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Qualitative Characterization of Benzoxazinoid Derivatives in Whole Grain Rye and Wheat by LC-MS Metabolite Profiling

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† Institute of Public Health and Clinical Nutrition, Food and Health Research Centre, University of Eastern Finland, P.O. Box 1627, FIN-70211 Kuopio, Finland
§ Department of Plant Sciences, Weizmann Institute of Science, P.O. Box 26, 76100 Rehovot, Israel
# VTT Technical Research Centre of Finland, P.O. Box 1000, FI-02044 VTT, Finland
*To whom correspondence should be addressed: [email protected]
Cite this: J. Agric. Food Chem. 2011, 59, 3, 921–927
Publication Date (Web):January 7, 2011
https://doi.org/10.1021/jf103612u
Copyright © 2011 American Chemical Society
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    Abstract

    Benzoxazinoids are metabolites occurring in a restricted group of plant species including crops such as rye, wheat, and maize. Focus on the analysis of benzoxazinoid metabolites has typically been due to their importance to plant biochemistry and physiology as highly bioactive molecules that plants use as alleochemicals to defend themselves against predators and infections. However, the potential dietary contribution of these compounds has not been addressed. This study conducted a detailed qualitative characterization of benzoxazinoid metabolites present in the whole grain rye and processed fractions of rye bran, and their presence was also detected in whole grain wheat samples. Several novel benzoxazinoid metabolites of the hydroxamic acids (2,4-dihydroxy-1,4-benzoxazin-3-one, DIBOA; 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one, DIMBOA), lactams (2-hydroxy-1,4-benzoxazin-3-one, HBOA), and benzoxazolinones (1,3-benzoxazol-2-one, BOA) were identified, including double-hexose derivatives of DIBOA, DIMBOA, and HBOA. This paper presents an important addition to the information on the phytochemical composition of rye and wheat grains, which deserves attention in the discussion of the potential health-promoting effects of these grains.

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    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
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    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

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