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discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Pathway: phloridzin 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

Some taxa known to possess this pathway include ? : Malus domestica , Malus hupehensis , Malus pumila , Malus sp.

Expected Taxonomic Range: Viridiplantae

Summary:
phlorizin is a phenylproponoid derivative also known as phloretin 2-beta glucoside, it is a dihydrochalcone and the structure closely resembles the precursors chalcones [Gosch10]. phlorizin was first discovered in 1835 as a bitter tasting compound in barks of apple trees. Its distribution in the plant kingdom seems more widely present in the Malus species. Tissue distribution of the compound differs considerably; in Malus pumila and Lithocarpus polystachyus it mainly exists in fruits, in Malus hupehensis it is found in the stem and root barks, young leaves and fruits. The root bark contained more of it than the stem bark [Wang10d]. In Malus domestica, 90% of the soluble phenolics in the leaves is that of the dihydrochalcone phlorizin.

This compound has been used for medicinal properties for a long time, modern medicine uses it in the control of blood sugar levels, protective agent to the heart from scavenging oxygen free radicals and antioxidant injuries. Studies have also shown that phlorizin has estrogenic and antiestrogenic activities [Wang10d]. Dihydrochalcones are related to flavonoids but very less is known about their biosynthetic route, some enzymes have been cloned and it seems to depend on the presence of a dehydrogenase that can convert the substrate 4-dihydrocoumaroyl-CoA from 4-coumaryl-CoA. No phlorizin biosynthesis occurs in Pyrus communis which is a closely related species of apples. This is due to the absence of the enzyme capable of catalyzing the first step of the biosynthesis namely the formation of 4-dihydrocoumaroyl-CoA from 4-coumaryl-CoA [Gosch09].

Credits:
Created 26-May-2010 by Pujar A , Boyce Thompson Institute


References

Gosch09: Gosch, Christian, Halbwirth, Heidi, Kuhn, Jasmin, Miosic, Silvija, Stich, Karl "Biosynthesis of phloridzin in apple (Malus domestica Borkh.) [electronic resource]." Plant science. [Ireland]: Elsevier Science Ireland Ltd. 2009 Feb., v. 176, no. 2 p. 223-231. AGRICOLA: IND44141307

Gosch10: Gosch C, Halbwirth H, Stich K (2010). "Phloridzin: biosynthesis, distribution and physiological relevance in plants." Phytochemistry 71(8-9);838-43. PMID: 20356611

Wang10d: Wang J, Chung MH, Xue B, Ma H, Ma C, Hattori M (2010). "Estrogenic and antiestrogenic activities of phloridzin." Biol Pharm Bull 33(4);592-7. PMID: 20410591

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

Jugde08: Jugde H, Nguy D, Moller I, Cooney JM, Atkinson RG (2008). "Isolation and characterization of a novel glycosyltransferase that converts phloretin to phlorizin, a potent antioxidant in apple." FEBS J 275(15);3804-14. PMID: 18573104

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


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 Thu Nov 27, 2014, BIOCYC14A.