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2-phenethyl rutinoside + H2O
2-phenylethanol + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
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Substrates: purified aromatic an terpenyl rutinosides are incubated as substrates, no activity in aqueous medium, 3.8% in 12% ethanol
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2-phenylethanol + hesperidin
2-phenylethyl beta-D-rutinoside + hesperetin
Substrates: -
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4-methylumbelliferyl-beta-D-glucopyranoside + H2O
4-methylumbelliferol + D-glucose
4-methylumbelliferyl-beta-D-rutinoside + H2O
4-methylumbelliferol + D-rutinose
4-nitrophenyl-beta-D-glucopyranoside + H2O
4-nitrophenol + D-glucose
Substrates: 1% activity compared to hesperidin
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4-nitrophenyl-beta-D-rutinoside + H2O
4-nitrophenol + D-rutinose
Substrates: 91% activity compared to hesperidin
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catechol + hesperidin
2-hydroxyphenyl beta-D-rutinoside + hesperetin
Substrates: -
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diosmin + H2O
didymin + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
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Substrates: a 7-O-beta-rutinoside, pH 5.0, 60°C, 3.3% relative activity compared to hesperidin as substrate
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eriocitrin + H2O
eriodictyol + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
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Substrates: a 7-O-beta-rutinoside, pH 5.0, 60°C, 89.7% relative activity compared to hesperidin as substrate
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geraniol + hesperidin
geranyl beta-D-rutinoside + hesperetin
Substrates: -
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geranyl rutinoside + H2O
geraniol + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
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Substrates: purified aromatic an terpenyl rutinosides are incubated as substrates, no activity in aqueous medium, 2.9% in 12% ethanol
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hesperidin + H2O
hesperetin + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
hesperidin + H2O
hesperetin + rutinose
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Substrates: -
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hesperidin + H2O
hesperitin + rutinose
hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
hydroquinone + hesperidin
4-hydroxyphenyl-beta-D-rutinoside + hesperetin
Substrates: -
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narirutin + H2O
naringenin + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
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Substrates: a 7-O-beta-rutinoside, pH 5.0, 60°C, 61% relative activity compared to hesperidin as substrate
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nerol + hesperidin
neryl beta-D-rutinoside + hesperetin
Substrates: -
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neryl rutinoside + H2O
nerol + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
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Substrates: purified aromatic an terpenyl rutinosides are incubated as substrates, no activity in aqueous medium, 2.9% in 12% ethanol
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phloroglucinol + hesperidin
3,5-dihydroxyphenyl beta-D-rutinoside + hesperetin
Substrates: -
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pyrogallol + hesperidin
2,3-dihydroxyphenyl beta-D-rutinoside + hesperetin
Substrates: -
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rutin + caffeic acid
quercetin + caffeic acid 3'-O-rutinoside
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Substrates: -
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rutin + ferulic acid
quercetin + ferulic acid 4'-O-rutinoside
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Substrates: -
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rutin + sinapic acid
quercetin + sinapic acid 4'-O-rutinoside
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Substrates: -
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rutin + vanillic acid
quercetin + vanillic acid 4'-O-rutinoside
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Substrates: -
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additional information
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4-methylumbelliferyl-beta-D-glucopyranoside + H2O
4-methylumbelliferol + D-glucose
Substrates: -
Products: -
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4-methylumbelliferyl-beta-D-glucopyranoside + H2O
4-methylumbelliferol + D-glucose
Substrates: -
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4-methylumbelliferyl-beta-D-glucopyranoside + H2O
4-methylumbelliferol + D-glucose
Substrates: -
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4-methylumbelliferyl-beta-D-glucopyranoside + H2O
4-methylumbelliferol + D-glucose
Substrates: -
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4-methylumbelliferyl-beta-D-glucopyranoside + H2O
4-methylumbelliferol + D-glucose
Substrates: -
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4-methylumbelliferyl-beta-D-glucopyranoside + H2O
4-methylumbelliferol + D-glucose
Substrates: -
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4-methylumbelliferyl-beta-D-glucopyranoside + H2O
4-methylumbelliferol + D-glucose
Substrates: -
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4-methylumbelliferyl-beta-D-glucopyranoside + H2O
4-methylumbelliferol + D-glucose
Substrates: -
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4-methylumbelliferyl-beta-D-rutinoside + H2O
4-methylumbelliferol + D-rutinose
Substrates: -
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4-methylumbelliferyl-beta-D-rutinoside + H2O
4-methylumbelliferol + D-rutinose
Substrates: -
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4-methylumbelliferyl-beta-D-rutinoside + H2O
4-methylumbelliferol + D-rutinose
Substrates: -
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4-methylumbelliferyl-beta-D-rutinoside + H2O
4-methylumbelliferol + D-rutinose
Substrates: -
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4-methylumbelliferyl-beta-D-rutinoside + H2O
4-methylumbelliferol + D-rutinose
Substrates: -
Products: -
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4-methylumbelliferyl-beta-D-rutinoside + H2O
4-methylumbelliferol + D-rutinose
Substrates: -
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4-methylumbelliferyl-beta-D-rutinoside + H2O
4-methylumbelliferol + D-rutinose
Substrates: -
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4-methylumbelliferyl-beta-D-rutinoside + H2O
4-methylumbelliferol + D-rutinose
Substrates: -
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hesperidin + H2O
hesperetin + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
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Substrates: -
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hesperidin + H2O
hesperetin + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
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Substrates: -
