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The three compounds were purified by column chromatography and HPLC. Spectroscopic analyses of 1, 2, and 3 suggested that they are amides of 4,5-dihydroxyanthranilic acid with caffeic, p-coumaric, and ferulic acids, respectively. Their identities were confirmed by comparing spectra and chromatographic behavior with compounds synthesized from 4,5-dihydroxyanthranilic acid and N-hyrdroxysuccinimide esters of hydroxycinnamic acids. LC-MS\/MS analysis with multiple reaction monitoring showed that the amounts of 1, 2, and 3 were 16.5\u201326.9% of corresponding avenanthamides with 5-hydroxyanthranilic acid. Compounds 1, 2, and 3 showed stronger 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging activity than the corresponding avenanthramides with 5-hydroxyanthranilic acid, indicating the involvement of 4,5-dihydroxyanthranilic acid moiety in the scavenging of DPPH radicals.<\/jats:p>","DOI":"10.1080\/09168451.2014.946390","type":"journal-article","created":{"date-parts":[[2014,8,13]],"date-time":"2014-08-13T15:32:40Z","timestamp":1407943960000},"page":"1975-1983","update-policy":"https:\/\/doi.org\/10.1080\/tandf_crossmark_01","source":"Crossref","is-referenced-by-count":36,"title":["New series of avenanthramides in oat seed"],"prefix":"10.1080","volume":"78","author":[{"given":"Atsushi","family":"Ishihara","sequence":"first","affiliation":[{"name":"Faculty of Agriculture, Tottori University, Tottori, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kana","family":"Kojima","sequence":"additional","affiliation":[{"name":"Faculty of Agriculture, Tottori University, Tottori, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Takeshi","family":"Fujita","sequence":"additional","affiliation":[{"name":"Faculty of Agriculture, Tottori University, Tottori, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yuya","family":"Yamamoto","sequence":"additional","affiliation":[{"name":"Faculty of Agriculture, Tottori University, Tottori, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hiromitsu","family":"Nakajima","sequence":"additional","affiliation":[{"name":"Faculty of Agriculture, Tottori University, Tottori, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"301","published-online":{"date-parts":[[2014,12,2]]},"reference":[{"key":"2021033108381649700_CIT0001","doi-asserted-by":"publisher","first-page":"60","DOI":"10.1021\/jf00085a015","article-title":"Oat phenolics: avenanthramides, novel substituted N-cinnamoylanthranilate alkaloids from oat groats and hulls","volume":"37","author":"Collins","year":"1989","journal-title":"J. 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