KEGG ORTHOLOGY: K13395

ORTHOLOGY: K13395

Entry

K13395                      KO

Symbol

CYP719A1_2_3_13

Name

(S)-stylopine/(S)-canadine/(S)-nandinine synthase [EC:1.14.19.64 1.14.19.68 1.14.19.73]

Pathway

map00950

Isoquinoline alkaloid biosynthesis

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

Module

M00945

Sanguinarine biosynthesis, (S)-reticuline => sanguinarine

M00946

Noscapine biosynthesis, (S)-reticuline => noscapine

Reaction

R04400

(S)-tetrahydrocolumbamine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (methylenedioxy-bridge-forming)

R04690

(S)-cheilanthifoline,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (methylenedioxy-bridge-forming)

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00950 Isoquinoline alkaloid biosynthesis
    K13395  CYP719A1_2_3_13; (S)-stylopine/(S)-canadine/(S)-nandinine synthase
09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K13395  CYP719A1_2_3_13; (S)-stylopine/(S)-canadine/(S)-nandinine synthase
Enzymes [BR:ko01000]
1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.19  With oxidation of a pair of donors resulting in the reduction of O2 to two molecules of water
    1.14.19.64  (S)-stylopine synthase
     K13395  CYP719A1_2_3_13; (S)-stylopine/(S)-canadine/(S)-nandinine synthase
    1.14.19.68  (S)-canadine synthase
     K13395  CYP719A1_2_3_13; (S)-stylopine/(S)-canadine/(S)-nandinine synthase
    1.14.19.73  (S)-nandinine synthase
     K13395  CYP719A1_2_3_13; (S)-stylopine/(S)-canadine/(S)-nandinine synthase
Cytochrome P450 [BR:ko00199]
Cytochrome P450, plant type
  CYP719 family
   K13395  CYP719A1_2_3_13; (S)-stylopine/(S)-canadine/(S)-nandinine synthase

Other DBs

GO:	0047052 0047056 0102632

Genes

NNU:

104604446

PSOM:

113322097 113347890

MSIN:

131224026 131255012 131255027 131255031 131255053 131255539 131258159 131258160 131258162 131258168 131258169 131258172 131258174

ACAK:

137940221 137942891 137942892

AG:	AAU20771 ABR14721(CYP719A13) BAB68769(CYP719A1) BAD98249(CYP719A3) BAD98250(CYP719A2)

Reference

PMID:15722473 (CYP719A)

Authors

Samanani N, Park SU, Facchini PJ

Title

Cell type-specific localization of transcripts encoding nine consecutive enzymes involved in protoberberine alkaloid biosynthesis.

Journal

Plant Cell 17:915-26 (2005)
DOI:10.1105/tpc.104.028654

Sequence

[ag:AAU20771]

Reference

PMID:12732624 (CYP719A1)

Authors

Ikezawa N, Tanaka M, Nagayoshi M, Shinkyo R, Sakaki T, Inouye K, Sato F

Title

Molecular cloning and characterization of CYP719, a methylenedioxy bridge-forming enzyme that belongs to a novel P450 family, from cultured Coptis japonica cells.

Journal

J Biol Chem 278:38557-65 (2003)
DOI:10.1074/jbc.M302470200

Sequence

[ag:BAB68769]

Reference

PMID:17250743 (CYP719A2 CYP719A3)

Authors

Ikezawa N, Iwasa K, Sato F

Title

Molecular cloning and characterization of methylenedioxy bridge-forming enzymes involved in stylopine biosynthesis in Eschscholzia californica.

Journal

FEBS J 274:1019-35 (2007)
DOI:10.1111/j.1742-4658.2007.05652.x

Sequence

[ag:BAD98250 BAD98249]

Reference

PMID:21094631 (CYP719A13)

Authors

Diaz Chavez ML, Rolf M, Gesell A, Kutchan TM

Title

Characterization of two methylenedioxy bridge-forming cytochrome P450-dependent enzymes of alkaloid formation in the Mexican prickly poppy Argemone mexicana.

