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2',3,4',6'-tetrahydroxy-4-methoxydihydrochalcone + H2O
phloroglucinol + ?
-
-
-
?
2',3,4',6'-tetrahydroxy-dihydrochalcone + H2O
phloroglucinol + ?
-
-
-
?
2',3,4,4',6'-pentahydroxy-dihydrochalcone 2'-beta-D-glucoside + H2O
phloroglucinol beta-D-glucoside + 3-(3,4-dihydroxyphenyl)propanoic acid
-
-
-
?
2',4'-dihydroxy-4-methoxydihydrochalcone + H2O
resorcinol + ?
-
-
-
?
2',4'-dihydroxypropiophenone + H2O
resorcinol
-
-
-
?
2',4,4',6'-tetrahydroxy-dihydrochalcone + H2O
phloroglucinol + ?
-
-
-
?
2',4,4'-trihydroxyhydrochalcone
?
-
-
-
-
?
2',6'-dihydroxy-4,4'-dimethoxydihydrochalcone + H2O
3-methoxyresorcinol + ?
-
-
-
?
3'-methylchloracetophenone + H2O
?
-
-
-
-
?
beta-methyl D-glucoside + H2O
?
-
-
-
-
?
cellobiose + H2O
2 D-glucose
-
-
-
?
cerebrosides + H2O
?
-
-
-
-
?
chloracetophenone + H2O
?
-
-
-
-
?
dihydrochalcone phloretin + H2O
phloroglucinol + phloretic acid
-
-
-
-
?
epimedin C + H2O
?
-
-
-
?
lactose + H2O
?
-
66% reduced activity towards the substrate in rats fed a low starch diet as compared to rats fed a high starch diet
-
-
?
lactose + H2O
beta-D-galactose + beta-D-glucose
lactose + H2O
D-galactose + D-glucose
lactose + H2O
D-glucose + D-galactose
lactose + H2O
glucose + galactose
-
-
-
-
?
monoacetylphloroglucinol + H2O
?
N-palmitoyldihydroglucosylceramide + H2O
?
-
-
-
-
?
o-nitrophenyl-beta-D-galactoside + H2O
o-nitrophenol + beta-D-galactose
-
-
-
?
o-nitrophenyl-beta-D-glucoside + H2O
o-nitrophenol + beta-D-glucose
-
-
-
?
p-nitrophenyl-beta-D-galactoside + H2O
p-nitrophenol + beta-D-galactose
-
-
-
?
p-nitrophenyl-beta-D-glucoside + H2O
p-nitrophenol + beta-D-glucose
-
-
-
?
phloretin + H2O
phloretate + phloroglucinol
phloretin + H2O
phloroglucinol + 3-(4-hydroxyphenyl)propionic acid
phlorhizin + H2O
3-(4-hydroxyphenyl)propanoate + arbutin
pyridoxine-5'-beta-D-glucoside + H2O
pyridoxine + D-glucose
pyridoxine-5'-beta-D-glucoside + lactose
pyridoxine + beta-D-glucose + pyridoxine disaccharide
-
-
product identification, product is formed by a pyridoxine molecule with the 5'-beta-gkucoside and another glucose or galactose moiety
-
?
salicin + H2O
?
-
-
-
-
?
sucrose + H2O
D-fructose + D-glucose
-
87% reduced activity towards the substrate in rats fed a low starch diet as compared to rats fed a high starch diet
-
-
?
additional information
?
-
baohuoside I + H2O
?
-
-
-
?
baohuoside I + H2O
?
-
-
-
?
epimedin A + H2O
?
-
-
-
?
epimedin A + H2O
?
-
-
-
?
epimedin B + H2O
?
-
-
-
?
epimedin B + H2O
?
-
-
-
?
icariin + H2O
?
-
-
-
?
icariin + H2O
?
the metabolic pathways of icariin by rat intestinal flora and enzyme solution are basically the same, including 3-O-rhamnose, 7-O-glucose hydrolysis or dual 3, 7-hydrolysis. Compared to 3-O-rhamnose and dual hydrolysis of 3, 7-, the 7-O-glucose hydrolysis is easier. The yielded metabolites contain M1 (icariside I), M2 (icaritin), and baohuoside I
-
-
?
lactose + H2O
beta-D-galactose + beta-D-glucose
-
-
-
-
?
lactose + H2O
beta-D-galactose + beta-D-glucose
-
-
-
-
?
lactose + H2O
D-galactose + D-glucose
-
-
-
-
?
lactose + H2O
D-galactose + D-glucose
-
-
-
?
lactose + H2O
D-galactose + D-glucose
-
-
-
?
lactose + H2O
D-glucose + D-galactose
-
-
-
-
?
lactose + H2O
D-glucose + D-galactose
-
-
-
?
monoacetylphloroglucinol + H2O
?
