title: Production of novel antioxidative phenolic amides through heterologous expression of the plant's chlorogenic acid biosynthesis genes in yeast.
abstract: Phenolic esters like chlorogenic acid play an important role in therapeutic properties of many plant extracts. We aimed to produce phenolic esters in baker's yeast, by expressing tobacco 4CL and globe artichoke HCT. Indeed yeast produced phenolic esters. However, the primary product was identified as N-(E)-p-coumaroyl-3-hydroxyanthranilic acid by NMR. This compound is an amide condensation product of p-coumaric acid, which was supplied to the yeast, with 3-hydroxyanthranilic acid, which was unexpectedly recruited from the yeast metabolism by the HCT enzyme. N-(E)-p-coumaroyl-3-hydroxyanthranilic acid has not been described before, and it shows structural similarity to avenanthramides, a group of inflammation-inhibiting compounds present in oat. When applied to mouse fibroblasts, N-(E)-p-coumaroyl-3-hydroxyanthranilic acid induced a reduction of intracellular reactive oxygen species, indicating a potential therapeutic value for this novel compound.
authors: DiVaPRA, Plant Genetics and Breeding, University of Torino, via L. da Vinci 44, 10095 Grugliasco (TO), Italy.
authors: Andrea
authors: A
authors: Moglia
authors: Cinzia
authors: C
authors: Comino
authors: Sergio
authors: S
authors: Lanteri
authors: Ric
authors: R
authors: de Vos
authors: Pieter
authors: P
authors: de Waard
authors: Teris A
authors: TA
authors: van Beek
authors: Luca
authors: L
authors: Goitre
authors: Saverio Francesco
authors: SF
authors: Retta
authors: Jules
authors: J
authors: Beekwilder
mesh_terms: D015095:3-Hydroxyanthranilic Acid / Q000378:metabolism; D000577:Amides / Q000378:metabolism; D000818:Animals; D002726:Chlorogenic Acid / Q000378:metabolism*; D003373:Coumaric Acids; D031943:Cynara scolymus / Q000235:genetics* / Q000378:metabolism*; D004952:Esters / Q000378:metabolism; D005796:Genes; D051379:Mice; D010636:Phenols / Q000378:metabolism; D010944:Plants / Q000201:enzymology* / Q000235:genetics / Q000378:metabolism*; D011422:Propionates; D012441:Saccharomyces cerevisiae / Q000235:genetics / Q000378:metabolism; D014026:Nicotiana / Q000235:genetics / Q000378:metabolism; D015003:Yeasts / Q000235:genetics / Q000378:metabolism
chemical_list: D000577:Amides; D003373:Coumaric Acids; D004952:Esters; D010636:Phenols; D011422:Propionates; D015095:3-Hydroxyanthranilic Acid; D002726:Chlorogenic Acid; C495469:p-coumaric acid