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Information on EC 1.14.14.95 - germacrene A hydroxylase for references in articles please use BRENDA:EC1.14.14.95
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IUBMB Comments A cytochrome P-450 (heme-thiolate) protein. This plant enzyme catalyses three steps in a pathway that leads to the biosynthesis of many sesquiterpenoid lactones.
The enzyme appears in viruses and cellular organisms
Synonyms
(+)-germacrene A hydroxylase, GAO, germacrene A oxidase, NADP+-dependent sesquiterpenoid dehydrogenase,
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(+)-germacrene A hydroxylase
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NADP+-dependent sesquiterpenoid dehydrogenase
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GAO
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germacrene A oxidase
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(+)-germacrene A + 3 [reduced NADPH-hemoprotein reductase] + 3 O2 = germacra-1(10),4,11(13)-trien-12-oate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
overall reaction
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(+)-germacrene A + O2 + [reduced NADPH-hemoprotein reductase] = germacra-1(10),4,11(13)-trien-12-ol + [oxidized NADPH-hemoprotein reductase] + H2O
(1a)
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germacra-1(10),4,11(13)-trien-12-al + O2 + [reduced NADPH-hemoprotein reductase] = germacra-1(10),4,11(13)-trien-12-oate + [oxidized NADPH-hemoprotein reductase] + H2O
(1c)
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germacra-1(10),4,11(13)-trien-12-ol + O2 + [reduced NADPH-hemoprotein reductase] = germacra-1(10),4,11(13)-trien-12-al + [oxidized NADPH-hemoprotein reductase] + 2 H2O
(1b)
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hydroxylation
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C13-hydroxylation
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(+)-germacrene-A,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (12-hydroxylating)
A cytochrome P-450 (heme-thiolate) protein. This plant enzyme catalyses three steps in a pathway that leads to the biosynthesis of many sesquiterpenoid lactones.
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(+)-germacrene A + [reduced NADPH-hemoprotein reductase] + O2
germacra-1(10),4,11(13)-trien-12-ol + [oxidized NADPH-hemoprotein reductase] + H2O
beta-elemene + [reduced NADPH-hemoprotein reductase] + O2
elema-1,3,11(13)-trien-12-ol + [oxidized NADPH-hemoprotein reductase] + H2O
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the amount of (+)-beta-elemene hydroxylated is 2times less than that of (-)-beta-elemene
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germacra-1(10),4,11(13)-trien-12-ol + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
germacra-1(10),4,11(13)-trien-12-oate + 2 [oxidized NADPH-hemoprotein reductase] + 3 H2O
germacrene A + [reduced NADPH-hemoprotein reductase] + O2
12-hydroxygermacrene A + [oxidized NADPH-hemoprotein reductase] + H2O
(+)-germacrene A + [reduced NADPH-hemoprotein reductase] + O2
germacra-1(10),4,11(13)-trien-12-ol + [oxidized NADPH-hemoprotein reductase] + H2O
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100% activity
germacra-1(10),4,11(13)-trien-12-ol is also named costol
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(+)-germacrene A + [reduced NADPH-hemoprotein reductase] + O2
germacra-1(10),4,11(13)-trien-12-ol + [oxidized NADPH-hemoprotein reductase] + H2O
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30% activity with NADH as compared to NADPH
germacra-1(10),4,11(13)-trien-12-ol is also named costol
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germacra-1(10),4,11(13)-trien-12-ol + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
germacra-1(10),4,11(13)-trien-12-oate + 2 [oxidized NADPH-hemoprotein reductase] + 3 H2O
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germacra-1(10),4,11(13)-trien-12-ol + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
germacra-1(10),4,11(13)-trien-12-oate + 2 [oxidized NADPH-hemoprotein reductase] + 3 H2O
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germacrene A + [reduced NADPH-hemoprotein reductase] + O2
12-hydroxygermacrene A + [oxidized NADPH-hemoprotein reductase] + H2O
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germacrene A + [reduced NADPH-hemoprotein reductase] + O2
12-hydroxygermacrene A + [oxidized NADPH-hemoprotein reductase] + H2O
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germacrene A + [reduced NADPH-hemoprotein reductase] + O2
12-hydroxygermacrene A + [oxidized NADPH-hemoprotein reductase] + H2O
