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Enzyme Nomenclature
Information on EC 1.14.13.102 - psoralen synthase
for references in articles please use BRENDA:EC1.14.13.102
Word Map on EC 1.14.13.102
- 1.14.13.102
-
furanocoumarins
- psoralens
- majus
- umbelliferone
-
elicitors
-
elicitor-induced
-
phytophthora
-
glycinea
- carthami
-
angular
-
alternaria
-
syn-elimination
- megasperma
- angelicin
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.14.13.102
-
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RECOMMENDED NAME
GeneOntology No.
psoralen synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(+)-marmesin + NADPH + H+ + O2 = psoralen + NADP+ + acetone + 2 H2O
-
-
-
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(+)-marmesin + NADPH + H+ + O2 = psoralen + NADP+ + acetone + 2 H2O
reaction mechanism
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(+)-marmesin + NADPH + H+ + O2 = psoralen + NADP+ + acetone + 2 H2O
reaction mechanism, analogy modeling and docking analysis of substrate binding, alignmant of recognition sites, modeling of the catalytic site, overview
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
(+)-marmesin,NADPH:oxygen oxidoreductase
This microsomal cytochrome P-450-dependent enzyme is specific for (+)-marmesin, and to a much lesser extent 5-hydroxymarmesin, as substrate. Furanocoumarins protect plants from fungal invasion and herbivore attack. (+)-Columbianetin, the angular furanocoumarin analogue of the linear furanocoumarin (+)-marmesin, is not a substrate for the enzyme but it is a competitive inhibitor.
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CAS REGISTRY NUMBER
COMMENTARY
106527-99-5
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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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
(+)-marmesin + NADPH + H+ + O2
psoralen + NADP+ + acetone + 2 H2O
-
-
-
-
?
(+)-marmesin + NADPH + H+ + O2
psoralen + NADP+ + acetone + H2O
the enzyme is the first committed monooxygenase of linear furanocoumarin biosynthesis, pathway overview
-
-
?
(+)-marmesin + NADPH + H+ + O2
psoralen + NADP+ + acetone + H2O
-
the substrate is synthesized from demethylsuberosin by the marmesin synthase, biosynthesis of furanocoumarin phytoalexin which are then excreted from the endoplasmic reticulum lumen into the cell culture medium
-
-
?
(+)-marmesin + NADPH + H+ + O2
psoralen + NADP+ + acetone + H2O
release of acetone by syn-elimination
-
-
?
(+)-marmesin + NADPH + H+ + O2
psoralen + NADP+ + acetone + H2O
-
-
-
?
(+)-marmesin + NADPH + H+ + O2
psoralen + NADP+ + acetone + H2O
-
-
-
?
(+)-marmesin + NADPH + H+ + O2
psoralen + NADP+ + acetone + H2O
-
-
-
-
?
(+)-marmesin + NADPH + H+ + O2
psoralen + NADP+ + acetone + H2O
-
very poor activity with (-)-marmesin, i.e. nodakenetin
-
-
?
5-hydroxymarmesin + NADPH + H+ + O2
bergaptol + acetone + NADP+ + H2O
low activity, psoralen 5-monoxygenase activity
-
-
?
5-hydroxymarmesin + NADPH + H+ + O2
bergaptol + acetone + NADP+ + H2O
-
-
-
?
5-hydroxymarmesin + NADPH + H+ + O2
bergaptol + acetone + NADP+ + H2O
-
-
-
?
additional information
?
-
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umbelliferone is a better precursor of psoralens than either demethylsuberosin or marmesin
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-
-
additional information
?
-
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no activity with (+)-columbianetin, the psoralen synthase is a cytochrome-P450-dependent monooxygenase
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-
-
additional information
?
-
no activity with (+)-columbianetin, the psoralen synthase is a cytochrome-P450-dependent monooxygenase
-
-
-
additional information
?
-
-
the psoralen synthase is a cytochrome-P450-dependent monooxygenase
-
-
-
additional information
?
-
-
the psoralen synthase is a cytochrome-P450-dependent monooxygenase
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-
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
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
(+)-marmesin + NADPH + H+ + O2
psoralen + NADP+ + acetone + 2 H2O
-
-
-
-
?
additional information
?
-
-
umbelliferone is a better precursor of psoralens than either demethylsuberosin or marmesin
-
-
-
(+)-marmesin + NADPH + H+ + O2
psoralen + NADP+ + acetone + H2O
Q6QNI4
the enzyme is the first committed monooxygenase of linear furanocoumarin biosynthesis, pathway overview
-
-
?
