Absorption and metabolic fate of bioactive dietary benzoxazinoids in humans

Adhikari, Khem B.; Laursen, Britt Elmedal; Gregersen, Per L.; Schnoor, Heidi Julius; Witten, Marianne; Poulsen, Lars K.; Jensen, Bettina M.; Fomsgaard, Inge S.

doi:10.1002/mnfr.201300107

Cited by 36 publications

(56 citation statements)

References 48 publications

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“…In rats, 3 benzoxazinoid compounds (HBOA, HBOA glucose, and DIBOA glucose) were detected in plasma 3 h after feeding (17). In humans, circulating plasma benzoxazinoids were detected 1-3 hours after the intake of a benzoxazinoid-rich breakfast and were identified as HBOA glucose and DIBOA glucose with negligible amount of HBOA (18). In our study, none of these benzoxazinoids were found based on their accurate mass and MS/MS fragmentation in the plasma.…”

Section: Discussioncontrasting

confidence: 68%

“…Recently, there were several targeted, quantitative approaches on the characterization of bioavailability and absorption of dietary benzoxazinoids in rats (17), pigs (16), and humans (18). In rats, 3 benzoxazinoid compounds (HBOA, HBOA glucose, and DIBOA glucose) were detected in plasma 3 h after feeding (17).…”

Section: Discussionmentioning

confidence: 99%

“…Several compounds of the benzoxazinoid class were detected in the plasma and urine of pigs (16) and rats (17) and in a human study showing the postprandial appearance of benzoxazinoids in circulation and urine (18). In addition to these studies using targeted, quantitative assays, a recent nontargeted metabolite profiling study indicated phenylacetamides as the predominant urine metabolites of benzoxazinoids (19).…”

Section: Introductionmentioning

confidence: 97%

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The Postprandial Plasma Rye Fingerprint Includes Benzoxazinoid-Derived Phenylacetamide Sulfates

Hanhineva

Keski‐Rahkonen

Lappi

et al. 2014

The Journal of Nutrition

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The bioavailability of whole-grain rye-derived phytochemicals has not yet been comprehensively characterized, and different baking and manufacturing processes can modulate the phytochemical composition of breads and other rye products. The aim of our study was to find key differences in the phytochemical profile of plasma after the consumption of 3 breads containing rye bran when compared with a plain white wheat bread control. Plasma metabolite profiles of 12 healthy middle-aged men and women were analyzed using LC quadrupole time-of-flight mass spectrometry metabolomics analysis while fasting and at 60 min, 120 min, 240 min, and 24 h after consuming a meal that contained either 100% whole-grain sourdough rye bread or white wheat bread enriched with native unprocessed rye bran or bioprocessed rye bran. White wheat bread was used as the control. The meals were served in random order after a 12-h overnight fast, with at least 3 d between each occasion. Two sulfonated phenylacetamides, hydroxy-N-(2-hydroxyphenyl) acetamide and N-(2-hydroxyphenyl) acetamide, potentially derived from the benzoxazinoid metabolites, were among the most discriminant postprandial plasma biomarkers distinguishing intake of breads containing whole-meal rye or rye bran from the control white wheat bread. Furthermore, subsequent metabolite profiling analysis of the consumed breads indicated that different bioprocessing/baking techniques involving exposure to microbial metabolism (e.g., sourdough fermentation) have a central role in modulating the phytochemical content of the whole-grain and bran-rich breads.

