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ecdysone + reduced acceptor + O2 = 20-hydroxyecdysone + acceptor + H2O
ecdysone + reduced acceptor + O2 = 20-hydroxyecdysone + acceptor + H2O
2 different isozymes of mitochondria and microsomes may have different inducers, electron donors, endogenous inhibitors, and physiological optima
-
ecdysone + reduced acceptor + O2 = 20-hydroxyecdysone + acceptor + H2O
2 different isozymes of mitochondria and microsomes may have different inducers, electron donors, endogenous inhibitors, and physiological optima
Parasarcophaga argyrostoma
-
ecdysone + reduced acceptor + O2 = 20-hydroxyecdysone + acceptor + H2O
NADPH-dependent monooxygenase containing cytochrome P-450, a heme-thiolate protein
-
ecdysone + reduced acceptor + O2 = 20-hydroxyecdysone + acceptor + H2O
NADPH-dependent monooxygenase containing cytochrome P-450, a heme-thiolate protein
-
ecdysone + reduced acceptor + O2 = 20-hydroxyecdysone + acceptor + H2O
NADPH-dependent monooxygenase containing cytochrome P-450, a heme-thiolate protein
-
ecdysone + reduced acceptor + O2 = 20-hydroxyecdysone + acceptor + H2O
NADPH-dependent monooxygenase containing cytochrome P-450, a heme-thiolate protein
-
ecdysone + reduced acceptor + O2 = 20-hydroxyecdysone + acceptor + H2O
NADPH-dependent monooxygenase containing cytochrome P-450, a heme-thiolate protein
-
ecdysone + reduced acceptor + O2 = 20-hydroxyecdysone + acceptor + H2O
NADPH-dependent monooxygenase containing cytochrome P-450, a heme-thiolate protein
-
ecdysone + reduced acceptor + O2 = 20-hydroxyecdysone + acceptor + H2O
ecdysteroid biosynthesis regulation
-
ecdysone + reduced acceptor + O2 = 20-hydroxyecdysone + acceptor + H2O
microsomal enzyme system contains NADPH-dependent cytochrome P-450 reductase without a second electron carrier type
-
ecdysone + reduced acceptor + O2 = 20-hydroxyecdysone + acceptor + H2O
a cytochrome P-450-dependent steroid hydroxylase as part of the mitochondrial enzyme system with both ferredoxin and cytochrome P-450 components
-
ecdysone + reduced acceptor + O2 = 20-hydroxyecdysone + acceptor + H2O
a cytochrome P-450-dependent steroid hydroxylase as part of the mitochondrial enzyme system with both ferredoxin and cytochrome P-450 components
-
ecdysone + reduced acceptor + O2 = 20-hydroxyecdysone + acceptor + H2O
NADPH-dependent monooxygenase containing cytochrome P-450, a heme-thiolate protein
-
-
ecdysone + reduced acceptor + O2 = 20-hydroxyecdysone + acceptor + H2O
-
-
-
-
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alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
ecdysone + AH2 + O2
20-hydroxyecdysone + A + H2O
ecdysone + NADPH + H+ + O2
20-hydroxyecdysone + NADP+ + H2O
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H+ + H2O
-
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
ecdysone + reduced acceptor + O2
20-hydroxyecdysone + acceptor + H2O
-
-
-
?
additional information
?
