BRENDA - Enzyme Database
show all sequences of 5.4.99.33

Oxidation of cucurbitadienol catalyzed by CYP87D18 in the biosynthesis of mogrosides from Siraitia grosvenorii

Zhang, J.; Dai, L.; Yang, J.; Liu, C.; Men, Y.; Zeng, Y.; Cai, Y.; Zhu, Y.; Sun, Y.; Plant Cell Physiol. 57, 1000-1007 (2016)

Data extracted from this reference:

Cloned(Commentary)
Cloned (Commentary)
Organism
gene CBS, subcloning in Escherichia coli strain DH5alpha, 11-oxo-24,25-epoxy cucurbitadienol as well as 11-oxocucurbitadienol and 11-hydroxycucurbitadienol are produced when enzyme CYP87D18 is co-expressed with Cyt P450 reductase and SgCbQ in Saccharomyces cerevisiae strain BY4741-Z35 microsomes, metabolite structures are confirmed by liquid chromatography-solid-phase extraction-nuclear magnetic resonance-mass spectrometry coupling (LC-SPE-NMR-MS). 11-Oxo-24,25-epoxycucurbitadienol might be a derivative of 24,25-epoxycucurbitadienol, which is assumed to be formed through cyclization of 2,3-(S)-22,23-(S)-dioxidosqualene in yeast cells by recombinant SgCbQ, and then sequentially oxidized by recombinant CYP87D18 at the C-11 position in BY4741-Z5 as the oxidation process of cucurbitadienol
Siraitia grosvenorii
Engineering
Protein Variants
Commentary
Organism
additional information
combination of SgCbQ with UGT74AC1 and CYP87D18 may potentially allow improvement in mogroside production by genetic transformation of Siraitia grosvenorii
Siraitia grosvenorii
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
(3S)-2,3-epoxy-2,3-dihydrosqualene
Siraitia grosvenorii
-
cucurbitadienol
-
-
?
Organism
Organism
UniProt
Commentary
Textmining
Siraitia grosvenorii
K7NBZ9
cultivated in Guangxi Province of China
-
Source Tissue
Source Tissue
Commentary
Organism
Textmining
fruit
-
Siraitia grosvenorii
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
(3S)-2,3-epoxy-2,3-dihydrosqualene
-
746042
Siraitia grosvenorii
cucurbitadienol
-
-
-
?
additional information
11-oxo-24,25-epoxy cucurbitadienol might be a derivative of 24,25-epoxy cucurbitadienol, which is assumed to be formed through cyclization of 2,3-(S)-22,23-(S)-dioxidosqualene in yeast cells by recombinant SgCbQ, and then sequentially oxidized by recombinant CYP87D18 (EC 1.14.14.71) at the C-11 position in BY4741-Z5 as the oxidation process of cucurbitadienol. Metabolite identification by TLC, metabolite structures are confirmed by liquid chromatography-solid-phase extraction-nuclear magnetic resonance-mass spectrometry coupling (LC-SPE-NMR-MS)
746042
Siraitia grosvenorii
?
-
-
-
-
Synonyms
Synonyms
Commentary
Organism
SgCbQ
-
Siraitia grosvenorii
Temperature Optimum [C]
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
30
-
coupled assay at
Siraitia grosvenorii
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.5
-
coupled assay at
Siraitia grosvenorii
Cloned(Commentary) (protein specific)
Commentary
Organism
gene CBS, subcloning in Escherichia coli strain DH5alpha, 11-oxo-24,25-epoxy cucurbitadienol as well as 11-oxocucurbitadienol and 11-hydroxycucurbitadienol are produced when enzyme CYP87D18 is co-expressed with Cyt P450 reductase and SgCbQ in Saccharomyces cerevisiae strain BY4741-Z35 microsomes, metabolite structures are confirmed by liquid chromatography-solid-phase extraction-nuclear magnetic resonance-mass spectrometry coupling (LC-SPE-NMR-MS). 11-Oxo-24,25-epoxycucurbitadienol might be a derivative of 24,25-epoxycucurbitadienol, which is assumed to be formed through cyclization of 2,3-(S)-22,23-(S)-dioxidosqualene in yeast cells by recombinant SgCbQ, and then sequentially oxidized by recombinant CYP87D18 at the C-11 position in BY4741-Z5 as the oxidation process of cucurbitadienol
Siraitia grosvenorii
Engineering (protein specific)
Protein Variants
Commentary
Organism
additional information
combination of SgCbQ with UGT74AC1 and CYP87D18 may potentially allow improvement in mogroside production by genetic transformation of Siraitia grosvenorii
Siraitia grosvenorii
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
(3S)-2,3-epoxy-2,3-dihydrosqualene
Siraitia grosvenorii
-
cucurbitadienol
-
-
?
Source Tissue (protein specific)
Source Tissue
Commentary
Organism
Textmining
fruit
-
Siraitia grosvenorii
-
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
(3S)-2,3-epoxy-2,3-dihydrosqualene
-
746042
Siraitia grosvenorii
cucurbitadienol
-
-
-
?
additional information
