3.2.1.168: hesperidin 6-O-alpha-L-rhamnosyl-beta-D-glucosidase
This is an abbreviated version!
For detailed information about hesperidin 6-O-alpha-L-rhamnosyl-beta-D-glucosidase, go to the full flat file.
Word Map on EC 3.2.1.168
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3.2.1.168
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diglycosidase
-
flavonoid
-
transglycosylation
-
glycoside
-
rutinose
-
hydrolyse
-
juice
-
aglycone
-
acremonium
-
citrus
-
sinensis
-
mandatory
-
orange
-
food industry
-
quercetin
-
deglycosylation
-
fagopyrum
-
niger
-
rutinosides
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utilises
-
biotechnology
- 3.2.1.168
-
diglycosidase
- flavonoid
-
transglycosylation
- glycoside
- rutinose
-
hydrolyse
- juice
-
aglycone
- acremonium
-
citrus
-
sinensis
-
mandatory
- orange
- food industry
- quercetin
-
deglycosylation
- fagopyrum
- niger
- rutinosides
-
utilises
- biotechnology
Reaction
Synonyms
6-O-alpha-rhamnosyl-beta-glucosidase, alpha-rhamnosyl-beta-glucosidase, alphaRbetaG, AMIS_8220, hesperidin deglycosylase, rutinase, rutinoside transferase
ECTree
3.2.1.168 hesperidin 6-O-alpha-L-rhamnosyl-beta-D-glucosidaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 3.2.1.168 - hesperidin 6-O-alpha-L-rhamnosyl-beta-D-glucosidase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2-phenethyl rutinoside + H2O
2-phenylethanol + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
-
purified aromatic an terpenyl rutinosides are incubated as substrates, no activity in aqueous medium, 3.8% in 12% ethanol
-
-
?
2-phenylethanol + hesperidin
2-phenylethyl beta-D-rutinoside + hesperetin
-
-
-
?
4-nitrophenyl-beta-D-glucopyranoside + H2O
4-nitrophenol + D-glucose
1% activity compared to hesperidin
-
-
?
4-nitrophenyl-beta-D-rutinoside + H2O
4-nitrophenol + D-rutinose
91% activity compared to hesperidin
-
-
?
catechol + hesperidin
2-hydroxyphenyl beta-D-rutinoside + hesperetin
-
-
-
?
diosmin + H2O
didymin + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
-
a 7-O-beta-rutinoside, pH 5.0, 60°C, 3.3% relative activity compared to hesperidin as substrate
-
-
?
eriocitrin + H2O
eriodictyol + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
-
a 7-O-beta-rutinoside, pH 5.0, 60°C, 89.7% relative activity compared to hesperidin as substrate
-
-
?
geraniol + hesperidin
geranyl beta-D-rutinoside + hesperetin
-
-
-
?
geranyl rutinoside + H2O
geraniol + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
-
purified aromatic an terpenyl rutinosides are incubated as substrates, no activity in aqueous medium, 2.9% in 12% ethanol
-
-
?
hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
hydroquinone + hesperidin
4-hydroxyphenyl-beta-D-rutinoside + hesperetin
-
-
-
?
narirutin + H2O
naringenin + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
-
a 7-O-beta-rutinoside, pH 5.0, 60°C, 61% relative activity compared to hesperidin as substrate
-
-
?
nerol + hesperidin
neryl beta-D-rutinoside + hesperetin
-
-
-
?
neryl rutinoside + H2O
nerol + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
-
purified aromatic an terpenyl rutinosides are incubated as substrates, no activity in aqueous medium, 2.9% in 12% ethanol
-
-
?
phloroglucinol + hesperidin
3,5-dihydroxyphenyl beta-D-rutinoside + hesperetin
-
-
-
?
pyrogallol + hesperidin
2,3-dihydroxyphenyl beta-D-rutinoside + hesperetin
-
-
-
?
rutin + vanillic acid
quercetin + vanillic acid 4'-O-rutinoside
-
-
-
-
?
4-methylumbelliferyl-beta-D-glucopyranoside + H2O
4-methylumbelliferol + D-glucose
-
-
-
?
4-methylumbelliferyl-beta-D-glucopyranoside + H2O
4-methylumbelliferol + D-glucose
-
-
-
?
4-methylumbelliferyl-beta-D-glucopyranoside + H2O
4-methylumbelliferol + D-glucose
-
-
-
?
4-methylumbelliferyl-beta-D-glucopyranoside + H2O
4-methylumbelliferol + D-glucose
-
-
-
?
4-methylumbelliferyl-beta-D-glucopyranoside + H2O
4-methylumbelliferol + D-glucose
-
-
-
?
4-methylumbelliferyl-beta-D-glucopyranoside + H2O
4-methylumbelliferol + D-glucose
-
-
-
?