-
-
-
-
?
monoacetylphloroglucinol + H2O
?
-
-
-
-
?
phloretin + H2O
phloretate + phloroglucinol
-
-
-
?
phloretin + H2O
phloretate + phloroglucinol
-
-
-
?
phloretin + H2O
phloretate + phloroglucinol
a C-C bond cleaving enzyme
-
-
?
phloretin + H2O
phloretate + phloroglucinol
phloretin hydrolase catalyzes the hydrolysis of the dihydrochalcone phloretin to phloroglucinol and phloretic acid, performing a formal retro-Friedel-Crafts acylation reaction on its substrate, it is a C-C bond cleaving enzyme
-
-
?
phloretin + H2O
phloretate + phloroglucinol
-
-
-
?
phloretin + H2O
phloretate + phloroglucinol
a C-C bond cleaving enzyme
-
-
?
phloretin + H2O
phloretate + phloroglucinol
-
-
-
-
?
phloretin + H2O
phloretate + phloroglucinol
-
-
-
?
phloretin + H2O
phloretate + phloroglucinol
-
-
-
?
phloretin + H2O
phloretate + phloroglucinol
-
-
-
?
phloretin + H2O
phloretate + phloroglucinol
-
-
-
?
phloretin + H2O
phloretate + phloroglucinol
-
-
-
-
?
phloretin + H2O
phloroglucinol + 3-(4-hydroxyphenyl)propionic acid
-
-
-
ir
phloretin + H2O
phloroglucinol + 3-(4-hydroxyphenyl)propionic acid
during flavonoid degradation
-
-
?
phloretin + H2O
phloroglucinol + 3-(4-hydroxyphenyl)propionic acid
-
-
-
ir
phloretin + H2O
phloroglucinol + 3-(4-hydroxyphenyl)propionic acid
-
-
-
-
?
phloretin + H2O
phloroglucinol + 3-(4-hydroxyphenyl)propionic acid
-
-
-
-
?
phlorhizin + H2O
3-(4-hydroxyphenyl)propanoate + arbutin
-
-
-
?
phlorhizin + H2O
3-(4-hydroxyphenyl)propanoate + arbutin
-
-
-
-
?
phlorhizin + H2O
3-(4-hydroxyphenyl)propanoate + arbutin
-
-
-
?
phlorhizin + H2O
3-(4-hydroxyphenyl)propanoate + arbutin
-
-
-
?
pyridoxine-5'-beta-D-glucoside + H2O
pyridoxine + D-glucose
-
-
-
-
?
pyridoxine-5'-beta-D-glucoside + H2O
pyridoxine + D-glucose
-
enzyme might play an important role in providing the bioavailability of pyridoxine-5'-beta-D-glucoside
-
-
?
additional information
?
-
no activity with phloretin-2'-glucoside, i.e. phloridzin, neohesperidin dihydrochalcone, 1,3-diphenyl-1,3-propandione, and trans-1,3-diphenyl-2,3-epoxy-propan-1-one
-
-
?
additional information
?
-
-
no activity with phloretin-2'-glucoside, i.e. phloridzin, neohesperidin dihydrochalcone, 1,3-diphenyl-1,3-propandione, and trans-1,3-diphenyl-2,3-epoxy-propan-1-one
-
-
?
additional information
?
-
no activity with 1,3-diphenyl 1,3-propanedione and diacetylphloroglucinol, a substrate of diacetyl phloroglucinol hydrolase, Phlg
-
-
?
additional information
?
-
no activity with glycosides phloretin-2'-glucoside (phloridzin) and neohesperidin dihydrochalcone, nor with compounds showing a structure similar to phloretin, such as 1,3-diphenyl-1,3-propandione and trans-1,3-diphenyl-2,3-epoxy-propan-1-one
-
-
?
additional information
?
-
-
no activity with glycosides phloretin-2'-glucoside (phloridzin) and neohesperidin dihydrochalcone, nor with compounds showing a structure similar to phloretin, such as 1,3-diphenyl-1,3-propandione and trans-1,3-diphenyl-2,3-epoxy-propan-1-one
-
-
?
additional information
?
-
no activity with phloretin-2'-glucoside, i.e. phloridzin, neohesperidin dihydrochalcone, 1,3-diphenyl-1,3-propandione, and trans-1,3-diphenyl-2,3-epoxy-propan-1-one
-
-
?
additional information
?