Products: i.e. hesperetin + rutinose
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hesperidin + H2O
hesperetin + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
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Substrates: pH 5.0, 60°C
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hesperidin + H2O
hesperetin + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
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Substrates: 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
Products: i.e. hesperetin + rutinose, substrates and products of the enzymatic reaction are analyzed by UV-Maldi-TOF/TOF mass spectrometry
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hesperidin + H2O
hesperetin + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
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Substrates: 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
Products: i.e. hesperetin + rutinose
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hesperidin + H2O
hesperetin + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
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Substrates: purified aromatic and terpenyl rutinosides are incubated as substrates, 14.3% relative activity in aqueous medium, 21.7% in 12% ethanol
Products: i.e. hesperetin + rutinose
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hesperidin + H2O
hesperitin + rutinose
Substrates: -
Products: -
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hesperidin + H2O
hesperitin + rutinose
Substrates: 6-O-alpha-rhamnosyl-beta-glucosidase activity
Products: -
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hesperidin + H2O
hesperitin + rutinose
Substrates: -
Products: -
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hesperidin + H2O
hesperitin + rutinose
Substrates: -
Products: -
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hesperidin + H2O
hesperitin + rutinose
Substrates: -
Products: -
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hesperidin + H2O
hesperitin + rutinose
Substrates: -
Products: -
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hesperidin + H2O
hesperitin + rutinose
Substrates: -
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hesperidin + H2O
hesperitin + rutinose
Substrates: -
Products: -
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hesperidin + H2O
hesperitin + rutinose
Substrates: -
Products: -
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hesperidin + H2O
hesperitin + rutinose
Substrates: -
Products: -
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hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
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Substrates: -
Products: -
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hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
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Substrates: a 7-O-beta-rutinoside, pH 5.0, 60°C, 58.5% relative activity compared to hesperidin as substrate
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hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
Substrates: 91% activity compared to hesperidin
Products: -
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hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
Substrates: 91% activity compared to hesperidin
Products: -
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hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
Substrates: 91% activity compared to hesperidin
Products: -
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hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
Substrates: 91% activity compared to hesperidin
Products: -
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hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
Substrates: 91% activity compared to hesperidin
Products: -
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hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
Substrates: 91% activity compared to hesperidin
Products: -
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hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
Substrates: 91% activity compared to hesperidin
Products: -
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hesperidin methylchalcone + H2O
hesperetin methylchalcone + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
Substrates: 91% activity compared to hesperidin
Products: -
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additional information
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Substrates: 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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Substrates: 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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Substrates: hydrolysis not detected in aqueous medium without ethanol
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additional information
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Substrates: 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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Substrates: 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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Substrates: 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
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additional information
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Substrates: 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
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additional information
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Substrates: 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
Products: -
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additional information
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Substrates: 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
Products: -
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additional information
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Substrates: 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
Products: -
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additional information
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Substrates: 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
Products: -
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additional information
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Substrates: 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
Products: -
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additional information
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Substrates: 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
Products: -
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additional information
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Substrates: 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
Products: -
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additional information
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Substrates: 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
Products: -
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Mazzaferro, L.; Pinuel, L.; Minig, M.; Breccia, J.D.
