Information on EC 4.2.1.125 - dammarenediol II synthase

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The expected taxonomic range for this enzyme is: Apiineae

EC NUMBER
COMMENTARY
4.2.1.125
-
RECOMMENDED NAME
GeneOntology No.
dammarenediol II synthase
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
dammarenediol II = (3S)-2,3-epoxy-2,3-dihydrosqualene + H2O
show the reaction diagram
cyclization initiated by protonation at the oxirane ring proceeds to form tetracycles. The resulting dammarenyl cation is trapped by stereospecific addition of water at C20 without further rearrangement
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
ginsenosides biosynthesis
-
-
Sesquiterpenoid and triterpenoid biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
(S)-squalene-2,3-epoxide hydro-lyase (dammarenediol-II forming)
The reaction occurs in the reverse direction.
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene PgDDS
SwissProt
Manually annotated by BRENDA team
gene PgDDS1
SwissProt
Manually annotated by BRENDA team
gene PqDS
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
-
the enzyme catalyzes the first step in biosynthetic pathway of ginsenosides, overview
metabolism
Q08IT1
the enzyme catalyzes the first step in the biosynthetic pathway for ginsenosides in Panax ginseng, overview
metabolism
Q08IT1
the enzyme catalyzes the first step in the synthesis of dammarane-type ginsenoside, the cyclization of 2,3-oxidosqualene to dammarenediol-II, overview
physiological function
-
Centella asiatica hairy roots overexpressing ginseng farnesyl diphosphate synthase show higher levels of dammarenediol synthase and cycloartenol synthase mRNA when compared with the controls. No differences are detected in expression of the squalene synthase gene. The upregulation of dammarenediol synthase transcripts suggests that FPS may result in alterations in triterpene biosynthesis capacity. Squalene contents in the T17, T24, and T27 lines increase to 1.1-, 1.3- and 1.5fold those in the controls, respectively. The total sterol contents in the T24 line are approximately three times higher than those of the controls
physiological function
Q08IT1
dammarenediol-II synthase catalyzes the cyclization of 2,3-oxidosqualene to dammarenediol-II, which is the basic triterpene skeleton in dammarene-type saponin (ginsenosides) in Panax ginseng. Dammarenediol-II is present in the roots of Panax ginseng in trace amounts because it is an intermediate product in triterpene biosynthesis
metabolism
-
the enzyme is involved in the ginsenoside biosynthetic pathway catalyzing the first committed step, the cyclization of 2,3-oxidosqualene to dammarenediol
additional information
-
close correlation of dammarenediol synthetase and saponin production in vitro
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(3S)-2,3-epoxy-2,3-dihydrosqualene + H2O
dammarenediol II
show the reaction diagram
-
-
-
-
?
(3S)-2,3-epoxy-2,3-dihydrosqualene + H2O
dammarenediol II
show the reaction diagram
Q08IT1
-
-
-
?
(3S)-2,3-epoxy-2,3-dihydrosqualene + H2O
dammarenediol II
show the reaction diagram
M4WEZ8
-
-
-
?
(3S)-2,3-epoxy-2,3-dihydrosqualene + H2O
dammarenediol II
show the reaction diagram
Q08IT1
-
GC-MS product analysis
-
?
(3S)-2,3-epoxy-2,3-dihydrosqualene + H2O
dammarenediol II
show the reaction diagram
Q08IT1
dammarenediol-II is a ginsenoside precursor
-
-
?
(3S)-2,3-oxidosqualene + H2O
(20S)-dammarenediol
show the reaction diagram
-
-
the accumulated product was confirmed as dammarenediol
-
?
(3S)-2,3-oxidosqualene + H2O
(20S)-dammarenediol
show the reaction diagram
-
substrate is folded in a pre-chair-chair-chair conformation
-
-
?
(S)-2,3-oxidosqualene + H2O
(20S)-dammarenediol
show the reaction diagram
Q08IT1
-
S-isomer is the sole product, water addition to the dammarenyl cation intermediate is stereospecific
-
?
(S)-2,3-oxidosqualene + H2O
(20S)-dammarenediol + hydroxydammarenone
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
LC-MS analysis of substrate and product amounts
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(3S)-2,3-epoxy-2,3-dihydrosqualene + H2O
dammarenediol II
show the reaction diagram
-
-
-
-
?