-
alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
3beta,14alpha,22,25-pentahydroxy-5beta-cholest-7-en-6-one, the 5alpha-epimer of ecdysone, 2beta-acetoxyecdysone, 3-hydroxyecdysone, 3-dehydro-ecdysone or ecdysterone are not hydroxylated
beta-ecdysone, ecdysterone
?
alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
Parasarcophaga argyrostoma
-
-
-
?
alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
alpha-ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
ecdysone + AH2 + O2
20-hydroxyecdysone + A + H2O
-
the enzyme is responsible for the conversion of the molting hormone ecdysone to its more physiologically active metabolite, 20-hydroxyecdysone
-
-
?
ecdysone + AH2 + O2
20-hydroxyecdysone + A + H2O
-
-
-
-
?
ecdysone + AH2 + O2
20-hydroxyecdysone + A + H2O
-
-
-
?
ecdysone + AH2 + O2
20-hydroxyecdysone + A + H2O
-
the enzyme is responsible for the conversion of the molting hormone ecdysone to its more physiologically active metabolite, 20-hydroxyecdysone
-
-
?
ecdysone + AH2 + O2
20-hydroxyecdysone + A + H2O
-
-
-
-
?
ecdysone + AH2 + O2
20-hydroxyecdysone + A + H2O
-
the enzyme is responsible for the conversion of the molting hormone ecdysone to its more physiologically active metabolite, 20-hydroxyecdysone
-
-
?
ecdysone + AH2 + O2
20-hydroxyecdysone + A + H2O
-
-
-
?
ecdysone + NADPH + H+ + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
-
?
ecdysone + NADPH + H+ + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
-
?
ecdysone + NADPH + H+ + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
serves as precursor of ecdysterone, the active moulting hormone in larval insects
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
serves as precursor of ecdysterone, the active moulting hormone in larval insects
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
serves as precursor of ecdysterone, the active moulting hormone in larval insects
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
serves as precursor of ecdysterone, the active moulting hormone in larval insects
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
serves as precursor of ecdysterone, the active moulting hormone in larval insects
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
serves as precursor of ecdysterone, the active moulting hormone in larval insects
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
alpha-ecdysone, a secretory product of prothoracic glands
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
last step in biosynthesis of insect molting hormone
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
last step in biosynthesis of insect molting hormone
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
midgut microsomes show higher specific activity with 2fold higher Vmax, while total activity is 8-10fold higher in mitochondria
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
Parasarcophaga argyrostoma
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
serves as precursor of ecdysterone, the active moulting hormone in larval insects
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
serves as precursor of ecdysterone, the active moulting hormone in larval insects
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
serves as precursor of ecdysterone, the active moulting hormone in larval insects
-
?
additional information
?
-
-
recombinant GST-fusion protein, expressed in E. coli, is also able to transfer electrons from NADPH to a microsomal steroid hydroxylase p-450 and support steroidogenesis
-
-
?
additional information
?
-
-
E20-M preferentially uses NADPH in catalyzing ecdysone conversion to the physiologically active molting hormone, 20-hydroxyecdysone
-
-
?
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ecdysone + AH2 + O2
20-hydroxyecdysone + A + H2O
ecdysone + NADPH + H+ + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
ecdysone + reduced acceptor + O2
20-hydroxyecdysone + acceptor + H2O
-
-
-
?
additional information
?
-
-
E20-M preferentially uses NADPH in catalyzing ecdysone conversion to the physiologically active molting hormone, 20-hydroxyecdysone
-
-
?
ecdysone + AH2 + O2
20-hydroxyecdysone + A + H2O
-
the enzyme is responsible for the conversion of the molting hormone ecdysone to its more physiologically active metabolite, 20-hydroxyecdysone
-
-
?
ecdysone + AH2 + O2
20-hydroxyecdysone + A + H2O
-
-
-
-
?
ecdysone + AH2 + O2
20-hydroxyecdysone + A + H2O
-
-
-
?
ecdysone + AH2 + O2
20-hydroxyecdysone + A + H2O
-
the enzyme is responsible for the conversion of the molting hormone ecdysone to its more physiologically active metabolite, 20-hydroxyecdysone
-
-
?
ecdysone + AH2 + O2
20-hydroxyecdysone + A + H2O
-
-
-
-
?
ecdysone + AH2 + O2
20-hydroxyecdysone + A + H2O
-
the enzyme is responsible for the conversion of the molting hormone ecdysone to its more physiologically active metabolite, 20-hydroxyecdysone
-
-
?
