The Enzyme Database

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EC 1.14.13.190      
Transferred entry: ferruginol synthase. Now EC 1.14.14.175, ferruginol synthase
[EC 1.14.13.190 created 2014, modified 2015, deleted 2020]
 
 
EC 1.14.14.60     
Accepted name: ferruginol monooxygenase
Reaction: ferruginol + [reduced NADPH—hemoprotein reductase] + O2 = 11-hydroxyferruginol + [oxidized NADPH—hemoprotein reductase] + H2O
For diagram of carnosic acid, salviol and suginol diterpenoids biosynthesis, click here
Glossary: ferruginol = abieta-8,11,13-trien-12-ol
Other name(s): CYP76AH24; CYP76AH3
Systematic name: ferruginol,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (11-hydroxyferruginol-forming)
Comments: A cytochrome P-450 (heme-thiolate) protein isolated from the plants Salvia pomifera (apple sage) and Salvia miltiorrhiza (danshen). 11-Hydroxyferruginol is a precursor of carnosic acid, a potent antioxidant.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Ignea, C., Athanasakoglou, A., Ioannou, E., Georgantea, P., Trikka, F.A., Loupassaki, S., Roussis, V., Makris, A.M. and Kampranis, S.C. Carnosic acid biosynthesis elucidated by a synthetic biology platform. Proc. Natl. Acad. Sci. USA 113 (2016) 3681–3686. [DOI] [PMID: 26976595]
2.  Scheler, U., Brandt, W., Porzel, A., Rothe, K., Manzano, D., Bozic, D., Papaefthimiou, D., Balcke, G.U., Henning, A., Lohse, S., Marillonnet, S., Kanellis, A.K., Ferrer, A. and Tissier, A. Elucidation of the biosynthesis of carnosic acid and its reconstitution in yeast. Nat. Commun. 7:12942 (2016). [DOI] [PMID: 27703160]
3.  Guo, J., Ma, X., Cai, Y., Ma, Y., Zhan, Z., Zhou, Y.J., Liu, W., Guan, M., Yang, J., Cui, G., Kang, L., Yang, L., Shen, Y., Tang, J., Lin, H., Ma, X., Jin, B., Liu, Z., Peters, R.J., Zhao, Z.K. and Huang, L. Cytochrome P450 promiscuity leads to a bifurcating biosynthetic pathway for tanshinones. New Phytol. 210 (2016) 525–534. [DOI] [PMID: 26682704]
[EC 1.14.14.60 created 2018]
 
 
EC 1.14.14.61     
Accepted name: carnosic acid synthase
Reaction: 11-hydroxyferruginol + 3 [reduced NADPH—hemoprotein reductase] + 3 O2 = carnosic acid + 3 [oxidized NADPH—hemoprotein reductase] + 4 H2O
For diagram of carnosic acid, salviol and suginol diterpenoids biosynthesis, click here
Glossary: carnosic acid = 11,12-dihydroxyabieta-8,11,13-trien-20-oic acid
Other name(s): CYP76AK6; CYP76AK7; CYP76AK8
Systematic name: 11-hydroxyferruginol,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase
Comments: A cytochrome P-450 (heme-thiolate) protein isolated from the plants Salvia pomifera (apple sage), S. miltiorrhiza (red sage), S. fruticosa (Greek sage) and Rosmarinus officinalis (Rosemary).
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Ignea, C., Athanasakoglou, A., Ioannou, E., Georgantea, P., Trikka, F.A., Loupassaki, S., Roussis, V., Makris, A.M. and Kampranis, S.C. Carnosic acid biosynthesis elucidated by a synthetic biology platform. Proc. Natl. Acad. Sci. USA 113 (2016) 3681–3686. [DOI] [PMID: 26976595]
2.  Scheler, U., Brandt, W., Porzel, A., Rothe, K., Manzano, D., Bozic, D., Papaefthimiou, D., Balcke, G.U., Henning, A., Lohse, S., Marillonnet, S., Kanellis, A.K., Ferrer, A. and Tissier, A. Elucidation of the biosynthesis of carnosic acid and its reconstitution in yeast. Nat. Commun. 7:12942 (2016). [DOI] [PMID: 27703160]
[EC 1.14.14.61 created 2018]
 
 
EC 1.14.14.62     
Accepted name: salviol synthase
Reaction: ferruginol + [reduced NADPH—hemoprotein reductase] + O2 = salviol + [oxidized NADPH—hemoprotein reductase] + H2O
For diagram of carnosic acid, salviol and suginol diterpenoids biosynthesis, click here
Glossary: salviol = abieta-8,11,13-triene-2α,12-diol
Other name(s): CYP71BE52
Systematic name: ferruginol,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (salviol-forming)
Comments: A cytochrome P-450 (heme-thiolate) protein isolated from the plant Salvia pomifera (apple sage).
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Ignea, C., Athanasakoglou, A., Ioannou, E., Georgantea, P., Trikka, F.A., Loupassaki, S., Roussis, V., Makris, A.M. and Kampranis, S.C. Carnosic acid biosynthesis elucidated by a synthetic biology platform. Proc. Natl. Acad. Sci. USA 113 (2016) 3681–3686. [DOI] [PMID: 26976595]
[EC 1.14.14.62 created 2018]
 