(+)-marmesin + NADPH + H+ + O2
psoralen + NADP+ + acetone + H2O
-
the substrate is synthesized from demethylsuberosin by the marmesin synthase, biosynthesis of furanocoumarin phytoalexin which are then excreted from the endoplasmic reticulum lumen into the cell culture medium
-
-
?
(+)-marmesin + NADPH + H+ + O2
psoralen + NADP+ + acetone + H2O
-
-
-
-
?
5-hydroxymarmesin + NADPH + H+ + O2
bergaptol + acetone + NADP+ + H2O
Q6QNI4
low activity, psoralen 5-monoxygenase activity
-
-
?
5-hydroxymarmesin + NADPH + H+ + O2
bergaptol + acetone + NADP+ + H2O
C0SJS4
-
-
-
?
5-hydroxymarmesin + NADPH + H+ + O2
bergaptol + acetone + NADP+ + H2O
C0SJS2
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADPH
-
dependent on, NADH acts synergisticallyy, but cannot substitute for NADPH
additional information
-
the psoralen synthase is a cytochrome-P450-dependent monooxygenase
-
additional information
-
the psoralen synthase is a cytochrome-P450-dependent monooxygenase
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(+)-columbianetin
i.e. (+)-3,4,2',3'-D4-columbianetin, competitive inhibition, binds to the active site, analogy modeling and docking analysis, mechanism-based inactivation
Ancymidole
-
48% inhibition of the psoralen synthase at 0.05 mM, 29% at 0.005 mM
BAS 110
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34% inhibition of the psoralen synthase at 0.001 mM, 30% at 0.0002 mM
BAS 111
-
complete inhibition of the psoralen synthase at 0.001 mM, 86% at 0.0002 mM
BAS 111
-
52% inhibition of the psoralen synthase at 0.001 mM, 33% at 0.0002 mM
BAS 978
-
complete inhibition of the psoralen synthase at 0.05 mM, 68% at 0.005 mM
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ketoconazole
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complete inhibition of the psoralen synthase at 0.001 mM, 74% at 0.0002 mM
ketoconazole
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38% inhibition of the psoralen synthase at 0.050 mM, 20% at 0.005 mM
Tetcyclacis
-
85% inhibition of the psoralen synthase at 0.001 mM, 25% at 0.0002 mM
Tetcyclacis
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47% inhibition of the psoralen synthase at 0.05 mM, 51% at 0.005 mM
additional information
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no inhibition by 5- and 8-methoxypsoralen, and angelicin
-
additional information
no inhibition by 5- and 8-methoxypsoralen, and angelicin
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additional information
-
no effect on enzyme activity by 2-mercaptoethanol and DTT
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADH
-
NADH acts synergistically with NADPH, but cannot substitute for NADPH
additional information
-
elicitor preparations from either Alternaria carthami Chowdhury or Phytophthora megasperma f.sp. glycinea induce the production of linear furanocoumarins in Ammi majus suspension culture
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additional information
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psoralen synthase is induced rapidly from negligible background levels upon elicitation, e.g. by crude Phytophthora sojae cell wall elicitor fraction, of cell cultures with transient maxima at 9-10 h, furanocoumarin composition in induced cells, overview
-
additional information
psoralen synthase is induced rapidly from negligible background levels upon elicitation, e.g. by crude Phytophthora sojae cell wall elicitor fraction, of cell cultures with transient maxima at 9-10 h, furanocoumarin composition in induced cells, overview
-
additional information
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no effect on enzyme activity by 2-mercaptoethanol and DTT, elicitor fractions isolated from cell walls of Alternaria carthami Chowdhury and of Phythophthora megasperma Drechsler f. sp. glycinea induce the enzyme, the endoplasmic reticulum of cultured parsley cells is the primary target in the differential induction by elicitors from these two non-pathogenic strains of fungi.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
20
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native enzyme partially by preparation of microsomes
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in yeast strain WAT 11
gene CYP71AJ1, DNA and amino acid sequence determination and analysis, phylogenetic analysis, functional expression of the wild-type enzyme in Escherichia coli and Saccharomyces cerevisiae strain WAT11 requiring swapping the N-terminal membrane anchor domain with that of CYP73A1, expression of the enzyme mutant in yeast cells
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.102)
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