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The Biosynthetic Pathway of Major Avenanthramides in Oat

Department of Food & Bioproduct Sciences, University of Saskatchewan, Saskatoon, SK S7N 5A8, Canada
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Author to whom correspondence should be addressed.
Current Address: Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology (SUSTech), Shenzhen 518055, China.
Metabolites 2019, 9(8), 163; https://doi.org/10.3390/metabo9080163
Received: 1 June 2019 / Revised: 17 July 2019 / Accepted: 2 August 2019 / Published: 7 August 2019
(This article belongs to the Special Issue Molecular Nutrition and Metabolism)
Avenanthramides are a group of N-cinnamoylanthranilic acids, with health-promoting properties mainly found in oat (Avena sativa L.). However, the biosynthetic mechanism for the main three types of avenanthramides (Avn-A, Avn-B and Avn-C) is not completely understood. In the present study, we report molecular identification and functional characterization of three different types of genes from oat encoding 4-coumarate-CoA ligase (4CL), hydroxycinnamoyl-CoA:hydroxyanthranilate N-hydroxycinnamoyl transferase (HHT) and a caffeoyl-CoA O-methyltransferase (CCoAOMT) enzymes, all involved in the biosynthesis of these avenanthramides. In vitro enzymatic assays using the proteins expressed in Escherichia coli showed that oat 4CL could convert p-coumaric acid, caffeic acid and ferulic acid to their CoA thioesters. Oat HHTs were only responsible for the biosynthesis of Avn-A and Avn-C using hydroxyanthranilic acid as an acyl acceptor and p-coumaroyl-CoA and caffeoyl-CoA as an acyl donor, respectively. Avn-B was synthesized by a CCoAOMT enzyme through the methylation of Avn-C. Collectively, these results have elucidated the molecular mechanisms for the biosynthesis of three major avenanthramides in vitro and paved the way for metabolic engineering of the biosynthetic pathway in heterologous systems to produce nutraceutically important compounds and make possible genetic improvement of this nutritional trait in oat through marker-assisted breeding. View Full-Text
Keywords: Avena sativa; avenanthramides; hydroxycinnamoyl-CoA:hydroxyanthranilate N-hydroxycinnamoyl transferase; caffeoyl-CoA O-methyltransferase; 4-coumarate-CoA ligase Avena sativa; avenanthramides; hydroxycinnamoyl-CoA:hydroxyanthranilate N-hydroxycinnamoyl transferase; caffeoyl-CoA O-methyltransferase; 4-coumarate-CoA ligase
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Li, Z.; Chen, Y.; Meesapyodsuk, D.; Qiu, X. The Biosynthetic Pathway of Major Avenanthramides in Oat. Metabolites 2019, 9, 163.

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