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ARS Home » Midwest Area » Madison, Wisconsin » Cereal Crops Research » Research » Publications at this Location » Publication #293506

Title: Chemo-enzymatic synthesis of physiologically modified avenanthramides

item CAHILL, NICHOLAS - University Of Wisconsin
item Wise, Mitchell

Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: 4/12/2013
Publication Date: N/A
Citation: N/A

Interpretive Summary:

Technical Abstract: Avenanthramides are a group of phenolic alkaloids produced, among food crops, uniquely by oats. These metabolites function as phytoalexins in vegetative tissue and they are produced in the grain where their function is unknown. In vitro the avenanthramides inhibit the activation of nuclear factor kappa beta. Thus, avenanthramides also demonstrate anti-inflammatory properties and are the active component in oat-meal salves used in folk medicine to relieve symptoms of skin irritation. They might also retard development of atherosclerosis and other inflammatory diseases. Like many phytonutrients, avenanthramides undergo hepatic modification in mammals. Plasma samples from rats gavaged with avenanthramides 2c, 2f and 2p show much higher avenanthramide content when treated with a mix of glucuronidase/sulfonase. The experiments reported here were undertaken to determine the extent to which the avenanthramides are modified by either glucuronidation or sulfonation and to determine the chemical structures of these modified compounds. Thus the synthesis of the three principal avenanthramides, 2c, 2f and 2p is described as well as the effect of treating these pure synthetic avenanthramides with rat liver extracts to yield the glucuronidated and the sulfonated forms. Recombinant human glucuronate- and sulfotransferases were also employed to modify these natural products.