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MetaCyc Pathway: vitamin E biosynthesis (tocopherols)
Inferred from experiment

Enzyme View:

Pathway diagram: vitamin E biosynthesis (tocopherols)

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: tocopherol biosynthesis

Superclasses: BiosynthesisCofactors, Prosthetic Groups, Electron Carriers BiosynthesisQuinol and Quinone Biosynthesis
BiosynthesisCofactors, Prosthetic Groups, Electron Carriers BiosynthesisVitamins Biosynthesis

Some taxa known to possess this pathway include : Arabidopsis thaliana colInferred from experiment [Collakova03], Synechocystis sp. PCC 6803

Expected Taxonomic Range: Chlorophyta, Cyanobacteria, Phaeophyceae, Rhodophyta, Viridiplantae

The term vitamin E (tocochromenols) is a collective term for the eight forms of tocotrienols and tocopherols, each existing as α, β, γ, and δ species.

Structurally tocotrienols and tocopherols differ only in the degree of unsaturation of their side-chain. The tocotrienol chain comprises three trans-double bonds, whereas the tocopherol chain is fully saturated. In addition, the α, β, γ, and δ species of both compound groups vary in the methylation pattern of the chromanol ring [Cahoon03].

Vitamin E compounds are synthesized only by photosynthetic organisms, although they are essential dietary components for animals (including humans), where they act primarily as antioxidants. Their presumed role in plants involve protection of chloroplast lipids and chlorophylls against oxidative damages. The tocotrienols are mostly found in monocots [Padley94] and a few dicots [Horvath], whereas tocopherols are wider spread in the plant kingdom and dominate in the dicots [KamalEldin96].

The tocopherols include α-tocopherol, β-tocopherol, γ-tocopherol and δ-tocopherol, which differ only in the number and position of methyl groups on the chromanol ring. α-tocopherol has been shown to possess the highest vitamin E activity.

The genes encoding all the of pathway enzymes have been cloned from Arabidopsis.

Citations: [Cheng03, Porfirova02]

Unification Links: AraCyc:PWY-1422

Created 15-Apr-2004 by Zhang P, TAIR


Cahoon03: Cahoon EB, Hall SE, Ripp KG, Ganzke TS, Hitz WD, Coughlan SJ (2003). "Metabolic redesign of vitamin E biosynthesis in plants for tocotrienol production and increased antioxidant content." Nat Biotechnol 21(9);1082-7. PMID: 12897790

Cheng03: Cheng Z, Sattler S, Maeda H, Sakuragi Y, Bryant DA, DellaPenna D (2003). "Highly divergent methyltransferases catalyze a conserved reaction in tocopherol and plastoquinone synthesis in cyanobacteria and photosynthetic eukaryotes." Plant Cell 15(10);2343-56. PMID: 14508009

Collakova03: Collakova E, DellaPenna D (2003). "Homogentisate phytyltransferase activity is limiting for tocopherol biosynthesis in Arabidopsis." Plant Physiol 131(2);632-42. PMID: 12586887

Horvath: Horvath G, Wessjohann L, Bigirimana J, Monica H, Jansen M, Guisez Y, Caubergs R, Horemans N "Accumulation of tocopherols and tocotrienols during seed development of grape (Vitis vinifera L. cv. Albert Lavallee)." Plant Physiol Biochem 44(11-12);724-31. PMID: 17110122

KamalEldin96: Kamal-Eldin A, Appelqvist LA (1996). "The chemistry and antioxidant properties of tocopherols and tocotrienols." Lipids 31(7);671-701. PMID: 8827691

Padley94: Padley FB, Gunstone FD, Harwood JL (1994). "The Lipid Handbook." In: The Lipid Handbook, 2nd Edn. (eds. Gunstone, F.D., Harwood, J.L., and Padley, F.B.) 130 Chapman & Hall, London,.

Porfirova02: Porfirova S, Bergmuller E, Tropf S, Lemke R, Dormann P (2002). "Isolation of an Arabidopsis mutant lacking vitamin E and identification of a cyclase essential for all tocopherol biosynthesis." Proc Natl Acad Sci U S A 99(19);12495-500. PMID: 12213958

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Albermann08a: Albermann C, Ghanegaonkar S, Lemuth K, Vallon T, Reuss M, Armbruster W, Sprenger GA (2008). "Biosynthesis of the vitamin E compound delta-tocotrienol in recombinant Escherichia coli cells." Chembiochem 9(15);2524-33. PMID: 18810749

Bradley86: Bradley FC, Lindstedt S, Lipscomb JD, Que L, Roe AL, Rundgren M (1986). "4-Hydroxyphenylpyruvate dioxygenase is an iron-tyrosinate protein." J Biol Chem 261(25);11693-6. PMID: 3017941

