1.14.19.64: (S)-stylopine synthase
This is an abbreviated version!
For detailed information about (S)-stylopine synthase, go to the full flat file.
Word Map on EC 1.14.19.64
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1.14.19.64
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californica
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eschscholzia
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sanguinarine
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coptis
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berberine
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benzophenanthridine
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japonica
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s-tetrahydrocolumbamine
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s-scoulerine
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mexicana
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isoquinoline
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cyp80b1
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argemone
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poppy
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benzylisoquinoline
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majus
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chelidonium
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6-hydroxylase
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protopine
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papaveraceae
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pharmacology
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synthesis
- 1.14.19.64
- californica
-
eschscholzia
- sanguinarine
- coptis
- berberine
-
benzophenanthridine
- japonica
-
s-tetrahydrocolumbamine
-
s-scoulerine
- mexicana
- isoquinoline
- cyp80b1
-
argemone
- poppy
-
benzylisoquinoline
- majus
-
chelidonium
-
6-hydroxylase
- protopine
- papaveraceae
- pharmacology
- synthesis
Reaction
Synonyms
(S)-cheilanthifoline oxidase (methylenedioxy-bridge-forming), CYP719A13, CYP719A2, CYP719A2/A3, CYP719A3, EC 1.1.3.32, EC 1.14.21.1, methylenedioxy bridge-forming enzyme, stylopine synthase, synthase, (S)-stylopine
ECTree
1.14.19.64 (S)-stylopine synthaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 1.14.19.64 - (S)-stylopine synthase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(R,S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
(R,S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
(R,S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
(S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
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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
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-
?
(R,S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2
(S)-nandinine + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
-
r
(S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
(S)-stylopine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
(S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
(S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
(S)-coreximine + [reduced NADPH-hemoprotein reductase] + O2
(S)-cheilanthifoline + [oxidized NADPH-hemoprotein reductase] + H2O
kcat (S)-coreximine: 1% compared to kcat (S)-cheilanthifoline: 100%
-
-
?
(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2
(S)-nandinine + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
-
?
(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2
?
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CYP719A3
-
-
?
(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2
nandinine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
(S)-tetrahydroberberine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
?
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CYP719A3
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-
?
(S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
(S)-stylopine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
the enzyme is involved in biosynthesis of stylopine
-
-
?
(S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
(S)-stylopine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
high substrate specificity. The only alternative substrate identified is scoulerine, which is converted by stylopine synthase to yield minor amounts of nandinine
-
-
?
(S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
(S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
(S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
(S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
(S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
-
NADPH is essential for activity, NADH displays only 0.5% turnover of that of NADPH
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?
(S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
(S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
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enzyme is induced 20 h after challenging the cell suspension culture with elicitor
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?
(S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
(S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
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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
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-
?
additional information
?
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the methylenedioxy bridge-forming enzyme is involved in stylopine biosynthesis in Eschscholzia californica, biosynthetic pathway for a variety of isoquinoline alkaloids, overview
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-
?
additional information
?
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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
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-
?