 
EC 1.14.14.65     
Accepted name: sugiol synthase
Reaction: ferruginol + 2 [reduced NADPH—hemoprotein reductase] + 2 O2 = sugiol + 2 [oxidized NADPH—hemoprotein reductase] + 3 H2O
For diagram of carnosic acid, salviol and suginol diterpenoids biosynthesis, click here
Glossary: ferruginol = abieta-8,11,13-trien-12-ol
sugiol = 12-hydroxyabieta-8,11,13-trien-7-one
Other name(s): CYP76AH3
Systematic name: ferruginol,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (sugiol-forming)
Comments: A cytochrome P-450 (heme-thiolate) protein isolated from the plant Salvia miltiorrhiza (danshen). The enzyme also oxidizes 11-hydroxyferruginol to 11-hydroxysugiol. It also oxidizes at C-12 of ferruginol (EC 1.14.14.60 ferruginol monooxygenase).
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Guo, J., Ma, X., Cai, Y., Ma, Y., Zhan, Z., Zhou, Y.J., Liu, W., Guan, M., Yang, J., Cui, G., Kang, L., Yang, L., Shen, Y., Tang, J., Lin, H., Ma, X., Jin, B., Liu, Z., Peters, R.J., Zhao, Z.K. and Huang, L. Cytochrome P450 promiscuity leads to a bifurcating biosynthetic pathway for tanshinones. New Phytol. 210 (2016) 525–534. [DOI] [PMID: 26682704]
[EC 1.14.14.65 created 2018]
 
 
EC 1.14.14.67     
Accepted name: 11-hydroxysugiol 20-monooxygenase
Reaction: 11-hydroxysugiol + [reduced NADPH—hemoprotein reductase] + O2 = 11,20-dihydroxysugiol + [oxidized NADPH—hemoprotein reductase] + H2O
For diagram of carnosic acid, salviol and suginol diterpenoids biosynthesis, click here
Glossary: ferruginol = abieta-8,11,13-trien-12-ol
sugiol = 12-hydroxyabieta-8,11,13-trien-7-one
Other name(s): CYP76AK1
Systematic name: 11-hydroxysugiol,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (11,20-dihydroxysugiol-forming)
Comments: A cytochrome P-450 (heme-thiolate) protein isolated from the plant Salvia miltiorrhiza (danshen). The enzyme also oxidizes 11-hydroxyferruginol to 11,20-dihydroxyferruginol.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Guo, J., Ma, X., Cai, Y., Ma, Y., Zhan, Z., Zhou, Y.J., Liu, W., Guan, M., Yang, J., Cui, G., Kang, L., Yang, L., Shen, Y., Tang, J., Lin, H., Ma, X., Jin, B., Liu, Z., Peters, R.J., Zhao, Z.K. and Huang, L. Cytochrome P450 promiscuity leads to a bifurcating biosynthetic pathway for tanshinones. New Phytol. 210 (2016) 525–534. [DOI] [PMID: 26682704]
[EC 1.14.14.67 created 2018]
 
 
EC 1.14.14.175     
Accepted name: ferruginol synthase
Reaction: abieta-8,11,13-triene + [reduced NADPH—hemoprotein reductase] + O2 = ferruginol + [oxidized NADPH—hemoprotein reductase] + H2O
For diagram of abietane diterpenoids biosynthesis, click here
Glossary: ferruginol = abieta-8,11,13-trien-12-ol
Other name(s): miltiradiene oxidase (incorrect); CYP76AH1; miltiradiene,NADPH:oxygen oxidoreductase (ferruginol forming) (incorrect)
Systematic name: abieta-8,11,13-triene,[reduced NADPH—hemoprotein reductase]:oxygen 12-oxidoreductase (ferruginol-forming)
Comments: A cytochrome P-450 (heme thiolate) enzyme found in some members of the Lamiaceae (mint family). The enzyme from Rosmarinus officinalis (rosemary) is involved in biosynthesis of carnosic acid, while the enzyme from the Chinese medicinal herb Salvia miltiorrhiza is involved in the biosynthesis of the tanshinones, abietane-type norditerpenoid naphthoquinones that are the main lipophilic bioactive components found in the plant.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  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. and Huang, L. CYP76AH1 catalyzes turnover of miltiradiene in tanshinones biosynthesis and enables heterologous production of ferruginol in yeasts. Proc. Natl. Acad. Sci. USA 110 (2013) 12108–12113. [DOI] [PMID: 23812755]
2.  Zi, J. and Peters, R.J. Characterization of CYP76AH4 clarifies phenolic diterpenoid biosynthesis in the Lamiaceae. Org. Biomol. Chem. 11 (2013) 7650–7652. [DOI] [PMID: 24108414]
3.  Bozic, D., Papaefthimiou, D., Bruckner, 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. and 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). [DOI] [PMID: 26020634]
[EC 1.14.14.175 created 2014 as EC 1.14.13.190, modified 2015, transferred 2020 to EC 1.14.14.175]
 
 


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