Hydroxylated phenylacetamides derived from bioactive benzoxazinoids are bioavailable in humans after habitual consumption of whole grain sourdough rye bread
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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 whole grain rye consumption. METHODS AND RESULTS: After a wash-out period, volunteers consumed 48-g whole grain rye foods per day for 4 wk and then doubled their intake for a further 4 wk. Samples of 24-h 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 whole grain rye products could not be discriminated adequately from their wash-out samples. However, discrimination was seen in urine samples from participants who reported high whole grain 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 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 whole grain sourdough rye bread consumption. CONCLUSION: Several potentially bioactive alkaloids have been identified in humans consuming fermented whole grain sourdough rye bread.
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Direct flow injection-MS has been used and offers the advantage of high-throughput analysis required for large-scale epidemiologic studies.
“Direct flow injection-MS has also been used (82,114), which offers the advantage of high-throughput analysis, as would be required for large-scale epidemiologic studies.”
From The food metabolome: a window over dietary exposure (2014) · cites this paper as [114]
The recent description of benzoxazinoids in rye helped identify some of their metabolites (2,4-dihydroxy-1,4-benzoxazin-3-one, 2-aminophenol sulfate, and hydroxylated phenylacetamides) in urinary profiles after rye bread consumption.
“As an example, the recent description of benzoxazinoids in rye facilitated the identification of some of their metabolites (2,4-dihydroxy-1,4-benzoxazin-3-one, 2-aminophenol sulfate, and hydroxylated phenylacetamides) in urinary metabolic profiles observed after rye bread consumption (86,114).”
From The food metabolome: a window over dietary exposure (2014) · cites this paper as [114]
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The food metabolome: a window over dietary exposure
Scalbert, A., Brennan, L., Manach, C., Andres-Lacueva, C., Dragsted, L. O., Draper, J., Rappaport, S. M., van der Hooft, J. J., & Wishart, D. S. (2014) · The American Journal of Clinical Nutrition · doi:10.3945/ajcn.113.076133 · Cited by 519 · see citing works
Self-citation
- Authors
- Beckmann, M., Lloyd, A. J., Haldar, S., Seal, C., Brandt, K., & Draper, J.
- Affiliations
- Aberystwyth University (GB)
- Newcastle University (GB)
- Corresponding author
- Draper, John
- Venue
- Molecular Nutrition & Food Research
- Publisher
- Wiley
- Published
- 2013-05-16
- Volume
- 57
- Issue
- 10
- Pages
- 1859-1873
- ISSN
- 1613-4125 (ISSN-L)
- 1613-4133
- OpenAlex
- W2137698854
- Cited by
- 55
- References
- 56
- Citations by year
- 2025: 1 · 2023: 4 · 2022: 5 · 2021: 8 · 2020: 5 · 2019: 5 · 2017: 3 · 2016: 8 · 2015: 8 · 2014: 8
- FWCI
- 7.42
- Type
- journal article
- Language
- en
- Open access
- green
- doi.org
- Licence
- Locations
- Molecular Nutrition & Food Research (publishedVersion)
- PubMed (publishedVersion)
- Newcastle University ePrints (Newcastle Univesity) (cc-by-nc)
- Funders
- UK Food Standard Agency (N05075)
- Topics
- Health Sciences › Nursing › Nutrition and Dietetics › Food composition and properties
- Health Sciences › Medicine › Biochemistry › Phytochemicals and Antioxidant Activities
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Mycotoxins in Agriculture and Food
- Keywords
- benzoxazinoids, urinary biomarkers, whole grain intake, bioavailability
- MeSH terms
- Acetanilides, Bread, Diet, Female, Fermentation, Humans, Hydroxylation, Male, Middle Aged, Secale, Mass Spectrometry, Reproducibility of Results, Multivariate Analysis, Benzoxazines
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