Information on EC 2.1.1.70 - 8-hydroxyfuranocoumarin 8-O-methyltransferase

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The expected taxonomic range for this enzyme is: Gunneridae

EC NUMBER
COMMENTARY
2.1.1.70
-
RECOMMENDED NAME
GeneOntology No.
8-hydroxyfuranocoumarin 8-O-methyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + an 8-hydroxyfurocoumarin = S-adenosyl-L-homocysteine + an 8-methoxyfurocoumarin
show the reaction diagram
-
-
-
-
S-adenosyl-L-methionine + xanthotoxol = S-adenosyl-L-homocysteine + xanthotoxin
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
methyl group transfer
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:8-hydroxyfurocoumarin 8-O-methyltransferase
Converts xanthotoxol into xanthotoxin, which has therapeutic potential in the treatment of psoriasis as it has photosensitizing and antiproliferative activities [4]. Methylates the 8-hydroxy group of some hydroxy- and methylcoumarins, but has little activity on non-coumarin phenols (see also EC 2.1.1.69, 5-hydroxyfuranocoumarin 5-O-methyltransferase).
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
furanocoumarin 8-methyltransferase
-
-
-
-
furanocoumarin 8-O-methyl-transferase
-
-
-
-
methyltransferase, xanthotoxol
-
-
-
-
XMT
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
101637-32-5
-
67339-13-3
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Heracleum maximum Michx.
Michx.
-
-
Manually annotated by BRENDA team
cv Hamburger Schnitt
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
S-adenosyl-L-methionine + 5-hydroxyxanthotoxin
S-adenosyl-L-homocysteine + isopimpinellin
show the reaction diagram
-
0.7% of the activity with xanthotoxol
-
?
S-adenosyl-L-methionine + 7,8-dihydroxycoumarin
?
show the reaction diagram
-
-
-
-
-
S-adenosyl-L-methionine + 8-hydroxybergapten
S-adenosyl-L-homocysteine + isopimpinellin
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + 8-hydroxybergapten
S-adenosyl-L-homocysteine + isopimpinellin
show the reaction diagram
-
-
-
-
-
S-adenosyl-L-methionine + 8-hydroxybergapten
S-adenosyl-L-homocysteine + isopimpinellin
show the reaction diagram
-
2% of the activity with xanthotoxol
-
?
S-adenosyl-L-methionine + 8-hydroxybergapten
S-adenosyl-L-homocysteine + isopimpinellin
show the reaction diagram
Heracleum maximum Michx.
-
-
-
-
-
S-adenosyl-L-methionine + bergaptol
S-adenosyl-L-homocysteine + bergapten
show the reaction diagram
-
0.5% of the activity with xanthotoxol
-
?
S-adenosyl-L-methionine + daphnetin
S-adenosyl-L-homocysteine + hydrangetin
show the reaction diagram
-
0.6% of the activity with xanthotoxol
-
?
S-adenosyl-L-methionine + xanthotoxol
S-adenosyl-L-homocysteine + xanthotoxin
show the reaction diagram
-
-
-
?
S-adenosyl-L-methionine + xanthotoxol
S-adenosyl-L-homocysteine + xanthotoxin
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + xanthotoxol
S-adenosyl-L-homocysteine + xanthotoxin
show the reaction diagram
-
-
-
-
-
S-adenosyl-L-methionine + xanthotoxol
S-adenosyl-L-homocysteine + xanthotoxin
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + xanthotoxol
S-adenosyl-L-homocysteine + xanthotoxin
show the reaction diagram
-
-
-
-
-
S-adenosyl-L-methionine + xanthotoxol
S-adenosyl-L-homocysteine + xanthotoxin
show the reaction diagram
-
furanocoumarin biosynthesis
-
-
-
S-adenosyl-L-methionine + xanthotoxol
S-adenosyl-L-homocysteine + xanthotoxin
show the reaction diagram
-
furanocoumarin biosynthesis
-
-
?
S-adenosyl-L-methionine + xanthotoxol
S-adenosyl-L-homocysteine + xanthotoxin
show the reaction diagram
-
final methylation in the biosynthesis of the furanocoumarin xanthotoxin
-
-
?
S-adenosyl-L-methionine + xanthotoxol
S-adenosyl-L-homocysteine + xanthotoxin
show the reaction diagram
Heracleum maximum Michx.
-
-
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
S-adenosyl-L-methionine + xanthotoxol
S-adenosyl-L-homocysteine + xanthotoxin
show the reaction diagram
-
furanocoumarin biosynthesis
-
-
-
S-adenosyl-L-methionine + xanthotoxol
S-adenosyl-L-homocysteine + xanthotoxin
show the reaction diagram
-
furanocoumarin biosynthesis
-
-
?
S-adenosyl-L-methionine + xanthotoxol
S-adenosyl-L-homocysteine + xanthotoxin
show the reaction diagram
-
final methylation in the biosynthesis of the furanocoumarin xanthotoxin
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
S-adenosyl-L-methionine
-
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
kinetin
-
strong inhibition
p-chloromercuribenzoic acid
-
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0044
S-adenosyl-L-methionine
-
-
0.0098
xanthotoxol
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.0000073
-
xanthotoxol
0.000033
-
8-hydroxybergapten
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.3 - 8
-
-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
from leaf petiole, cells treated with an elicitor from Phytophtora megasperma, no activity in untreated cells
Manually annotated by BRENDA team
-
activity decreases from high activity in young cotyledons to low activity in late stages of cotyledon development
Manually annotated by BRENDA team
-
sterile leaf cell culture
Manually annotated by BRENDA team
Heracleum maximum Michx.
-
-
-
Manually annotated by BRENDA team
-
cell suspension culture
Manually annotated by BRENDA team
-
young shoots of field-grown plants
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
enzyme activity is stimulated by elicitor treatment of protoplasts, increase in activity up to 30 h post treatment, no activity is detected in untreated or UV-irradiated protoplasts
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
67000
-
gel filtration
485668
850000
-
gel filtration
485549
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
-
2 * 34000, SDS-PAGE
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5
-
30 min, inactivation below
485668
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
2-mercaptoethanol stabilizes during purification and storage
-
marked loss of activity against xanthotoxol after resalting
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, stable for 20 days in 50% v/v glycerol
-
-20°C, stored and refrozen, activity against xanthotoxol falls rapidly to less than half of the initial value in 1 week and to only 10% after 4 weeks
-
0°C, stored below undesalted, 40% loss of activity after 5 weeks
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE