2O | enzyme does not catalyze the methylenedioxy bridge-formation in ring D of scoulerine but strictly recognizes ring A of the substrate | ? | |
| 1.14.19.73 | (S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2 | Eschscholzia californica | - |
(S)-tetrahydroberberine + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.19.73 | additional information | Eschscholzia californica | no substrates: columbamine, (R,S)-reticuline, (R,S)-norreticuline, (S)-N-methylcoclaurine, (S)-coclaurine, (R,S)-6-O-methylnorlaudanosoline, and magnoflorine | ? | - |
? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.14.19.64 | Eschscholzia californica | - |
two full-length P450 cDNAs, CYP719A2 and CYP7193A, isolated | - |
| 1.14.19.64 | Eschscholzia californica | - |
CYP719A2 and CYP719A3 | - |
| 1.14.19.73 | Eschscholzia californica | Q50LH4 | - |
- |
Source Tissue
| EC Number | Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|---|
| 1.14.19.64 | additional information | tissue expression patterns of CYP719A2 and CYP719A3, overview | Eschscholzia californica | - |
| 1.14.19.64 | root | specific expression of CYP719A3 | Eschscholzia californica | - |
| 1.14.19.64 | seedling | - |
Eschscholzia californica | - |
| 1.14.19.73 | leaf | - |
Eschscholzia californica | - |
| 1.14.19.73 | root | 30fold higher expression than in leaf | Eschscholzia californica | - |
| 1.14.19.73 | stem | - |
Eschscholzia californica | - |
Specific Activity [micromol/min/mg]
| EC Number | Specific Activity Minimum [µmol/min/mg] | Specific Activity Maximum [µmol/min/mg] | Comment | Organism |
|---|---|---|---|---|
| 1.14.19.64 | additional information | - |
0.43 pmol/min/pmol P450 for the CYP719A2 variant, (R,S)-scoulerine as substrate | Eschscholzia californica |
| 1.14.19.64 | additional information | - |
CYP719A2 variant uses only (R,S)-cheilanthifoline as substrate to produce stylopine when incubating with a mixture of 0.4 microM (R,S)-cheilanthifoline and 0.4 microM S-scoulerine as substrates | Eschscholzia californica |
| 1.14.19.64 | additional information | - |
CYP719A3 and CYP719A2 do not react with columbamine, (R,S)-reticuline, (R,S)-norreticuline, (S)-N-methylcoclaurine, (S)-coclaurine, (R,S)-6-O-methylnorlaudanosoline and magnoflorine to make corresponding products with a methylenedioxy bridge | Eschscholzia californica |
| 1.14.19.64 | additional information | - |
CYP719A3 but not CYP719A2 variant converts (S)-tetrahydrocolumbamine to (S)-tetrahydroberberine | Eschscholzia californica |
| 1.14.19.64 | additional information | - |
CYP719A3 converts a mixture of 0.4 microM (R,S)-cheilanthifoline and 0.4 microM S-scoulerine as substrates to stylopine and nandinine | Eschscholzia californica |
| 1.14.19.64 | 0.0000045 | - |
CYP719A3 variant, (S)-scoulerine as substrate, microsomal protein used for determination | Eschscholzia californica |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.19.64 | (R,S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2 | - |
Eschscholzia californica | (R,S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.19.64 | (R,S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2 | both CYP719A2 and CYP719A3 have stylopine synthase activity to catalyze methylenedioxy bridge-formation from cheilanthifoline to stylopine, but not cheilanthifoline synthase activity to convert scoulerine to cheilanthifoline, overview | Eschscholzia californica | (S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.19.64 | (R,S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2 | - |
Eschscholzia californica | (S)-nandinine + [oxidized NADPH-hemoprotein reductase] + H2O | - |
r | |
| 1.14.19.64 | (S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2 | stylopine biosynthesis involves the sequential formation of two methylenedioxy bridges, (S)-stylopine is an important intermediate in the biosynthesis of benzophenanthridine alkaloids, such as sanguinarine | Eschscholzia californica | (S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.19.64 | (S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2 | - |
Eschscholzia californica | (S)-nandinine + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.19.64 | (S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2 | CYP719A3 | Eschscholzia californica | ? | - |
? | |
| 1.14.19.64 | (S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2 | CYP719A3 | Eschscholzia californica | ? | - |
? | |
| 1.14.19.64 | additional information | the methylenedioxy bridge-forming enzyme is involved in stylopine biosynthesis in Eschscholzia californica, biosynthetic pathway for a variety of isoquinoline alkaloids, overview | Eschscholzia californica | ? | - |
? | |
| 1.14.19.64 | additional information | CYP719A2 has high substrate affinity only toward (R,S)-cheilanthifoline, whereas CYP719A3 has high affinity toward the three similar substrates (R,S)-cheilanthifoline, (S)-scoulerine, and (S)-tetrahydrocolumbamine, both show no activity with columbamine, (R,S)-reticuline, (R,S)-norreticuline, (S)-N-methylcoclaurine, (S)-coclaurine, (R,S)-6-O-methylnorlaudanosoline, and magnoflorine, overview | Eschscholzia californica | ? | - |
? | |
| 1.14.19.73 | (R,S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2 | - |
Eschscholzia californica | (R,S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.19.73 | (R,S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2 | - |
Eschscholzia californica | stylopine + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.19.73 | (S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2 | - |
Eschscholzia californica | (S)-nandinine + [oxidized NADPH-hemoprotein reductase] + H2O | enzyme does not catalyze the methylenedioxy bridge-formation in ring D of scoulerine but strictly recognizes ring A of the substrate | ? | |
| 1.14.19.73 | (S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2 | - |
Eschscholzia californica | (S)-tetrahydroberberine + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.19.73 | additional information | no substrates: columbamine, (R,S)-reticuline, (R,S)-norreticuline, (S)-N-methylcoclaurine, (S)-coclaurine, (R,S)-6-O-methylnorlaudanosoline, and magnoflorine | Eschscholzia californica | ? | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 1.14.19.64 | CYP719A2 | - |
Eschscholzia californica |
| 1.14.19.64 | CYP719A3 | - |
Eschscholzia californica |
| 1.14.19.64 | methylenedioxy bridge-forming enzyme | - |
Eschscholzia californica |
| 1.14.19.64 | stylopine synthase | - |
Eschscholzia californica |
| 1.14.19.73 | (S)-stylopine synthase 2 | - |
Eschscholzia californica |
| 1.14.19.73 | CYP719A3 | - |
Eschscholzia californica |
Expression
| EC Number | Organism | Comment | Expression |
|---|---|---|---|
| 1.14.19.73 | Eschscholzia californica | treatment with methyl jasmonate induces expression of both CYP719A2 and CYP719A3 | up |
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