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Literature summary extracted from
- Multifunctional oxidosqualene cyclases and cytochrome P450 involved in the biosynthesis of apple fruit triterpenic acids (2016), New Phytol., 211, 1279-1294 .
Cloned(Commentary)
| EC Number | Cloned (Comment) | Organism |
|---|---|---|
| 1.14.14.126 | gene CYP716A175, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, quantitative real-time PCR expression analysis, transient recombinant expression in Nicotiana benthamiana using the transformation method via Agrobacterium tumefaciens strain GV3101. The higher oxidizing efficiency of CYP716A175 for lupeol and beta-amyrin compared with germanicol preferentially drives the whole reaction chain to the production of betulinate and oleanolate rather than morolic acid. Transient expression in Saccharomyces cerevisiae shows the presence of the intermediate erythrodiol in addition to oleanolate, but not of oleanolic aldehyde. Sequential three-step oxidation reaction leading to oleanolate, low efficiency of CYP716A75 to oxidize erythrodiol in yeast | Malus domestica |
| 5.4.99.34 | gene OSC4, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, quantitative real-time PCR expression analysis of the enzyme in apple fruits, functional recombinant expression in Nicotiana benthamiana via transformation by Agrobacterium tumefaciens strain GV3101 resulting in production of germanicol, beta-amyrin, and lupeol | Malus domestica |
| 5.4.99.39 | gene OSC1, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, quantitative real-time PCR expression analysis of the enzyme in apple fruits, functional recombinant expression in Nicotiana benthamiana via transformation by Agrobacterium tumefaciens strain GV3101 resulting in production of alpha-amyrin, beta-amyrin, and lupeol. MdOSC1 produces predominantly alpha-amyrin, beta-amyrin to a lesser extent, and small amounts of lupeol | Malus domestica |
| 5.4.99.40 | gene OSC1, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, quantitative real-time PCR expression analysis of the enzyme in apple fruits, functional recombinant expression in Nicotiana benthamiana via transformation by Agrobacterium tumefaciens strain GV3101 resulting in production of alpha-amyrin, beta-amyrin, and lupeol. MdOSC1 produces predominantly alpha-amyrin, beta-amyrin to a lesser extent, and small amounts of lupeol | Malus domestica |
| 5.4.99.40 | gene OSC3, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, quantitative real-time PCR expression analysis of the enzyme in apple fruits, recombinant expression in Nicotiana benthamiana via transformation by Agrobacterium tumefaciens strain GV3101 resulting in production of alpha-amyrin, beta-amyrin, and lupeol | Malus domestica |
| 5.4.99.41 | gene OSC1, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, quantitative real-time PCR expression analysis of the enzyme in apple fruits, functional recombinant expression in Nicotiana benthamiana leaves via transformation by Agrobacterium tumefaciens strain GV3101 resulting in production of alpha-amyrin, beta-amyrin, and lupeol. Cells transiently expressing MdOSC5 cDNA are found to generate lupeol as a major component and beta-amyrin as a minor product, in a ratio of 95:5 | Malus domestica |
Protein Variants
| EC Number | Protein Variants | Comment | Organism |
|---|---|---|---|
| 5.4.99.39 | additional information | transient expression of MdOSC1 and MdOSC5 together with CYP716A175 confirms the ratio between the different triterpene backbones observed after transient expression of MdOSC1 and MDOSC5 alone, overview | Malus domestica |
| 5.4.99.40 | additional information | transient expression of MdOSC1 and MdOSC5 together with CYP716A175 confirms the ratio between the different triterpene backbones observed after transient expression of MdOSC1 and MDOSC5 alone, overview | Malus domestica |
