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abieta-8,11,13-triene + O2
ferruginol + H2O
-
abieta-8,11,13-triene is formed spontaneously from miltiradiene. This reaction may be catalyzed by a not yet identified enzyme
-
-
?
abieta-8,11,13-triene + [reduced NADPH-hemoprotein reductase] + O2
abieta-8,11,13-trien-12-ol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
abieta-8,11,13-triene + [reduced NADPH-hemoprotein reductase] + O2
ferruginol + [oxidized NADPH-hemoprotein reductase] + H2O
miltiradiene + [reduced NADPH-hemoprotein reductase] + O2
11-oxomiltiradiene + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
additional information
?
-
CYP76AH1, catalyzes a four-electron oxidation cascade on miltiradiene to produce ferruginol both in vitro and in vivo
-
-
-
abieta-8,11,13-triene + [reduced NADPH-hemoprotein reductase] + O2
ferruginol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
abieta-8,11,13-triene + [reduced NADPH-hemoprotein reductase] + O2
ferruginol + [oxidized NADPH-hemoprotein reductase] + H2O
-
enzymes carry out not a single but two successive oxidations leading to 11-hydroxyferruginol from abieta-8,11,13-triene, i.e. reactions of EC 1.14.14.175 and 1.14.14.60
-
-
?
abieta-8,11,13-triene + [reduced NADPH-hemoprotein reductase] + O2
ferruginol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
abieta-8,11,13-triene + [reduced NADPH-hemoprotein reductase] + O2
ferruginol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
abieta-8,11,13-triene + [reduced NADPH-hemoprotein reductase] + O2
ferruginol + [oxidized NADPH-hemoprotein reductase] + H2O
i.e. miltiradiene
-
-
?
abieta-8,11,13-triene + [reduced NADPH-hemoprotein reductase] + O2
ferruginol + [oxidized NADPH-hemoprotein reductase] + H2O
-
enzyme catalyzes two successive oxidations leading to 11-hydroxyferruginol from abieta-8,11,13-triene, i.e. reactions of EC 1.14.14.175 and 1.14.14.60
-
-
?
abieta-8,11,13-triene + [reduced NADPH-hemoprotein reductase] + O2
ferruginol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
abieta-8,11,13-triene + [reduced NADPH-hemoprotein reductase] + O2
ferruginol + [oxidized NADPH-hemoprotein reductase] + H2O
-
enzymes carry out not a single but two successive oxidations leading to 11-hydroxyferruginol from abieta-8,11,13-triene, i.e. reactions of EC 1.14.14.175 and 1.14.14.60
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
abieta-8,11,13-triene + O2
ferruginol + H2O
-
abieta-8,11,13-triene is formed spontaneously from miltiradiene. This reaction may be catalyzed by a not yet identified enzyme
-
-
?
abieta-8,11,13-triene + [reduced NADPH-hemoprotein reductase] + O2
abieta-8,11,13-trien-12-ol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
abieta-8,11,13-triene + [reduced NADPH-hemoprotein reductase] + O2
ferruginol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
additional information
?
-
CYP76AH1, catalyzes a four-electron oxidation cascade on miltiradiene to produce ferruginol both in vitro and in vivo
-
-
-
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D301E/N303S/V479F
mutation leads to a second oxidation of product to give 11-hydroxyferruginol, i.e. reaction of EC 1.14.14.60
F112L
-
mutant catalyzes ferruginol production in yeast 2 times more efficiently than the wild-type enzyme, while production of 11-hydroxy-ferruginol is abolished. mutant does not oxidize miltiradiene
V296L
-
mutant produces 1.5 times more ferruginol, but 8fold less 11-hydroxy-ferruginol and 20fold less 11beta-hydroxy-manoyl oxide than the wild-type enzyme. mutant does not oxidize miltiradiene
additional information
RNAi-mediated silencing of CYP76AH1 in hairy roots, construction of a CYP76AH1 RNAi system for hairy roots using transformation via Agrobacterium rhizogenes strain C58C1. Metabolic analysis of RNAi-AH1 hairy root lines shows a significantly increased accumulation of miltiradiene and decreased concentration of ferruginol compared to the control lines. The content of tanshinones decreases significantly after silencing of CYP76AH1
additional information
-
RNAi-mediated silencing of CYP76AH1 in hairy roots, construction of a CYP76AH1 RNAi system for hairy roots using transformation via Agrobacterium rhizogenes strain C58C1. Metabolic analysis of RNAi-AH1 hairy root lines shows a significantly increased accumulation of miltiradiene and decreased concentration of ferruginol compared to the control lines. The content of tanshinones decreases significantly after silencing of CYP76AH1
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Zi, J.; Peters, R.J.