11-oxo-24,25-epoxy cucurbitadienol might be a derivative of 24,25-epoxy cucurbitadienol, which is assumed to be formed through cyclization of 2,3-(S)-22,23-(S)-dioxidosqualene in yeast cells by recombinant SgCbQ, and then sequentially oxidized by recombinant CYP87D18 (EC 1.14.14.71) at the C-11 position in BY4741-Z5 as the oxidation process of cucurbitadienol. Metabolite identification by TLC, metabolite structures are confirmed by liquid chromatography-solid-phase extraction-nuclear magnetic resonance-mass spectrometry coupling (LC-SPE-NMR-MS)
746042
Siraitia grosvenorii
?
-
-
-
-
Temperature Optimum [C] (protein specific)
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
30
-
coupled assay at
Siraitia grosvenorii
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.5
-
coupled assay at
Siraitia grosvenorii
General Information
General Information
Commentary
Organism
metabolism
cucurbitadienol synthase and a multifunctional P450, CYP87D18, are involved in biosynthesis of mogrosides in Siraitia grosvenorii. Cucurbitadienol synthase synthesizes cucurbitadienol, that is oxidized by CYP87D18 (EC 1.14.14.71) at C-11 to produce 11-oxo cucurbitadienol and 11-hydroxy cucurbitadienol. Proposed biosynthetic pathway of mogrosides, overview
Siraitia grosvenorii
physiological function
cyclization of 2,3-oxidosqualene to cucurbitadienol catalyzed by cucurbitadienol synthase SgCbQ in the biosynthesis of mogrosides, the major bioactive components isolated from the fruits of Siraitia grosvenorii. Mogrosides are a family of cucurbitane-type tetracyclic triterpenoid saponins that are used worldwide as high-potency sweeteners and possess a variety of notable pharmacological activities
Siraitia grosvenorii
General Information (protein specific)
General Information
Commentary
Organism
metabolism
cucurbitadienol synthase and a multifunctional P450, CYP87D18, are involved in biosynthesis of mogrosides in Siraitia grosvenorii. Cucurbitadienol synthase synthesizes cucurbitadienol, that is oxidized by CYP87D18 (EC 1.14.14.71) at C-11 to produce 11-oxo cucurbitadienol and 11-hydroxy cucurbitadienol. Proposed biosynthetic pathway of mogrosides, overview
Siraitia grosvenorii
physiological function
cyclization of 2,3-oxidosqualene to cucurbitadienol catalyzed by cucurbitadienol synthase SgCbQ in the biosynthesis of mogrosides, the major bioactive components isolated from the fruits of Siraitia grosvenorii. Mogrosides are a family of cucurbitane-type tetracyclic triterpenoid saponins that are used worldwide as high-potency sweeteners and possess a variety of notable pharmacological activities
Siraitia grosvenorii
Other publictions for EC 5.4.99.33
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Synonyms
Temperature Optimum [C]
Temperature Range [C]
Temperature Stability [C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [C] (protein specific)
Temperature Range [C] (protein specific)
Temperature Stability [C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
746042
Zhang
Oxidation of cucurbitadienol ...
Siraitia grosvenorii
Plant Cell Physiol.
57
1000-1007
2016
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3
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1
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1
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2
2
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746038
Dai
Functional characterization o ...
Siraitia grosvenorii
Plant Cell Physiol.
56
1172-1182
2015
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1
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2
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4
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2
2
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749428
Davidovich-Rikanati
Recombinant yeast as a functi ...
Citrullus colocynthis, Cucurbita pepo, no activity in Citrullus lanatus var. lanatus
Yeast
32
103-114
2015
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2
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2
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9
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4
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4
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2
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716949
Shibuya
-
Cucurbitadienol synthase, the ...
Cucurbita pepo
Tetrahedron
60
6995-7003
2004
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1
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3
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