Extracellular monoenzyme deglycosylation system of 7-O-linked flavonoid beta-rutinosides and its disaccharide transglycosylation activity from Stilbella fimetaria
Arch. Microbiol.
192
383-393
2010
Acremonium sp.
brenda
Mazzaferro, L.; Pinuel, L.; Minig, M.; Breccia, J.D.
Erratum: Extracellular monoenzyme deglycosylation system of 7-O-linked flavonoid beta-rutinosides and its disaccharide transglycosylation activity from Stilbella fimetaria
Arch. Microbiol.
193
461
2011
Acremonium sp.
-
brenda
Mazzaferro, L.S.; Breccia, J.D.
Functional and biotechnological insights into diglycosidases
Biocatal. Biotransform.
29
103-112
2011
Acremonium sp.
-
brenda
Mazzaferro, L.S.; Pinuel, L.; Erra-Balsells, R.; Giudicessi, S.L.; Breccia, J.D.
Transglycosylation specificity of Acremonium sp. alpha-rhamnosyl-beta-glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinosid
Carbohydr. Res.
347
69-75
2012
Acremonium sp.
brenda
Minig, M.; Mazzaferro, L.S.; Erra-Balsells, R.; Petroselli, G.; Breccia, J.D.
alpha-Rhamnosyl-beta-glucosidase-catalyzed reactions for analysis and biotransformations of plant-based foods
J. Agric. Food Chem.
59
11238-11243
2011
Acremonium sp.
brenda
Pinuel, L.; Mazzaferro, L.; Breccia, J.D.
Operational stabilization of fungal alpha-rhamnosyl-beta-glucosidase by immobilization on chitosan composites
Process Biochem.
46
2330-2335
2011
Acremonium sp.
-
brenda
Neher, B.D.; Mazzaferro, L.S.; Kotik, M.; Oyhenart, J.; Halada, P.; Kren, V.; Breccia, J.D.
Bacteria as source of diglycosidase activity Actinoplanes missouriensis produces 6-O-alpha-L-rhamnosyl-beta-D-glucosidase active on flavonoids
Appl. Microbiol. Biotechnol.
100
3061-3070
2016
Actinoplanes missouriensis (I0GZ55), Actinoplanes missouriensis, Actinoplanes missouriensis 431 (I0GZ55), Actinoplanes missouriensis ATCC 14538 (I0GZ55), Actinoplanes missouriensis CBS 188.64 (I0GZ55), Actinoplanes missouriensis DSM 43046 (I0GZ55), Actinoplanes missouriensis JCM 3121 (I0GZ55), Actinoplanes missouriensis NBRC 102363 (I0GZ55), Actinoplanes missouriensis NCIMB 12654 (I0GZ55)
brenda
Minig, M.; Mazzaferro, L.; Capecce, A.; Breccia, J.
Polyethyleneimine coating of magnetic particles increased the stability of an immobilized diglycosidase
Biotechnol. Appl. Biochem.
62
94-100
2015
Acremonium sp. DSM 24697 (A0A286JZ59)
brenda
Mazzaferro, L.S.; Weiz, G.; Braun, L.; Kotik, M.; Pelantova, H.; Kren, V.; Breccia, J.D.
Enzyme-mediated transglycosylation of rutinose (6-O-alpha-L-rhamnosyl-D-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697
Biotechnol. Appl. Biochem.
66
53-59
2019
Acremonium sp. DSM 24697 (A0A286JZ59)
brenda
Katayama, S.; Ohno, F.; Yamauchi, Y.; Kato, M.; Makabe, H.; Nakamura, S.
Enzymatic synthesis of novel phenol acid rutinosides using rutinase and their antiviral activity in vitro
J. Agric. Food Chem.
61
9617-9622
2013
Fagopyrum tataricum
brenda