title: A Stilbenoid-Specific Prenyltransferase Utilizes Dimethylallyl Pyrophosphate from the Plastidic Terpenoid Pathway.
abstract: Prenylated stilbenoids synthesized in some legumes exhibit plant pathogen defense properties and pharmacological activities with potential benefits to human health. Despite their importance, the biosynthetic pathways of these compounds remain to be elucidated. Peanut (Arachis hypogaea) hairy root cultures produce a diverse array of prenylated stilbenoids upon treatment with elicitors. Using metabolic inhibitors of the plastidic and cytosolic isoprenoid biosynthetic pathways, we demonstrated that the prenyl moiety on the prenylated stilbenoids derives from a plastidic pathway. We further characterized, to our knowledge for the first time, a membrane-bound stilbenoid-specific prenyltransferase activity from the microsomal fraction of peanut hairy roots. This microsomal fraction-derived resveratrol 4-dimethylallyl transferase utilizes 3,3-dimethylallyl pyrophosphate as a prenyl donor and prenylates resveratrol to form arachidin-2. It also prenylates pinosylvin to chiricanine A and piceatannol to arachidin-5, a prenylated stilbenoid identified, to our knowledge, for the first time in this study. This prenyltransferase exhibits strict substrate specificity for stilbenoids and does not prenylate flavanone, flavone, or isoflavone backbones, even though it shares several common features with flavonoid-specific prenyltransferases.
authors.affiliation: Arkansas Biosciences Institute (T.Y., L.F., F.M.-B.), Molecular Biosciences Graduate Program (T.Y.), and Department of Biological Sciences (L.F., F.M.-B.), Arkansas State University, Jonesboro, Arkansas 72467;Natural Products Utilization Research Unit, Agricultural Research Service, U.S. Department of Agriculture, University, Mississippi 38677 (A.M.R.);National Peanut Research Laboratory, Dawson, Georgia 39842 (V.S.); andPervasive Technology Institute and Department of Biology, Indiana University, Bloomington, Indiana 47408 (K.M.).
authors.forename: Tianhong
authors.identifier: 0000-0002-3873-0602
authors.initials: T
authors.lastname: Yang
authors.affiliation: Arkansas Biosciences Institute (T.Y., L.F., F.M.-B.), Molecular Biosciences Graduate Program (T.Y.), and Department of Biological Sciences (L.F., F.M.-B.), Arkansas State University, Jonesboro, Arkansas 72467;Natural Products Utilization Research Unit, Agricultural Research Service, U.S. Department of Agriculture, University, Mississippi 38677 (A.M.R.);National Peanut Research Laboratory, Dawson, Georgia 39842 (V.S.); andPervasive Technology Institute and Department of Biology, Indiana University, Bloomington, Indiana 47408 (K.M.).
authors.forename: Lingling
authors.identifier: 0000-0003-2938-9155
authors.initials: L
authors.lastname: Fang
authors.affiliation: Arkansas Biosciences Institute (T.Y., L.F., F.M.-B.), Molecular Biosciences Graduate Program (T.Y.), and Department of Biological Sciences (L.F., F.M.-B.), Arkansas State University, Jonesboro, Arkansas 72467;Natural Products Utilization Research Unit, Agricultural Research Service, U.S. Department of Agriculture, University, Mississippi 38677 (A.M.R.);National Peanut Research Laboratory, Dawson, Georgia 39842 (V.S.); andPervasive Technology Institute and Department of Biology, Indiana University, Bloomington, Indiana 47408 (K.M.).
authors.forename: Agnes M
authors.identifier: 0000-0001-8229-8506
authors.initials: AM
authors.lastname: Rimando
authors.affiliation: Arkansas Biosciences Institute (T.Y., L.F., F.M.-B.), Molecular Biosciences Graduate Program (T.Y.), and Department of Biological Sciences (L.F., F.M.-B.), Arkansas State University, Jonesboro, Arkansas 72467;Natural Products Utilization Research Unit, Agricultural Research Service, U.S. Department of Agriculture, University, Mississippi 38677 (A.M.R.);National Peanut Research Laboratory, Dawson, Georgia 39842 (V.S.); andPervasive Technology Institute and Department of Biology, Indiana University, Bloomington, Indiana 47408 (K.M.).
authors.forename: Victor
authors.identifier: 0000-0001-5352-9539
authors.initials: V
authors.lastname: Sobolev
authors.affiliation: Arkansas Biosciences Institute (T.Y., L.F., F.M.-B.), Molecular Biosciences Graduate Program (T.Y.), and Department of Biological Sciences (L.F., F.M.-B.), Arkansas State University, Jonesboro, Arkansas 72467;Natural Products Utilization Research Unit, Agricultural Research Service, U.S. Department of Agriculture, University, Mississippi 38677 (A.M.R.);National Peanut Research Laboratory, Dawson, Georgia 39842 (V.S.); andPervasive Technology Institute and Department of Biology, Indiana University, Bloomington, Indiana 47408 (K.M.).
authors.forename: Keithanne
authors.identifier: 0000-0001-6123-8424
authors.initials: K
authors.lastname: Mockaitis
authors.affiliation: Arkansas Biosciences Institute (T.Y., L.F., F.M.-B.), Molecular Biosciences Graduate Program (T.Y.), and Department of Biological Sciences (L.F., F.M.-B.), Arkansas State University, Jonesboro, Arkansas 72467;Natural Products Utilization Research Unit, Agricultural Research Service, U.S. Department of Agriculture, University, Mississippi 38677 (A.M.R.);National Peanut Research Laboratory, Dawson, Georgia 39842 (V.S.); andPervasive Technology Institute and Department of Biology, Indiana University, Bloomington, Indiana 47408 (K.M.) fmedinabolivar@astate.edu.
authors.forename: Fabricio
authors.identifier: 0000-0002-6237-1232
authors.initials: F
authors.lastname: Medina-Bolivar
mesh_terms: D010367:Arachis / Q000737:chemistry / Q000201:enzymology*; D004122:Dimethylallyltranstransferase / Q000378:metabolism*; D045782:Hemiterpenes / Q000737:chemistry / Q000378:metabolism*; D009943:Organophosphorus Compounds / Q000737:chemistry / Q000378:metabolism*; D010940:Plant Proteins / Q000378:metabolism; D018517:Plant Roots / Q000737:chemistry / Q000201:enzymology; D018087:Plastids / Q000737:chemistry / Q000201:enzymology; D054876:Prenylation; D000077185:Resveratrol; D012639:Seeds / Q000737:chemistry / Q000201:enzymology / Q000378:metabolism; D013267:Stilbenes / Q000737:chemistry / Q000378:metabolism; D013379:Substrate Specificity; D013729:Terpenes / Q000737:chemistry / Q000378:metabolism*; D000094162:Phytoalexins
chemical_list: D004122:Dimethylallyltranstransferase; D045782:Hemiterpenes; D009943:Organophosphorus Compounds; D010940:Plant Proteins; D000077185:Resveratrol; D013267:Stilbenes; D013729:Terpenes; C043060:3,3-dimethylallyl pyrophosphate; C041525:3,3',4,5'-tetrahydroxystilbene; C049032:pinosylvin; D000094162:Phytoalexins