Information on EC 1.14.13.101 - senecionine N-oxygenase

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The expected taxonomic range for this enzyme is: Eukaryota

EC NUMBER
COMMENTARY
1.14.13.101
-
RECOMMENDED NAME
GeneOntology No.
senecionine N-oxygenase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
senecionine + NADPH + H+ + O2 = senecionine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
oxidation
-
-
-
-
oxidation
Q8MP06
-
redox reaction
-
-
-
-
redox reaction
Q8MP06
-
reduction
-
-
-
-
reduction
Q8MP06
-
PATHWAY
KEGG Link
MetaCyc Link
senecionine N-oxide biosynthesis
-
Tropane, piperidine and pyridine alkaloid biosynthesis
-
SYSTEMATIC NAME
IUBMB Comments
senecionine,NADPH:oxygen oxidoreductase (N-oxide-forming)
A flavoprotein. NADH cannot replace NADPH. While pyrrolizidine alkaloids of the senecionine and monocrotaline types are generally good substrates (e.g. senecionine, retrorsine and monocrotaline), the enzyme does not use ester alkaloids lacking an hydroxy group at C-7 (e.g. supinine and phalaenopsine), 1,2-dihydro-alkaloids (e.g. sarracine) or unesterified necine bases (e.g. senkirkine) as substrates [1]. Senecionine N-oxide is used by insects as a chemical defense: senecionine N-oxide is non-toxic, but it is bioactivated to a toxic form by the action of cytochrome P-450 oxidase when absorbed by insectivores.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
GgPNO
D6CHF2
-
oxygenase, senecionine N-
Q8MP06
-
senecionine monooxygenase (N-oxide-forming)
-
-
-
-
senecionine N-oxygenase
Q8MP06
-
SNO
Q8MP06
-
TjSNO
Q8MP06
-
CAS REGISTRY NUMBER
COMMENTARY
220581-68-0
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
Amerila phaedra
-
-
-
Manually annotated by BRENDA team
Arctia intercalaris
-
-
-
Manually annotated by BRENDA team
no activity in Spodoptera littoralis
-
-
-
Manually annotated by BRENDA team
sinnabar moth
SwissProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
atropine + NADPH + O2
atropine N-oxide + NADP+ + H2O
show the reaction diagram
D6CHF2, -
21% of the activity with monocrotaline
-
-
?
axillaridine + NADPH + O2
axillaridine N-oxide + NADP+ + H2O
show the reaction diagram
-
76% of the activity with senecionine
-
?
axillaridine + NADPH + O2
axillaridine N-oxide + NADP+ + H2O
show the reaction diagram
-
79% of the activity with senecionine
-
?
axillaridine + NADPH + O2
axillaridine N-oxide + NADP+ + H2O
show the reaction diagram
-
93% of the activity with senecionine
-
?
axillarine + NADPH + O2
axillarine N-oxide + NADP+ + H2O
show the reaction diagram
-
38% of the activity with senecionine
-
?
axillarine + NADPH + O2
axillarine N-oxide + NADP+ + H2O
show the reaction diagram
-
55% of the activity with senecionine
-
?
axillarine + NADPH + O2
axillarine N-oxide + NADP+ + H2O
show the reaction diagram
-
74% of the activity with senecionine
-
?
axillarine + NADPH + O2
axillarine N-oxide + NADP+ + H2O
show the reaction diagram
Q8MP06, -
74% of the activity with senecionine, native enzyme. 83% of the activity with senecionine, recombinant enzyme
-
?
axillarine + NADPH + O2
axillarine N-oxide + NADP+ + H2O
show the reaction diagram
D6CHF2, -
69% of the activity with monocrotaline
-
-
?
heliotrine + NADPH + O2
heliotrine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
-
heliotrine + NADPH + O2
heliotrine N-oxide + NADP+ + H2O
show the reaction diagram
-
115% of the activity with senecionine
-
?
heliotrine + NADPH + O2
heliotrine N-oxide + NADP+ + H2O
show the reaction diagram
-
25% of the activity with senecionine
-
?
heliotrine + NADPH + O2
heliotrine N-oxide + NADP+ + H2O
show the reaction diagram
Q8MP06, -
25% of the activity with senecionine, native enzyme. 49% of the activity with senecionine, recombinant enzyme
-
?
heliotrine + NADPH + O2
heliotrine N-oxide + NADP+ + H2O
show the reaction diagram
-
86% of the activity with senecionine
-
?
heliotrine + NADPH + O2
heliotrine N-oxide + NADP+ + H2O
show the reaction diagram
D6CHF2, -
49% of the activity with monocrotaline
-
-
?
indicine + NADPH + O2
indicine N-oxide + NADP+ + H2O
show the reaction diagram
-
35% of the activity with senecionine
-
?
indicine + NADPH + O2
indicine N-oxide + NADP+ + H2O
show the reaction diagram
-
78% of the activity with senecionine
-
?
indicine + NADPH + O2
indicine N-oxide + NADP+ + H2O
show the reaction diagram
-
90% of the activity with senecionine
-
?