ecdysone + AH2 + O2
20-hydroxyecdysone + A + H2O
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
serves as precursor of ecdysterone, the active moulting hormone in larval insects
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
serves as precursor of ecdysterone, the active moulting hormone in larval insects
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
serves as precursor of ecdysterone, the active moulting hormone in larval insects
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
serves as precursor of ecdysterone, the active moulting hormone in larval insects
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
serves as precursor of ecdysterone, the active moulting hormone in larval insects
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
serves as precursor of ecdysterone, the active moulting hormone in larval insects
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
alpha-ecdysone, a secretory product of prothoracic glands
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
last step in biosynthesis of insect molting hormone
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
last step in biosynthesis of insect molting hormone
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
midgut microsomes show higher specific activity with 2fold higher Vmax, while total activity is 8-10fold higher in mitochondria
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
Parasarcophaga argyrostoma
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
serves as precursor of ecdysterone, the active moulting hormone in larval insects
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
serves as precursor of ecdysterone, the active moulting hormone in larval insects
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
-
-
?
ecdysone + NADPH + O2
20-hydroxyecdysone + NADP+ + H2O
-
serves as precursor of ecdysterone, the active moulting hormone in larval insects
-
?
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1,4-anthraquinone
-
about 20% residual activity at 10 mM
1H-[1,2,4]oxadizolo[4,3-a]-quinoxalin-1-one
-
a guanylate cyclase inhibitor, applied with ecdysone agonist RH-5849 results in 63% reduced E20M activity
2-isopropoxy-1,4-naphthoquinone
2-methoxy-1,4-anthraquinone
-
about 18% residual activity at 1 mM
2-methoxy-1,4-naphthoquinone
2-propoxy-1,4-naphthoquinone
6-anilinoquinoline-5,6-quinone
-
LY-38583, a guanylate cyclase inhibitor, applied with ecdysone agonist RH-5849 results in 80% reduced E20M activity, addition of guanylate cyclase activator S levels the activity to 78% of control activity
7-O-Hemisuccinyl-7-deacetyl-forskolin
9-hydroxy-1,4-anthraquinone
-
about 40% residual activity at 10 mM
9-methoxy-1,4-anthraquinone
-
about 45% residual activity at 10 mM
ecdysterone
-
competitive inhibition
KK-42
-
i.e. 1-benzyl-5[(E)-2,6-dimethyl-1,5-heptadienyl]imidazole
methylene blue
-
a guanylate cyclase inhibitor, applied with ecdysone agonist RH-5849 results in 86% reduced E20M activity, reversed by addition of dibutyryl-cGMP/theophylline to 87% of control activity
NADP+
-
competitive inhibition
Non-ionic detergents
-
Tween 20, Tween 80 and Triton X-100
-
oxidized cytochrome c
-
reversed by KCN
-
quinizarin
-
about 60% residual activity at 10 mM
1,9-Dideoxyforskolin
-
dose dependent inhibition
1,9-Dideoxyforskolin
-
dose dependent inhibition
2-isopropoxy-1,4-naphthoquinone
-
synthetic compound
2-isopropoxy-1,4-naphthoquinone
-
synthetic compound
2-isopropoxy-1,4-naphthoquinone
-
synthetic compound
2-methoxy-1,4-naphthoquinone
