KEGG   ORTHOLOGY: K14040
Entry
K14040            Tight     KO                                     
Symbol
CYP720B, PTAO
Name
abieta-7,13-dien-18-ol hydroxylase [EC:1.14.14.145]
Pathway
map00904  Diterpenoid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Reaction
R06354  abietinol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (18-hydroxylating)
R10077  
R10078  
R12123  
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00904 Diterpenoid biosynthesis
    K14040  CYP720B, PTAO; abieta-7,13-dien-18-ol hydroxylase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K14040  CYP720B, PTAO; abieta-7,13-dien-18-ol hydroxylase
Enzymes [BR:ko01000]
 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
    1.14.14.145  abieta-7,13-dien-18-ol hydroxylase
     K14040  CYP720B, PTAO; abieta-7,13-dien-18-ol hydroxylase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP720 family
   K14040  CYP720B, PTAO; abieta-7,13-dien-18-ol hydroxylase
Other DBs
GO: 0036204
Genes
AG: AAX07431(CYP720B1) ADR78276(CYP720B4)
Reference
PMID:15911762 (CYP720B1)
  Authors
Ro DK, Arimura G, Lau SY, Piers E, Bohlmann J
  Title
Loblolly pine abietadienol/abietadienal oxidase PtAO (CYP720B1) is a multifunctional, multisubstrate cytochrome P450 monooxygenase.
  Journal
Proc Natl Acad Sci U S A 102:8060-5 (2005)
DOI:10.1073/pnas.0500825102
  Sequence
Reference
  Authors
Ro DK, Bohlmann J
  Title
Diterpene resin acid biosynthesis in loblolly pine (Pinus taeda): functional characterization of abietadiene/levopimaradiene synthase (PtTPS-LAS) cDNA and subcellular targeting of PtTPS-LAS and abietadienol/abietadienal oxidase (PtAO, CYP720B1).
  Journal
Phytochemistry 67:1572-8 (2006)
DOI:10.1016/j.phytochem.2006.01.011
Reference
PMID:21994349 (CYP720B4)
  Authors
Hamberger B, Ohnishi T, Hamberger B, Seguin A, Bohlmann J
  Title
Evolution of diterpene metabolism: Sitka spruce CYP720B4 catalyzes multiple oxidations in resin acid biosynthesis of conifer defense against insects.
  Journal
Plant Physiol 157:1677-95 (2011)
DOI:10.1104/pp.111.185843
  Sequence
LinkDB

KEGG   ENZYME: 1.14.14.145
Entry
EC 1.14.14.145              Enzyme                                 
Name
abieta-7,13-dien-18-ol hydroxylase;
CYP720B1;
PtAO;
abietadienol hydroxylase (ambiguous)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
abieta-7,13-dien-18-ol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (18-hydroxylating)
Reaction(IUBMB)
abieta-7,13-dien-18-ol + 2 [reduced NADPH---hemoprotein reductase] + 2 O2 = abieta-7,13-dien-18-oate + 2 [oxidized NADPH---hemoprotein reductase] + 3 H2O (overall reaction) [RN:R12122];
(1a) abieta-7,13-dien-18-ol + [reduced NADPH---hemoprotein reductase] + O2 = abieta-7,13-dien-18,18-diol + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R10077];
(1b) abieta-7,13-dien-18,18-diol = abieta-7,13-dien-18-al + H2O (spontaneous) [RN:R10078];
(1c) abieta-7,13-dien-18-al + [reduced NADPH---hemoprotein reductase] + O2 = abieta-7,13-dien-18-oate + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R12123]
Reaction(KEGG)
R10077 R10078 R12122 R12123;
(other) R06354
Substrate
abieta-7,13-dien-18-ol [CPD:C11882];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
abieta-7,13-dien-18,18-diol [CPD:C20329];
abieta-7,13-dien-18-al [CPD:C11887]
Product
abieta-7,13-dien-18-oate [CPD:C06087];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
abieta-7,13-dien-18,18-diol [CPD:C20329];
abieta-7,13-dien-18-al [CPD:C11887]
Comment
A cytochrome P-450 (heme-thiolate) protein. This enzyme catalyses a step in the pathway of abietic acid biosynthesis. The activity has been demonstrated in cell-free stem extracts of Abies grandis (grand fir) and Pinus contorta (lodgepole pine) [1], and the gene encoding the enzyme has been identified in Pinus taeda (loblolly pine) [3]. The recombinant enzyme catalyses the oxidation of multiple diterpene alcohol and aldehydes, including levopimaradienol, isopimara-7,15-dienol, isopimara-7,15-dienal, dehydroabietadienol and dehydroabietadienal. It is not able to oxidize abietadiene.
History
EC 1.14.14.145 created 2009 as EC 1.14.13.109, modified 2012, transferred 2018 to EC 1.14.14.145
Pathway
ec00904  Diterpenoid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K14040  abieta-7,13-dien-18-ol hydroxylase
Reference
1  [PMID:8311462]
  Authors
Funk C, Croteau R
  Title
Diterpenoid resin acid biosynthesis in conifers: characterization of two cytochrome P450-dependent monooxygenases and an aldehyde dehydrogenase involved in abietic acid biosynthesis.
  Journal
Arch Biochem Biophys 308:258-66 (1994)
DOI:10.1006/abbi.1994.1036
Reference
2  [PMID:12232380]
  Authors
Funk C, Lewinsohn E, Vogel BS, Steele CL, Croteau R
  Title
Regulation of Oleoresinosis in Grand Fir (Abies grandis) (Coordinate Induction of Monoterpene and Diterpene Cyclases and Two Cytochrome P450-Dependent Diterpenoid Hydroxylases by Stem Wounding).
  Journal
Plant Physiol 106:999-1005 (1994)
DOI:10.1104/pp.106.3.999
Reference
3  [PMID:15911762]
  Authors
Ro DK, Arimura G, Lau SY, Piers E, Bohlmann J
  Title
Loblolly pine abietadienol/abietadienal oxidase PtAO (CYP720B1) is a multifunctional, multisubstrate cytochrome P450 monooxygenase.
  Journal
Proc Natl Acad Sci U S A 102:8060-5 (2005)
DOI:10.1073/pnas.0500825102
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.145
IUBMB Enzyme Nomenclature: 1.14.14.145
ExPASy - ENZYME nomenclature database: 1.14.14.145
BRENDA, the Enzyme Database: 1.14.14.145
LinkDB

KEGG   REACTION: R06354
Entry
R06354                      Reaction                               
Name
abietinol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (18-hydroxylating)
Definition
Abietinol + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Abietal + [Oxidized NADPH---hemoprotein reductase] + 2 H2O
Equation
Reaction class
RC00893  C11882_C11887
Enzyme
Pathway
rn00904  Diterpenoid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  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
    1.14.14.145
     R06354  Abietinol + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Abietal + [Oxidized NADPH---hemoprotein reductase] + 2 H2O
Orthology
K14040  abieta-7,13-dien-18-ol hydroxylase [EC:1.14.14.145]
Other DBs
RHEA: 26224
LinkDB

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