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Ligand delphinidin 3-O-beta-D-glucoside

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

KEGG

Anthocyanin biosynthesis, Biosynthesis of secondary metabolites

MetaCyc

anthocyanidin 3-malylglucoside biosynthesis (acyl-glucose dependent), anthocyanidin sambubioside biosynthesis, anthocyanidin sophoroside metabolism, anthocyanin biosynthesis (delphinidin 3-O-glucoside), delphinidin diglucoside biosynthesis (acyl-glucose dependent), gentiodelphin biosynthesis, superpathway of anthocyanin biosynthesis (from delphinidin 3-O-glucoside), ternatin C5 biosynthesis, violdelphin biosynthesis more

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (7 results)

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Show Natural Substrate (7 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.267

S-adenosyl-L-methionine + delphinidin 3-O-glucoside = S-adenosyl-L-homocysteine + 3'-methoxydelphinidin 3-O-glucoside

757956

-

2.1.1.267

S-adenosyl-L-methionine + delphinidin 3-O-glucoside = S-adenosyl-L-homocysteine + petunidin 3-O-beta-D-glucoside

721944

-

2.1.1.267

2 entries

2.3.1.171

malonyl-CoA + delphinidin 3-O-beta-D-glucoside = CoA + delphinidin 3-O-(6-malonyl-beta-D-glucoside)

656963

-

2.3.1.215

4-hydroxycinnamoyl-CoA + delphinidin 3-O-beta-D-glucoside = CoA + ?

720758

-

2.3.1.215

caffeoyl-CoA + delphinidin 3-O-beta-D-glucoside = CoA + ?

720758

-

2.3.1.215

2 entries

2.4.1.298

UDP-alpha-D-glucose + delphinidin 3-O-beta-D-glucoside = UDP + delphinidin 3,5-di-O-beta-D-glucoside

722872

-

2.4.2.51

UDP-alpha-D-xylose + delphinidin 3-O-beta-D-glucoside = UDP + delphinidin 3-O-beta-D-sambubioside

720781

-

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

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Show Natural Product (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.115

UDP-glucose + delphinidin = UDP + delphinidin 3-O-beta-D-glucoside

0

-

2.4.1.115

UDP-D-glucose + delphinidin = UDP + delphinidin-3-O-beta-D-glucoside

0

-

2.4.1.115

2 entries

Substrate in Enzyme-catalyzed Reactions (20 results)

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Show Substrate (20 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.267

S-adenosyl-L-methionine + delphinidin 3-O-beta-D-glucoside = S-adenosyl-L-homocysteine + petunidin 3-O-beta-D-glucoside

736999

-

2.1.1.267

S-adenosyl-L-methionine + delphinidin 3-O-glucoside = S-adenosyl-L-homocysteine + 3'-methoxydelphinidin 3-O-glucoside

757323, 757956

-

2.1.1.267

S-adenosyl-L-methionine + delphinidin 3-O-glucoside = S-adenosyl-L-homocysteine + petunidin 3-O-beta-D-glucoside

721944

-

2.1.1.267

S-adenosyl-L-methionine + delphinidin 3-O-glucoside = S-adenosyl-L-homocysteine + petunidin 3-O-glucoside

757955

-

2.3.1.171

malonyl-CoA + delphinidin 3-O-beta-D-glucoside = CoA + delphinidin 3-O-(6-malonyl-beta-D-glucoside)

656963

-

2.3.1.171

malonyl-CoA + delphinidin 3-O-beta-D-glucoside = CoA + delphinidin 3-O-(6-O-malonyl-beta-D-glucoside)

656933, 657110, 674809, 656938, 656935, 656963

-

2.3.1.215

4-hydroxycinnamoyl-CoA + delphinidin 3-O-beta-D-glucoside = CoA + ?

720758

-

2.3.1.215

4-hydroxycinnamoyl-CoA + delphinidin 3-O-beta-D-glucoside = CoA + delphinidin 3-O-[6-O-(4-hydroxycinnamoyl)-beta-D-glucoside]

723385

-

2.3.1.215

caffeoyl-CoA + delphinidin 3-O-beta-D-glucoside = CoA + ?

