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Ligand naringenin 7-O-beta-D-glucoside

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Natural Substrate (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.236

UDP-L-rhamnose + naringenin 7-O-glucoside = UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]

723433, 488818, 655963, 759382

-

2.4.1.B53

UDP-L-rhamnose + naringenin 7-O-beta-D-glucoside = UDP + naringenin 7-O-[alpha-L-rhamnosyl-(1->6)-beta-D-glucoside]

723433

-

3.2.1.21

naringenin-7-beta-glucopyranoside + H2O = naringenin + beta-D-glucose

654522

-

Substrate in Enzyme-catalyzed Reactions (7 results)

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Show Substrate (7 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.3.1.115

malonyl-CoA + naringenin 7-O-glucoside = ?

706233

-

2.3.1.115

naringenin 7-O-glucoside + malonyl-CoA = CoA + naringenin 7-O-glucoside 6''-O-malonylester

486144

-

2.4.1.236

UDP-L-rhamnose + naringenin 7-O-glucoside = UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]

759382, 723433, 488818, 655963

-

2.4.1.236

UDP-beta-L-rhamnose + naringenin-7-O-glucoside = UDP + naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]

735522

-

2.3.1.115

2 entries

2.4.1.236

2 entries

2.4.1.B53

UDP-L-rhamnose + naringenin 7-O-beta-D-glucoside = UDP + naringenin 7-O-[alpha-L-rhamnosyl-(1->6)-beta-D-glucoside]

735522, 723433

-

3.2.1.21

naringenin-7-beta-D-glucopyranoside + H2O = naringenin + beta-D-glucose

655434

-

3.2.1.21

naringenin-7-beta-glucopyranoside + H2O = naringenin + beta-D-glucose

654522, 655762

-

3.2.1.21

2 entries

Product in Enzyme-catalyzed Reactions (7 results)

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Show Product (7 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.170

UDP-glucose + naringenin = UDP + naringenin 7-O-beta-D-glucoside

0

-

2.4.1.185

UDP-glucose + naringenin = UDP + naringenin 7-O-beta-D-glucoside

0

-

2.4.1.185

UDP-glucose + naringenin = UDP + naringenin 7-O-glucoside

0

-

2.4.1.185

2 entries

2.4.1.237

UDP-glucose + naringenin = UDP + naringenin 7-O-beta-D-glucoside

0

-

2.4.1.357

UDP-alpha-D-glucose + naringenin = UDP + naringenin-7-O-glucoside

0

-

2.4.1.81

UDP-glucose + naringenin = UDP + 7-O-beta-D-glucosyl-naringenin

0

-

2.4.1.81

UDP-alpha-D-glucose + naringenin = UDP + 7-O-beta-D-glucosylnaringenin

0

-

2.4.1.81

2 entries

Inhibitor in Enzyme-catalyzed Reactions (2 results)

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Show Inhibitors (2 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.14.20.5

competitive with respect to (2S)-naringenin

439113

-

3.2.1.40

-

655015

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (3 results)

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Show Turnover Number (3 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

3.2.1.21

1.4

-

recombinant wild-type enzyme

681442

3.2.1.21

2.6

-

37°C, pH 6.5

655434

3.2.1.21

2.6

-

50°C, pH 6.5

654522

3.2.1.21

3 entries

K_M Value (7 results)

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Show KM Value (7 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.3.1.115

0.028

-

-

706233

2.3.1.115

0.1004

-

-

706233

2.3.1.115

0.1256

-

-

706233

2.3.1.115

3 entries

2.4.1.236

0.0024

-

pH 7.5, 37°C

655963

3.2.1.21

0.43

-

37°C, pH 6.5

655434

3.2.1.21

148

-

recombinant wild-type enzyme

681442

3.2.1.21

432

-

50°C, pH 6.5

654522

3.2.1.21

3 entries

K_i Value (2 results)

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Show KI Value (2 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.20.5

0.057

-

-

439113

3.2.1.40

2.6

-

pH 5.5, 40°C

655015

References & Links

Literature References (13)

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Show Reference (13 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

439113

2221917

Purification and characterization of flavone synthase I, a 2-oxoglutarate-dependent desaturase

1990

Britsch, L.

