Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
twitter

MetaCyc Pathway: zeaxanthin, antheraxanthin and violaxanthin interconversion

Enzyme View:

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: xanthophyll cycle

Superclasses: Activation/Inactivation/Interconversion Interconversions
Biosynthesis Secondary Metabolites Biosynthesis Terpenoids Biosynthesis Carotenoids Biosynthesis
Biosynthesis Secondary Metabolites Biosynthesis Terpenoids Biosynthesis Tetraterpenoids Biosynthesis

Some taxa known to possess this pathway include ? : Arabidopsis thaliana col , Capsicum annuum , Chlamydomonas reinhardtii Inferred from experiment [Niyogi97], Lactuca sativa romaine , Nicotiana plumbaginifolia , Solanum lycopersicum , Solanum tuberosum , Xanthophyllomyces dendrorhous

Expected Taxonomic Range: Cyanobacteria , Fungi , Rhodophyta , Viridiplantae

Summary:
General Background

Carotenoids with cyclic ends are integral constituents of plants, algae and cyanobacteria photosynthetic reaction centers [Goodwin80, Young93]. Animals, including humans, cannot synthesize carotenoids, although they are an essential source of retinoids and vitamin A. These isoprenoids pigments are lipid-soluble and are involved in a variety of functions including: protection against photooxidative stress through energy-dissipation of excess light absorbed by the antenna pigments; light-harvest for photosynthesis; the prominent lutein, as well as zeaxanthin, are involved in the reduction of cataract and macular degeneration; others are exploited as coloring agents in flowers and fruits to attract pollinators (and in industry as food colorant) and agents of seed dispersal; finally they are precursors for the plant growth hormone abscisic acid and vitamin A (for a succinct review of the applications of carotenoids, see [Cunningham98b]).

Carotenoids are C40 isoprenoids which consist of eight isoprene units and can be divided in two major groups: carotene and xanthophylls. Carotenes are linear or cyclized hydrocarbons such as lycopene, α-carotene and β-carotene. Xanthophylls are oxygenated derivatives (epoxy, keto or hydroxyl groups) of carotenes; for example: lutein, zeaxanthin. The carotenoid composition varies from species to species; the concentration and composition of xanthophylls are affected by light intensity and the accumulation of specific carotenoids in fruit and flower chromoplasts is a highly, developmentally regulated process [Fraser94, Giuliano93]. Important carotenoids variations are observed during fruit ripening (for review, see [Ronen99]). Higher plant chloroplasts typically accumulate lutein, β-carotene, violaxanthin and neoxanthin in the thylakoid membrane-bound photosystems [Peter91, Ryberg93]. β-Carotene is generally found in the reaction center where it plays a critical photoprotective role by quenching triplet chlorophyll and singlet oxygen, and can undergo rapid degradation during photooxidation [Young93a]. Adjacent to the reaction centers, in the core complex proteins, β-carotene and lutein can be found [Peter91, Bassi93]. Finally, the surrounding antenna complexes contain xanthophylls (lutein, violaxanthin and neoxanthin) [Peter91, Bassi93]. In the chromoplasts of ripening fruits and flower petals, and in the chloroplasts of senescing leaves, the carotenoids are found in membranes or in oil bodies or other structures within the stroma.

About This Pathway

The epoxidation reaction of the xanthophyll cycle consists of the conversion of zeaxanthin to antheraxanthin and violaxanthin and is carried out by the zeaxanthin epoxidase. The isolated cDNA for this enzyme from tobacco was used to identify potential epoxidases of other plants. It has been demonstrated that in Arabidopsis plants defective in osmotic stress-regulated gene induction the LOS6/ABA1 gene encodes a zeaxanthin epoxidase that functions in ABA biosynthesis [Xiong02].

Superpathways: superpathway of carotenoid biosynthesis

Credits:
Created 29-May-2008 by Caspi R , SRI International


References

Bassi93: Bassi R, Pineau B, Dainese P, Marquardt J (1993). "Carotenoid-binding proteins of photosystem II." Eur J Biochem 212(2);297-303. PMID: 8444169

Cunningham98b: Cunningham FX, Gantt E (1998). "Genes and enzymes of carotenoid biosynthesis in plants." Annu Rev Plant Physiol Plant Mol Biol 49;557-583. PMID: 15012246

Fraser94: Fraser PD, Truesdale MR, Bird CR, Schuch W, Bramley PM (1994). "Carotenoid Biosynthesis during Tomato Fruit Development (Evidence for Tissue-Specific Gene Expression)." Plant Physiol 105(1);405-413. PMID: 12232210

Giuliano93: Giuliano G, Bartley GE, Scolnik PA (1993). "Regulation of carotenoid biosynthesis during tomato development." Plant Cell 5(4);379-87. PMID: 8485401

Goodwin80: Goodwin, T.W. (1980). "The biochemistry of carotenoids." 2nd Edition, Vol. 1 (London: Chapman and Hall), pp. 261-320.