720758

-

2.3.1.215

caffeoyl-CoA + delphinidin 3-O-beta-D-glucoside = CoA + delphinidin 3-O-[6-O-caffeoyl-beta-D-glucoside]

723385

-

2.3.1.215

delphinidin 3-O-beta-D-glucoside + acetyl-CoA = CoA + delphinidin 3-O-(6-O-acetyl)-beta-D-glucoside

737034

-

2.1.1.267

4 entries

2.3.1.171

2 entries

2.3.1.215

5 entries

2.4.1.238

UDP-glucose + delphinidin 3-glucoside = UDP + delphinidin 3,3'-diglucoside

657052

-

2.4.1.249

UDP-D-glucose + delphinidin 3-O-beta-D-glucoside = UDP + delphinidin 3,3'-di-O-beta-D-glucoside

694767

-

2.4.1.297

UDP-alpha-D-glucose + delphinidin 3-O-beta-D-glucoside = UDP + delphinidin 3-O-sophoroside

737241

-

2.4.1.298

UDP-alpha-D-glucose + delphinidin 3-O-beta-D-glucoside = UDP + delphinidin 3,5-di-O-beta-D-glucoside

737289, 722615, 722872, 720319, 736957

-

2.4.1.299

1-O-vanilloyl-beta-D-glucose + delphinidin 3-O-beta-D-glucoside = vanillate + delphinidin 3,5-di-O-beta-D-glucoside

720677

-

2.4.1.300

1-O-vanilloyl-beta-D-glucose + delphinidin 3-O-beta-D-glucoside = vanillate + delphinidin 3,7-di-O-beta-D-glucoside

720677

-

2.4.1.300

4-hydroxybenzoyl-beta-D-glucose + delphinidin 3-O-beta-D-glucoside = 4-hydroxybenzoic acid + delphinidin 3,7-di-O-beta-D-glucoside

736964

-

2.4.2.51

UDP-alpha-D-xylose + delphinidin 3-O-beta-D-glucoside = UDP + delphinidin 3-O-beta-D-sambubioside

720781, 723428

-

2.4.2.51

UDP-D-xylose + delphinidin 3-O-beta-D-glucoside = UDP + delphinidin 3-O-(beta-D-xylosyl-(1->2)-beta-D-glucoside)

723428

-

2.4.1.300

2 entries

2.4.2.51

2 entries

Product in Enzyme-catalyzed Reactions (6 results)

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Show Product (6 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.115

UDP-glucose + delphinidin = UDP + delphinidin 3-O-beta-D-glucoside

0

-

2.4.1.115

UDP-glucose + delphinidin = UDP + delphinidin 3-O-glucoside

488476, 0

-

2.4.1.115

UDP-D-glucose + delphinidin = UDP + delphinidin-3-O-beta-D-glucoside

0

-

2.4.1.115

UDP-glucose + delphinidin = UDP + delphinidin-3-O-beta-D-glucoside

0

-

2.4.1.91

UDP-alpha-D-glucose + delphinidin = UDP + delphinidin 3-O-beta-D-glucoside

0

-

2.4.1.91

UDP-glucose + delphinidin = UDP + delphinidin 3-O-glucoside

0

-

2.4.1.115

4 entries

2.4.1.91

2 entries

Inhibitor in Enzyme-catalyzed Reactions (5 results)

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Show Inhibitors (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.13.11.12

from Vaccinium myrtillus berries, most effective inhibitor, uncompetitive type, inhibits in a concentration-dependent manner

705797

-

1.13.11.34

from Vaccinium myrtillus berries, strong inhibitor, in a concentration-dependent manner

