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Information on EC 1.14.14.61 - carnosic acid synthase

for references in articles please use BRENDA:EC1.14.14.61

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EC Tree

1 Oxidoreductases

1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen

1.14.14 With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor

1.14.14.61 carnosic acid synthase

IUBMB 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).

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The expected taxonomic range for this enzyme is: Salvia

Reaction Schemes

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11-hydroxyferruginol

[reduced NADPH-hemoprotein reductase]

carnosic acid

[oxidized NADPH-hemoprotein reductase]

H2O

Synonyms

CYP76AK6, CYP76AK7, CYP76AK8, show all synonyms

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SYNONYM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

CYP76AK6

CYP76AK7

CYP76AK8

CYP76AK6

CYP76AK7

CYP76AK8

CYP76AK8

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REACTION

REACTION DIAGRAM

COMMENTARY

ORGANISM

UNIPROT

LITERATURE

11-hydroxyferruginol + 3 [reduced NADPH-hemoprotein reductase] + 3 O2 = carnosic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O

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Go to Pathway Search

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PATHWAY SOURCE

PATHWAYS

KEGG

Biosynthesis of secondary metabolites, Diterpenoid biosynthesis

MetaCyc

carnosate bioynthesis

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SYSTEMATIC NAME

IUBMB Comments

11-hydroxyferruginol,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase

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).

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SUBSTRATE

PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

Reversibility
r=reversible
ir=irreversible
?=not specified

11-hydroxyferruginol + 3 [reduced NADPH-hemoprotein reductase] + 3 O2

carnosic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O

3 entries

ferruginol + 3 [reduced NADPH-hemoprotein reductase] + 3 O2

pisiferic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O

2 entries

additional information

5 entries

11-hydroxyferruginol + 3 [reduced NADPH-hemoprotein reductase] + 3 O2

carnosic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O

Salvia fruticosa

745860

11-hydroxyferruginol + 3 [reduced NADPH-hemoprotein reductase] + 3 O2

carnosic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O

Salvia pomifera

A0A0S1TPC7

745860, 746312

11-hydroxyferruginol + 3 [reduced NADPH-hemoprotein reductase] + 3 O2

carnosic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O

Salvia rosmarinus

745860, 746312

ferruginol + 3 [reduced NADPH-hemoprotein reductase] + 3 O2

pisiferic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O

Salvia pomifera

A0A0S1TPC7

746312

ferruginol + 3 [reduced NADPH-hemoprotein reductase] + 3 O2

pisiferic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O

Salvia rosmarinus

746312

additional information

Salvia fruticosa

reaction intermediates are 11,20-dohydroxyferruginol and carnosaldehyde, which itself spontaneously oxidizes to carnosol. The enzyme can also oxidize miltiradiene and ferruginol, thelatter leading to pisifieric acid, albeit with much lower efficiency, indicating 11-hydroxyferruginol is their preferred substrate

745860

additional information

Salvia pomifera

A0A0S1TPC7

CYP76AK6 is a multifunctional enzyme that catalyzes successive oxidation events at C-20 of the labdane skeleton

746312

additional information

Salvia pomifera

A0A0S1TPC7

reaction intermediates are 11,20-dohydroxyferruginol and carnosaldehyde, which itself spontaneously oxidizes to carnosol. The enzyme can also oxidize miltiradiene and ferruginol, the latter leading to pisifieric acid, albeit with much lower efficiency, indicating 11-hydroxyferruginol is their preferred substrate

745860

additional information

Salvia rosmarinus

CYP76AK6 is a multifunctional enzyme that catalyzes successive oxidation events at C-20 of the labdane skeleton

746312

additional information

Salvia rosmarinus

reaction intermediates are 11,20-dohydroxyferruginol and carnosaldehyde, which itself spontaneously oxidizes to carnosol. The enzyme can also oxidize miltiradiene and ferruginol, the latter leading to pisifieric acid, albeit with much lower efficiency, indicating 11-hydroxyferruginol is their preferred substrate

745860

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COFACTOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

cytochrome P450

cytochrome P450

cytochrome P450

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ORGANISM

COMMENTARY

LITERATURE

UNIPROT

SEQUENCE DB

SOURCE

brenda

UniProt

brenda

Salvia rosmarinus

745860, 746312

brenda

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SOURCE TISSUE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

SOURCE

glandular trichome

brenda

glandular trichome

brenda

Go to AA Sequence and Transmembrane Helices SearchGo to Localization Prediction

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UNIPROT

ENTRY NAME

ORGANISM

NO. OF AA

NO. OF TRANSM. HELICES

MOLECULAR WEIGHT[Da]

SOURCE

SEQUENCE

LOCALIZATION PREDICTION

The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).

A0A1D8QMD1 pBLAST

C76K6_SALFT

Salvia fruticosa

500

56138

Swiss-Prot

Show Sequence

Mitochondrion (Reliability: 4)

A0A0S1TPC7 pBLAST

C76K6_SALPM

Salvia pomifera

500

56161

Swiss-Prot

Show Sequence

Mitochondrion (Reliability: 4)

A0A1D8QMD2 pBLAST

C76K7_ROSOF

Rosmarinus officinalis

507

57245

Swiss-Prot

Show Sequence

Secretory Pathway (Reliability: 5)

A0A1D8QMG4 pBLAST

C76K8_ROSOF

Rosmarinus officinalis

504

56686

Swiss-Prot

Show Sequence

Mitochondrion (Reliability: 5)

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CLONED (Commentary)

ORGANISM

UNIPROT

LITERATURE

expression in Nicotiana benthamiana leaf

2 entries

expression in Nicotiana benthamiana leaf

Salvia rosmarinus

745860

expression in Nicotiana benthamiana leaf

Salvia fruticosa

745860

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REF.

AUTHORS

TITLE

JOURNAL

VOL.

PAGES

YEAR

ORGANISM (UNIPROT)

PUBMED ID

SOURCE

745860

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.

12942

2016

Salvia fruticosa, Salvia rosmarinus, Salvia pomifera (A0A0S1TPC7)

27703160

brenda

746312

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