lycopsamine + NADPH + O2
lycopsamine N-oxide + NADP+ + H2O
show the reaction diagram
-
20% of the activity with senecionine
-
?
lycopsamine + NADPH + O2
lycopsamine N-oxide + NADP+ + H2O
show the reaction diagram
-
75% of the activity with senecionine
-
?
lycopsamine + NADPH + O2
lycopsamine N-oxide + NADP+ + H2O
show the reaction diagram
-
93% of the activity with senecionine
-
?
monocrotaline + NADPH + O2
monocrotaline N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
-
monocrotaline + NADPH + O2
monocrotaline N-oxide + NADP+ + H2O
show the reaction diagram
D6CHF2, -
-
-
-
?
monocrotaline + NADPH + O2
monocrotaline N-oxide + NADP+ + H2O
show the reaction diagram
-
103% of the activity with senecionine
-
?
monocrotaline + NADPH + O2
monocrotaline N-oxide + NADP+ + H2O
show the reaction diagram
-
110% of the activity with senecionine
-
?
monocrotaline + NADPH + O2
monocrotaline N-oxide + NADP+ + H2O
show the reaction diagram
-
92% of the activity with senecionine
-
?
phalaenopsine + NADPH + O2
phalaenopsine N-oxide + NADP+ + H2O
show the reaction diagram
D6CHF2, -
19% of the activity with monocrotaline
-
-
?
retrorsine + NADPH + O2
retrorsine N-oxide + NADP+ + H2O
show the reaction diagram
-
93% of the activity with senecionine
-
?
retrorsine + NADPH + O2
retrorsine N-oxide + NADP+ + H2O
show the reaction diagram
-
97% of the activity with senecionine
-
?
retrorsine + NADPH + O2
retrorsine N-oxide + NADP+ + H2O
show the reaction diagram
-
as active as senecionine
-
?
rinderine + NADPH + O2
rinderine N-oxide + NADP+ + H2O
show the reaction diagram
-
23% of the activity with senecionine
-
?
rinderine + NADPH + O2
rinderine N-oxide + NADP+ + H2O
show the reaction diagram
-
79% of the activity with senecionine
-
?
rinderine + NADPH + O2
rinderine N-oxide + NADP+ + H2O
show the reaction diagram
-
81% of the activity with senecionine
-
?
rinderine + NADPH + O2
rinderine N-oxide + NADP+ + H2O
show the reaction diagram
D6CHF2, -
43% of the activity with monocrotaline
-
-
?
senecionine + NADPH + H+ + O2
senecionine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
senecionine + NADPH + O2
senecionine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
?
senecionine + NADPH + O2
senecionine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
-
senecionine + NADPH + O2
senecionine N-oxide + NADP+ + H2O
show the reaction diagram
Q8MP06, -
-
-
?
senecionine + NADPH + O2
senecionine N-oxide + NADP+ + H2O
show the reaction diagram
Q8MP06
-
-
-
?
senecionine + NADPH + O2
senecionine N-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
?
senecionine + NADPH + O2
senecionine N-oxide + NADP+ + H2O
show the reaction diagram
D6CHF2, -
61% of the activity with monocrotaline
-
-
?
seneciphylline + NADPH + O2
seneciphylline N-oxide + NADP+ + H2O
show the reaction diagram
-
117% of the activity with senecionine
-
?
seneciphylline + NADPH + O2
seneciphylline N-oxide + NADP+ + H2O
show the reaction diagram
-
119% of the activity with senecionine
-
?
seneciphylline + NADPH + O2
seneciphylline N-oxide + NADP+ + H2O
show the reaction diagram
-
95% of the activity with senecionine
-
?
seneciphylline + NADPH + O2
seneciphylline N-oxide + NADP+ + H2O
show the reaction diagram
Q8MP06, -
95% of the activity with senecionine, native enzyme. 93% of the activity with senecionine, recombinant enzyme
-
?
seneciphylline + NADPH + O2
seneciphylline N-oxide + NADP+ + H2O
show the reaction diagram
D6CHF2, -
59% of the activity with monocrotaline
-
-
?
senecivernine + NADPH + O2
senecivernine N-oxide + NADP+ + H2O
show the reaction diagram
-
107% of the activity with senecionine
-
?
senecivernine + NADPH + O2
senecivernine N-oxide + NADP+ + H2O
show the reaction diagram
-
113% of the activity with senecionine
-
?
senecivernine + NADPH + O2
senecivernine N-oxide + NADP+ + H2O
show the reaction diagram
-
81% of the activity with senecionine
-
?
triangularine + NADPH + O2
triangularine N-oxide + NADP+ + H2O
show the reaction diagram
-
60% of the activity with senecionine
-
?
monocrotaline + NADPH + O2
monocrotaline N-oxide + NADP+ + H2O
show the reaction diagram
Q8MP06, -
92% of the activity with senecionine, native enzyme. 94% of the activity with senecionine, recombinant enzyme
-
?
additional information
?