705797

-

1.4.3.4

-

713198

-

3.1.4.35

-

669021

-

3.3.2.10

noncompetitive inhibition

753841

-

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

2.1.1.267

0.025

-

pH 7.0, 30°C

736999

2.1.1.267

0.0947

-

recombinant enzyme, pH 7.5, temperature not specified in the publication

757323

2.1.1.267

2 entries

2.3.1.215

67.89

-

pH 6.5, 30°C

737034

K_M Value (6 results)

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Show KM Value (6 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.1.1.267

0.00411

-

recombinant enzyme, pH 7.5, temperature not specified in the publication

757323

2.1.1.267

0.012

-

pH 7.0, 30°C

736999

2.1.1.267

0.103

-

pH 7.5, 37°C, recombinant enzyme

757955

2.1.1.267

3 entries

2.3.1.215

0.765

-

pH 6.5, 30°C

737034

2.4.1.298

0.0295

-

pH 8.5, 30°C

722872

2.4.1.298

0.0535

-

pH 8.0, 35°C

737289

2.4.1.298

2 entries

IC₅₀ Value (5 results)

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Show IC50 Value (5 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.13.11.12

0.00043

-

-

705797

1.13.11.34

0.00215

-

-

705797

1.4.3.4

0.0294

-

pH not specified in the publication, temperature not specified in the publication, MAO-A

713198

1.4.3.4

0.0314

-

pH not specified in the publication, temperature not specified in the publication, MAO-B

713198

1.4.3.4

2 entries

3.3.2.10

0.0253

-

pH 7.0, 37°C

753841

References & Links

Literature References (31)

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Show Reference (31 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

488476

751640

Identification and properties of UDP-glucose: cyanidin-3-O-glucosyltransferase isolated from petals of the red campion (Silene dioica)

1978

Kamsteeg, J.; van Brederode, J.; van Nigtevecht, G.

Biochem. Genet.

16

1045-1058

656933

-

Malonyl-coenzyme A:anthocyanidin 3-glucoside malonyltransferase from flowers of Callistephus chinensis

1987

Teusch, M.; Forkmann, G.

Phytochemistry

26

2181-2183

656935

-

Cyanidin 3-malonylglucoside and malonyl-coenzyme A: anthocyanidin malonyltransferase in Lactuca sativa leaves

1996

Yamaguchi, M.A.; Kawanobu, S.; Maki, T.; Ino, I.

Phytochemistry

42

661-663

656938

-

Anthocyanidin 3-glucoside malonyltransferase from Dahlia variabilis

1999

Yamaguchi, M.A.; Oshida, N.; Nakayama, M.; Koshioka, M.; Yamaguchi, Y.; Ino, I.

Phytochemistry

52

15-18

656963

-

Identification of a cDNA encoding malonyl-coenzyme A:anthocyanidin 3-O-glucoside 6''-O-malonyltransferase from cineraria (Senecio cruentus) flowers

2003

Suzuki, H.; Sawada, S.; Yonekura-Sakakibara, K.; Nakayama, T.; Yamaguchi, M.; Nishino, T.

Plant Biotechnol.

20

229-234

657052

12857844

Biochemical and molecular characterization of a novel UDP-glucose:anthocyanin 3'-O-glucosyltransferase, a key enzyme for blue anthocyanin biosynthesis, from gentian

2003

Fukuchi-Mizutani, M.; Okuhara, H.; Fukui, Y.; Nakao, M.; Katsumoto, Y.; Yonekura-Sakakibara, K.; Kusumi, T.; Hase, T.; Tanaka, Y.

Plant Physiol.

132

1652-1663

657110

100140121

cDNA cloning and characterization of two Dendranthema x morifolium anthocyanin malonyltransferases with different functional activities.

2004

Suzuki, H.; Nakayama, T.; Yamaguchi, M.a.; Nishino, T.

Plant Sci.

166

89-96

669021

15769121

In vitro inhibition of human cGMP-specific phosphodiesterase-5 by polyphenols from red grapes

2005

Dell'Agli, M.; Galli, G.V.; Vrhovsek, U.; Mattivi, F.; Bosisio, E.

