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(3alpha,4alpha,5alpha,10alpha,13alpha,20S)-4-methyl-9,19-cycloergosta-7,24(28)-dien-3-ol + 6 ferrocytochrome b5 + 3 O2 + 6 H+
(3alpha,4alpha,5alpha,10alpha,13alpha,20S)-3-hydroxy-9,19-cycloergosta-7,24(28)-diene-4-carboxylic acid + 6 ferricytochrome b5 + 4 H2O
-
-
-
-
ir
(3alpha,4alpha,5alpha,10alpha,13alpha,20S)-4-methylcholest-7-en-3-ol + 6 ferrocytochrome b5 + 3 O2 + 6 H+
(3alpha,4alpha,5alpha,10alpha,13alpha,20S)-3-hydroxycholest-7-ene-4-carboxylic acid + 6 ferricytochrome b5 + 4 H2O
-
-
-
-
ir
24-ethylidenelophenol + 6 ferrocytochrome b5 + 3 O2 + 6 H+
(3beta,4alpha,5alpha,24Z)-3-hydroxystigmasta-7,24(28)-diene-4-carboxylic acid + 6 ferricytochrome b5 + 4 H2O
-
-
-
-
ir
24-ethylidenelophenol + 6 ferrocytochrome b5 + 3 O2 + 6 H+
3beta,4alpha,5alpha-3-hydroxystigmasta-7,24(28)-diene-4-carboxylate + 6 ferricytochrome b5 + 4 H2O
24-ethylidenelophenol + NAD(P)H + O2 + H+
?
-
100% activity
-
-
?
24-methylidenelophenol + 6 ferrocytochrome b5 + 3 O2 + 6 H+
3beta-hydroxyergosta-7,24(241)-dien-4alpha-carboxylate + 6 ferricytochrome b5 + 4 H2O
-
-
-
-
ir
24-methylidenelophenol + 6 ferrocytochrome b5 + 3 O2 + 6 H+
3beta-hydroxyergosta-7,24(241)-diene-4alpha-carboxylate + 6 ferricytochrome b5 + 4 H2O
-
-
-
-
?
24-methylidenelophenol + NAD(P)H + H+
?
-
59% activity compared to 24-ethylidenelophenol
-
-
?
24zeta(241)-dihydrocycloeucalenol + NAD(P)H + H+
?
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10% activity compared to 24-ethylidenelophenol
-
-
?
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde + a ferrocytochrome + O2
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carboxylate + a ferricytochrome + H2O
4,4-dimethyl-5alpha-cholest-7-en-3beta-ol + a ferrocytochrome + O2
4beta-hydroxymethyl-4alpha-methyl-5alpha-cholest-7-en-3beta-ol + a ferricytochrome + H2O
4beta-hydroxymethyl-4alpha-methyl-5alpha-cholest-7-en-3beta-ol + a ferrocytochrome + O2
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde + a ferricytochrome + H2O
cycloeucalenol + NAD(P)H + H+
?
-
10% activity compared to 24-ethylidenelophenol
-
-
?
lophenol + NAD(P)H + H+
?
-
38% activity compared to 24-ethylidenelophenol
-
-
?
additional information
?
-
24-ethylidenelophenol + 6 ferrocytochrome b5 + 3 O2 + 6 H+
3beta,4alpha,5alpha-3-hydroxystigmasta-7,24(28)-diene-4-carboxylate + 6 ferricytochrome b5 + 4 H2O
-
-
-
-
?
24-ethylidenelophenol + 6 ferrocytochrome b5 + 3 O2 + 6 H+
3beta,4alpha,5alpha-3-hydroxystigmasta-7,24(28)-diene-4-carboxylate + 6 ferricytochrome b5 + 4 H2O
-
-
-
-
?
24-ethylidenelophenol + 6 ferrocytochrome b5 + 3 O2 + 6 H+
3beta,4alpha,5alpha-3-hydroxystigmasta-7,24(28)-diene-4-carboxylate + 6 ferricytochrome b5 + 4 H2O
-
-
-
-
?
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde + a ferrocytochrome + O2
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carboxylate + a ferricytochrome + H2O
step 3 of 3 of the overall reaction
-
-
?
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde + a ferrocytochrome + O2
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carboxylate + a ferricytochrome + H2O
step 3 of 3 of the overall reaction
-
-
?
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde + a ferrocytochrome + O2
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carboxylate + a ferricytochrome + H2O
step 3 of 3 of the overall reaction
-
-
?
4,4-dimethyl-5alpha-cholest-7-en-3beta-ol + a ferrocytochrome + O2
4beta-hydroxymethyl-4alpha-methyl-5alpha-cholest-7-en-3beta-ol + a ferricytochrome + H2O
step 1 of 3 of the overall reaction
-
-
?
4,4-dimethyl-5alpha-cholest-7-en-3beta-ol + a ferrocytochrome + O2
4beta-hydroxymethyl-4alpha-methyl-5alpha-cholest-7-en-3beta-ol + a ferricytochrome + H2O
step 1 of 3 of the overall reaction
-
-
?
