Information on EC 1.14.13.190 - ferruginol synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.13.190
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RECOMMENDED NAME
GeneOntology No.
ferruginol synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
abieta-8,11,13-triene + NADPH + H+ + O2 = ferruginol + NADP+ + H2O
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydroxylation
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
carnosate bioynthesis
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Diterpenoid biosynthesis
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
miltiradiene,NADPH:oxygen oxidoreductase (ferruginol forming)
The enzyme is found in some members of the Lamiaceae (mint family). The enzyme from Rosmarinus officinalis (rosemary) is involved in biosynthesis of carnosic acid, while the enzyme from the Chinese medicinal herb Salvia miltiorrhiza is involved in the biosynthesis of the tanshinones, abietane-type norditerpenoid naphthoquinones that are the main lipophilic bioactive components found in the plant.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
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the enzyme catalyzes the first committed step in the biosynthesis of tanshinones, pathay overview
physiological function
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CYP76AH1 catalyzes the conversion of the carbon skeleton miltiradiene into the intermediate ferruginol, which is involved in the biosynthesis of tanshinones, the chief bioactive ingredients of Salvia miltiorrhiza
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
abieta-8,11,13-triene + NADPH + H+ + O2
ferruginol + NADP+ + H2O
show the reaction diagram
abieta-8,11,13-triene + O2
ferruginol + H2O
show the reaction diagram
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abieta-8,11,13-triene is formed spontaneously from miltiradiene. This reaction may be catalyzed by a not yet identified enzyme
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?
miltiradiene + NADPH + H+ + O2
11-oxomiltiradiene + NADP+ + H2O
show the reaction diagram
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?
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
abieta-8,11,13-triene + NADPH + H+ + O2
ferruginol + NADP+ + H2O
show the reaction diagram
S4UX02
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?
abieta-8,11,13-triene + O2
ferruginol + H2O
show the reaction diagram
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abieta-8,11,13-triene is formed spontaneously from miltiradiene. This reaction may be catalyzed by a not yet identified enzyme
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?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P-450
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cytochrome P450
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.025
abieta-8,11,13-triene
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pH and temperature not specified in the publication
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
PDB
SCOP
CATH
UNIPROT
ORGANISM
Salvia miltiorrhiza;
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
molecular modeling of structure
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
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expression in Saccharomyces cerevisiae
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expression Saccaromyces cerevisiae
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D301E/N303S/V479F
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mutation leads to a second oxidation of product to give 11-hydroxyferruginol, i.e. reaction of EC 1.14.14.60
F112L
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mutant catalyzes ferruginol production in yeast 2 times more efficiently than the wild-type enzyme, while production of 11-hydroxy-ferruginol is abolished. mutant does not oxidize miltiradiene
V296L
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mutant produces 1.5 times more ferruginol, but 8fold less 11-hydroxy-ferruginol and 20fold less 11beta-hydroxy-manoyl oxide than the wild-type enzyme. mutant does not oxidize miltiradiene
additional information
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RNAi-mediated silencing of CYP76AH1 in hairy roots, construction of a CYP76AH1 RNAi system for hairy roots using transformation via Agrobacterium rhizogenes strain C58C1. Metabolic analysis of RNAi-AH1 hairy root lines shows a significantly increased accumulation of miltiradiene and decreased concentration of ferruginol compared to the control lines. The content of tanshinones decreases significantly after silencing of CYP76AH1
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
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coexpression of mutant F112L or mutant V296L and cytochrome Cyp76AK6 in yeast leads to overall improvements of 24- and 14fold for pisiferic acid and salviol, respectively, compared to wild-type