Niyogi97: Niyogi KK, Bjorkman O, Grossman AR (1997). "Chlamydomonas Xanthophyll Cycle Mutants Identified by Video Imaging of Chlorophyll Fluorescence Quenching." Plant Cell 9(8);1369-1380. PMID: 12237386

Peter91: Peter GF, Thornber JP (1991). "Biochemical composition and organization of higher plant photosystem II light-harvesting pigment-proteins." J Biol Chem 266(25);16745-54. PMID: 1885603

Ronen99: Ronen G, Cohen M, Zamir D, Hirschberg J (1999). "Regulation of carotenoid biosynthesis during tomato fruit development: expression of the gene for lycopene epsilon-cyclase is down-regulated during ripening and is elevated in the mutant Delta." Plant J 17(4);341-51. PMID: 10205893

Ryberg93: Ryberg, H., Ryberg, M., Sundqvist, C. (1993). "Plastid ultrastructure and development." In "Pigment-protein complexes in plastids: synthesis and assembly', C.Sundqvist and M. Ryberg, eds, London: Academic Press, pp. 25-62.

Xiong02: Xiong L, Lee H, Ishitani M, Zhu JK (2002). "Regulation of osmotic stress-responsive gene expression by the LOS6/ABA1 locus in Arabidopsis." J Biol Chem 277(10);8588-96. PMID: 11779861

Young93: Young, A. (1993). "Occurence and distribution of carotenoids in photosynthetic systems." Carotenoids in Photosynthesis, eds. Young, A.J. & Britton, G. (Chapman & Hall, London), pp. 16-71.

Young93a: Young AJ (1993). "Factors that affect the carotenoid composition of higer plants and algae." In 'Carotenoids in photosynthesis' A.J. Young and G. Britton, eds, London: Chapman and Hall, pp. 161-205.

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

Baroli03: Baroli I, Do AD, Yamane T, Niyogi KK (2003). "Zeaxanthin accumulation in the absence of a functional xanthophyll cycle protects Chlamydomonas reinhardtii from photooxidative stress." Plant Cell 15(4);992-1008. PMID: 12671093

Bouvier96: Bouvier F, d'Harlingue A, Hugueney P, Marin E, Marion-Poll A, Camara B (1996). "Xanthophyll biosynthesis. Cloning, expression, functional reconstitution, and regulation of beta-cyclohexenyl carotenoid epoxidase from pepper (Capsicum annuum)." J Biol Chem 271(46);28861-7. PMID: 8910532

Bugos96: Bugos RC, Yamamoto HY (1996). "Molecular cloning of violaxanthin de-epoxidase from romaine lettuce and expression in Escherichia coli." Proc Natl Acad Sci U S A 93(13);6320-5. PMID: 8692813

Chae11: Chae, Lee (2011). "The functional annotation of protein sequences was performed by the in-house Ensemble Enzyme Prediction Pipeline (E2P2, version 1.0). E2P2 systematically integrates results from three molecular function annotation algorithms using an ensemble classification scheme. For a given genome, all protein sequences are submitted as individual queries against the base-level annotation methods. The individual methods rely on homology transfer to annotate protein sequences, using single sequence (BLAST, E-value cutoff <= 1e-30, subset of SwissProt 15.3) and multiple sequence (Priam, November 2010; CatFam, version 2.0, 1% FDR profile library) models of enzymatic functions. The base-level predictions are then integrated into a final set of annotations using an average weighted integration algorithm, where the weight of each prediction from each individual method was determined via a 0.632 bootstrap process over 1000 rounds of testing. The training and testing data for E2P2 and the BLAST reference database were drawn from protein sequences with experimental support of existence, compiled from SwissProt release 15.3."

DestefanoBeltra06: Destefano-Beltran L, Knauber D, Huckle L, Suttle JC (2006). "Effects of postharvest storage and dormancy status on ABA content, metabolism, and expression of genes involved in ABA biosynthesis and metabolism in potato tuber tissues." Plant Mol Biol 61(4-5);687-97. PMID: 16897484

Frechilla99: Frechilla S, Zhu J, Talbott LD, Zeiger E (1999). "Stomata from npq1, a zeaxanthin-less Arabidopsis mutant, lack a specific response to blue light." Plant Cell Physiol 40(9);949-54. PMID: 10588066

Green05: Green MA, Fry SC (2005). "Vitamin C degradation in plant cells via enzymatic hydrolysis of 4-O-oxalyl-L-threonate." Nature 433(7021);83-7. PMID: 15608627

