title: Molecular Characterization of Soybean Pterocarpan 2-Dimethylallyltransferase in Glyceollin Biosynthesis: Local Gene and Whole-Genome Duplications of Prenyltransferase Genes Led to the Structural Diversity of Soybean Prenylated Isoflavonoids.
abstract: Soybean (Glycine max) accumulates several prenylated isoflavonoid phytoalexins, collectively referred to as glyceollins. Glyceollins (I, II, III, IV and V) possess modified pterocarpan skeletons with C5moieties from dimethylallyl diphosphate, and they are commonly produced from (6aS, 11aS)-3,9,6a-trihydroxypterocarpan [(-)-glycinol]. The metabolic fate of (-)-glycinol is determined by the enzymatic introduction of a dimethylallyl group into C-4 or C-2, which is reportedly catalyzed by regiospecific prenyltransferases (PTs). 4-Dimethylallyl (-)-glycinol and 2-dimethylallyl (-)-glycinol are precursors of glyceollin I and other glyceollins, respectively. Although multiple genes encoding (-)-glycinol biosynthetic enzymes have been identified, those involved in the later steps of glyceollin formation mostly remain unidentified, except for (-)-glycinol 4-dimethylallyltransferase (G4DT), which is involved in glyceollin I biosynthesis. In this study, we identified four genes that encode isoflavonoid PTs, including (-)-glycinol 2-dimethylallyltransferase (G2DT), using homology-based in silico screening and biochemical characterization in yeast expression systems. Transcript analyses illustrated that changes in G2DT gene expression were correlated with the induction of glyceollins II, III, IV and V in elicitor-treated soybean cells and leaves, suggesting its involvement in glyceollin biosynthesis. Moreover, the genomic signatures of these PT genes revealed that G4DT and G2DT are paralogs derived from whole-genome duplications of the soybean genome, whereas other PT genes [isoflavone dimethylallyltransferase 1 (IDT1) and IDT2] were derived via local gene duplication on soybean chromosome 11.
authors.affiliation: Department of Applied Biological Sciences, Nihon University, Fujisawa, Kanagawa, 252-0880 Japan.
authors.forename: Keisuke
authors.initials: K
authors.lastname: Yoneyama
authors.affiliation: Department of Applied Biological Sciences, Nihon University, Fujisawa, Kanagawa, 252-0880 Japan.
authors.forename: Tomoyoshi
authors.initials: T
authors.lastname: Akashi
authors.affiliation: Department of Applied Biological Sciences, Nihon University, Fujisawa, Kanagawa, 252-0880 Japan aoki.toshio@nihon-u.ac.jp.
authors.forename: Toshio
authors.initials: T
authors.lastname: Aoki
mesh_terms: D004122:Dimethylallyltranstransferase / Q000235:genetics* / Q000378:metabolism; D044948:Flavonols / Q000737:chemistry / Q000378:metabolism*; D020440:Gene Duplication; D023061:Gene Order; D018745:Genome, Plant / Q000235:genetics*; D007529:Isoflavones / Q000737:chemistry / Q000378:metabolism*; D010802:Phylogeny; D018515:Plant Leaves / Q000737:chemistry / Q000201:enzymology / Q000235:genetics; D010940:Plant Proteins / Q000235:genetics / Q000378:metabolism; D036343:Pterocarpans / Q000737:chemistry / Q000378:metabolism*; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism; D013025:Glycine max / Q000737:chemistry / Q000201:enzymology* / Q000235:genetics; D000094162:Phytoalexins
chemical_list: D044948:Flavonols; D007529:Isoflavones; D010940:Plant Proteins; D036343:Pterocarpans; D012717:Sesquiterpenes; C017343:glyceollin; D004122:Dimethylallyltranstransferase; C540862:glycinol; D000094162:Phytoalexins
keywords: Gene duplication; Isoflavonoid; Phytoalexin; Prenyltransferase; Soybean