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Ligand alpha-tocopherol

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

vitamin E metabolism

KEGG

Biosynthesis of cofactors, Biosynthesis of plant secondary metabolites, Biosynthesis of secondary metabolites, Ferroptosis, Ubiquinone and other terpenoid-quinone biosynthesis, Vitamin digestion and absorption more

MetaCyc

alpha-tocopherol degradation, vitamin E biosynthesis (tocopherols)

Show all BRENDA pathways known for alpha-tocopherol

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Roles as Enzyme Ligand

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.95

S-adenosyl-L-methionine + gamma-tocopherol = S-adenosyl-L-homocysteine + alpha-tocopherol

0, 485679, 485680, 485682, 485675, 485676, 485677, 485678, 485681

-

Substrate in Enzyme-catalyzed Reactions (2 results)

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Show Substrate (2 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.94

alpha-tocopherol + [reduced NADPH-hemoprotein reductase] + O2 = alpha-13'-hydroxy-tocopherol + [oxidized NADPH-hemoprotein reductase] + H2O

712833

-

7.1.1.8

alpha-tocopheryl hydroquinone + ferricytochrome c + H+ = alpha-tocopherol + ferrocytochrome c + H2O

686076

-

Product in Enzyme-catalyzed Reactions (3 results)

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Show Product (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.95

S-adenosyl-L-methionine + gamma-tocopherol = S-adenosyl-L-homocysteine + alpha-tocopherol

485679, 485680, 0, 485675, 485676, 485677, 485678, 485681, 485682

-

5.5.1.24

2,3,5-trimethyl-6-[(2E,7S,11S)-3,7,11,15-tetramethylhexadec-2-en-1-yl]benzene-1,4-diol = alpha-tocopherol

0

-

7.1.1.8

alpha-tocopheryl hydroquinone + ferricytochrome c + H+ = alpha-tocopherol + ferrocytochrome c + H2O

0

-

Activator in Enzyme-catalyzed Reactions (2 results)

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Show Activating Compound (2 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.49

in concert with nicotine the enzyme from testis brain and liver is inhibited, while the enzyme from muscle and stomach is activated by 36% and 20%, respectively, overview

675105

-

3.5.3.18

-

697831

-

Inhibitor in Enzyme-catalyzed Reactions (10 results)

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Show Inhibitors (10 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.49

in concert with nicotine the enzyme from testis brain and liver is inhibited, while the enzyme from muscle and stomach is activated, overview

675105

-

1.10.3.3

-

439889

-

1.11.1.12

complete inhibition of glutathione oxidation

394876

-

1.11.1.7

58% inhibition at 0.1 mM

439733

-

1.13.11.12

competitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction

704118

-

1.13.11.87

1 mM, 40% inhibition

744096

-

1.6.5.2

-

692722

-

2.1.1.95

noncompetitive

485682

-

2.5.1.18

significant inhibition

684841

-

2.5.1.54

-

738155

-

3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (1 entry)

EC NUMBER

ENZYME 3D STRUCTURE

3.1.1.4

1kpm, 3D-view

Enzyme Kinetic Parameters

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

1.11.1.12

0.019

-

-

394876

1.13.11.12

1.1

-

-

704118

IC₅₀ Value (2 results)

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Show IC50 Value (2 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

2.5.1.18

0.25

-

-

684841

2.5.1.54

0.021

-

pH and temperature not specified in the publication

738155

References & Links

Literature References (20)

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Show Reference (20 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

394876

8436014

Purification of phospholipid hydroperoxide glutathione peroxidase from bovine retina

1993

Lam, K.W.; Wang, L.; Hong, B.S.; Treble, D.

Curr. Eye Res.

12

9-15

439733

11557069

Characterization of peroxidase-mediated chlorophyll bleaching in strawberry fruit

2001

Martinez, G.A.; Civello, P.M.; Chaves, A.R.; Anon, M.C.

Phytochemistry

58

379-387

439889

-

Ascorbic acid oxidase

1963

Stark, G.R.; Dawson, C.R.

The Enzymes, 2nd Ed (Boyer, P. D. , Lardy, H. , Myrbäck, K. , eds. )

8

297-311

485675

24253640

Demonstration and solubilization of S-adenosylmethionine:gamma-tocopherol methyltransferase from Capsicum chromoplasts

1985

Camara, B.; D'Harlingue, A.

