Production of novel antioxidative phenolic amides through heterologous expression of the plant's chlorogenic acid biosynthesis genes in yeast.
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.
Moglia
Andrea
A
DiVaPRA, Plant Genetics and Breeding, University of Torino, via L. da Vinci 44, 10095 Grugliasco (TO), Italy.
Comino
Cinzia
C
Lanteri
Sergio
S
de Vos
Ric
R
de Waard
Pieter
P
van Beek
Teris A
TA
Goitre
Luca
L
Retta
Saverio Francesco
SF
Beekwilder
Jules
J
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
D000577:Amides; D003373:Coumaric Acids; D004952:Esters; D010636:Phenols; D011422:Propionates; D015095:3-Hydroxyanthranilic Acid; D002726:Chlorogenic Acid; C495469:p-coumaric acid