MetaCyc Pathway: quercetin sulfate biosynthesis
Inferred from experiment

Pathway diagram: quercetin sulfate biosynthesis

If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: quercetin sulphate biosynthesis

Superclasses: BiosynthesisSecondary Metabolites BiosynthesisPhenylpropanoid Derivatives BiosynthesisFlavonoids BiosynthesisFlavonols Biosynthesis

Some taxa known to possess this pathway include : Arabidopsis thaliana col, Flaveria bidentis, Flaveria chlorifolia

Expected Taxonomic Range: Viridiplantae

Flavonoids are a class of plant secondary metabolites widely distributed in the plant kingdom. Over 10,000 flavonoids have been described in the literature [Tahara07]. They display important functions as attractants for pollinators, protective agents against UV light and various pathogens, antibiotics, and signal molecules involved in symbiosis with Rhizobia. Apart from their biological functions, they are also known for their antioxidant and anticancer and other bioactivities in humans.

Flavonoids are usually found as water-soluble glycosides. However, the occurrence of methoxylated, acylated or sulfated derivatives of flavonoids have also been reported in plants. The presence of over 80 different flavonoids sulfates has been reported from various plant species [Barron88].

Enzymatic sulfonation of flavonoids is catalyzed by a family of sulfotransferases (STs) that transfer the sulfonate group of 3'-phosphoadenylyl-sulfate to the hydroxyl group of a flavonoid to produce a sulfate flavonoid ester.

Citations: [Gidda, Varin92a , Varin92, Varin89]

Superpathways: superpathway of flavones and derivatives biosynthesis

Created 02-Apr-2009 by Karthikeyan AS, TAIR


Barron88: Barron, D, Varin, L, Ibrahim, R.K, Harborne, J.B, Williams C.A. (1988). "Sulphated flavonoids." Phytochemistry 27: 2375-2395.

Gidda: Gidda SK, Varin L "Biochemical and molecular characterization of flavonoid 7-sulfotransferase from Arabidopsis thaliana." Plant Physiol Biochem 44(11-12);628-36. PMID: 17095238

Tahara07: Tahara S (2007). "A journey of twenty-five years through the ecological biochemistry of flavonoids." Biosci Biotechnol Biochem 71(6);1387-404. PMID: 17587669

Varin89: Varin L, Ibrahim RK (1989). "Partial Purification and Characterization of Three Flavonol-Specific Sulfotransferases from Flaveria chloraefolia." Plant Physiol 90(3);977-981. PMID: 16666908

Varin92: Varin L, DeLuca V, Ibrahim RK, Brisson N (1992). "Molecular characterization of two plant flavonol sulfotransferases." Proc Natl Acad Sci U S A 89(4);1286-90. PMID: 1741382

Varin92a: Varin L, Ibrahim RK (1992). "Novel flavonol 3-sulfotransferase. Purification, kinetic properties, and partial amino acid sequence." J Biol Chem 267(3);1858-63. PMID: 1309801

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

Ananvoranich94: Ananvoranich S, Varin L, Gulick P, Ibrahim R (1994). "Cloning and regulation of flavonol 3-sulfotransferase in cell-suspension cultures of Flaveria bidentis." Plant Physiol 106(2);485-91. PMID: 7991681

Gauthier98: Gauthier A, Gulick PJ, Ibrahim RK (1998). "Characterization of two cDNA clones which encode O-methyltransferases for the methylation of both flavonoid and phenylpropanoid compounds." Arch Biochem Biophys 351(2);243-9. PMID: 9514654

Ibdah03: Ibdah M, Zhang XH, Schmidt J, Vogt T (2003). "A novel Mg(2+)-dependent O-methyltransferase in the phenylpropanoid metabolism of Mesembryanthemum crystallinum." J Biol Chem 278(45);43961-72. PMID: 12941960

Kim06: Kim BG, Lee HJ, Park Y, Lim Y, Ahn JH (2006). "Characterization of an O-methyltransferase from soybean." Plant Physiol Biochem 44(4);236-41. PMID: 16777424

Kopycki08: Kopycki JG, Rauh D, Chumanevich AA, Neumann P, Vogt T, Stubbs MT (2008). "Biochemical and structural analysis of substrate promiscuity in plant Mg2+-dependent O-methyltransferases." J Mol Biol 378(1);154-64. PMID: 18342334

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

Lin13: Lin Y, Sun X, Yuan Q, Yan Y (2013). "Combinatorial biosynthesis of plant-specific coumarins in bacteria." Metab Eng 18;69-77. PMID: 23644174

Muzac00: Muzac I, Wang J, Anzellotti D, Zhang H, Ibrahim RK (2000). "Functional expression of an Arabidopsis cDNA clone encoding a flavonol 3'-O-methyltransferase and characterization of the gene product." Arch Biochem Biophys 2000;375(2);385-8. PMID: 10700397

Schmidt11: Schmidt A, Li C, Shi F, Jones AD, Pichersky E (2011). "Polymethylated myricetin in trichomes of the wild tomato species Solanum habrochaites and characterization of trichome-specific 3'/5'- and 7/4'-myricetin O-methyltransferases." Plant Physiol 155(4);1999-2009. PMID: 21343428

Varin87: Varin, L, Barront, D, Ibrahim, R,K (1987). "Enzymatic synthesis of sulphated flavonols in Flaveria." Phytochemistry 26: 135-138.

Wils13: Wils CR, Brandt W, Manke K, Vogt T (2013). "A single amino acid determines position specificity of an Arabidopsis thaliana CCoAOMT-like O-methyltransferase." FEBS Lett 587(6);683-9. PMID: 23416302

Zhang97: Zhang H, Wang J, Goodman HM (1997). "An Arabidopsis gene encoding a putative 14-3-3-interacting protein, caffeic acid/5-hydroxyferulic acid O-methyltransferase." Biochim Biophys Acta 1997;1353(3);199-202. PMID: 9349713

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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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