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MetaCyc Pathway: apigenin glycosides biosynthesis
Author statementInferred from experiment

Enzyme View:

Pathway diagram: apigenin glycosides biosynthesis

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: BiosynthesisSecondary Metabolites BiosynthesisPhenylpropanoid Derivatives BiosynthesisFlavonoids BiosynthesisFlavones Biosynthesis

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

Expected Taxonomic Range: Viridiplantae

Flavonoids represent a highly diverse class of plant secondary metabolites. The basic chemical structure of flavonoids is a C15 skeleton which consists of two aromatic rings linked by a C3 chain. About 9000 compounds have been identified so far [Martens05]. They are involved in a wide range of biological processes in higher plants such as UV protection, flower coloration, and antimicrobial activity [Harborne00]. They also have demonstrated antioxidant and anticancer properties [Le02] [Long08].


Flavones are a class of flavonoids synthesized directly from flavanones. Flavone formation in various tissues of a wide range of higher and lower plant species is catalyzed by a flavone synthase which belongs to the plant cytochrome P450 superfamily [Long08]. The flavones can be classified into several subgroups based on (i) hydroxylation, (ii) O-methylation, (iii) C-methylation, (iv) isoprenylation, or (v) methylenedioxy substitutions.

Most of the flavonoids, including flavones such as apigenin occur as glycosides. Glycosylation increases the chemical stability, bioavailability and bioactivity [Vogt00] of flavonoids and potentially improves their intrinsic pharmacological properties for human health [Ross02]. The formation of apigenin-7-O-gentiobioside is catalyzed by a flavonoid 1,6-glucosyltransferase characterized from Catharanthus roseus which adds β-D-glucopyranose to the β-D-glucopyranose attached to the A-ring 7-O-position of apigenin 7-O-β-D-glucoside yielding the corresponding gentiobioside, hence contributing yet another structural variety of apigenin glycosides as displayed in the pathway [Masada09].

Created 13-Aug-2008 by Karthikeyan AS, TAIR
Revised 12-Oct-2012 by Foerster H, Boyce Thompson Institute


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

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

Le02: Le Marchand L (2002). "Cancer preventive effects of flavonoids--a review." Biomed Pharmacother 56(6);296-301. PMID: 12224601

Long08: Long X, Fan M, Bigsby RM, Nephew KP (2008). "Apigenin inhibits antiestrogen-resistant breast cancer cell growth through estrogen receptor-alpha-dependent and estrogen receptor-alpha-independent mechanisms." Mol Cancer Ther 7(7);2096-108. PMID: 18645020

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

Ross02: Ross JA, Kasum CM (2002). "Dietary flavonoids: bioavailability, metabolic effects, and safety." Annu Rev Nutr 22;19-34. PMID: 12055336

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

Vogt00: Vogt T, Jones P (2000). "Glycosyltransferases in plant natural product synthesis: characterization of a supergene family." Trends Plant Sci 5(9);380-6. PMID: 10973093

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

Koester84: Koester J, Bussmann R, Barz W (1984). "Malonyl-coenzyme A:isoflavone 7-O-glucoside-6"-O-malonyltransferase from roots of chick pea (Cicer arietinum L.)." Arch Biochem Biophys 234(2);513-21. PMID: 6497385

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

Matern83: Matern U, Feser C, Hammer D (1983). "Further characterization and regulation of malonyl-coenzyme A: flavonoid glucoside malonyltransferases from parsley cell suspension cultures." Arch Biochem Biophys 226(1);206-17. PMID: 6639051

Ortmann72: Ortmann R, Sutter A, Grisebach H (1972). "Purification and properties of udpapiose: 7-O-( -D-glucosyl)-flavone apiosyltransferase from cell suspension cultures of parsley." Biochim Biophys Acta 289(2);293-302. PMID: 4650134

Rubio06: Rubio S, Larson TR, Gonzalez-Guzman M, Alejandro S, Graham IA, Serrano R, Rodriguez PL (2006). "An Arabidopsis mutant impaired in coenzyme A biosynthesis is sugar dependent for seedling establishment." Plant Physiol 140(3);830-43. PMID: 16415216

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 Pathway Tools version 19.5 (software by SRI International) on Sun May 1, 2016, biocyc11.