4-methylumbelliferyl-beta-D-glucopyranoside + H2O
4-methylumbelliferol + D-glucose
-
-
-
?
4-methylumbelliferyl-beta-D-glucopyranoside + H2O
4-methylumbelliferol + D-glucose
-
-
-
?
4-methylumbelliferyl-beta-D-rutinoside + H2O
4-methylumbelliferol + D-rutinose
-
-
-
?
4-methylumbelliferyl-beta-D-rutinoside + H2O
4-methylumbelliferol + D-rutinose
-
-
-
?
4-methylumbelliferyl-beta-D-rutinoside + H2O
4-methylumbelliferol + D-rutinose
-
-
-
?
4-methylumbelliferyl-beta-D-rutinoside + H2O
4-methylumbelliferol + D-rutinose
-
-
-
?
4-methylumbelliferyl-beta-D-rutinoside + H2O
4-methylumbelliferol + D-rutinose
-
-
-
?
4-methylumbelliferyl-beta-D-rutinoside + H2O
4-methylumbelliferol + D-rutinose
-
-
-
?
4-methylumbelliferyl-beta-D-rutinoside + H2O
4-methylumbelliferol + D-rutinose
-
-
-
?
4-methylumbelliferyl-beta-D-rutinoside + H2O
4-methylumbelliferol + D-rutinose
-
-
-
?
hesperidin + H2O
hesperetin + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
-
-
-
-
?
hesperidin + H2O
hesperetin + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
-
-
i.e. hesperetin + rutinose
-
?
hesperidin + H2O
hesperetin + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
-
pH 5.0, 60°C
-
-
?
hesperidin + H2O
hesperetin + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
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i.e. hesperitin 7-(6-O-alpha-rhamnopyranosyl)-beta-D-glucopyranoside, pH 5.0, 60°C, substrates and products of the enzymatic reaction are analyzed by UV-MALDI-TOF/TOF mass spectrometry
i.e. hesperetin + rutinose, substrates and products of the enzymatic reaction are analyzed by UV-Maldi-TOF/TOF mass spectrometry
-
?
hesperidin + H2O
hesperetin + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
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herperidin occurs in lemons and oranges in high concentrations and contributes to juice clouding. Enzymatic hydrolysis via the diglycosidase is useful to remove the unpleasant taste or for juice clarification, a deglycosylation (hydrolysis and transglycosylation) in a single step
i.e. hesperetin + rutinose
-
?
hesperidin + H2O
hesperetin + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
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purified aromatic and terpenyl rutinosides are incubated as substrates, 14.3% relative activity in aqueous medium, 21.7% in 12% ethanol
i.e. hesperetin + rutinose
-
?
hesperidin + H2O
hesperitin + rutinose
6-O-alpha-rhamnosyl-beta-glucosidase activity
-
-
?
hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
-
-
-
-
?
hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
-
a 7-O-beta-rutinoside, pH 5.0, 60°C, 58.5% relative activity compared to hesperidin as substrate
-
-
?
hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
91% activity compared to hesperidin
-
-
?
hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
91% activity compared to hesperidin
-
-
?
hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
91% activity compared to hesperidin
-
-
?
hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
91% activity compared to hesperidin
-
-
?
hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
91% activity compared to hesperidin
-
-
?
hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
91% activity compared to hesperidin
-
-
?
hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
91% activity compared to hesperidin
-
-
?
hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
91% activity compared to hesperidin
-
-
?
additional information
?
-
-
in addition, when incubated with 5% (v/v) ethanol as acceptor and hesperidin and hesperidin methylchalcone as sugar donors another glycosylated product is found as a result of a transglycosylation reaction: ethyl rutinoside, indicating that alpha-rhamnosyl-beta-glucosidase is able to transfer disaccharide units to OH-acceptors in an aqueous medium
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-
?
additional information
?
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-
no dectectable enzyme activity using the 7-O-beta-neohesperidosides: naringin and neohesperidin as substrates, or the 3-O-beta-rutinoside rutin
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-
?
additional information
?
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-
hydrolysis not detected in aqueous medium without ethanol
-
-
?
additional information
?
-
-
the enzyme shows a high alpha-rhamnosyl-beta-glucosidase transglycosylation activity with hesperidin and 4-methylumbelliferone resulting in formation of 4-methylumbelliferyl-rutinoside nd hesperetin, overview
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-
?
additional information
?