-
no activity with glycosides phloretin-2'-glucoside (phloridzin) and neohesperidin dihydrochalcone, nor with compounds showing a structure similar to phloretin, such as 1,3-diphenyl-1,3-propandione and trans-1,3-diphenyl-2,3-epoxy-propan-1-one
-
-
?
additional information
?
-
-
the enzyme interacts with ER chaperones, immunglobulin binding protein, and calnexin at non-permissive temperatures in the ER
-
-
?
additional information
?
-
-
the enzyme preparation also shows maltase-glucoamylase activity, EC 3.2.1.20, at 3.8 U/mg
-
-
?
additional information
?
-
hydrolysis of prenylated flavonoids from Epimedium sp., Epimedii herba, used for a tranditional chinese medicine tonic, Yinyanghuo. Comparison of hydrolysis rates and substrate specificities of intestinal flora and intestinal enzymes, especially lactase phlorizin hydrolase, with the flavonoid substrates, overview. Flavonoid metabolic rates with rat intestinal enzyme are higher than those with intestinal flora. The intestinal hydrolysis of glycosides by intestinal enzymes is rapid. Even icariin is completely metabolized in 6 h and the epimedin A is totally metabolized in 12 h in incubation with intestinal enzyme
-
-
?
additional information
?
-
the enzyme has two distinct catalytic active sites, one for the hydrolysis of lactose and flavonoid glucosides and another, phlorizin hydrolase, for the hydrolysis of phlorizin and phlorizin-glucosylceramides
-
-
?
additional information
?
-
hydrolysis of prenylated flavonoids from Epimedium sp., Epimedii herba, used for a tranditional chinese medicine tonic, Yinyanghuo. Comparison of hydrolysis rates and substrate specificities of intestinal flora and intestinal enzymes, especially lactase phlorizin hydrolase, with the flavonoid substrates, overview. Flavonoid metabolic rates with rat intestinal enzyme are higher than those with intestinal flora. The intestinal hydrolysis of glycosides by intestinal enzymes is rapid. Even icariin is completely metabolized in 6 h and the epimedin A is totally metabolized in 12 h in incubation with intestinal enzyme
-
-
?
additional information
?
-
the enzyme has two distinct catalytic active sites, one for the hydrolysis of lactose and flavonoid glucosides and another, phlorizin hydrolase, for the hydrolysis of phlorizin and phlorizin-glucosylceramides
-
-
?
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dihydrochalcone phloretin + H2O
phloroglucinol + phloretic acid
-
-
-
-
?
epimedin C + H2O
?
-
-
-
?
icariin + H2O
?
the metabolic pathways of icariin by rat intestinal flora and enzyme solution are basically the same, including 3-O-rhamnose, 7-O-glucose hydrolysis or dual 3, 7-hydrolysis. Compared to 3-O-rhamnose and dual hydrolysis of 3, 7-, the 7-O-glucose hydrolysis is easier. The yielded metabolites contain M1 (icariside I), M2 (icaritin), and baohuoside I
-
-
?
monoacetylphloroglucinol + H2O
?
phloretin + H2O
phloretate + phloroglucinol
phloretin + H2O
phloroglucinol + 3-(4-hydroxyphenyl)propionic acid
pyridoxine-5'-beta-D-glucoside + H2O
pyridoxine + D-glucose
-
enzyme might play an important role in providing the bioavailability of pyridoxine-5'-beta-D-glucoside
-
-
?
additional information
?
-
baohuoside I + H2O
?
-
-
-
?
baohuoside I + H2O
?
-
-
-
?
epimedin A + H2O
?
-
-
-
?
epimedin A + H2O
?
-
-
-
?
epimedin B + H2O
?
-
-
-
?
epimedin B + H2O
?
-
-
-
?
monoacetylphloroglucinol + H2O
?
-
-
-
-
?
monoacetylphloroglucinol + H2O
?
-
-
-
-
?
phloretin + H2O
phloretate + phloroglucinol
-
-
-
?
phloretin + H2O
phloretate + phloroglucinol
-
-
-
?
phloretin + H2O
phloretate + phloroglucinol
-
-
-
-
?
phloretin + H2O
phloretate + phloroglucinol
-
-
-
?
phloretin + H2O
phloretate + phloroglucinol
-
-
-
-
?
phloretin + H2O
phloroglucinol + 3-(4-hydroxyphenyl)propionic acid
during flavonoid degradation
-
-
?
phloretin + H2O
phloroglucinol + 3-(4-hydroxyphenyl)propionic acid
-
-
-
-
?
phloretin + H2O
phloroglucinol + 3-(4-hydroxyphenyl)propionic acid
-
-
-
-
?
additional information
?
