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Information on EC 1.14.14.141 - psoralen synthase
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EC Tree
1.14.14.141 psoralen synthaseIUBMB Comments
This microsomal cytochrome P-450 (heme-thiolate) enzyme is rather specific for (+)-marmesin, although it can also accept 5-hydroxymarmesin to a much lesser extent. Furanocoumarins protect plants from fungal invasion and herbivore attack. (+)-Columbianetin, the angular furanocoumarin analogue of the linear furanocoumarin (+)-marmesin, acts as a competitive inhibitor even though it is not a substrate.
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Word Map
- 1.14.14.141
-
furanocoumarins
- psoralens
- majus
- angelicin
- umbelliferone
- elicitors
- monooxygenase
-
columbianetin
-
angular
- carthami
-
glycinea
-
p-coumaroyl
- megasperma
-
syn-elimination
-
phytophthora
- acetone
-
elicitor-induced
-
alternaria
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
psoralen synthase, cyp71aj3, cyp71aj1, cyp71aj2, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
EC 1.14.13.102
-
-
formerly
-
psoralen synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(+)-marmesin + [reduced NADPH-hemoprotein reductase] + O2 = psoralen + [oxidized NADPH-hemoprotein reductase] + acetone + 2 H2O
(+)-marmesin + [reduced NADPH-hemoprotein reductase] + O2 = psoralen + [oxidized NADPH-hemoprotein reductase] + acetone + 2 H2O
-
-
-
-
(+)-marmesin + [reduced NADPH-hemoprotein reductase] + O2 = psoralen + [oxidized NADPH-hemoprotein reductase] + acetone + 2 H2O
reaction mechanism
-
(+)-marmesin + [reduced NADPH-hemoprotein reductase] + O2 = psoralen + [oxidized NADPH-hemoprotein reductase] + 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 SOURCE
PATHWAYS
-
-
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SYSTEMATIC NAME
IUBMB Comments
(+)-marmesin,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase
This microsomal cytochrome P-450 (heme-thiolate) enzyme is rather specific for (+)-marmesin, although it can also accept 5-hydroxymarmesin to a much lesser extent. Furanocoumarins protect plants from fungal invasion and herbivore attack. (+)-Columbianetin, the angular furanocoumarin analogue of the linear furanocoumarin (+)-marmesin, acts as a competitive inhibitor even though it is not a substrate.
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CAS REGISTRY NUMBER
COMMENTARY
106527-99-5
-
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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 + NADP + H+ + O2
psoralen + [oxidized NADPH-hemoprotein reductase] + acetone + H2O
-
-
-
-
r
(+)-marmesin + [reduced NADPH-hemoprotein reductase] + O2
psoralen + acetone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
(+)-marmesin + [reduced NADPH-hemoprotein reductase] + O2
psoralen + [oxidized NADPH-hemoprotein reductase] + acetone + 2 H2O
(+)-marmesin + [reduced NADPH-hemoprotein reductase] + O2
psoralen + [oxidized NADPH-hemoprotein reductase] + acetone + H2O
-
-
-
?
5-hydroxymarmesin + [reduced NADPH-hemoprotein reductase] + O2
bergaptol + acetone + [oxidized NADPH-hemoprotein reductase] + H2O
(+)-marmesin + [reduced NADPH-hemoprotein reductase] + O2
psoralen + [oxidized NADPH-hemoprotein reductase] + acetone + 2 H2O
-
-
-
-
?
(+)-marmesin + [reduced NADPH-hemoprotein reductase] + O2
psoralen + [oxidized NADPH-hemoprotein reductase] + acetone + 2 H2O
the enzyme is the first committed monooxygenase of linear furanocoumarin biosynthesis, pathway overview
-
-
?
(+)-marmesin + [reduced NADPH-hemoprotein reductase] + O2
psoralen + [oxidized NADPH-hemoprotein reductase] + acetone + 2 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 + [reduced NADPH-hemoprotein reductase] + O2
psoralen + [oxidized NADPH-hemoprotein reductase] + acetone + 2 H2O
release of acetone by syn-elimination
-
-
?