Arch. Biochem. Biophys.

282

152-160

486144

7259181

Two flavonoid-specific malonyltransferases from cell suspension cultures of Petroselinum hortense: partial purification and some properties of malonyl-coenzyme A: flavone/flavonol-7-O-glycoside malonyltransferase and malonyl-coenzyme A: flavonol-3-O-glucoside malonyltransferase

1981

Matern, U.; Potts, J.R.M.; Hahlbrock, K.

Arch. Biochem. Biophys.

208

233-241

488818

16667183

Flavanone glycoside biosynthesis in Citrus. Chalcone synthase, UDP-glucose: flavanone-7-O-glucosyltransferase and -rhamnosyltransferase activities in cell-free extracts

1989

Lewinsohn, E.; Britsch, L.; Mazur, Y.; Gressel, J.

Plant Physiol.

91

1323-1328

654522

12667141

Substrate (aglycone) specificity of human cytosolic beta-glucosidase

2003

Berrin, J.G.; Czjzek, M.; Kroon, P.A.; McLauchlan, W.R.; Puigserver, A.; Williamson, G.; Juge, N.

Biochem. J.

373

41-48

655015

12224626

Thermal inactivation and product inhibition of Aspergillus terreus CECT 2663 alpha-L-rhamnosidase and their role on hydrolysis of naringin solutions

2002

Soria, F.; Ellenrieder, G.

Biosci. Biotechnol. Biochem.

66

1442-1449

655434

11784319

Functional expression of human liver cytosolic beta-glucosidase in Pichia pastoris. Insights into its role in the metabolism of dietary glucosides

2002

Berrin, J.G.; McLauchlan, W.R.; Needs, P.; Williamson, G.; Puigserver, A.; Kroon, P.A.; Juge, N.

Eur. J. Biochem.

269

249-258

655762

11559154

Purification and characterization of a beta-glucosidase from Citrus sinensis var. Valencia fruit tissue

2001

Cameron, R.G.; Manthey, J.A.; Baker, R.A.; Grohmann, K.

J. Agric. Food Chem.

49

4457-4462

655963

1939145

UDP-rhamnose:flavanone-7-O-glucoside-2''-O-rhamnosyltransferase. Purification and characterization of an enzyme catalyzing the production of bitter compounds in citrus

1991

Bar-Peled, M.; Lewinsohn, E.; Fluhr, R.; Gressel, J.

J. Biol. Chem.

266

20953-20959

681442

17555766

The crystal structure of human cytosolic beta-glucosidase unravels the substrate aglycone specificity of a family 1 glycoside hydrolase

2007

Tribolo, S.; Berrin, J.G.; Kroon, P.A.; Czjzek, M.; Juge, N.

J. Mol. Biol.

370

964-975

706233

18419782

Nucleocytoplasmic-localized acyltransferases catalyze the malonylation of 7-O-glycosidic (iso)flavones in Medicago truncatula

2008

Yu, X.; Chen, M.; Liu, C.

Plant J.

55

382-396

723433

22989156

The molecular and enzymatic basis of bitter/non-bitter flavor of citrus fruit: evolution of branch-forming rhamnosyltransferases under domestication

2013

Frydman, A.; Liberman, R.; Huhman, D.V.; Carmeli-Weissberg, M.; Sapir-Mir, M.; Ophir, R.; W Sumner, L.; Eyal, Y.

Plant J.

73

166-178

735522

26433966

Substrate preference of citrus naringenin rhamnosyltransferases and their application to flavonoid glycoside production in fission yeast

2016

Ohashi, T.; Hasegawa, Y.; Misaki, R.; Fujiyama, K.

Appl. Microbiol. Biotechnol.

100

687-696

759382

27808514

Variation in key flavonoid biosynthetic enzymes and phytochemicals in Rio Red Grapefruit (Citrus paradisi Macf.) during fruit development

2016

Chaudhary, P.R.; Bang, H.; Jayaprakasha, G.K.; Patil, B.S.

J. Agric. Food Chem.

64

9022-9032

Links to other databases for naringenin 7-O-beta-D-glucoside

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Show Links (1 entry)

ChEBI

PubChem