Brownlee04: Brownlee JM, Johnson-Winters K, Harrison DH, Moran GR (2004). "Structure of the ferrous form of (4-hydroxyphenyl)pyruvate dioxygenase from Streptomyces avermitilis in complex with the therapeutic herbicide, NTBC." Biochemistry 43(21);6370-7. PMID: 15157070

Collakova01: Collakova E, DellaPenna D (2001). "Isolation and functional analysis of homogentisate phytyltransferase from Synechocystis sp. PCC 6803 and Arabidopsis." Plant Physiol 127(3);1113-24. PMID: 11706191

Dahnhardt02: Dahnhardt D, Falk J, Appel J, van der Kooij TA, Schulz-Friedrich R, Krupinska K (2002). "The hydroxyphenylpyruvate dioxygenase from Synechocystis sp. PCC 6803 is not required for plastoquinone biosynthesis." FEBS Lett 523(1-3);177-81. PMID: 12123828

DellaPenna05: DellaPenna D (2005). "A decade of progress in understanding vitamin E synthesis in plants." J Plant Physiol 162(7);729-37. PMID: 16008096

Garcia00: Garcia I, Job D, Matringe M (2000). "Inhibition of p-hydroxyphenylpyruvate dioxygenase by the diketonitrile of isoxaflutole: a case of half-site reactivity." Biochemistry 39(25);7501-7. PMID: 10858299

Garcia99: Garcia I, Rodgers M, Pepin R, Hsieh TF, Matringe M (1999). "Characterization and subcellular compartmentation of recombinant 4-hydroxyphenylpyruvate dioxygenase from Arabidopsis in transgenic tobacco." Plant Physiol 119(4);1507-16. PMID: 10198110

Gunsior04: Gunsior M, Ravel J, Challis GL, Townsend CA (2004). "Engineering p-hydroxyphenylpyruvate dioxygenase to a p-hydroxymandelate synthase and evidence for the proposed benzene oxide intermediate in homogentisate formation." Biochemistry 43(3);663-74. PMID: 14730970

Koch03: Koch M, Lemke R, Heise KP, Mock HP (2003). "Characterization of gamma-tocopherol methyltransferases from Capsicum annuum L and Arabidopsis thaliana." Eur J Biochem 270(1);84-92. PMID: 12492478

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Lindstedt87: Lindstedt S, Odelhog B (1987). "4-Hydroxyphenylpyruvate dioxygenase from Pseudomonas." Methods Enzymol 142;143-8. PMID: 3037255

Lindstedt87a: Lindstedt S, Odelhog B (1987). "4-Hydroxyphenylpyruvate dioxygenase from human liver." Methods Enzymol 142;139-42. PMID: 3037254

Lipka13: Lipka AE, Gore MA, Magallanes-Lundback M, Mesberg A, Lin H, Tiede T, Chen C, Buell CR, Buckler ES, Rocheford T, DellaPenna D (2013). "Genome-wide association study and pathway-level analysis of tocochromanol levels in maize grain." G3 (Bethesda) 3(8);1287-99. PMID: 23733887

Moran05: Moran GR (2005). "4-Hydroxyphenylpyruvate dioxygenase." Arch Biochem Biophys 433(1);117-28. PMID: 15581571

Motohashi03: Motohashi R, Ito T, Kobayashi M, Taji T, Nagata N, Asami T, Yoshida S, Yamaguchi-Shinozaki K, Shinozaki K (2003). "Functional analysis of the 37 kDa inner envelope membrane polypeptide in chloroplast biogenesis using a Ds-tagged Arabidopsis pale-green mutant." Plant J 34(5);719-31. PMID: 12787252

Norris98: Norris SR, Shen X, DellaPenna D (1998). "Complementation of the Arabidopsis pds1 mutation with the gene encoding p-hydroxyphenylpyruvate dioxygenase." Plant Physiol 117(4);1317-23. PMID: 9701587

Pascal85: Pascal RA, Oliver MA, Chen YC (1985). "Alternate substrates and inhibitors of bacterial 4-hydroxyphenylpyruvate dioxygenase." Biochemistry 24(13);3158-65. PMID: 4027238

Ruetschi97: Ruetschi U, Rymo L, Lindstedt S (1997). "Human 4-hydroxyphenylpyruvate dioxygenase gene (HPD)." Genomics 44(3);292-9. PMID: 9325050

Sattler03: Sattler SE, Cahoon EB, Coughlan SJ, DellaPenna D (2003). "Characterization of tocopherol cyclases from higher plants and cyanobacteria. Evolutionary implications for tocopherol synthesis and function." Plant Physiol 132(4);2184-95. PMID: 12913173

Showing only 20 references. To show more, press the button "Show all references".

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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