TY - JOUR
T1 - Production of novel antioxidative phenolic amides through heterologous expression of the plant’s chlorogenic acid biosynthesis genes in yeast
AU - Moglia, A.
AU - Comino, C.
AU - Lanteri, S.
AU - de Vos, C.H.
AU - de Waard, P.
AU - van Beek, T.A.
AU - Goitre, L.
AU - Retta, S.F.
AU - Beekwilder, M.J.
PY - 2010
Y1 - 2010
N2 - 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.
AB - 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.
KW - cell-suspension cultures
KW - saccharomyces-cerevisiae
KW - escherichia-coli
KW - phenylpropanoid metabolism
KW - functional-characterization
KW - recombinant microorganisms
KW - liquid-chromatography
KW - globe artichoke
KW - avenanthramides
KW - purification
U2 - 10.1016/j.ymben.2009.11.003
DO - 10.1016/j.ymben.2009.11.003
M3 - Article
VL - 12
SP - 223
EP - 232
JO - Metabolic Engineering
JF - Metabolic Engineering
SN - 1096-7176
IS - 3
ER -