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MetaCyc Pathway: dalcochinin biosynthesis
Inferred from experiment

Pathway diagram: dalcochinin 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: dalcochinin glucoside hydrolysis, dalbergia isoflavonoid β-glucoside hydrolysis

Superclasses: BiosynthesisSecondary Metabolites BiosynthesisPhenylpropanoid Derivatives BiosynthesisFlavonoids BiosynthesisIsoflavonoids Biosynthesis

Some taxa known to possess this pathway include : Dalbergia cochinchinensis

Expected Taxonomic Range: Fabaceae

The isoflavonoid glycosides in legumes have conserved patterns of glycosylations, the monosaccharides and dissacharides are usually β-glucopyranosides. Dissacharides among the isoflavonoid glucosides are known to occur less frequently. Nevertheless, unusual isoflavone glycosides are reported every year, for example the uncommon sugar β-apiofuranose has been found a s a monosaccharid invariably O-linked to C-4' of the isoflavone aglycone or as a terminal sugar of various disaccharids [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. In Dalbergia cochinchinensis, an isoflavonoid β-glucosidase called dalcochinase had been isolated and cloned [Chuankhayan07]. This enzyme hydrolyzes the rotenoid glycoside dalcochinin-8'-O-β-glucoside [Toonkool06]. Dalcochinase has also been shown to carry out reverse hydrolysis of saccharides in the presence of excess sugars.

Created 27-Feb-2008 by Pujar A, Cornell University
Reviewed 18-Jul-2012 by Foerster H, Boyce Thompson Institute


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

Ketudat00: Ketudat Cairns JR, Champattanachai V, Srisomsap C, Wittman-Liebold B, Thiede B, Svasti J (2000). "Sequence and expression of Thai Rosewood beta-glucosidase/beta-fucosidase, a family 1 glycosyl hydrolase glycoprotein." J Biochem 128(6);999-1008. PMID: 11098143

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

Srisomsap96: Srisomsap C, Svasti J, Surarit R, Champattanachai V, Sawangareetrakul P, Boonpuan K, Subhasitanont P, Chokchaichamnankit D (1996). "Isolation and characterization of an enzyme with beta-glucosidase and beta-fucosidase activities from Dalbergia cochinchinensis Pierre." J Biochem 119(3);585-90. PMID: 8830058

Svasti99: Svasti, J., Srisomsap, C., Techasakul, S, Surarit, R (1999). "Dalcochinin-8'-O-β-D-glucoside and its β-glucosidase enzyme from Dalbergia cochinchinensis." Phytochemistry, 50, 739-743.

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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, biocyc14.