J. Agric. Food Chem.

53

1960-1965

674809

17383962

Structural and mutational studies of anthocyanin malonyltransferases establish the features of BAHD enzyme catalysis

2007

Unno, H.; Ichimaida, F.; Suzuki, H.; Takahashi, S.; Tanaka, Y.; Saito, A.; Nishino, T.; Kusunoki, M.; Nakayama, T.

J. Biol. Chem.

282

15812-15822

694767

17668234

Purification and characterization of UDP-glucose: anthocyanin 3',5'-O-glucosyltransferase from Clitoria ternatea

2007

Kogawa, K.; Kato, N.; Kazuma, K.; Noda, N.; Suzuki, M.

Planta

226

1501-1509

705797

19072887

Anthocyanins as lipoxygenase inhibitors

2009

Knaup, B.; Oehme, A.; Valotis, A.; Schreier, P.

Mol. Nutr. Food Res.

53

617-624

713198

19416630

Berry anthocyanins and their aglycons inhibit monoamine oxidases A and B

2009

Dreiseitel, A.; Korte, G.; Schreier, P.; Oehme, A.; Locher, S.; Domani, M.; Hajak, G.; Sand, P.G.

Pharmacol. Res.

59

306-311

720319

-

Isolation and characterization of anthocyanin 5-O-glucosyltransferase from flowers of Dahlia variabilis

2001

Ogata, J.; Sakamoto, T.; Yamaguchi, M.; Kawanobu, S.; Yoshitama, K.

J. Plant Physiol.

158

709-714

720677

20971893

A novel glucosylation reaction on anthocyanins catalyzed by acyl-glucose-dependent glucosyltransferase in the petals of carnation and delphinium

2010

Matsuba, Y.; Sasaki, N.; Tera, M.; Okamura, M.; Abe, Y.; Okamoto, E.; Nakamura, H.; Funabashi, H.; Takatsu, M.; Saito, M.; Matsuoka, H.; Nagasawa, K.; Ozeki, Y.

Plant Cell

22

3374-3389

720758

-

Purification and characterization of anthocyanin 3-aromatic acyltransferase from Perilla frutescens

1998

Fujiwara, H.; Tanaka, Y.; Fukui, Y.; Ashikari, T.; Yamaguchi, M.; Kusumi, T.

Plant Sci.

137

87-94

720781

24232765

Uridine 5'-diphosphate-xylose:anthocyanidin 3-O-glucose-xylosyltransferase from petals of Matthiola incana R.Br

1986

Teusch, M.

Planta

169

559-563

721944

22171701

Genetic mechanisms underlying the methylation level of anthocyanins in grape (Vitis vinifera L.)

2011

Fournier-Level, A.; Hugueney, P.; Verries, C.; This, P.; Ageorges, A.

BMC Plant Biol.

11

179

722615

10066805

Molecular cloning and biochemical characterization of a novel anthocyanin 5-O-glucosyltransferase by mRNA differential display for plant forms regarding anthocyanin

1999

Yamazaki, M.; Gong, Z.; Fukuchi-Mizutani, M.; Fukui, Y.; Tanaka, Y.; Kusumi, T.; Saito, K.

J. Biol. Chem.

274

7405-7411

722872

18375606

Cloning and characterization of the UDP-glucose:anthocyanin 5-O-glucosyltransferase gene from blue-flowered gentian

2008

Nakatsuka, T.; Sato, K.; Takahashi, H.; Yamamura, S.; Nishihara, M.

J. Exp. Bot.

59

1241-1252

723385

10845463

Molecular and biochemical characterization of a novel hydroxycinnamoyl-CoA:anthocyanin 3-O-glucoside-6-O-acyltransferase from Perilla frutescens

2000

Yonekura-Sakakibara, K.; Tanaka, Y.; Fukuchi-Mizutani, M.; Fujiwara, H.; Fukui, Y.; Ashikari, T.; Murakami, Y.; Yamaguchi, M.; Kusumi, T.

Plant Cell Physiol.