| 5.4.99.41 | additional information | transient expression of MdOSC1 and MdOSC5 together with CYP716A175 confirms the ratio between the different triterpene backbones observed after transient expression of MdOSC1 and MDOSC5 alone, overview | Malus domestica |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.14.126 | alpha-amyrin + 3 O2 + 3 NADPH + 3 H+ | Malus domestica | overall reaction | ursolate + 3 NADP+ + 4 H2O | - |
? |  |
| 1.14.14.126 | beta-amyrin + 3 O2 + 3 NADPH + 3 H+ | Malus domestica | overall reaction | oleanolate + 3 NADP+ + 4 H2O | - |
? | |
| 1.14.14.126 | germanicol + 3 O2 + 3 NADPH + 3 H+ | Malus domestica | overall reaction | morolate + 3 NADP+ + 4 H2O | - |
? | |
| 1.14.14.126 | lupeol + 3 O2 + 3 NADPH + 3 H+ | Malus domestica | overall reaction | betulinate + 3 NADP+ + 4 H2O | - |
? | |
| 1.14.14.126 | additional information | Malus domestica | CYP716A175 catalyses the C-28 oxidation of alpha-amyrin, beta-amyrin, lupeol and germanicol, producing ursolic acid, oleanolic acid, betulinic acid, and putatively morolic acid. CYP716A175 catalyses the three-step oxidation of triterpene backbones at the C-28 position | ? | - |
? | |
| 5.4.99.34 | (3S)-2,3-epoxy-2,3-dihydrosqualene | Malus domestica | - |
germanicol | - |
r | |
| 5.4.99.34 | additional information | Malus domestica | although the MdOSC4 gene was expressed in the skins of all apple varieties under investigation, no germanicol or derivatives were detected at the metabolite level | ? | - |
? | |
| 5.4.99.39 | (S)-2,3-oxidosqualene | Malus domestica | via dammarenyl cation | beta-amyrin | - |
r | |
| 5.4.99.40 | (S)-2,3-oxidosqualene | Malus domestica | via dammarenyl cation | beta-amyrin | - |
r | |
| 5.4.99.40 | (S)-2,3-oxidosqualene | Malus domestica | via dammarenyl cation | lupeol | - |
r | |
| 5.4.99.40 | (S)-2,3-oxidosqualene | Malus domestica | via dammarenyl cation | alpha-amyrin | - |
r | |
| 5.4.99.41 | (S)-2,3-oxidosqualene | Malus domestica | via dammarenyl cation, low activity | beta-amyrin | - |
r | |
| 5.4.99.41 | (S)-2,3-oxidosqualene | Malus domestica | via dammarenyl cation | lupeol | - |
r | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.14.14.126 | Malus domestica | EB148173 | - |
- |
| 5.4.99.34 | Malus domestica | A0A142LT03 | - |
- |
| 5.4.99.39 | Malus domestica | C7SCX0 | hybrid | - |
| 5.4.99.40 | Malus domestica | C7SCX0 | hybrid | - |
| 5.4.99.40 | Malus domestica | C7SCX2 | hybrid, cultivars Merton Russet and Royal Gala, grown in New Zealand | - |
| 5.4.99.41 | Malus domestica | A0A142LT04 | hybrid | - |
Source Tissue
| EC Number | Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|---|
| 1.14.14.126 | additional information | gene expression pattern analysis of CYP716A175 in 20 apple cultivars | Malus domestica | - |
| 5.4.99.34 | fruit | - |
Malus domestica | - |
| 5.4.99.34 | additional information | although the MdOSC4 gene was expressed in the skins of all apple varieties under investigation, no germanicol or derivatives were detected at the metabolite level | Malus domestica | - |
| 5.4.99.34 | plant epidermis | - |
Malus domestica | - |
| 5.4.99.39 | epidermis | - |
Malus domestica | - |
| 5.4.99.39 | fruit | - |
Malus domestica | - |
| 5.4.99.40 | epidermis | - |
Malus domestica | - |
| 5.4.99.40 | fruit | - |
Malus domestica | - |
| 5.4.99.41 | epidermis | - |
Malus domestica | - |
| 5.4.99.41 | fruit | - |
Malus domestica | - |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.14.126 | alpha-amyrin + 3 O2 + 3 NADPH + 3 H+ | overall reaction | Malus domestica | ursolate + 3 NADP+ + 4 H2O | - |
? | |
| 1.14.14.126 | beta-amyrin + 3 O2 + 3 NADPH + 3 H+ | overall reaction | Malus domestica | oleanolate + 3 NADP+ + 4 H2O | - |
? | |
| 1.14.14.126 | germanicol + 3 O2 + 3 NADPH + 3 H+ | overall reaction | Malus domestica | morolate + 3 NADP+ + 4 H2O | - |