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germacrene A + [reduced NADPH-hemoprotein reductase] + O2
12-hydroxygermacrene A + [oxidized NADPH-hemoprotein reductase] + H2O
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germacrene A + [reduced NADPH-hemoprotein reductase] + O2
12-hydroxygermacrene A + [oxidized NADPH-hemoprotein reductase] + H2O
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flavin
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an assay buffer without flavins (FAD and FMN) gives 18% loss of hydroxylase activity. However, omitting these flavins from the extraction buffer results in a loss of more than 70% in enzyme activity
cytochrome P-450
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cytochrome P-450
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required for activity, the combination of NADPH with NADH shows an additive effect on enzyme activity (120%)
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aminobenzotriazole
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26% inhibition at 0.1 mM
carbon monoxide
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blue-light reversible inhibition, an atmosphere of 80% CO plus 20% O2 inhibits (+)-germacrene A hydroxylase by 69%
clotrimazole
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016% inhibition at 0.1 mM
cytochrome c
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97% inhibition at 0.1 mM
Metyrapone
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23% inhibition at 1 mM
miconazole
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30% inhibition at 0.1 mM
additional information
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flushing the reaction mixture for 1.5 min with argon prior to incubation causes a 69% decrease of enzyme activity because of O2 depletion
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6 - 9
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60% of maximal enzyme activity at pH 7.5 and 9.0 (no difference in activity between bis-Tris and Tris buffer)
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UniProt
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UniProt
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UniProt
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UniProt
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UniProt
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brenda
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GAO_BARSP
496
0
55699
Swiss-Prot
GAO_CICIN
488
0
54972
Swiss-Prot
GAO_HELAN
488
0
55088
Swiss-Prot
GAO_LACSA
488
0
54963
Swiss-Prot
GAO_SAUCO
488
0
55032
Swiss-Prot
GAO_TANPA
488
0
55063
Swiss-Prot
A0A3Q8QEF5_CICIN
488
0
54972
TrEMBL
A0A396I508_MEDTR
316
1
35732
TrEMBL
A0A3S8NUY8_CICEN
488
0
54963
TrEMBL
A0A251SU99_HELAN
488
0
55088
TrEMBL
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54900
calculated from amino acid sequence
54900
calculated from amino acid sequence
54900
calculated from amino acid sequence
54900
calculated from amino acid sequence
54900
calculated from amino acid sequence
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expressed in Saccharomyces cerevisiae strain YPL 154C:Pep4 KO; expressed in the protease-deficient Saccharomyces cerevisiae YPL 154C:Pep4 KO strain
expressed in the protease-deficient Saccharomyces cerevisiae YPL 154C:Pep4 KO strain
expressed in the protease-deficient Saccharomyces cerevisiae YPL 154C:Pep4 KO strain
expressed in the protease-deficient Saccharomyces cerevisiae YPL 154C:Pep4 KO strain
expressed in the protease-deficient Saccharomyces cerevisiae YPL 154C:Pep4 KO strain
expressed in the protease-deficient Saccharomyces cerevisiae YPL 154C:Pep4 KO strain
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Nguyen, D.; Goepfert, J.; Ikezawa, N.; MacNevin, G.; Kathiresan, M.; Conrad, J.; Spring, O.; Ro, D.
Biochemical conservation and evolution of germacrene A oxidase in Asteraceae
J. Biol. Chem.
285
16588-16598
2010
Barnadesia spinosa, Barnadesia spinosa (D5JBX1), Cichorium intybus, Cichorium intybus (D5JBW8), Helianthus annuus (D5JBX0), Lactuca sativa (D5J9U8), Saussurea costus (D5JBW9)
brenda
De Kraker, K.J.; Franssen, M.; Dalm, M.; de, G.A.; Bouwmeester, H.
Biosynthesis of germacrene A carboxylic acid in chicory roots. Demonstration of a cytochrome P450 (+)-germacrene a hydroxylase and NADP+-dependent sesquiterpenoid dehydrogenase(s) involved in sesquiterpene lactone biosynthesis
Plant Physiol.
125
1930-1940
2001
Cichorium intybus
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1.14.14.95 germacrene A hydroxylase
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