41

495-502

723428

21899608

Two glycosyltransferases involved in anthocyanin modification delineated by transcriptome independent component analysis in Arabidopsis thaliana

2012

Yonekura-Sakakibara, K.; Fukushima, A.; Nakabayashi, R.; Hanada, K.; Matsuda, F.; Sugawara, S.; Inoue, E.; Kuromori, T.; Ito, T.; Shinozaki, K.; Wangwattana, B.; Yamazaki, M.; Saito, K.

Plant J.

69

154-167

736957

26159788

Molecular and biochemical characterization of the UDP-glucose:anthocyanin 5-O-glucosyltransferase from Vitis amurensis

2015

He, F.; Chen, W.K.; Yu, K.J.; Ji, X.N.; Duan, C.Q.; Reeves, M.J.; Wang, J.

Phytochemistry

117

363-372

736964

-

Isolation of anthocyanin 7-O-glucosyltransferase from Canterbury bells (Campanula medium)

2014

Miyahara, T.; Tani, T.; Takahashi, M.; Nishizaki, Y.; Ozeki, Y.; Sasaki, N.

Plant Biotechnol.

31

555-559

736999

25227758

An O-methyltransferase modifies accumulation of methylated anthocyanins in seedlings of tomato

2014

Gomez Roldan, M.V.; Outchkourov, N.; van Houwelingen, A.; Lammers, M.; Romero de la Fuente, I.; Ziklo, N.; Aharoni, A.; Hall, R.D.; Beekwilder, J.

Plant J.

80

695-708

737034

26395841

A grapevine anthocyanin acyltransferase, transcriptionally regulated by VvMYBA, can produce most acylated anthocyanins present in grape skins

2015

Rinaldo, A.R.; Cavallini, E.; Jia, Y.; Moss, S.M.; McDavid, D.A.; Hooper, L.C.; Robinson, S.P.; Tornielli, G.B.; Zenoni, S.; Ford, C.M.; Boss, P.K.; Walker, A.R.

Plant Physiol.

169

1897-1916

737241

-

Major anthocyanin biosynthesis in the brilliant crimson petals from Erythrina crista-galli L

2014

Arita, T.; Miyazaki, S.; Teramoto, S.; Yoshitama, K.

Sci. Hortic.

168

272-280

737289

-

Biosynthesis of galactofuranose-containing glycans in filamentous fungi

2016

Oka, T.; Goto, M.

Trends Glycosci. Glycotechnol.

28

E39-E45

753841

29447963

In vitro and in silico investigation of anthocyanin derivatives as soluble epoxide hydrolase inhibitors

2018

Kim, J.H.; Cho, I.S.; Ryu, J.; Lee, J.S.; Kang, J.S.; Kang, S.Y.; Kim, Y.H.

Int. J. Biol. Macromol.

112

961-967

757323

26208646

Methylation mediated by an anthocyanin, O-methyltransferase, is involved in purple flower coloration in Paeonia

2015

Du, H.; Wu, J.; Ji, K.X.; Zeng, Q.Y.; Bhuiya, M.W.; Su, S.; Shu, Q.Y.; Ren, H.X.; Liu, Z.A.; Wang, L.S.

J. Exp. Bot.

66

6563-6577

757955

-

Flower color modification in Rosa hybrida by expressing the S-adenosylmethionine anthocyanin 3',5'-O-methyltransferase gene from Torenia hybrida

2015

Nakamura, N.; Katsumoto, Y.; Brugliera, F.; Demelis, L.; Nakajima, D.; Suzuki, H.; Tanaka, Y.

Plant Biotechnol.

32

109-117

757956

31275032

Molecular cloning of flavonoid biosynthetic genes and biochemical characterization of anthocyanin O-methyltransferase of Nemophila menziesii Hook. and Arn

2018

Okitsu, N.; Mizuno, T.; Matsui, K.; Choi, S.H.; Tanaka, Y.

Plant Biotechnol.

35

9-16

Links to other databases for delphinidin 3-O-beta-D-glucoside

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Show Links (1 entry)

ChEBI

PubChem