? | |
| 1.14.14.126 | lupeol + 3 O2 + 3 NADPH + 3 H+ | overall reaction | Malus domestica | betulinate + 3 NADP+ + 4 H2O | - |
? | |
| 1.14.14.126 | additional information | CYP716A175 catalyses the C-28 oxidation of alpha-amyrin, beta-amyrin, lupeol and germanicol, producing ursolic acid, oleanolic acid, betulinic acid, and putatively morolic acid. CYP716A175 catalyses the three-step oxidation of triterpene backbones at the C-28 position | Malus domestica | ? | - |
? | |
| 1.14.14.126 | additional information | CYP716A175 catalyses the three-step oxidation of triterpene backbones at the C-28 position. CYP716A175 has a similar oxidizing capacity for the triterpene scaffold alpha-amyrin, beta-amyrin, and lupeol but not for germanicol | Malus domestica | ? | - |
? | |
| 5.4.99.34 | (3S)-2,3-epoxy-2,3-dihydrosqualene | - |
Malus domestica | germanicol | - |
r | |
| 5.4.99.34 | (S)-2,3-oxidosqualene | via dammarenyl cation, low activity | Malus domestica | beta-amyrin | - |
r | |
| 5.4.99.34 | (S)-2,3-oxidosqualene | via dammarenyl cation, low activity | Malus domestica | lupeol | - |
r | |
| 5.4.99.34 | additional information | although the MdOSC4 gene was expressed in the skins of all apple varieties under investigation, no germanicol or derivatives were detected at the metabolite level | Malus domestica | ? | - |
? | |
| 5.4.99.34 | additional information | gene MdOSC4 encodes a multifunctional oxidosqualene cyclase producing an oleanane-type triterpene, putatively identified as germanicol, as well as beta-amyrin and lupeol, in the proportion 82:14:4 | Malus domestica | ? | - |
? | |
| 5.4.99.39 | (S)-2,3-oxidosqualene | via dammarenyl cation | Malus domestica | beta-amyrin | - |
r | |
| 5.4.99.39 | additional information | MdOSC1 is a mixed amyrin synthase, with a 5:1 ratio of alpha-amyrin to beta-amyrin. The alpha-amyrin to beta-amyrin to lupeol production ratio for MdOSC1 from (S)-2,3-oxidosqualene is 85:13:2 | Malus domestica | ? | - |
? | |
| 5.4.99.40 | (S)-2,3-oxidosqualene | via dammarenyl cation | Malus domestica | beta-amyrin | - |
r | |
| 5.4.99.40 | (S)-2,3-oxidosqualene | via dammarenyl cation | Malus domestica | lupeol | - |
r | |
| 5.4.99.40 | (S)-2,3-oxidosqualene | via dammarenyl cation | Malus domestica | alpha-amyrin | - |
r | |
| 5.4.99.40 | additional information | MdOSC1 is a mixed amyrin synthase, with a 5:1 ratio of alpha-amyrin to beta-amyrin. The alpha-amyrin to beta-amyrin to lupeol production ratio for MdOSC1 is 85:13:2 | Malus domestica | ? | - |
? | |
| 5.4.99.41 | (S)-2,3-oxidosqualene | via dammarenyl cation, low activity | Malus domestica | beta-amyrin | - |
r | |
| 5.4.99.41 | (S)-2,3-oxidosqualene | via dammarenyl cation | Malus domestica | lupeol | - |
r | |
| 5.4.99.41 | additional information | MdOSC5 cyclizes 2,3-oxidosqualene into lupeol and beta-amyrin at a ratio of 95:5 | Malus domestica | ? | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 1.14.14.126 | C-28 oxidase | - |
Malus domestica |
| 1.14.14.126 | CYP716A175 | - |
Malus domestica |
| 1.14.14.126 | multifunctional P450 | - |
Malus domestica |
| 1.14.14.126 | triterpene monooxygenase | - |
Malus domestica |
| 5.4.99.34 | OCS4 | - |
Malus domestica |
| 5.4.99.39 | MdOSC1 | - |
Malus domestica |
| 5.4.99.39 | OPSC 1 | - |
Malus domestica |
| 5.4.99.40 | MdOSC1 | - |
Malus domestica |
| 5.4.99.40 | MdOSC3 | - |
- |
| 5.4.99.40 | MdOSC3 | - |
Malus domestica |
| 5.4.99.40 | OPSC 1 | - |
- |
| 5.4.99.40 | OPSC 1 | - |
Malus domestica |
| 5.4.99.40 | OSC3 | - |
- |
| 5.4.99.40 | OSC3 | - |
Malus domestica |
| 5.4.99.41 | MdOSC5 | - |
Malus domestica |
| 5.4.99.41 | OSC5 | - |
Malus domestica |
Cofactor
| EC Number | Cofactor | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.14.14.126 | cytochrome P450 | - |
Malus domestica |
General Information