-
hydrolysis of prenylated flavonoids from Epimedium sp., Epimedii herba, used for a tranditional chinese medicine tonic, Yinyanghuo. Comparison of hydrolysis rates and substrate specificities of intestinal flora and intestinal enzymes, especially lactase phlorizin hydrolase, with the flavonoid substrates, overview. Flavonoid metabolic rates with rat intestinal enzyme are higher than those with intestinal flora. The intestinal hydrolysis of glycosides by intestinal enzymes is rapid. Even icariin is completely metabolized in 6 h and the epimedin A is totally metabolized in 12 h in incubation with intestinal enzyme
-
-
?
additional information
?
-
hydrolysis of prenylated flavonoids from Epimedium sp., Epimedii herba, used for a tranditional chinese medicine tonic, Yinyanghuo. Comparison of hydrolysis rates and substrate specificities of intestinal flora and intestinal enzymes, especially lactase phlorizin hydrolase, with the flavonoid substrates, overview. Flavonoid metabolic rates with rat intestinal enzyme are higher than those with intestinal flora. The intestinal hydrolysis of glycosides by intestinal enzymes is rapid. Even icariin is completely metabolized in 6 h and the epimedin A is totally metabolized in 12 h in incubation with intestinal enzyme
-
-
?
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additional information
comparison of the enzyme phloretin hydrolase Phy from Eubacterium ramulus with the diacetyl phloroglucinol hydrolase (Phlg) from Pseudomonas fluorescens, which catalyses a similar, hydrolytic, de-acylation of its substrate, homology modeling of Phy based on the structure of Phlg, PDB ID 3HWP
evolution
C-C-cleaving hydrolases catalyzing reactions similar to the reaction carried out by phloretin hydrolase belong to the alpha/beta-hydrolase fold superfamily, but since the phloretin hydrolase sequence of Eubacterium ramulus has no sequence similarity to other C-C-cleaving hydrolases and also does not contain the conserved sequence motif GXSXG, it can be assumed that this enzyme belongs to another enzyme family. The sequences of phloretin hydrolase, Phy, and 2,4-diacetylphloroglucinol hydrolase, PhlG, show no similarities to any other protein sequences with known functions deposited in database
evolution
-
C-C-cleaving hydrolases catalyzing reactions similar to the reaction carried out by phloretin hydrolase belong to the alpha/beta-hydrolase fold superfamily, but since the phloretin hydrolase sequence of Eubacterium ramulus has no sequence similarity to other C-C-cleaving hydrolases and also does not contain the conserved sequence motif GXSXG, it can be assumed that this enzyme belongs to another enzyme family. The sequences of phloretin hydrolase, Phy, and 2,4-diacetylphloroglucinol hydrolase, PhlG, show no similarities to any other protein sequences with known functions deposited in database
-
metabolism
the enzyme is involved in the metabolic pathway of icariin, epimedin A, B, and C, and f baohuoside I in intestinal flora and enzyme of rats, detailed overview
metabolism
-
the enzyme is involved in the metabolic pathway of icariin, epimedin A, B, and C, and f baohuoside I in intestinal flora and enzyme of rats, detailed overview
-
physiological function
phloretin hydrolase catalyzes the hydrolytic C-C cleavage of phloretin to phloroglucinol and 3-(4-hydroxyphenyl) propionic acid during flavonoid degradation in Eubacterium ramulus
physiological function
the enzyme catalyses the degradation of plant-derived dihydrochalcone phloretin
physiological function
the enzyme plays a major role in the deglycosylation of daidzin
physiological function
-
the enzyme plays a major role in the deglycosylation of daidzin
-
physiological function
-
phloretin hydrolase catalyzes the hydrolytic C-C cleavage of phloretin to phloroglucinol and 3-(4-hydroxyphenyl) propionic acid during flavonoid degradation in Eubacterium ramulus
-
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A126S
site-directed mutagenesis
F218Y
site-directed mutagenesis
N1340Q
-
the variant lacks the closest potential N-glycosylation site to Asp1338
N1814Q
-
the variant lacks the N-glycosylation site in the domain IV
N821Q
-
the variant lacks the N-glycosylation site in the domain II
A213S
-
the mutant completely loses catalytic activity towards phloretin
E164A
-
the mutation completely abolishes the hydrolytic activity towards phloretin