(3S)-2,3-epoxy-2,3-dihydrosqualene + H2O
dammarenediol II
show the reaction diagram
Q08IT1
-
-
-
?
(3S)-2,3-epoxy-2,3-dihydrosqualene + H2O
dammarenediol II
show the reaction diagram
M4WEZ8
-
-
-
?
(3S)-2,3-epoxy-2,3-dihydrosqualene + H2O
dammarenediol II
show the reaction diagram
Q08IT1
dammarenediol-II is a ginsenoside precursor
-
-
?
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
3-((3-cholamidopropyl)dimethylammonio)-1-propanesulfonate
-
i.e. CHAPS, 0.1%, 30% residual activity
deoxycholate
-
0.1%, 92% residual activity
n-octyl-beta-D-glucoside
-
0.1%, 58% residual activity
Triton X-100
-
0.1%, 64% residual activity
Tween 20
-
0.1%, 23% residual activity
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
methyl jasmonate
-
up-regulation of enzyme expression
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
hairy root culture
Manually annotated by BRENDA team
-
higher expression compared with root, leaf and petiole
Manually annotated by BRENDA team
-
higher expression in flower bud compared with root, leaf and petiole
Manually annotated by BRENDA team
-
higher expression in flower bud compared with root, leaf and petiole
Manually annotated by BRENDA team
-
hairy root
Manually annotated by BRENDA team
-
hairy root culture
Manually annotated by BRENDA team
-
higher expression in flower bud compared with root, leaf and petiole
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
transmembrane enzyme
Manually annotated by BRENDA team
-
exclusive localization
-
Manually annotated by BRENDA team
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
-
x * 88300, calculated
?
-
x * 88400, calculated
?
-
x * 84600, about, sequence calculation, x * 89000, recombinant His-tagged enzyme, SDS-PAGE
?
M4WEZ8
x * 88400, about, sequence calculation
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged enzyme from Escherichia coli strains Origami B (DE3) amd Rosetta (DE3) by nickel affinity chromatography
-
recombinnat enzyme from Saccharomyces cerevisiae strain 31147 lipid particles, solubilization by Triton X-100
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Saccharomyces cerevisiae
-
DNA and amino acid sequence determination and analysis, recombinant expression of functional His-tagged enzyme in Escherichia coli strains Origami B (DE3) amd Rosetta (DE3)
-
expression in an engineered strain of Saccharomyces cerevisiae strain 31147 from vector pAUR123, the enzyme is contained in microsomes, lipid particles, and total yeast homogenate
-
functional expression in Sacchaormyces cerevisiae
-
gene PgDDS, functional expression in Nicotiana tabacum cv. Xanthi leaves using Agrobacterium strain GV3101, the heterologous expression confers resistance to Tobacco mosaic virus. Expression profile of PgDDS trangenic tobacco plants, overview. Production of dammarenediol-II in transgenic tobacco stimulates the expression of tobacco pathogenesis-related genes (PR1 and PR2) under both virus-untreated and -treated conditions
Q08IT1
recombinant expression in Nicotiana tabacum cv. Xanthi leaves using transfection via Agrobacterium tumefaciens strain LBA4404, accumulation of dammarenediol-II in transgenic tobacco plants occurred in an organ-specific manner in descending order: roots, stems, leaves, flower buds, and transgenic cell suspension line 14 exhibits a high amount, overview
Q08IT1
gene PqDS, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree, ectopic heterologous co-expression with cytochrome P450 gene PqD12H in Saccharomyces cerevisiae
M4WEZ8
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
induction by methyl jasmonate, overview
Q08IT1
transcription increase of gene PqDS in the methyl jasmonate-induced hairy roots
M4WEZ8
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
functionally expressed in the lanosterol synthase-deficient yeast mutant erg7
additional information
-
expression in Saccharomyces cerevisiae mutant lacking lanosterol synthase results in production of dammarenediol and hydroxydammarenone. Silencing of gene expression by RNAi leads to a reduction of ginsenoide production to 84.5% in roots
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
Q08IT1
the production of dammarenediol-II in a cell suspension culture of transgenic tobacco can be applied to the large-scale production of this compound and utilized as a source of pharmacologically active medicinal materials