KEGG   ENZYME: 1.14.14.126Help
Entry
EC 1.14.14.126              Enzyme                                 

Name
beta-amyrin 28-monooxygenase;
CYP716A52v2;
CYP716A12;
CYP16A75;
beta-amyrin 28-oxidase
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
BRITE hierarchy
Sysname
beta-amyrin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (28-hydroxylating)
Reaction(IUBMB)
beta-amyrin + 3 O2 + 3 [reduced NADPH---hemoprotein reductase] = oleanolate + 3 [oxidized NADPH---hemoprotein reductase] + 4 H2O (overall reaction) [RN:R10924];
(1a) beta-amyrin + O2 + [reduced NADPH---hemoprotein reductase] = erythrodiol + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R10921];
(1b) erythrodiol + O2 + [reduced NADPH---hemoprotein reductase] = oleanolic aldehyde + [oxidized NADPH---hemoprotein reductase] + 2 H2O [RN:R10922];
(1c) oleanolic aldehyde + O2 + [reduced NADPH---hemoprotein reductase] = oleanolate + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R10923]
Reaction(KEGG)
Substrate
beta-amyrin [CPD:C08616];
O2 [CPD:C00007];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
erythrodiol [CPD:C20945];
oleanolic aldehyde [CPD:C20946]
Product
oleanolate [CPD:C17148];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
erythrodiol [CPD:C20945];
oleanolic aldehyde [CPD:C20946]
Comment
A cytochrome P-450 (heme-thiolate) protein found in plants. The enzyme is involved in the biosynthesis of oleanane-type triterpenoids, such as ginsenoside Ro. The enzyme from Medicago truncatula (barrel medic) (CYP716A12) can also convert alpha-amyrin and lupeol to ursolic acid and betulinic acid, respectively. The enzyme from Maesa lanceolata (false assegai) (CYP16A75) does not catalyse the reaction to completion, resulting in accumulation of both intermediates.
History
EC 1.14.14.126 created 2015 as EC 1.14.13.201, transferred 2018 to EC 1.14.14.126
Orthology
K20667  beta-amyrin 28-monooxygenase
Genes
ATH: AT5G36110(CYP716A1) AT5G36130 AT5G36140(CYP716A2)
ALY: ARALYDRAFT_493652
CRB: 17878597
CSAT: 104719298 104724031 104732576
EUS: EUTSA_v10027740mg EUTSA_v10028112mg
THJ: 104808921
CPAP: 110811366
CIT: 102613788 102620622 102623975 102625141 102625960
CIC: CICLE_v10001024mg CICLE_v10010450mg CICLE_v10015070mg CICLE_v10018316mg CICLE_v10019890mg CICLE_v10019893mg CICLE_v10030148mg
TCC: 18587560 18589551 18593052 18593053 18593056 18595104 18595548 18595550
LJA: Lj0g3v0291119.1(Lj0g3v0291119.1) Lj0g3v0312269.1(Lj0g3v0312269.1) Lj4g3v2666330.1(Lj4g3v2666330.1) Lj4g3v2666330.2(Lj4g3v2666330.2) Lj4g3v2666360.1(Lj4g3v2666360.1) Lj4g3v2704710.1(Lj4g3v2704710.1) Lj4g3v3014670.1(Lj4g3v3014670.1)
CSV: 101206033
CMO: 103487187
CMAX: 111485071
CMOS: 111461545
CPEP: 111780629
 » show all
Taxonomy
Reference
1  [PMID:22039103]
  Authors
Fukushima EO, Seki H, Ohyama K, Ono E, Umemoto N, Mizutani M, Saito K, Muranaka T
  Title
CYP716A subfamily members are multifunctional oxidases in triterpenoid biosynthesis.
  Journal
Plant Cell Physiol 52:2050-61 (2011)
DOI:10.1093/pcp/pcr146
Reference
2  [PMID:24092881]
  Authors
Han JY, Kim MJ, Ban YW, Hwang HS, Choi YE
  Title
The involvement of beta-amyrin 28-oxidase (CYP716A52v2) in oleanane-type ginsenoside biosynthesis in Panax ginseng.
  Journal
Plant Cell Physiol 54:2034-46 (2013)
DOI:10.1093/pcp/pct141
  Sequence
Reference
3  [PMID:25578277]
  Authors
Moses T, Pollier J, Faizal A, Apers S, Pieters L, Thevelein JM, Geelen D, Goossens A
  Title
Unraveling the triterpenoid saponin biosynthesis of the African shrub Maesa lanceolata.
  Journal
Mol Plant 8:122-35 (2015)
DOI:10.1016/j.molp.2014.11.004
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.126
IUBMB Enzyme Nomenclature: 1.14.14.126
ExPASy - ENZYME nomenclature database: 1.14.14.126
BRENDA, the Enzyme Database: 1.14.14.126

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