title: Differential production of meta hydroxylated phenylpropanoids in sweet basil peltate glandular trichomes and leaves is controlled by the activities of specific acyltransferases and hydroxylases.
abstract: Sweet basil (Ocimum basilicum) peltate glandular trichomes produce a variety of small molecular weight phenylpropanoids, such as eugenol, caffeic acid, and rosmarinic acid, that result from meta hydroxylation reactions. Some basil lines do not synthesize eugenol but instead synthesize chavicol, a phenylpropanoid that does not contain a meta hydroxyl group. Two distinct acyltransferases, p-coumaroyl-coenzyme A:shikimic acid p-coumaroyl transferase and p-coumaroyl-coenzyme A:4-hydroxyphenyllactic acid p-coumaroyl transferase, responsible for the production of p-coumaroyl shikimate and of p-coumaroyl 4-hydroxyphenyllactate, respectively, were partially purified and shown to be specific for their substrates. p-Coumaroyl-coenzyme A:shikimic acid p-coumaroyl transferase is expressed in basil peltate glands that are actively producing eugenol and is not active in glands of noneugenol-producing basil plants, suggesting that the levels of this activity determine the levels of synthesis of some meta-hydroxylated phenylpropanoids in these glands such as eugenol. Two basil cDNAs encoding isozymes of cytochrome P450 CYP98A13, which meta hydroxylates p-coumaroyl shikimate, were isolated and found to be highly similar (90% identity) to the Arabidopsis homolog, CYP98A3. Like the Arabidopsis enzyme, the basil enzymes were found to be very specific for p-coumaroyl shikimate. Finally, additional hydroxylase activities were identified in basil peltate glands that convert p-coumaroyl 4-hydroxyphenyllactic acid to its caffeoyl derivative and p-coumaric acid to caffeic acid.
authors.affiliation: Department of Molecular, Cellular, and Developmental Biology, University of Michigan, Ann Arbor, Michigan 48109-1048, USA. gang@ag.arizona.edu
authors.forename: David R
authors.initials: DR
authors.lastname: Gang
authors.forename: Till
authors.initials: T
authors.lastname: Beuerle
authors.forename: Pascaline
authors.initials: P
authors.lastname: Ullmann
authors.forename: Daniéle
authors.initials: D
authors.lastname: Werck-Reichhart
authors.forename: Eran
authors.initials: E
authors.lastname: Pichersky
mesh_terms: D000214:Acyl Coenzyme A / Q000378:metabolism; D000217:Acyltransferases / Q000235:genetics / Q000378:metabolism*; D029681:Arabidopsis Proteins; D002109:Caffeic Acids / Q000737:chemistry / Q000378:metabolism; D022081:Cell Surface Extensions / Q000235:genetics / Q000378:metabolism*; D002934:Cinnamates / Q000737:chemistry / Q000378:metabolism; D003373:Coumaric Acids / Q000737:chemistry / Q000378:metabolism; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism; D018076:DNA, Complementary / Q000235:genetics / Q000302:isolation & purification; D053630:Depsides; D005054:Eugenol / Q000737:chemistry / Q000378:metabolism; D006899:Mixed Function Oxygenases / Q000235:genetics / Q000378:metabolism*; D018649:Ocimum basilicum / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*; D010666:Phenylpropionates / Q000737:chemistry / Q000378:metabolism; D018515:Plant Leaves / Q000235:genetics / Q000378:metabolism*; D011422:Propionates; D000097123:Rosmarinic Acid
chemical_list: D000214:Acyl Coenzyme A; D000217:Acyltransferases; D029681:Arabidopsis Proteins; D002109:Caffeic Acids; D002934:Cinnamates; D003373:Coumaric Acids; D003577:Cytochrome P-450 Enzyme System; D018076:DNA, Complementary; D053630:Depsides; D005054:Eugenol; D006899:Mixed Function Oxygenases; D010666:Phenylpropionates; D011422:Propionates; D000097123:Rosmarinic Acid; C058644:4-coumaroyl-coenzyme A; C001418:4-hydroxyphenyllactic acid; C438015:CYP98A3 protein, Arabidopsis; C495469:p-coumaric acid; C040048:caffeic acid