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Section: Discussioncontrasting

confidence: 68%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

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The Postprandial Plasma Rye Fingerprint Includes Benzoxazinoid-Derived Phenylacetamide Sulfates

Hanhineva

Keski‐Rahkonen

Lappi

et al. 2014

The Journal of Nutrition

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“…Recent metabolomic studies have reported an increase in urinary excretions of some benzoxazinoid metabolites in human intervention studies with different types of whole-grain breads (Beckmann et al 2013;Bondia-Pons et al 2013) and after a 5-week dietary intervention with high fibre doses (Johansson-Persson et al 2013). Furthermore, Adhikari et al (2013) were also tentatively identified. Their levels were higher among WGB consumers.…”

Section: Biological Interpretationmentioning

confidence: 99%

Nutrimetabolomics fingerprinting to identify biomarkers of bread exposure in a free-living population from the PREDIMED study cohort

et al. 2014

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Bread is one of the most widely consumed foods. Its impact on human health is currently of special interest for researchers. We aimed to identify biomarkers of bread consumption by applying a nutrimetabolomic approach to a free-living population. An untargeted HPLC-q-TOF-MS and multivariate analysis was applied to human urine from 155 subjects stratified by habitual bread consumption in three groups: non-consumers of bread (NCB, n=56), white-bread consumers (WHB, n=48) and whole-grain bread consumers (WGB, n=51). The most differential metabolites (VIP ≥1.5) included compounds originating from cereal plant phytochemicals such as benzoxazinoids and alkylresorcinol metabolites, and compounds produced by gut microbiota (such as enterolactones, hydroxybenzoic and dihydroferulic acid metabolites). Pyrraline, riboflavin, 3-indolecarboxylic acid glucuronide, 2,8-dihydroxyquinoline glucuronide and N-α-acetylcitrulline were also tentatively identified. In order to combine multiple metabolites 2 in a model to predict bread consumption, a stepwise logistic regression analysis was used.Receiver operating curves were constructed to evaluate the global performance of individual metabolites and their combination. The area under the curve values [AUC (95% CI)] of combined models ranged from 77.8% (69.1%-86.4%) to 93.7% (89.4%-98.1%), whereas the AUC for the metabolites included in the models had weak values when they were evaluated individually: from 58.1 % (46.6-69.7 %) to 78.4% (69.8%-87.1%). Our study showed that a daily bread intake significantly impacted on the urinary metabolome, despite being examined under uncontrolled free-living conditions. We further concluded that a combination of several biomarkers of exposure is better than a single biomarker for the predictive ability of discriminative analysis.

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“…in minor amounts. The benzoxazinoids can serve as biomarkers of whole grain as they are absorbed and metabolized by the body (Adhikari et al, 2013). Anti-inflammatory, anti-allergic, and anticarcinogenic effects of individual benzoxazinoids were reported (Poupaert, Carato, & Colacillo, 2005).…”

Section: Functional Properties Of Miscellaneous Bioactive Phytochemicalsmentioning

confidence: 99%

Bioactive phytochemicals in wheat: Extraction, analysis, processing, and functional properties

Luthria

John

2015

Journal of Functional Foods

105

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Available online A B S T R A C TWhole wheat provides a rich source of bioactive phytochemicals namely, phenolic acids, carotenoids, tocopherols, alkylresorcinols, benzoxazinoids, phytosterols, and lignans. This review provides information on the distribution, extractability, analysis, and functional properties of bioactive phytochemicals present in wheat. Understanding the impact of processing on wheat phytochemicals allows us to develop improved processes with higher retention of bioactive compounds in processed wheat foods. Details of extraction, analytical methodologies and processing effects on bioactive phytochemicals in wheat are presented in tabulated form.Published by Elsevier Ltd.

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Absorption and metabolic fate of bioactive dietary benzoxazinoids in humans

Abstract: These results indicate that following ingestion in healthy humans, a range of unmetabolized bioactive dietary benzoxazinoids and their sulfate and glucuronide conjugates appear in circulation and urine.

Cited by 36 publications

References 48 publications

The Postprandial Plasma Rye Fingerprint Includes Benzoxazinoid-Derived Phenylacetamide Sulfates

The Postprandial Plasma Rye Fingerprint Includes Benzoxazinoid-Derived Phenylacetamide Sulfates

Nutrimetabolomics fingerprinting to identify biomarkers of bread exposure in a free-living population from the PREDIMED study cohort

Bioactive phytochemicals in wheat: Extraction, analysis, processing, and functional properties

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