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Literature summary extracted from
- Interdependent evolution of biosynthetic gene clusters for momilactone production in rice (2021), Plant Cell, 33, 290-305.
Metals/Ions
| EC Number | Metals/Ions | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.1.1.295 | Fe2+ | required, in the cytochrome P450 heme | Oryza sativa Japonica Group |  |
| 1.14.14.123 | Fe2+ | required, in the heme | Oryza sativa Japonica Group | |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.1.1.295 | 3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NADP+ | Oryza sativa Japonica Group | - |
momilactone A + NADPH + H+ | - |
? | |
| 1.14.14.123 | ent-sandaracopimaradien-3beta-ol + [reduced NADPH-hemoprotein reductase] + O2 | Oryza sativa Japonica Group | - |
oryzalexin D + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.1.1.295 | Oryza sativa Japonica Group | Q7FAE1 | - |
- |
| 1.14.14.123 | Oryza sativa Japonica Group | Q6YTF1 | - |
- |
Source Tissue
| EC Number | Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|---|
| 1.1.1.295 | leaf | - |
Oryza sativa Japonica Group | - |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.1.1.295 | 3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NADP+ | - |
Oryza sativa Japonica Group | momilactone A + NADPH + H+ | - |
? | |
| 1.1.1.295 | additional information | besides the 3-hydroxylation of ent-sandaracopimara-814,15-diene and 9beta-pimara-7,15-diene (EC 1.14.14.70 and EC 1.14.14.68, respectively), enzyme CYP701A8 can further react beyond initial production of the C3beta-hydroxy derivative to produce the characteristic C3-oxo group of momilactone A. CYP701A8 can synthesize 3beta,6beta-dihydroxy-syn-pimaradiene and convert syn-pimaradien-19,6beta-olide to momilactone A | Oryza sativa Japonica Group | ? | - |
? | |
| 1.14.14.123 | ent-sandaracopimaradien-3beta-ol + [reduced NADPH-hemoprotein reductase] + O2 | - |
Oryza sativa Japonica Group | oryzalexin D + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.14.123 | additional information | the enzyme is active with ent-sandaracopimaradiene, ent-pimaradiene, ent-isokaurene, ent-cassadiene, ent-kaurene, and syn-pimaradiene as substrates. CYP701A8 can convert syn-pimaradien-19,6 beta-olide to momilactone A, EC 1.1.1.295 | Oryza sativa Japonica Group | ? | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 1.1.1.295 | CYP701A8 | - |
Oryza sativa Japonica Group |
| 1.1.1.295 | momilactone synthase | - |
Oryza sativa Japonica Group |
| 1.1.1.295 | additional information | cf. EC 1.14.14.68 and EC 1.14.14.70 | Oryza sativa Japonica Group |
| 1.14.14.123 | CYP76M8 | - |
Oryza sativa Japonica Group |
| 1.14.14.123 | additional information | see also EC 1.14.14.112, ent-cassa-12,15-diene 11-hydroxylase | Oryza sativa Japonica Group |
Temperature Optimum [°C]
| EC Number | Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|---|
| 1.14.14.123 | 32 | - |
assay at | Oryza sativa Japonica Group |
pH Optimum
| EC Number | pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|---|
| 1.14.14.123 | 7.5 | - |
assay at | Oryza sativa Japonica Group |
Cofactor
| EC Number | Cofactor | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.1.1.295 | cytochrome P450 | the enzyme is a cytochrome P450 monooxygenase | Oryza sativa Japonica Group | |
| 1.1.1.295 | heme | - |
Oryza sativa Japonica Group | |
| 1.1.1.295 | NADPH | - |
Oryza sativa Japonica Group | |
| 1.14.14.123 | cytochrome P450 | the enzyme is a cytochrome P450 monooxygenase | Oryza sativa Japonica Group | |
| 1.14.14.123 | heme | - |
Oryza sativa Japonica Group | |
Expression
| EC Number | Organism | Comment | Expression |
|---|---|---|---|
| 1.1.1.295 | Oryza sativa Japonica Group | the enzyme is induced by CuCl2 | up |
General Information
| EC Number | General Information | Comment | Organism |
|---|---|---|---|
| 1.1.1.295 | evolution | interdependent evolution of biosynthetic gene clusters for momilactone production in rice. Plants are limited to vertical gene transmission, implying that their biosynthetic gene clusters (BGCs) may exhibit distinct inheritance patterns. Rice (Oryza sativa) contains two unlinked BGCs involved in diterpenoid phytoalexin metabolism, with one clearly required for momilactone biosynthesis, while the other is associated with production of phytocassanes, interdependent evolution of these two BGCs, highlighting the distinct nature of BGC assembly in plants. CYP701A8 belongs to the c4BGC gene cluster. Expression of all the genes from the momilactone c4BGC and several from the c2BGC, including all those from the CYP76M subfamily, as well as CYP701A8 and the closely related CYP701A9, are examined | Oryza sativa Japonica Group |
| 1.1.1.295 | metabolism | the enzyme is involved in momilactone A biosynthesis, proposed momilactone A biosynthetic pathway, overview | Oryza sativa Japonica Group |
| 1.14.14.123 | evolution | CYP76M8 falls within a phylogenetic clade of the CYP76M subfamily that, in addition to CYP76M5, CYP76M6, and CYP76M7, which also are found in the c2BGC, has members located elsewhere in the rice genome. Interdependent evolution of biosynthetic gene clusters for momilactone production in rice. Plants are limited to vertical gene transmission, implying that their biosynthetic gene clusters (BGCs) may exhibit distinct inheritance patterns. Rice (Oryza sativa) contains two unlinked BGCs involved in diterpenoid phytoalexin metabolism, with one clearly required for momilactone biosynthesis, while the other is associated with production of phytocassanes. The presence of CYP76M8 in the other phytocassane BGC indicates interdependent evolution of these two BGCs, highlighting the distinct nature of BGC assembly in plants | Oryza sativa Japonica Group |
| 1.14.14.123 | metabolism | the momilactone biosynthetic gene cluster (BGC) is not only incomplete, but also fractured by the need for CYP76M8 to act in between steps catalyzed by enzymes from this BGC. The presence of CYP76M8 in the other phytocassane BGC indicates interdependent evolution of these two BGCs, highlighting the distinct nature of BGC assembly in plants. CYP76M7 is primarily responsible for phytocassane production. CYP76M8 acts after CYP99A2 and/or CYP99A3 from the momilactone BGC, with the resulting hemiacetal further oxidized to the eponymous lactone by the OsMS1 and/or OsMS2 also from this BGC | Oryza sativa Japonica Group |
| 1.14.14.123 | physiological function | role for cytochrome P450 (CYP) monooxygenase CYP76M8 from the phytocassane BGC. This CYP76M8 acts after the CYP99A2/3 from the momilactone BGC, producing a hemiacetal intermediate that is oxidized to the eponymous lactone by a short-chain alcohol dehydrogenase also from this BGC | Oryza sativa Japonica Group |
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