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Literature summary extracted from
- Oxidation of cucurbitadienol catalyzed by CYP87D18 in the biosynthesis of mogrosides from Siraitia grosvenorii (2016), Plant Cell Physiol., 57, 1000-1007 .
Cloned(Commentary)
| EC Number | Cloned (Comment) | Organism |
|---|---|---|
| 1.14.14.71 | expression in Saccharomyces cerevisiae | Siraitia grosvenorii |
| 5.4.99.33 | 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 |
Protein Variants
| EC Number | Protein Variants | Comment | Organism |
|---|---|---|---|
| 5.4.99.33 | 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)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 2.4.1.350 | UDP-alpha-D-glucose + mogrol | Siraitia grosvenorii | - |
mogroside IE + UDP | - |
? |  |
| 5.4.99.33 | (3S)-2,3-epoxy-2,3-dihydrosqualene | Siraitia grosvenorii | - |
cucurbitadienol | - |
? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.14.14.71 | Siraitia grosvenorii | - |
- |
- |
| 2.4.1.350 | Siraitia grosvenorii | - |
- |
- |
| 5.4.99.33 | Siraitia grosvenorii | K7NBZ9 | cultivated in Guangxi Province of China | - |
Source Tissue
| EC Number | Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|---|
| 5.4.99.33 | fruit | - |
Siraitia grosvenorii | - |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.14.71 | 11-hydroxycucurbitadienol + [reduced NADPH-hemoprotein reductase] + O2 | - |
Siraitia grosvenorii | 11-oxocucurbitadienol + [oxidized NADPH-hemoprotein reductase] + 2 H2O | - |
? | |
| 1.14.14.71 | cucurbitadienol + 2 [reduced NADPH-hemoprotein reductase] + 2 O2 | - |
Siraitia grosvenorii | 11-oxocucurbitadienol + 2 [oxidized NADPH-hemoprotein reductase] + 3 H2O | - |
? | |
| 1.14.14.71 | cucurbitadienol + [reduced NADPH-hemoprotein reductase] + O2 | - |
Siraitia grosvenorii | 11-hydroxycucurbitadienol + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 2.4.1.350 | UDP-alpha-D-glucose + mogrol | - |
Siraitia grosvenorii | mogroside IE + UDP | - |
? | |
| 5.4.99.33 | (3S)-2,3-epoxy-2,3-dihydrosqualene | - |
Siraitia grosvenorii | cucurbitadienol | - |
? | |
| 5.4.99.33 | 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) | Siraitia grosvenorii | ? | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 1.14.14.71 | CYP87D18 | - |
Siraitia grosvenorii |
| 2.4.1.350 | mogrol C-3 hydroxyl glycosyltransferase | - |
Siraitia grosvenorii |
| 2.4.1.350 | UGT74AC1 | - |
Siraitia grosvenorii |
| 5.4.99.33 | SgCbQ | - |
Siraitia grosvenorii |
Temperature Optimum [°C]
| EC Number | Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|---|
| 5.4.99.33 | 30 | - |
coupled assay at | Siraitia grosvenorii |
pH Optimum
| EC Number | pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|---|
| 5.4.99.33 | 7.5 | - |
coupled assay at | Siraitia grosvenorii |
General Information
| EC Number | General Information | Comment | Organism |
|---|---|---|---|
| 1.14.14.71 | physiological function | coexpression of CYP87D18 and cucurbitadienol synthase Cbq in Saccharomyces cerevisiae results in synthesis of 11-oxocucurbitadienol and 11-hydroxycucurbitadienol | Siraitia grosvenorii |
| 5.4.99.33 | 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 |
| 5.4.99.33 | 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 |
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