-
Q8MP06, -
the enzyme is highly specific for toxic pyrrolizidine alkaloids. No activity with: senkirkine, dimethylaniline, L-Pro, caffeine, atropine, supinidine, retronecine, phalaenopsine
-
?
additional information
?
-
-
the enzyme N-oxidizes only alkaloids with structural elements which are essential for hepatotoxic and genotoxic pyrrolizidine alkaloids, i.e. 1,2-double bond, esterification of the allylic hydroxyl group, presence of a second free or esterified hydroxyl group at carbon 7. No activity with: senkirkine, sarracine, supinine, phalaenopsine, retronecine, heliotridine, supinidine, isoretronecanol, nicotine, caffeine, tropane alkaloids, quinolizidine alkaloids, indole alkaloids, isoquinolines and synthetic heterocyclic tertiary amines
-
?
additional information
?
-
-
the enzyme N-oxidizes only alkaloids with structural elements which are essential for hepatotoxic and genotoxic pyrrolizidine alkaloids, i.e. 1,2-double bond, esterification of the allylic hydroxyl group, presence of a second free or esterified hydroxyl group at carbon 7. No activity with: triangularine, senkirkine, sarracine, supinine, phalaenopsine, retronecine, heliotridine, supinidine, isoretronecanol, nicotine, caffeine, tropane alkaloids, quinolizidine alkaloids, indole alkaloids, isoquinolines and synthetic heterocyclic tertiary amines
-
?
additional information
?
-
Q8MP06, -
the enzyme allows the larvae to feed on pyrrolizidine alkaloid-containing plants and to accumulate predation-deterrent pyrrolizidine alkaloids in the hemolymph
-
?
additional information
?
-
D6CHF2, -
the enzyme shows activity with glutathione (41% of the activity with monocrotaline)
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
senecionine + NADPH + O2
senecionine N-oxide + NADP+ + H2O
show the reaction diagram
Q8MP06
-
-
-
?
additional information
?
-
Q8MP06, -
the enzyme allows the larvae to feed on pyrrolizidine alkaloid-containing plants and to accumulate predation-deterrent pyrrolizidine alkaloids in the hemolymph
-
?
COFACTOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
FAD
-
molar apoenzyme/FAD ratio of 0.4
NADPH
-
strictly dependent on
NADPH
-
strictly dependent on, no reaction with NADH
NADPH
Q8MP06
dependent on
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
guanethidine
-
enhances activity
Metyrapone
-
enhances activity
n-octylamine
-
activity of solubilized enzyme is 1.6fold increased by 0.5 mM n-octylamine
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0186
-
heliotrine
-
pH 7.0, 37C
0.0229
-
heliotrine
-
pH 7.0, 37C
0.284
-
heliotrine
-
pH 7.0, 37C
0.0029
-
monocrotaline
-
pH 7.0, 37C
0.0051
-
monocrotaline
-
pH 7.0, 37C
0.0125
-
monocrotaline
-
pH 7.0, 37C
0.0013
-
NADPH
-
pH 7.0, pH 37C
0.0014
-
senecionine
-
pH 7.0, 37C
0.0031
-
senecionine
-
pH 7.0, 37C
0.0048
-
senecionine
-
pH 7.0, 37C
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
3.3
-
D6CHF2, -
purified enzyme with senecionine as substrate
4.67
-
-
-
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7.5
-
-
solubilized partially purified enzyme
8
-
D6CHF2, -
assay at
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
37
-
D6CHF2, -
assay at
40
45
-
solubilized partially purified enzyme
pI VALUE
pI VALUE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
4.9
-
-
determination on an Ampholine PAGplate pH 3.5-9.5 using a horizantal electrophoresis system
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
Amerila phaedra
-
-
Manually annotated by BRENDA team
-
from late instar larvae
Manually annotated by BRENDA team
Q8MP06
fat body and head
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
additional information
-
not a microsomal enzyme
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
200000
-
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
tetramer
-
4 * 51000, SDS-PAGE
TEMPERATURE STABILITY
TEMPERATURE STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
37
-
-
20 min, solubilized enzyme is completely inactivated in absence of NADPH, preincubation the presence of NADPH has no effect
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expressing GgPNO without the signal peptide in at least a partially soluble and active form. Betaine is added to the medium and promotes its uptake by osmotic stress by sorbitol. Further improvements are achieved by coexpression with the Escherichia coli chaperones DnaK/DnaJ/GrpE by using the plasmid pRDKJG and by reducing the expression temperature to 4C
D6CHF2, -
expression in active form in Escherichia coli BL21
Q8MP06
the heterologous expression results in the formation of an insoluble and inactive protein. Despite the finding that protein solubilization and subsequent renaturation results in an active protein, the specific activity remains low. Active SNO is detected by using an an Sf9 insect cell expression system, but the yield of protein is too low for further biochemical characterization. Using an alignment of senecionine N-oxygenase of Tyria jacobaeae and of flavin-dependent monooxygenase-like sequences of the dipteran species Drosophila melanogaster and Anopheles gambiae, several new flavin-dependent monooxygenase sequences of arctiids and other Lepidoptera are idenified
Q8MP06