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diglycosidase enzyme mediates transglycosylation of rutinose (6-O-alpha-L-rhamnosyl-D-glucose) to phenolic compounds. The enzyme 6-O-alpha-rhamnosyl-beta-glucosidase has the capacity to transfer the rutinosyl moiety (6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranose) from 7-O-rutinosylated flavonoids to hydroxylated organic compounds. This transglycosylation reaction is optimized using hydroquinone (HQ) and hesperidin as rutinose acceptor and donor, respectively. Formation of 4-hydroxyphenyl-beta-rutinoside, NMR analysis. The highest yield of 4-hydroxyphenyl-beta-rutinoside (38%, regarding hesperidin) is achieved in a 2-h process at pH 5.0 and 30°C, with 36 mM OH-acceptor and 5% v/v cosolvent. Under the same conditions, the enzyme synthesized glycoconjugates of various phenolic compounds (phloroglucinol, resorcinol, pyrogallol, catechol), with yields between 12% and 28% and an apparent direct linear relationship between the yield and the pKa value of the aglycon. Use of organic cosolvents (e.g. DMF or DMSO) as a means to increase the availability of the substrate in the reaction medium. The enzyme also efficiently rutinosylates specific hydroxy-acceptor compounds such as 2-phenylethanol, geraniol, and nerol without displaying significant hydrolysis activities
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-
?
additional information
?
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no activity with rutin, diosmin, isoquercitrin, naringin, or laminarin, and no activity with 4-nitrophenyl-alpha-L-rhamnopyranoside. The enzyme shows specificity for 7-O-rutinosylated flavonoids
-
-
?
additional information
?
-
-
no activity with rutin, diosmin, isoquercitrin, naringin, or laminarin, and no activity with 4-nitrophenyl-alpha-L-rhamnopyranoside. The enzyme shows specificity for 7-O-rutinosylated flavonoids
-
-
?
additional information
?
-
no activity with rutin, diosmin, isoquercitrin, naringin, or laminarin, and no activity with 4-nitrophenyl-alpha-L-rhamnopyranoside. The enzyme shows specificity for 7-O-rutinosylated flavonoids
-
-
?
additional information
?
-
no activity with rutin, diosmin, isoquercitrin, naringin, or laminarin, and no activity with 4-nitrophenyl-alpha-L-rhamnopyranoside. The enzyme shows specificity for 7-O-rutinosylated flavonoids
-
-
?
additional information
?
-
no activity with rutin, diosmin, isoquercitrin, naringin, or laminarin, and no activity with 4-nitrophenyl-alpha-L-rhamnopyranoside. The enzyme shows specificity for 7-O-rutinosylated flavonoids
-
-
?
additional information
?
-
no activity with rutin, diosmin, isoquercitrin, naringin, or laminarin, and no activity with 4-nitrophenyl-alpha-L-rhamnopyranoside. The enzyme shows specificity for 7-O-rutinosylated flavonoids
-
-
?
additional information
?
-
no activity with rutin, diosmin, isoquercitrin, naringin, or laminarin, and no activity with 4-nitrophenyl-alpha-L-rhamnopyranoside. The enzyme shows specificity for 7-O-rutinosylated flavonoids
-
-
?
additional information
?
-
no activity with rutin, diosmin, isoquercitrin, naringin, or laminarin, and no activity with 4-nitrophenyl-alpha-L-rhamnopyranoside. The enzyme shows specificity for 7-O-rutinosylated flavonoids
-
-
?
additional information
?
-
no activity with rutin, diosmin, isoquercitrin, naringin, or laminarin, and no activity with 4-nitrophenyl-alpha-L-rhamnopyranoside. The enzyme shows specificity for 7-O-rutinosylated flavonoids
-
-
?
additional information
?
-
-
catalysis of rutin hydrolysis (EC 3.2.1.168) and transglycosylation of phenol acceptors by rutinase. Preparation of rutinosides of phenolic acids (vanillic acid, sinapic acid, ferulic acid, and caffeic acid) using the reverse reaction of hydrolysis by rutinase, derived from tartary buckwheat (Fagopyrum tataricum) seeds. Rutinase is used to transfer the rutinose moiety from rutin (sugar donor) to the phenolic acids. The transglycosylation products are detected by NMR spectroscopy. Rutinosylation proceeds at the primary hydroxyl group of rutinose. In the rutinosylation of vanillic acid, sinapic acid, and ferulic acid, a hydroxyl group at the 4-position of the aromatic ring was rutinosylated. When caffeic acid, which contains two hydroxyl groups in the ortho position, is used as the acceptor, the hydroxyl group at the 3-position of the aromatic ring was conjugated to rutinose. Rutinase has high substrate specificity for rutin (quercetin-3-rutinoside) and does not degrade structural homologues such as naringin (naringenin-7-rhamnoglucoside) and quercitrin (quercetin 3-rhamnoside). Phenolic compounds containing two terminal aromatic groups, such as curcumin, nordihydroguaiaretic acid (NDGA), and resveratrol, do not form rutinosides
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