Characterization of CYP76AH4 clarifies phenolic diterpenoid biosynthesis in the Lamiaceae
Org. Biomol. Chem.
11
7650-7652
2013
Salvia rosmarinus
brenda
Ma, Y.; Ma, X.H.; Meng, F.Y.; Zhan, Z.L.; Guo, J.; Huang, L.Q.
RNA interference targeting CYP76AH1 in hairy roots of Salvia miltiorrhiza reveals its key role in the biosynthetic pathway of tanshinones
Biochem. Biophys. Res. Commun.
477
155-160
2016
Salvia miltiorrhiza (S4UX02), Salvia miltiorrhiza
brenda
Scheler, U.; Brandt, W.; Porzel, A.; Rothe, K.; Manzano, D.; Bozic, D.; Papaefthimiou, D.; Balcke, G.; Henning, A.; Lohse, S.; Marillonnet, S.; Kanellis, A.; Ferrer, A.; Tissier, A.
Elucidation of the biosynthesis of carnosic acid and its reconstitution in yeast
Nat. Commun.
7
12942
2016
Salvia fruticosa, Salvia rosmarinus, Salvia miltiorrhiza (S4UX02), Salvia miltiorrhiza
brenda
Ignea, C.; Athanasakoglou, A.; Ioannou, E.; Georgantea, P.; Trikka, F.A.; Loupassaki, S.; Roussis, V.; Makris, A.M.; Kampranis, S.C.
Carnosic acid biosynthesis elucidated by a synthetic biology platform
Proc. Natl. Acad. Sci. USA
113
3681-3686
2016
Salvia pomifera
brenda
Ignea, C.; Athanasakoglou, A.; Andreadelli, A.; Apostolaki, M.; Iakovides, M.; Stephanou, E.G.; Makris, A.M.; Kampranis, S.C.
Overcoming the plasticity of plant specialized metabolism for selective diterpene production in yeast
Sci. Rep.
7
8855
2017
Salvia pomifera
brenda
Bozic, D.; Papaefthimiou, D.; Brueckner, K.; de Vos, R.C.; Tsoleridis, C.A.; Katsarou, D.; Papanikolaou, A.; Pateraki, I.; Chatzopoulou, F.M.; Dimitriadou, E.; Kostas, S.; Manzano, D.; Scheler, U.; Ferrer, A.; Tissier, A.; Makris, A.M.; Kampranis, S.C.; Kanellis, A.K.
Towards elucidating carnosic acid biosynthesis in Lamiaceae Functional characterization of the three first steps of the pathway in Salvia fruticosa and Rosmarinus officinalis
PLoS ONE
10
e0124106
2015
Salvia rosmarinus (A0A0C5Q4Y6), Salvia rosmarinus (A0A0C5QEW3), Salvia fruticosa (A0A0C5QRZ2)
brenda
Guo, J.; Zhou, Y.J.; Hillwig, M.L.; Shen, Y.; Yang, L.; Wang, Y.; Zhang, X.; Liu, W.; Peters, R.J.; Chen, X.; Zhao, Z.K.; Huang, L.
CYP76AH1 catalyzes turnover of miltiradiene in tanshinones biosynthesis and enables heterologous production of ferruginol in yeasts
Proc. Natl. Acad. Sci. USA
110
12108-12113
2013
Salvia miltiorrhiza (S4UX02)
brenda
1.14.14.175 ferruginol synthase
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