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MetaCyc Pathway: luteolin glycosides biosynthesis

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.

Superclasses: Biosynthesis Secondary Metabolites Biosynthesis Phenylpropanoid Derivatives Biosynthesis Flavonoids Biosynthesis Flavones Biosynthesis

Some taxa known to possess this pathway include ? : Catharanthus roseus , Citrus maxima , Petroselinum crispum

Expected Taxonomic Range: Viridiplantae

Summary:
Flavonoids are widely distributed in the plant kingdom. Flavonoids are a highly diverse class of plant secondary metabolites (with about 9000 compounds identified so far [Martens05]) derived from the phenylpropanoid pathway. Based on core structures and chemical modifications flavonoids are classified as chalcones, aurones, flavonols, flavones, flavanones, isoflavones and anthocyanins. Flavonoids serve as pigments (red and purple anthocyanin pigments), act as signals for pollinators and other organisms, participate in plant hormone signaling, facilitate pollen-tube growth, protect plants from UV-B radiation, and function as phytoalexins [Harborne00], [Pietta00], [WinkelShirley01].

Flavone and flavonol-O-glycosides make up one of the largest classes of flavonoid constituents with over 2000 known structures. Although β-D-glucose [Sutter72] and β-L-rhamnopyranose [BarPeled91] are the most frequent O-glycoside conjugates found on flavones and flavonols, the presence of arabinose, xylose, and glucuronic acid has also been reported. The formation of luteolin-7-O-gentiobioside from luteolin 7-O-glucoside catalyzed by a flavonoid 1,6-glucosyltransferase isolated from cultured cells of Catharanthus roseus [Masada09] [Oguchi07] further extends the structural complexity of luteolin glycosides occurring in plants.

Luteolin and glycosidic derivatives thereof belong to the more common flavones found in plants. Several potential functions have been ascribed to luteolin and its glycosides. In humans these compounds have been shown to exhibit anti-oxidant [Hu04b], [Schlupper06], and anti-inflammatory activities [Chen07f].

Credits:
Created 28-Apr-2009 by Karthikeyan AS , TAIR
Revised 12-Oct-2012 by Foerster H , Boyce Thompson Institute
Revised 28-Jan-2014 by Foerster H , Boyce Thompson Institute


References

BarPeled91: Bar-Peled M, Lewinsohn E, Fluhr R, Gressel J (1991). "UDP-rhamnose:flavanone-7-O-glucoside-2''-O-rhamnosyltransferase. Purification and characterization of an enzyme catalyzing the production of bitter compounds in citrus." J Biol Chem 266(31);20953-9. PMID: 1939145

Chen07f: Chen CY, Peng WH, Tsai KD, Hsu SL (2007). "Luteolin suppresses inflammation-associated gene expression by blocking NF-kappaB and AP-1 activation pathway in mouse alveolar macrophages." Life Sci 81(23-24);1602-14. PMID: 17977562

Harborne00: Harborne JB, Williams CA (2000). "Advances in flavonoid research since 1992." Phytochemistry 55(6);481-504. PMID: 11130659

Hu04b: Hu C, Kitts DD (2004). "Luteolin and luteolin-7-O-glucoside from dandelion flower suppress iNOS and COX-2 in RAW264.7 cells." Mol Cell Biochem 265(1-2);107-13. PMID: 15543940

Martens05: Martens S, Mithofer A (2005). "Flavones and flavone synthases." Phytochemistry 66(20);2399-407. PMID: 16137727

Masada09: Masada S, Terasaka K, Oguchi Y, Okazaki S, Mizushima T, Mizukami H (2009). "Functional and structural characterization of a flavonoid glucoside 1,6-glucosyltransferase from Catharanthus roseus." Plant Cell Physiol 50(8);1401-15. PMID: 19561332

Oguchi07: Oguchi Y, Masada S, Kondo T, Terasaka K, Mizukami H (2007). "Purification and characterization of UDP-glucose : curcumin glucoside 1,6-glucosyltransferase from Catharanthus roseus cell suspension cultures." Plant Cell Physiol 48(11);1635-43. PMID: 17940060

Pietta00: Pietta PG (2000). "Flavonoids as antioxidants." J Nat Prod 63(7);1035-42. PMID: 10924197

Schlupper06: Schlupper D, Giesa S, Gebhardt R (2006). "Influence of biotransformation of luteolin, luteolin 7-O-glucoside, 3',4'-dihydroxyflavone and apigenin by cultured rat hepatocytes on antioxidative capacity and inhibition of EGF receptor tyrosine kinase activity." Planta Med 72(7);596-603. PMID: 16732514

Schulz88: Schulz, M, Weissenböck, G (1988). "Three specific UDP-glucuronate-flavone-glucuronosyl-transferases from primary leaves of Secale cereale." Phytochemistry 27:1261-1267.

Sutter72: Sutter A, Ortmann R, Grisebach H (1972). "Purification and properties of an enzyme from cell suspension cultures of parsley catalyzing the transfer of D-glucose from UDP-D-glucose to flavonoids." Biochim Biophys Acta 258(1);71-87. PMID: 5058406

WinkelShirley01: Winkel-Shirley B (2001). "Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology, and biotechnology." Plant Physiol 126(2);485-93. PMID: 11402179

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

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

Lazarowski03: Lazarowski ER, Shea DA, Boucher RC, Harden TK (2003). "Release of cellular UDP-glucose as a potential extracellular signaling molecule." Mol Pharmacol 63(5);1190-7. PMID: 12695547


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 Tue Nov 25, 2014, BIOCYC13A.