-
isolated from the leaves of Impatiens glandulifera
2-methoxy-1,4-naphthoquinone
-
isolated from the leaves of Impatiens glandulifera
2-methoxy-1,4-naphthoquinone
-
isolated from the leaves of Impatiens glandulifera
2-propoxy-1,4-naphthoquinone
-
synthetic compound
2-propoxy-1,4-naphthoquinone
-
synthetic compound
2-propoxy-1,4-naphthoquinone
-
synthetic compound
20-hydroxyecdysone
-
competitive inhibition
20-hydroxyecdysone
-
competitive inhibition
7-O-Hemisuccinyl-7-deacetyl-forskolin
-
-
7-O-Hemisuccinyl-7-deacetyl-forskolin
-
-
CO
-
partially reversible by irradiation with monochromatic light
CO
-
partially reversible by irradiation with monochromatic light
CO
-
partially reversible by irradiation with monochromatic light
diquat dibromide
Parasarcophaga argyrostoma
-
-
forskolin
-
7beta-acetoxy-8,13-epoxy-1alpha,6beta,9alpha-dihydroxylabd-14-en-11-one, adenylate cyclase activator
forskolin
-
7beta-acetoxy-8,13-epoxy-1alpha,6beta,9alpha-dihydroxylabd-14-en-11-one, adenylate cyclase activator
Metyrapone
-
-
Metyrapone
-
2-methyl-1,2-di-3'-pyridylpropan-1-one, up to 80% inhibition
Tween 80
Parasarcophaga argyrostoma
-
microsomal isozyme
Tween 80
-
microsomal isozyme
additional information
-
inhibition profiles
-
additional information
-
inhibition profiles
-
additional information
-
inhibition profiles
-
additional information
-
inhibitory effects of guanylate cyclase inhibitors with RH-5849 in vivo, overview
-
additional information
-
2-hydroxy-1,4-anthraquinone is essentially without effect on enzyme activity
-
additional information
-
in pure N2 atmosphere, enzyme activity is 50% inhibited due to missing oxygen
-
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Johnson, P.; Rees, H.H
The mechanism of C-20 hydroxylation of alpha-ecdysone in the desert locust, Schistocerca gregaria
Biochem. J.
168
513-520
1977
Schistocerca gregaria
brenda
Keogh, D.P.; Mitchell, M.J.; Crooks, J.R.; Smith, S.L.
Effects of the adenylate cyclase activator forskolin and its inactive derivative 1,9-dideoxyforskolin on insect cytochrome P-450 dependent steroid hydroxylase activity
Experientia
48
39-41
1991
Drosophila melanogaster, Drosophila melanogaster Canton S, Manduca sexta
brenda
Feyereisen, R.; Durst, F.
Ecdysterone biosynthesis: a microsomal cytochrome-P-450-linked ecdysone 20-monooxygenase from tissues of the African migratory locust
Eur. J. Biochem.
88
37-47
1978
Locusta migratoria migratorioides
brenda
Greenwood, D.R.; Rees, H.H.
Ecdysone 20-mono-oxygenase in the desert locust, Schistocerca gregaria
Biochem. J.
223
837-847
1984
Schistocerca gregaria
brenda
Weirich, G.F.
Ecdysone 20-monooxygenase
Methods Enzymol.
3
454-458
1985
Manduca sexta
-
brenda
Grebenok, R.J.; Galbraith, D.W.; Benveniste, I.; Feyereisen, R.
Ecdysone 20-monooxygenase , a cytochrome P-450 enzyme from spinach, Spinacia oleracea
Phytochemistry
42
927-933
1996
Spinacia oleracea
-
brenda
Shergill, J.K.; Cammack, R.; Chen, J.H.; Fisher, M.J.; Madden, S.; Rees, H.H.
EPR spectroscopic characterization of the iron-sulphur proteins and cytochrome P-450 in mitochondria from the insect Spodoptera littoralis (cotton leafworm)
Biochem. J.
307
719-728
1995
Spodoptera littoralis
-
brenda
Weirich, G.F.; Williams, V.P.; Feldlaufer, M.F.
Ecdysone 20-hydroxylation in Manduca sexta midgut: kinetic parameters of mitochondrial and microsomal ecdysone 20-monooxygenases
Arch. Insect Biochem. Physiol.
31
305-312
1996
Manduca sexta
-
brenda
Darvas, B.; Rees, H.H.; Hoggard, N.
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