(+)-marmesin + [reduced NADPH-hemoprotein reductase] + O2
psoralen + [oxidized NADPH-hemoprotein reductase] + acetone + 2 H2O
-
-
-
?
(+)-marmesin + [reduced NADPH-hemoprotein reductase] + O2
psoralen + [oxidized NADPH-hemoprotein reductase] + acetone + 2 H2O
-
-
-
?
(+)-marmesin + [reduced NADPH-hemoprotein reductase] + O2
psoralen + [oxidized NADPH-hemoprotein reductase] + acetone + 2 H2O
-
-
-
-
?
(+)-marmesin + [reduced NADPH-hemoprotein reductase] + O2
psoralen + [oxidized NADPH-hemoprotein reductase] + acetone + 2 H2O
-
very poor activity with (-)-marmesin, i.e. nodakenetin
-
-
?
5-hydroxymarmesin + [reduced NADPH-hemoprotein reductase] + O2
bergaptol + acetone + [oxidized NADPH-hemoprotein reductase] + H2O
low activity, psoralen 5-monoxygenase activity
-
-
?
5-hydroxymarmesin + [reduced NADPH-hemoprotein reductase] + O2
bergaptol + acetone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
5-hydroxymarmesin + [reduced NADPH-hemoprotein reductase] + O2
bergaptol + acetone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
additional information
?
-
-
umbelliferone is a better precursor of psoralens than either demethylsuberosin or marmesin
-
-
?
additional information
?
-
no activity with (+)-columbianetin, the psoralen synthase is a cytochrome-P450-dependent monooxygenase
-
-
?
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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NATURAL SUBSTRATE
NATURAL 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 + [reduced NADPH-hemoprotein reductase] + O2
psoralen + acetone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
(+)-marmesin + [reduced NADPH-hemoprotein reductase] + O2
psoralen + [oxidized NADPH-hemoprotein reductase] + acetone + 2 H2O
5-hydroxymarmesin + [reduced NADPH-hemoprotein reductase] + O2
bergaptol + acetone + [oxidized NADPH-hemoprotein reductase] + H2O
additional information
?
-
-
umbelliferone is a better precursor of psoralens than either demethylsuberosin or marmesin
-
-
?
(+)-marmesin + [reduced NADPH-hemoprotein reductase] + O2
psoralen + [oxidized NADPH-hemoprotein reductase] + acetone + 2 H2O
the enzyme is the first committed monooxygenase of linear furanocoumarin biosynthesis, pathway overview
-
-
?
(+)-marmesin + [reduced NADPH-hemoprotein reductase] + O2
psoralen + [oxidized NADPH-hemoprotein reductase] + acetone + 2 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 + [reduced NADPH-hemoprotein reductase] + O2
psoralen + [oxidized NADPH-hemoprotein reductase] + acetone + 2 H2O
-
-
-
-
?
5-hydroxymarmesin + [reduced NADPH-hemoprotein reductase] + O2
bergaptol + acetone + [oxidized NADPH-hemoprotein reductase] + H2O
low activity, psoralen 5-monoxygenase activity
-
-
?
