title: 4-Hydroxycinnamoyl-CoA hydratase/lyase, an enzyme of phenylpropanoid cleavage from Pseudomonas, causes formation of C(6)-C(1) acid and alcohol glucose conjugates when expressed in hairy roots of Datura stramonium L.
abstract: 4-Hydroxycinnamoyl-CoA hydratase/lyase (HCHL), a crotonase homologue of phenylpropanoid catabolism from Pseudomonas fluorescens strain AN103, led to the formation of 4-hydroxybenzaldehyde metabolites when expressed in hairy root cultures of Datura stramonium L. established by transformation with Agrobacterium rhizogenes. The principal new compounds observed were the glucoside and glucose ester of 4-hydroxybenzoic acid, together with 4-hydroxybenzyl alcohol- O-beta- D-glucoside. In lines actively expressing HCHL, these together amounted to around 0.5% of tissue fresh mass. No protocatechuic derivatives were found, although a trace of vanillic acid-beta- D-glucoside was detected. There was no accumulation of 4-hydroxybenzaldehydes, whether free or in the form of their glucose conjugates. There was some evidence suggesting a diminished availability of feruloyl-CoA for the production of feruloyl putrescine and coniferyl alcohol. The findings are discussed in the context of a diversion of phenylpropanoid metabolism, and the ability of plants and plant cultures to conjugate phenolic compounds.
authors.affiliation: Food Safety Science Division, Institute of Food Research, Norwich Resesrch Park, Colney, Norwich NR4 7UA, UK.
authors.forename: Adinpunya
authors.initials: A
authors.lastname: Mitra
authors.forename: Melinda J
authors.initials: MJ
authors.lastname: Mayer
authors.forename: Fred A
authors.initials: FA
authors.lastname: Mellon
authors.forename: Anthony J
authors.initials: AJ
authors.lastname: Michael
authors.forename: Arjan
authors.initials: A
authors.lastname: Narbad
authors.forename: Adrian J
authors.initials: AJ
authors.lastname: Parr
authors.forename: Keith W
authors.initials: KW
authors.lastname: Waldron
authors.forename: Nicholas J
authors.initials: NJ
authors.lastname: Walton
mesh_terms: D001547:Benzaldehydes / Q000378:metabolism; D013286:Datura stramonium / Q000235:genetics*; D004746:Enoyl-CoA Hydratase / Q000378:metabolism; D015971:Gene Expression Regulation, Enzymologic; D005947:Glucose / Q000378:metabolism; D006836:Hydro-Lyases / Q000235:genetics / Q000378:metabolism*; D008031:Lignin / Q000378:metabolism; D010226:Parabens / Q000378:metabolism; D010636:Phenols / Q000378:metabolism; D018517:Plant Roots / Q000235:genetics*; D030821:Plants, Genetically Modified; D020005:Propanols / Q000378:metabolism*; D011551:Pseudomonas fluorescens / Q000201:enzymology*; D014641:Vanillic Acid / Q000378:metabolism
chemical_list: D001547:Benzaldehydes; D010226:Parabens; D010636:Phenols; D020005:Propanols; C439395:1-phenylpropanol; D008031:Lignin; C010559:coniferyl alcohol; C119166:4-hydroxycinnamoyl-CoA hydratase-lyase; D006836:Hydro-Lyases; D004746:Enoyl-CoA Hydratase; D014641:Vanillic Acid; D005947:Glucose; C038193:4-hydroxybenzoic acid; C011483:4-hydroxybenzaldehyde