KEGG   ORTHOLOGY: K22092
Entry
K22092            Tight     KO                                     
Symbol
GLU1
Name
ipecoside beta-D-glucosidase [EC:3.2.1.220]
Pathway
map00950  Isoquinoline alkaloid biosynthesis
map01110  Biosynthesis of secondary metabolites
Reaction
R11682  6-O-methyldeacetylisoipecoside:beta-glucosidase
R13191  ipecoside glucohydrolase
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00950 Isoquinoline alkaloid biosynthesis
    K22092  GLU1; ipecoside beta-D-glucosidase
Enzymes [BR:ko01000]
 3. Hydrolases
  3.2  Glycosylases
   3.2.1  Glycosidases, i.e. enzymes that hydrolyse O- and S-glycosyl compounds
    3.2.1.220  ipecoside beta-D-glucosidase
     K22092  GLU1; ipecoside beta-D-glucosidase
Genes
AG: BAH02544(Glu1)
Reference
  Authors
Nomura T, Quesada AL, Kutchan TM
  Title
The new beta-D-glucosidase in terpenoid-isoquinoline alkaloid biosynthesis in Psychotria ipecacuanha.
  Journal
J Biol Chem 283:34650-9 (2008)
DOI:10.1074/jbc.M806953200
  Sequence
LinkDB

KEGG   ENZYME: 3.2.1.220
Entry
EC 3.2.1.220                Enzyme                                 
Name
ipecoside beta-D-glucosidase;
6-O-methyl-deacetylisoipecoside beta-glucosidase;
IpeGlu1
Class
Hydrolases;
Glycosylases;
Glycosidases, i.e. enzymes that hydrolyse O- and S-glycosyl compounds
Sysname
ipecoside glucohydrolase
Reaction(IUBMB)
(1) ipecoside + H2O = ipecoside aglycone + D-glucopyranose [RN:R13191];
(2) N-deacetylipecoside + H2O = N-deacetylipecoside aglycone + D-glucopyranose [RN:R13253];
(3) 6-O-methyl-N-deacetylipecoside + H2O = 6-O-methyl-N-deacetylipecoside aglycone + D-glucopyranose [RN:R13254]
Reaction(KEGG)
R13191 R13253 R13254;
(other) R11682
Substrate
ipecoside [CPD:C09464];
H2O [CPD:C00001];
N-deacetylipecoside [CPD:C07307];
6-O-methyl-N-deacetylipecoside [CPD:C22883]
Product
ipecoside aglycone [CPD:C22694];
D-glucopyranose [CPD:C00031];
N-deacetylipecoside aglycone [CPD:C22882];
6-O-methyl-N-deacetylipecoside aglycone [CPD:C22884]
Comment
The enzyme, isolated from the roots of the plant Carapichea ipecacuanha, preferentially hydrolyses glucosidic ipecoside alkaloids except for their lactams, but shows poor or no activity toward other substrates. IpeGlu1 activity is extremely poor toward 7-O-methyl and 6,7-O,O-dimethyl derivatives. However, 6-O-methyl derivatives are hydrolysed as efficiently as non-methylated substrates. IpeGlu1 accepts both 1alpha(S)-N-deacetylisoipecoside and 1beta(R)-N-deacetylipecoside epimers as substrate, with preference for the 1beta(R)-epimer. 6-O-methyl-N-deacetylisoipecoside is an intermediate in the biosynthesis of the medicinal alkaloid emetine.
History
EC 3.2.1.220 created 2023
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
Orthology
K22092  ipecoside beta-D-glucosidase
Reference
1  [PMID:18927081]
  Authors
Nomura T, Quesada AL, Kutchan TM
  Title
The new beta-D-glucosidase in terpenoid-isoquinoline alkaloid biosynthesis in Psychotria ipecacuanha.
  Journal
J Biol Chem 283:34650-9 (2008)
DOI:10.1074/jbc.M806953200
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 3.2.1.220
IUBMB Enzyme Nomenclature: 3.2.1.220
ExPASy - ENZYME nomenclature database: 3.2.1.220
BRENDA, the Enzyme Database: 3.2.1.220
LinkDB

KEGG   REACTION: R13191
Entry
R13191                      Reaction                               
Name
ipecoside glucohydrolase
Definition
Ipecoside + H2O <=> Ipecoside aglycone + D-Glucose
Equation
Enzyme
Pathway
rn00950  Isoquinoline alkaloid biosynthesis
Brite
Enzymatic reactions [BR:br08201]
 3. Hydrolase reactions
  3.2  Glycosylases
   3.2.1  Glycosidases, i.e. enzymes that hydrolyse O- and S-glycosyl compounds
    3.2.1.220
     R13191  Ipecoside + H2O <=> Ipecoside aglycone + D-Glucose
Orthology
K22092  ipecoside beta-D-glucosidase [EC:3.2.1.220]
Other DBs
RHEA: 78746
LinkDB

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