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MetaCyc Chimeric Pathway: wighteone and luteone 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 Isoflavonoids Biosynthesis
Biosynthesis Secondary Metabolites Biosynthesis Phytoalexins Biosynthesis Isoflavonoid Phytoalexins Biosynthesis

Some taxa known to possess parts of the pathway include ? : Glycine max , Glycyrrhiza echinata , Lupinus albus

Expected Taxonomic Range: Fabaceae

Note: This is a chimeric pathway, comprising reactions from multiple organisms, and typically will not occur in its entirety in a single organism. The taxa listed here are likely to catalyze only subsets of the reactions depicted in this pathway.

Summary:
General Background

Wighteone and luteone are complex prenylated isoflavones frequently found within the tribe Phaseolae of the legume family [Ingham90]. Their isomers isowighteone and lupiwighteone as well as phaseoluteone have also been isolated from various legume plants [Woodward79] [Stobiecki99]. Monoprenylated isoflavones are both involved in defense mechanisms against pathogens [Abe87] and nod gene induction [Gagnon98].

Prenylated isoflavones such as wighteone and luteone along with the prenylated isoflavanone kievitone have been observed to be more active against pathogens then their non-prenylated analogues (dalbergioidin, genistein, 2'-hydroxygenistein). It has been proposed that the greater lipid-solubility of the prenylated compounds may improve their efficiency [ONeill83]. Interestingly, monoprenylated isoflavones have been characterized as pre-infectional antifungal agent in the genus Lupinus [Harborne76] [Gagnon97] which is different from other phytoalexins which accumulate post-infectional in response to pathogens [Gagnon97].

About This Pathway

The hydroxylation of genistein is carried out by the isoflavone-2'-hydroxylase (I2'H). However, the enzyme(s) isolated from different species have demonstrated various substrate preferences. While I2'H does not hydroxylate genistein in chickpea [Hinderer] [Clemens] the 2'-hydroxylation is carried out in soybean [Kochs86] and licorice [Akashi98]. The intermediate 2'-hydroxygenistein is a branch point leading to the biosynthesis of prenylated isoflavanones such as dalbergioidin and kievitone (kievitone biosynthesis).

Lupinus albus possesses the enzymatic ability to monoprenylate genistein and its 2'-hydroxyl derivative. The enzyme activity is strongly increased upon wounding but the enzyme does not respond to elicitors [Schroeder79]. However, the question of how the mixture of isomers is obtained remains to be investigated.

Superpathways: superpathway of isoflavonoids (via naringenin)

Credits:
Created 31-Aug-2005 by Foerster H , TAIR


References

Abe87: Abe N, Sato H, Sakamura S "Antifungal stress compounds from Adzuki Bean, Vigna angularis, treated with Cephalosporium gregatum type B." Agric. Biol. Chem. (1987), 51(2), 349-353.

Akashi98: Akashi T, Aoki T, Ayabe S (1998). "CYP81E1, a cytochrome P450 cDNA of licorice (Glycyrrhiza echinata L.), encodes isoflavone 2'-hydroxylase." Biochem Biophys Res Commun 251(1);67-70. PMID: 9790908

Clemens: Clemens S, Hinderer W, Wittkampg U, Barz W, (1993) "Characterization of cytochrome P450-dependent isoflavone hydroxylase from chickpea." Phytochemistry, 32(3), 653-657.

Gagnon97: Gagnon H, Ibrahim RK, (1997) "Effects of various elicitors on the accumulation and secretion of isoflavonoids in white lupin." Phytochemistry (1997), 44(8), 1463-1467.

Gagnon98: Gagnon H, Ibrahim RK, (1998) "Aldonic Acids: A Novel Family of nod Gene Inducers of Mesorhizobium loti, Rhizobium lupini, and Sinorhizobium meliloti." Molecular Plant-Microbe Interactions (1998), 11(10), 988-998.

Harborne76: Harborne JB, Ingham JL, King L, Payne M, (1076) "The isopentenyl isoflavone luteone as a pre-infectional antifungal agent in the genus lupinus." Phytochemistry (1976), 15, 1485-1487.

Hinderer: Hinderer W, Flentje U, Barz W, (1987) "Microsomal isoflavone 2'- and 3'-hydroxylases from chickpea (Cicer arietinum L.) cell suspensions induced for pterocarpan phytoalexin formation." FEBS Letters, 214(1), 101-106.

Ingham90: Ingham JL, (1990) "Systematic aspects of phytoalexin in formation within tribe Phaseoleae of the Leguminosae (subfamily Papilionoideae)." Biochemical Systematics and Ecology (1990), 18(5), 329-343.

Kochs86: Kochs G, Grisebach H (1986). "Enzymic synthesis of isoflavones." Eur J Biochem 155(2);311-8. PMID: 3956488

ONeill83: O'Neill MJ, Adesanya SA, Roberts MF, (1983) "Antifungal phytoalexins in Phaseolus aureus Roxb." Z. Naturforsch. (1983), 38c, 693-697.

Schroeder79: Schroeder G, Zaehringer U, Heller W, Ebel J, Grisebach H, (1979) "Biosynthesis of antifungal isoflavonoids in Lupinus albus. Enzymatic prenylation of genistein and 2'-hydroxygenistein." Archives of Biochemistry and Biophysics (1979), 194(2), 635-636.

Stobiecki99: Stobiecki M, Malosse C, Kerhoas L, Wojlaszek P, Einhorn J, (1999) "Detection of Isoflavonoids and their Glycosides by Liquid Chromatography/Electrospray Ionization Mass Spectrometry in Root Extracts of Lupin (Lupinus albus)." Phytochem. Anal. (1999) 10, 198-207.

Woodward79: Woodward MD, (1979) "Phaseoluteone and other 5-hydroxyisoflavonoids from Phaseolus vulgaris." Phytochemistry (1979), 18, 363-365.

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

Kim05f: Kim H, Seo S, Lee BG, Lee Y (2005). "Identification of Tyrosinase Inhibitors from Glycyrrhiza uralensis ." Planta Medica 71(08);785-787.

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


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, biocyc11.