Journal

Arch Biochem Biophys 507:186-93 (2011)
DOI:10.1016/j.abb.2010.11.016

Sequence

[ag:ABR14721]

LinkDB

ENZYME: 1.14.19.68

Entry

EC 1.14.19.68               Enzyme

Name

(S)-canadine synthase;
(S)-tetrahydroberberine synthase;
(S)-tetrahydrocolumbamine oxidase (methylenedioxy-bridge-forming);
CYP719A (gene name)

Class

Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With oxidation of a pair of donors resulting in the reduction of O2 to two molecules of water

Sysname

(S)-tetrahydrocolumbamine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (methylenedioxy-bridge-forming)

Reaction(IUBMB)

(S)-tetrahydrocolumbamine + [reduced NADPH---hemoprotein reductase] + O2 = (S)-canadine + [oxidized NADPH---hemoprotein reductase] + 2 H2O [RN:R04400]

Reaction(KEGG)

R04400

Substrate

(S)-tetrahydrocolumbamine [CPD:C04118];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]

Product

(S)-canadine [CPD:C03329];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]

Comment

A cytochrome P-450 (heme-thiolate) protein found in plants. The enzyme catalyses an oxidative reaction that does not incorporate oxygen into the product. Oxidation of the methoxyphenol group of the alkaloid tetrahydrocolumbamine results in the formation of the methylenedioxy bridge of canadine.

History

EC 1.14.19.68 created 1999 as EC 1.1.3.36, transferred 2002 to EC 1.14.21.5, transferred 2018 to EC 1.14.19.68

Pathway

ec00950

Isoquinoline alkaloid biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K13395

(S)-stylopine/(S)-canadine/(S)-nandinine synthase

Genes

NNU:

104604446

PSOM:

113322097 113347890

MSIN:

131224026 131255012 131255027 131255031 131255053 131255539 131258159 131258160 131258162 131258168 131258169 131258172 131258174

ACAK:

137940221 137942891 137942892

CJF:	131032608 131032609 131034188 131034189 131034190 131034192 131044335 131044336 131044337 131046129 131046132 131046134 131046135 131047207 131060490 131060494 131060495 131060496 131060497 131060498 131856931 131856932 131856933

Reference

Authors

Rueffer M, Zenk MH.

Title

Canadine synthase from Thalictrum tuberosum cell cultures catalyses the formation of the methylenedioxy bridge in berberine synthesis.

Journal

Phytochemistry 36:1219-1223 (1994)

Reference

2 [PMID:12732624]

Authors

Ikezawa N, Tanaka M, Nagayoshi M, Shinkyo R, Sakaki T, Inouye K, Sato F

Title

Molecular cloning and characterization of CYP719, a methylenedioxy bridge-forming enzyme that belongs to a novel P450 family, from cultured Coptis japonica cells.

Journal

J Biol Chem 278:38557-65 (2003)
DOI:10.1074/jbc.M302470200

Sequence

[ag:BAB68769]

Reference

3 [PMID:24316226]

Authors

Dang TT, Facchini PJ

Title

Cloning and characterization of canadine synthase involved in noscapine biosynthesis in opium poppy.

Journal

FEBS Lett 588:198-204 (2014)
DOI:10.1016/j.febslet.2013.11.037

Other DBs

ExplorEnz - The Enzyme Database:

1.14.19.68

IUBMB Enzyme Nomenclature:

1.14.19.68

ExPASy - ENZYME nomenclature database:

1.14.19.68

BRENDA, the Enzyme Database:

1.14.19.68

CAS:	114308-22-4

LinkDB

REACTION: R04400

Entry

R04400                      Reaction

Name

(S)-tetrahydrocolumbamine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (methylenedioxy-bridge-forming)

Definition

Isocorypalmine + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> (S)-Canadine + [Oxidized NADPH---hemoprotein reductase] + 2 H2O

Equation

C04118 + C03024 + C00007 <=> C03329 + C03161 + 2 C00001

Reaction class

RC00925

C03329_C04118

Enzyme

1.14.19.68

Pathway

rn00950

Isoquinoline alkaloid biosynthesis

rn01100

Metabolic pathways

rn01110

Biosynthesis of secondary metabolites

Module

M00946

Noscapine biosynthesis, (S)-reticuline => noscapine

Brite

Enzymatic reactions [BR:br08201]
1. Oxidoreductase reactions
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.19  With oxidation of a pair of donors resulting in the reduction of O2 to two molecules of water
    1.14.19.68
     R04400  Isocorypalmine + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> (S)-Canadine + [Oxidized NADPH---hemoprotein reductase] + 2 H2O

Orthology

K13395

(S)-stylopine/(S)-canadine/(S)-nandinine synthase [EC:1.14.19.64 1.14.19.68 1.14.19.73]

Other DBs

RHEA:

21459

LinkDB

DBGET integrated database retrieval system