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.

Authors: 
A. Moglia, C. Comino, S. Lanteri, R.C.H. de Vos, P. de Waard, T.A. van Beek, L. Goitre, S.F. Retta, J. Beekwilder
Authors from the NMC: 
Publication data (text): 
2010
DOI: 
10.1016/j.ymben.2009.11.003
Pages: 
2010; 12 (3): 223-232
Publisher: 
Elsevier
Published in: 
Metabolic Engineering
Date of publication: 
May, 2010
Status of the publication: 
Published/accepted