MetaCyc Pathway: dalpatein and dalnigrein biosynthesis
Inferred from experiment

Pathway diagram: dalpatein and dalnigrein 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.

Synonyms: dalpatein glycoside hydrolysis, dalnigrein glycoside hydrolysis, dalpatein and dalnigrein biosynthesis

Superclasses: BiosynthesisSecondary Metabolites BiosynthesisPhenylpropanoid Derivatives BiosynthesisFlavonoids BiosynthesisIsoflavonoids Biosynthesis

Some taxa known to possess this pathway include : Dalbergia nigrescens

Expected Taxonomic Range: Fabaceae

The isoflavonoid glycosides in legumes have conserved patterns of glycosylations, the more abundant monosaccharides are usually β-glucopyranosides and the fewer dissacharides are also of the β-glucopyranosides type. There are some uncommon sugars reported, among them β-apiofuranose which is found invariably linked to C-4' of the isoflavone aglycone and also appears as a terminal sugar on various disaccharides [Vietch07].

The biosynthesis of legume isoflavonoid glycosides is poorly understood. A few isoflavonoid-specific glucotransferases have been cloned providing some insight into the mechanism of isoflavonoid production in legumes. Most of the plant glucosidases belong to the glucosyl hydrolase family (GH1). The 3 dimensional structure of these enzymes reveal a common α-/β- barrel [Toonkool06].

In Dalbergia nigrescens, an isoflavonoid β-glucosidase has been isolated and cloned [Chuankhayan07]. This enzyme hydrolyzes the natural substrates dalpatein and dalnigrein [Chuankhayan05] by cleaving off only dissacharides, i.e. β-D-apiofuranosyl-(1->6)-D-glucose and not monosaccharides.

Created 29-Feb-2008 by Pujar A, Cornell University
Reviewed 18-Jul-2012 by Foerster H, Boyce Thompson Institute


Chuankhayan05: Chuankhayan P, Hua Y, Svasti J, Sakdarat S, Sullivan PA, Ketudat Cairns JR (2005). "Purification of an isoflavonoid 7-O-beta-apiosyl-glucoside beta-glycosidase and its substrates from Dalbergia nigrescens Kurz." Phytochemistry 66(16);1880-9. PMID: 16098548

Chuankhayan07: Chuankhayan P, Rimlumduan T, Tantanuch W, Mothong N, Kongsaeree PT, Metheenukul P, Svasti J, Jensen ON, Cairns JR (2007). "Functional and structural differences between isoflavonoid beta-glycosidases from Dalbergia sp." Arch Biochem Biophys 468(2);205-16. PMID: 17998137

Toonkool06: Toonkool P, Metheenukul P, Sujiwattanarat P, Paiboon P, Tongtubtim N, Ketudat-Cairns M, Ketudat-Cairns J, Svasti J (2006). "Expression and purification of dalcochinase, a beta-glucosidase from Dalbergia cochinchinensis Pierre, in yeast and bacterial hosts." Protein Expr Purif 48(2);195-204. PMID: 16814564

Vietch07: Vietch, N.C (2007). "Isoflavonoids of the Leguminosae." Natural Product Reports, 24, 417-464.

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

Ahn04: Ahn YO, Mizutani M, Saino H, Sakata K (2004). "Furcatin hydrolase from Viburnum furcatum Blume is a novel disaccharide-specific acuminosidase in glycosyl hydrolase family 1." J Biol Chem 279(22);23405-14. PMID: 14976214

Chuankhayan07a: Chuankhayan P, Rimlumduan T, Svasti J, Cairns JR (2007). "Hydrolysis of soybean isoflavonoid glycosides by Dalbergia beta-glucosidases." J Agric Food Chem 55(6);2407-12. PMID: 17311399

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 Pathway Tools version 20.0 (software by SRI International) on Fri May 6, 2016, BIOCYC13B.