E273A
-
the mutation completely abolishes the hydrolytic activity towards phloretin
H118A
-
the mutant completely loses catalytic activity towards phloretin
H133A
-
the kcat value for phloretin is decreased at least by 1 order of magnitude, whereas the corresponding Km value is barely affected compared to the wild type enzyme
H160A
-
the mutant completely loses catalytic activity towards phloretin
H160F
-
the mutant completely loses catalytic activity towards phloretin
H217A
-
the mutant has a Km value increased by 3fold and a kcat value decreased by 6fold compared to the wild type enzyme
H269A
-
the kcat value for phloretin is decreased at least by 1 order of magnitude, whereas the corresponding Km value is barely affected compared to the wild type enzyme
I162A
-
the mutant completely loses catalytic activity towards phloretin
Q266F
-
the mutant completely loses catalytic activity towards phloretin
Y125A
-
the mutant completely loses catalytic activity towards phloretin
Y232A
-
the Km value for phloretin increases by 3fold and the kcat value decreases by 5fold compared to the wild type enzyme
E164A
-
the mutation completely abolishes the hydrolytic activity towards phloretin
-
E273A
-
the mutation completely abolishes the hydrolytic activity towards phloretin
-
H118A
-
the mutant completely loses catalytic activity towards phloretin
-
H160A
-
the mutant completely loses catalytic activity towards phloretin
-
H160F
-
the mutant completely loses catalytic activity towards phloretin
-
additional information
mutation of His123, His251, Glu154 and Glu255 (conserved zinc binding residues) results in variants that were either poorly expressed, or of much reduced activity. Mutation of Tyr115 and His203, thought to bind the phenol groups in the 1-and 3-positions of the phloroglucinol ring respectively, results in variants of 15-fold reduced activity and an inactive variant
additional information
-
hypolactasia seems to be strongly corretated with genotype C/C of the genetic variant C->T-13910 upstream of the lactase-phlorizin hydrolase gene
additional information
-
the genetic variant C/T-13910 upstream of the lactase-phlorizin hydrolase gene is strongly correlated with the lactase persistence/nonperistence trait
additional information
the mutations C/T-13910 and G/A-22018 of the lactase-phlorizin hydrolase gene are correlated with lactose absorption
additional information
-
Gata4 mutant, LPH mRNA abundance is significantly attenuated
additional information
-
deletions of the LPH 5' flanking sequence and fusion 5' to the human growth hormone reporter gene
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Ramaswamy, S.; Radhakrishnan, A.N.
Lactase-phlorizin hydrolase complex from monkey small intestine. Purification, properties and evidence for two catalytic sites
Biochim. Biophys. Acta
403
446-455
1975
Platyrrhini
brenda
Birkenmeier, E.; Alpers, D.H.
Enzymatic properties of rat lactase-phlorizin hydrolase
Biochim. Biophys. Acta
350
100-112
1974
Rattus norvegicus
brenda
Minamikawa, T.; Jayasankar, N.P.; Bohm, B.A.; Taylor, I.E.P.; Towers, G.H.N.
An inducible hydrolase from Aspergillus niger, acting on carbon-carbon bonds, for phlorrhizin and other C-acylated phenols
Biochem. J.
116
889-897
1970
Aspergillus niger
brenda
Chatterjee, A.K.; Gibbins, L.N.
Metabolism of phloridzin by Erwinia herbicola: nature of the degradation products, and the purification and properties of phloretin hydrolase
J. Bacteriol.
100
594-600
1969
Pantoea agglomerans, Pantoea agglomerans Y46
brenda
Schoefer, L.; Braune, A.; Blaut, M.
Cloning and Expression of a Phloretin Hydrolase Gene from Eubacterium ramulus and Characterization of the Recombinant Enzyme
Appl. Environ. Microbiol.
70
6131-6137
2004
Eubacterium ramulus (Q715L4), Eubacterium ramulus, Eubacterium ramulus wK1 (Q715L4)
brenda
Mackey, A.D.; Henderson, G.N.; Gregory, J.F., 3rd
Enzymatic hydrolysis of pyridoxine-5'-beta-D-glucoside is catalyzed by intestinal lactase-phlorizin hydrolase
J. Biol. Chem.
277
26858-26864
2002
Rattus norvegicus
brenda
Jacob, R.; Peters, K.; Naim, H.Y.
Prosequence of human lactase-phlorizin hydrolase modulates the folding of mature enzyme
J. Biol. Chem.
277
8217-8225
2002
Homo sapiens
brenda
Tseung, C.W.; McMahon, L.G.; Vazquez, J.; Pohl, J.; Gregory, J.F.
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