Han10b: Han H, Gao S, Li B, Dong XC, Feng HL, Meng QW (2010). "Overexpression of violaxanthin de-epoxidase gene alleviates photoinhibition of PSII and PSI in tomato during high light and chilling stress." J Plant Physiol 167(3);176-83. PMID: 19767125

Hieber00: Hieber AD, Bugos RC, Yamamoto HY (2000). "Plant lipocalins: violaxanthin de-epoxidase and zeaxanthin epoxidase." Biochim Biophys Acta 2000;1482(1-2);84-91. PMID: 11058750

Hieber02: Hieber AD, Bugos RC, Verhoeven AS, Yamamoto HY (2002). "Overexpression of violaxanthin de-epoxidase: properties of C-terminal deletions on activity and pH-dependent lipid binding." Planta 214(3);476-83. PMID: 11855651

Kerber08: Kerber, R. C. (2008). ""As simple as possible, but not simpler" - the case of dehydroascorbic acid." J. Chem. Ed. 85(9):1237-1242.

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

Marin96: Marin E, Nussaume L, Quesada A, Gonneau M, Sotta B, Hugueney P, Frey A, Marion-Poll A (1996). "Molecular identification of zeaxanthin epoxidase of Nicotiana plumbaginifolia, a gene involved in abscisic acid biosynthesis and corresponding to the ABA locus of Arabidopsis thaliana." EMBO J 15(10);2331-42. PMID: 8665840

Merchant07: Merchant SS, Prochnik SE, Vallon O, Harris EH, Karpowicz SJ, Witman GB, Terry A, Salamov A, Fritz-Laylin LK, Marechal-Drouard L, Marshall WF, Qu LH, Nelson DR, Sanderfoot AA, Spalding MH, Kapitonov VV, Ren Q, Ferris P, Lindquist E, Shapiro H, Lucas SM, Grimwood J, Schmutz J, Cardol P, Cerutti H, Chanfreau G, Chen CL, Cognat V, Croft MT, Dent R, Dutcher S, Fernandez E, Fukuzawa H, Gonzalez-Ballester D, Gonzalez-Halphen D, Hallmann A, Hanikenne M, Hippler M, Inwood W, Jabbari K, Kalanon M, Kuras R, Lefebvre PA, Lemaire SD, Lobanov AV, Lohr M, Manuell A, Meier I, Mets L, Mittag M, Mittelmeier T, Moroney JV, Moseley J, Napoli C, Nedelcu AM, Niyogi K, Novoselov SV, Paulsen IT, Pazour G, Purton S, Ral JP, Riano-Pachon DM, Riekhof W, Rymarquis L, Schroda M, Stern D, Umen J, Willows R, Wilson N, Zimmer SL, Allmer J, Balk J, Bisova K, Chen CJ, Elias M, Gendler K, Hauser C, Lamb MR, Ledford H, Long JC, Minagawa J, Page MD, Pan J, Pootakham W, Roje S, Rose A, Stahlberg E, Terauchi AM, Yang P, Ball S, Bowler C, Dieckmann CL, Gladyshev VN, Green P, Jorgensen R, Mayfield S, Mueller-Roeber B, Rajamani S, Sayre RT, Brokstein P, Dubchak I, Goodstein D, Hornick L, Huang YW, Jhaveri J, Luo Y, Martinez D, Ngau WC, Otillar B, Poliakov A, Porter A, Szajkowski L, Werner G, Zhou K, Grigoriev IV, Rokhsar DS, Grossman AR (2007). "The Chlamydomonas genome reveals the evolution of key animal and plant functions." Science 318(5848);245-50. PMID: 17932292

Niyogi98: Niyogi KK, Grossman AR, Bjorkman O (1998). "Arabidopsis mutants define a central role for the xanthophyll cycle in the regulation of photosynthetic energy conversion." Plant Cell 1998;10(7);1121-34. PMID: 9668132

Rockholm96: Rockholm DC, Yamamoto HY (1996). "Violaxanthin de-epoxidase." Plant Physiol 110(2);697-703. PMID: 8742341

Simpson00: Simpson GL, Ortwerth BJ (2000). "The non-oxidative degradation of ascorbic acid at physiological conditions." Biochim Biophys Acta 1501(1);12-24. PMID: 10727845

Wang08b: Wang N, Fang W, Han H, Sui N, Li B, Meng QW (2008). "Overexpression of zeaxanthin epoxidase gene enhances the sensitivity of tomato PSII photoinhibition to high light and chilling stress." Physiol Plant 132(3);384-96. PMID: 18275469


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Sun Dec 21, 2014, biocyc14.