Plant Cell Rep.

4

31-32

485676

16662717

Terpenoid metabolism in plastids. Localization of alpha-tocopherol synthesis in Capsicum chromoplasts

1982

Camara, B.; Bardat, F.; Seye, A.; D'Harlingue, A.; Moneger, R.

Plant Physiol.

70

1562-1563

485677

-

S-Adenosylmethionine:gamma-tocopherol methyltransferase (Capsicum chromoplasts)

1985

Camara, B.

Methods Enzymol.

111

544-547

485678

4066669

Plastid enzymes of terpenoid biosynthesis. Purification and characterization of gamma-tocopherol methyltransferase from Capsicum chromoplasts

1985

D'Harlingue, A.; Camara, B.

J. Biol. Chem.

260

15200-15203

485679

1420294

Isolation and properties of gamma-tocopherol methyltransferase in Euglena gracilis

1992

Shigeoka, S.; Ishiko, H.; Nakano, Y.; Mitsunaga, T.

Biochim. Biophys. Acta

1128

220-226

485680

-

Some properties of gamma-tocopherol methyltransferase solubilized from spinach chloroplasts

1992

Ishiko, H.; Shigeoka, S.; Nakano, Y.; Mitsunaga, T.

Phytochemistry

31

1499-1500

485681

-

Factors influencing a-tocopherol synthesis in pepper fruits

2002

Koch, M.; Arango, Y.; Mock, H.P.; Heise, K.P.

J. Plant Physiol.

159

1015-1019

485682

12492478

Characterization of gamma-tocopherol methyltransferases from Capsicum annuum L. and Arabidopsis thaliana

2003

Koch, M.; Lemke, R.; Heise, K.P.; Mock, H.P.

Eur. J. Biochem.

270

84-92

675105

16335059

Effects of nicotine and vitamin E on glucose 6-phosphate dehydrogenase activity in some rat tissues in vivo and in vitro

2005

Gumustekin, K.; Ciftci, M.; Coban, A.; Altikat, S.; Aktas, O.; Gul, M.; Timur, H.; Dane, S.

J. Enzyme Inhib. Med. Chem.

20

497-502

684841

17367761

MALDI mass sequencing and characterization of filarial glutathione-S-transferase

2007

Gupta, S.; Singh, A.; Yadav, M.; Singh, K.; Rathaur, S.

Biochem. Biophys. Res. Commun.

356

381-385

686076

17381131

A new ubiquinone metabolite and its activity at the mitochondrial bc1 complex

2007

Gille, L.; Stamberg, W.; Jaeger, W.; Reznicek, G.; Netscher, T.; Rosenau, T.

Chem. Res. Toxicol.

20

591-599

692722

18512942

In vitro activity of almond skin polyphenols for scavenging free radicals and inducing quinone reductase

2008

Chen, C.Y.; Blumberg, J.B.

J. Agric. Food Chem.

56

4427-4434

697831

19331593

Dimethylarginine dimethylaminohydrolase regulation: a novel therapeutic target in cardiovascular disease

2009

Wadham, C.; Mangoni, A.A.

Expert. Opin. Drug Metab. Toxicol.

5

303-319

704118

19785421

New tool to evaluate a comprehensive antioxidant activity in food extracts: Bleaching of 4-nitroso-N,N-dimethylaniline catalyzed by soybean lipoxygenase-1

2009

Pastore, D.; Laus, M.N.; Tozzi, D.; Fogliano, V.; Soccio, M.; Flagella, Z.

J. Agric. Food Chem.

28

9682-9292

712833

20861217

Common variants of cytochrome P450 4F2 exhibit altered vitamin E-omega-hydroxylase specific activity

2010

Bardowell, S.A.; Stec, D.E.; Parker, R.S.

J. Nutr.

140

1901-1906

738155

26491981

Inhibition of 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase from Mycobacterium tuberculosis: in silico screening and in vitro validation

2015

Nirmal, C.R.; Rao, R.; Hopper, W.

Eur. J. Med. Chem.

105

182-193

744096

24907333

Rubber oxygenase and latex clearing protein cleave rubber to different products and use different cleavage mechanisms

2014

Birke, J.; Jendrossek, D.

Appl. Environ. Microbiol.

80

5012-5020

Links to other databases for alpha-tocopherol

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Show Links (1 entry)

ChEBI

PubChem