<br/>Epidemiologic studies have suggested that a high intake of whole grain foods is associated with a lower risk of chronic disease, such as type 2 diabetes, obesity, cancer, and cardiovascular diseases. Oat, a cereal grain belonging to the family of Poaceae/Gramineae, is the third leading crop produced in the United States and the fourth most important crop worldwide. Oats contain a unique type of compounds, avenanthramides (AVAs), which are the group of substituted N-cinnamoylanthranilic acids with a single double bond (e.g. 2p, 2c and 2f) and N-avenalumoylanthranilic acids with two double bonds (e.g. 2pd, 2cd and 2fd) in structures. All AVAs are composed of an anthranilic acid moiety and a cinnamic acid or an avenalumic acid residue, where the substitution pattern on anthranilic acid or avenalumic acid moiety is what distinguishes the different AVAs from each other. N-cinnamoylanthranilic acids have been reported to have a variety of biological activities, such as anti-oxidative, anti-inflammatory, anti-itching, and anti-cancer activities. Biotransformation studies showed that N-avenalumoylanthranilic acids have a higher bioavailability than N-cinnamoylanthranilic acids in human plasma. However, no studies have been conducted on the bioactivity and biotransformation of N-avenalumoylanthranilic acids. We recently isolated and identified several N-avenalumoylanthranilic acids with two double bonds from sprout oat. Using these purified AVAs as standards, we developed a LC-MS method to establish the chemical profile of N-avenalumoylanthranilic acids with two double bonds and further quantify their levels in commercial available sprout oat and regular oat products. We studied the biotransformation of 2pd, one of the major N-avenalumoylanthranilic acids with two double bonds in oat, in mice. Microbial metabolism of 2pd by human gut microbiota was also investigated. The major metabolites of 2pd, including phase I and phase II metabolites in mice as well as microbial-derived metabolites from human gut microbiota, have been identified and will be discussed in this presentation.

Quantitative analysis, bioactive evaluation, and biotransformation of oat avenanthramides with two double bonds

2019 Fall National Meeting

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