5-hydroxymarmesin + [reduced NADPH-hemoprotein reductase] + O2
bergaptol + acetone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
5-hydroxymarmesin + [reduced NADPH-hemoprotein reductase] + O2
bergaptol + acetone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
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
-
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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INHIBITOR
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
-
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
-
ketoconazole
-
complete inhibition of the psoralen synthase at 0.001 mM, 74% at 0.0002 mM
ketoconazole
-
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
-
47% inhibition of the psoralen synthase at 0.05 mM, 51% at 0.005 mM
additional information
no inhibition by 5- and 8-methoxypsoralen, and angelicin
-
additional information
-
no inhibition by 5- and 8-methoxypsoralen, and angelicin
-
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
-
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
-
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
-
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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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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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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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). C71AJ_AMMMJ
494
1
55891
Swiss-Prot
Secretory Pathway (Reliability: 2)
C71AJ_APIGR
476
0
53543
Swiss-Prot
Mitochondrion (Reliability: 5)
C71AJ_PASSA
473
0
53246
Swiss-Prot
Mitochondrion (Reliability: 5)
A0A2P6RUL8_ROSCH
183
0
20380
TrEMBL
other Location (Reliability: 2)
A0A2P6P6U3_ROSCH
173
0
20005
TrEMBL
other Location (Reliability: 2)
A0A2G9HN93_9LAMI
123
0
13973
TrEMBL
other Location (Reliability: 3)
A0A2P6RE82_ROSCH
53
0
5914
TrEMBL
Secretory Pathway (Reliability: 5)
A0A2G9HNG5_9LAMI
494
1
56393
TrEMBL
Secretory Pathway (Reliability: 4)
A0A2G9FYA3_9LAMI
494
1
56617
TrEMBL
Secretory Pathway (Reliability: 5)
A0A396IXJ2_MEDTR
125
0
14214
TrEMBL
Mitochondrion (Reliability: 3)
A0A396IVK1_MEDTR
138
0
15831
TrEMBL
other Location (Reliability: 4)
A0A2P6P5I3_ROSCH
442
1
49504
TrEMBL
Secretory Pathway (Reliability: 3)
A0A2P6SD74_ROSCH
151
0
16879
TrEMBL
other Location (Reliability: 5)
A0A2P6P544_ROSCH
135
0
14520
TrEMBL
Secretory Pathway (Reliability: 2)
A0A2P6P5G1_ROSCH
199
1
22743
TrEMBL
Secretory Pathway (Reliability: 1)
A0A2P6QBJ5_ROSCH
275
0
31602
TrEMBL
Secretory Pathway (Reliability: 5)
A0A2P6RE79_ROSCH
111
0
12741
TrEMBL
other Location (Reliability: 2)
A0A2P6P559_ROSCH
129
0
14625
TrEMBL
other Location (Reliability: 2)
A0A2P6SD77_ROSCH
536
0
60964
TrEMBL
Secretory Pathway (Reliability: 5)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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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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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
transcript levels of are down-regulated under UV, cold, hot, oxidative stress and methyl jasmonate treatment
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Wendorff, H.; Matern, U.
Differential response of cultured parsley cells to elicitors from two non-pathogenic strains of fungi. Microsomal conversion of (+)marmesin into psoralen
Eur. J. Biochem.
161
391-398
1986
Petroselinum crispum
brenda
Hamerski, D.; Matern, U.
Elicitor-induced biosynthesis of psoralens in Ammi majus L. suspension cultures. Microsomal conversion of demethylsuberosin into (+)marmesin and psoralen
Eur. J. Biochem.
171
369-375
1988
Ammi majus
brenda
Larbat, R.; Kellner, S.; Specker, S.; Hehn, A.; Gontier, E.; Hans, J.; Bourgaud, F.; Matern, U.
Molecular cloning and functional characterization of psoralen synthase, the first committed monooxygenase of furanocoumarin biosynthesis
J. Biol. Chem.
282
542-554
2007
Ammi majus (Q6QNI4), Ammi majus
brenda
Larbat, R.; Hehn, A.; Hans, J.; Schneider, S.; Jugde, H.; Schneider, B.; Matern, U.; Bourgaud, F.
Isolation and functional characterization of CYP71AJ4 encoding for the first P450 monooxygenase of angular furanocoumarin biosynthesis
J. Biol. Chem.
284
4776-4785
2009
Pastinaca sativa (C0SJS2), Pastinaca sativa, Apium graveolens (C0SJS4), Apium graveolens
brenda
Parast, B.M.; Chetri, S.K.; Sharma, K.; Agrawal, V.
In vitro isolation, elicitation of psoralen in callus cultures of Psoralea corylifolia and cloning of psoralen synthase gene
Plant Physiol. Biochem.
49
1138-1146
2011
Cullen corylifolium
brenda
Jian, X.; Zhao, Y.; Wang, Z.; Li, S.; Li, L.; Luo, J.; Kong, L.
Two CYP71AJ enzymes function as psoralen synthase and angelicin synthase in the biosynthesis of furanocoumarins in Peucedanum praeruptorum Dunn
Plant Mol. Biol.
104
327-337
2020
Peucedanum praeruptorum (A0A6B9R5D4), Peucedanum praeruptorum
brenda
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