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Hydroxylated phenylacetamides derived from bioactive benzoxazinoids are bioavailable in humans after habitual consumption of whole grain sourdough rye bread

Lookup NU author(s): Dr Sumanto Haldar, Emeritus Professor Chris SealORCiD, Dr Kirsten BrandtORCiD



Scope: Understanding relationships between dietary whole grain and health is hindered by incomplete knowledge of potentially bioactive metabolites derived from these foods. We aimed to discover compounds in urine correlated with changes in amounts of wholegrain rye consumption. Methods and Results: After a wash-out period, volunteers consumed 48 g wholegrain rye foods per day for 4 weeks and then doubled their intake for a further 4 weeks. 24 hour urines were analyzed by flow infusion electrospray MS followed by supervised multivariate data analysis. Urine samples from participants who reported high intakes of rye flakes, rye pasta or total wholegrain rye products could not be discriminated adequately from their wash-out samples. However, discrimination was seen in urine samples from participants who reported high wholegrain sourdough rye bread consumption. Accurate mass analysis of explanatory signals followed by fragmentation identified conjugates of the benzoxazinoid lactam 2-hydroxy-1,4-benzoxazin-3-one (HBOA) and hydroxylated phenyl acetamide derivatives. Statistical validation showed sensitivities of 84–96% and specificities of 70–81% (P values <0·05) for elevated concentrations of these signals after preferential wholegrain sourdough rye bread consumption. Conclusion: Several potentially bioactive alkaloids have been identified in humans consuming fermented wholegrain sourdough rye bread.

Publication metadata

Author(s): Beckmann M, Lloyd AJ, Haldar S, Seal CJ, Brandt K, Draper J

Publication type: Article

Publication status: Published

Journal: Molecular Nutrition & Food Research

Year: 2013

Volume: 57

Issue: 10

Pages: 1859-1873

Print publication date: 16/05/2013

Date deposited: 28/03/2013

ISSN (print): 1613-4125

ISSN (electronic): 1613-4133

Publisher: Wiley - V C H Verlag GmbH & Co. KGaA


DOI: 10.1002/mnfr.201200777


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Funder referenceFunder name
N05075UK Food Standard Agency