4,4-dimethyl-5alpha-cholest-7-en-3beta-ol + a ferrocytochrome + O2
4beta-hydroxymethyl-4alpha-methyl-5alpha-cholest-7-en-3beta-ol + a ferricytochrome + H2O
step 1 of 3 of the overall reaction
-
-
?
4beta-hydroxymethyl-4alpha-methyl-5alpha-cholest-7-en-3beta-ol + a ferrocytochrome + O2
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde + a ferricytochrome + H2O
step 2 of 3 of the overall reaction
-
-
?
4beta-hydroxymethyl-4alpha-methyl-5alpha-cholest-7-en-3beta-ol + a ferrocytochrome + O2
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde + a ferricytochrome + H2O
step 2 of 3 of the overall reaction
-
-
?
4beta-hydroxymethyl-4alpha-methyl-5alpha-cholest-7-en-3beta-ol + a ferrocytochrome + O2
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde + a ferricytochrome + H2O
step 2 of 3 of the overall reaction
-
-
?
additional information
?
-
conversion of cycloartenol into functional phytosterol requires the removal of 2 methyl groups at C4 by the enzymic complex including the sterol 4alpha-methyl oxidase SMO
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-
?
additional information
?
-
conversion of cycloartenol into functional phytosterol requires the removal of 2 methyl groups at C4 by the enzymic complex including the sterol 4alpha-methyl oxidase SMO
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-
?
additional information
?
-
conversion of cycloartenol into functional phytosterol requires the removal of 2 methyl groups at C4 by the enzymic complex including the sterol 4alpha-methyl oxidase SMO, sterol spectrum in wild-type and transgenic gene-silenced plants, accumulation of 4alpha-methyl-DELTA7-sterols, overview
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?
additional information
?
-
conversion of cycloartenol into functional phytosterol requires the removal of 2 methyl groups at C4 by the enzymic complex including the sterol 4alpha-methyl oxidase SMO
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-
?
additional information
?
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no activity with cyclobranol, cycloartenol, 24-methylenelanosterol, lanosterol, 24(25)-dihydrolanosterol, parkeol, 4,4-dimethyl-7,22-ergostadienol, beta-amyrine, 4alpha,14alpha,dimethyl-5alpha-cholesta-7-en-3beta-ol, obtusifoliol, 24zeta(241)-dihydroobtusifoliol, 29-norlanosterol, 24(25)-dihydro-29-norlanosterol, 4alpha-dimethyl-5alpha-cholestanol, 4alpha,14alpha,24zeta-trimethyl-5alpha-cholesta-9(11)-en-3beta-ol, and 4beta-24zeta(241)-dihydrocycloeucalenol
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-
?
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Darnet, S.; Rahier, A.
Plant sterol biosynthesis: identification of two distinct families of sterol 4alpha-methyl oxidases
Biochem. J.
378
889-898
2004
Nicotiana benthamiana (Q5J954), Nicotiana tabacum (Q6YAU6), Arabidopsis thaliana (Q8VWZ8), Arabidopsis thaliana (Q9ZW22)
brenda
Rahier, A.; Smith, M.; Taton, M.
The role of cytochrome b5, in 4alpha-methyl-oxidation and C5(6) desaturation of plant sterol precursors
Biochem. Biophys. Res. Commun.
236
434-437
1997
Zea mays
brenda
Darnet, S.; Bard, M.; Rahier, A.
Functional identification of sterol-4alpha-methyl oxidase cDNAs from Arabidopsis thaliana by complementation of a yeast erg25 mutant lacking sterol-4alpha-methyl oxidation
FEBS Lett.
508
39-43
2001
Arabidopsis thaliana (Q9ZW22)
brenda
Zhang, J.; Li, X.; Lu, F.; Wang, S.; An, Y.; Su, X.; Li, X.; Ma, L.; Han, G.
De novo sequencing and transcriptome analysis reveal key genes regulating steroid metabolism in leaves, roots, adventitious roots and calli of Periploca sepium Bunge
Front. Plant Sci.
8
594
2017
Periploca sepium
brenda
Pascal, S.; Taton, M.; Rahier, A.
Plant sterol biosynthesis. Identification and characterization of two distinct microsomal oxidative enzymatic systems involved in sterol C4-demethylation
J. Biol. Chem.
268
11639-11654
1993
Zea mays
brenda
Ramadan, A.; Azeiz, A.; Baabad, S.; Hassanein, S.; Gadalla, N.; Hassan, S.; Algandaby, M.; Bakr, S.; Khan, T.; Abouseadaa, H.; Ali, H.; Al-Ghamdi, A.; Osman, G.; Edris, S.; Eissa, H.; Bahieldin, A.
Control of beta-sitosterol biosynthesis under light and watering in desert plant Calotropis procera
Steroids
141
1-8
2019
Calotropis procera
brenda
Rahier, A.
Dissecting the sterol C-4 demethylation process in higher plants. From structures and genes to catalytic mechanism
Steroids
76
340-352
2011
Arabidopsis thaliana
brenda
1.14.18.11 plant 4alpha-monomethylsterol monooxygenase
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