| EC Number | General Information | Comment | Organism |
|---|---|---|---|
| 1.14.14.126 | evolution | CYP716A175 is clearly grouped with the CYP716A subfamily. Expression patterns of triterpene-related genes in different apple cultivars, overview | Malus domestica |
| 5.4.99.34 | evolution | MdOSC4 contains the highly conserved DCTAE motif, which is implicated in substrate binding, and six repeats of the QW motifs, typical of the triterpene synthase superfamily, sequence comparisons and phylogenetic analysis | Malus domestica |
| 5.4.99.34 | metabolism | analysis of biosynthetic pathway of triterpenic acids in apple fruits, overview | Malus domestica |
| 5.4.99.34 | additional information | analysis of triterpenes from apple fruits in a collection of 20 contrasting apple cultivars, expression patterns of triterpene-related genes in different apple cultivars, overview | Malus domestica |
| 5.4.99.34 | physiological function | the enzyme is involved in the biosynthesis of pentacyclic triterpenes, which, in apple, account for 32-70% of the epicuticular waxes, depending on the cultivar | Malus domestica |
| 5.4.99.39 | metabolism | MdOSC1 and MdOSC5 are key genes in apple fruit triterpene biosynthesis, analysis of biosynthetic pathway of triterpenic acids in apple, overview. The gene expression of MdOSC1 is linked to the concentrations of ursolic and oleanolic acid | Malus domestica |
| 5.4.99.39 | additional information | analysis of triterpenes from apple fruits in a collection of 20 contrasting apple cultivars, expression patterns of triterpene-related genes in different apple cultivars, overview | Malus domestica |
| 5.4.99.39 | physiological function | the enzyme is involved in the biosynthesis of pentacyclic triterpenes, which, in apple, account for 32-70% of the epicuticular waxes, depending on the cultivar | Malus domestica |
| 5.4.99.40 | metabolism | analysis of biosynthetic pathway of triterpenic acids in apple fruits, overview | Malus domestica |
| 5.4.99.40 | metabolism | MdOSC1 and MdOSC5 are key genes in apple fruit triterpene biosynthesis, analysis of biosynthetic pathway of triterpenic acids in apple, overview. The gene expression of MdOSC1 is linked to the concentrations of ursolic and oleanolic acid | Malus domestica |
| 5.4.99.40 | additional information | analysis of triterpenes from apple fruits in a collection of 20 contrasting apple cultivars, expression patterns of triterpene-related genes in different apple cultivars, overview | Malus domestica |
| 5.4.99.40 | physiological function | the enzyme is involved in the biosynthesis of pentacyclic triterpenes, which, in apple, account for 32-70% of the epicuticular waxes, depending on the cultivar | Malus domestica |
| 5.4.99.41 | evolution | enzyme MdOSC5 contain the highly conserved DCTAE motif, which is implicated in substrate binding, and six repeats of the QW motifs, typical of the triterpene synthase superfamily. MdOSC5 is located in linkage group LG17, sequence comparisons and phylogenetic analysis | Malus domestica |
| 5.4.99.41 | metabolism | MdOSC1 and MdOSC5 are key genes in apple fruit triterpene biosynthesis, analysis of biosynthetic pathway of triterpenic acids in apple, overview. The gene expression of MdOSC1 is linked to the concentrations of ursolic and oleanolic acid | Malus domestica |
| 5.4.99.41 | additional information | analysis of triterpenes from apple fruits in a collection of 20 contrasting apple cultivars, expression patterns of triterpene-related genes in different apple cultivars, overview | Malus domestica |
| 5.4.99.41 | physiological function | the enzyme is involved in the biosynthesis of pentacyclic triterpenes, which, in apple, account for 32-70% of the epicuticular waxes, depending on the cultivar | Malus domestica |
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