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MetaCyc Pathway: formononetin conjugates 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.

Superclasses: Activation/Inactivation/Interconversion Interconversions
Biosynthesis Secondary Metabolites Biosynthesis Phenylpropanoid Derivatives Biosynthesis Flavonoids Biosynthesis Isoflavonoids Biosynthesis
Biosynthesis Secondary Metabolites Biosynthesis Phytoalexins Biosynthesis Isoflavonoid Phytoalexins Biosynthesis

Some taxa known to possess this pathway include ? : Cicer arietinum , Glycine max

Expected Taxonomic Range: Fabaceae

Summary:
Malonyl glucosides have been frequently overlooked due to their lability and inadequate isolation procedures. Numerous N-and O-malonyl conjugates have been reported in different plant species, including isoflavones, isoflavanones and isoflavonoids but also xenobiotics, D-amino acids and the ethylene precursor 1-aminocyclopropane-1-carboxylic acid.

The latter are considered to be detoxification products [Koester84], whereas the former may serve as pools for the release of free aglycons. Released isoflavones can be either incorporated into the biosynthetic pathway of phytoalexins or act as phytoanticipins [Hsieh01].

The finding that isoflavone conjugates are sometimes constitutively present in considerable amounts in legumes [Graham91], support such a possible role as preformed toxins (phytoanticipins).

Glucosides and malonyl glucosides of isoflavones, such as biochanin A and formononetin and further metabolic derivatives (e.g. cicerin, medicarpin) are exclusively located in the vacuole [Mackenbrock92] and it has been speculated, that acylation of these compounds could precede and facilitate their transport through the tonoplast [Matern83].

Superpathways: superpathway of formononetin derivative biosynthesis

Credits:
Created 15-Feb-2005 by Foerster H , TAIR


References

Graham91: Graham TL, (1991) "Flavonoid and isoflavonoid distribution in developing soybean seedling tissues and in seed and root exudates." Plant Physiology (1991), 95, 594-603.

Hsieh01: Hsieh MC, Graham TL (2001). "Partial purification and characterization of a soybean β-glucosidase with high specific activity towards isoflavone conjugates." Phytochemistry 58(7);995-1005. PMID: 11730862

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

Mackenbrock92: Mackenbrock U, Vogelsang R, Barz W, (1992) "Isoflavone and pterocarpan malonylglucosides and β-1,3-glucan- and chitin hydrolases are vacuolar constituents in chick pea (Cicer arietinum L.)." Z. Naturforsch (1992) 47c, 815-822.

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

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

Bentley52: Bentley, L.E. (1952). "Occurrence of malonic acid in plants." Nature 170(4333);847-8. PMID: 13013230

Davenport72: Davenport HE, Dupont MS (1972). "The enzymic hydrolysis of malonated flavone glycosides." Biochem J 129(2);18P-19P. PMID: 4643301

Dimroth97: Dimroth P, Hilbi H (1997). "Enzymic and genetic basis for bacterial growth on malonate." Mol Microbiol 25(1);3-10. PMID: 11902724

Hinderer86: Hinderer W, Koster J, Barz W (1986). "Purfication and properties of a specific isoflavone 7-O-glucoside-6''-malonate malonyestrase from roots of chickpea (Cicer arietinum L.)." Arch Biochem Biophys 248(2);570-8. PMID: 3740841

Hosel75: Hosel W, Barz W (1975). "β-Glucosidases from Cicer arietinum L. Purification and Properties of isoflavone-7-O-glucoside-specific β-glucosidases." Eur J Biochem 57(2);607-16. PMID: 240725

Koster81: Koster J, Barz W (1981). "UDP-glucose:isoflavone 7-O-glucosyltransferase from roots of chick pea (Cicer arietinum L.)." Arch Biochem Biophys 212(1);98-104. PMID: 6458246

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

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

Vogels76: Vogels GD, Van der Drift C (1976). "Degradation of purines and pyrimidines by microorganisms." Bacteriol Rev 40(2);403-68. PMID: 786256


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 Wed Nov 26, 2014, BIOCYC13B.