Quantitative Analysis of Absorption, Metabolism, and Excretion of Benzoxazinoids in Humans After the Consumption of High- and Low-benzoxazinoid Diets with Similar Contents of Cereal Dietary Fibres: a Crossover Study

Overview

Journal Eur J Nutr

Specialty Nutritional Sciences

Date 2015 Nov 1

PMID 26519282

Citations 7

Authors

Bettina M Jensen

Khem B Adhikari

Heidi J Schnoor

Nanna Juel-Berg

Inge S Fomsgaard

Lars K Poulsen

Affiliations

Soon will be listed here.

Abstract

Purpose: Benzoxazinoids (BXs) are a group of wholegrain phytochemicals with potential pharmacological properties; however, limited information exists on their absorption, metabolism, and excretion in humans. The aim of this study was to investigate the dose-dependent uptake and excretion of dietary BXs in a healthy population.

Methods: Blood and urine were collected from 19 healthy participants from a crossover study after a washout, a LOW BX diet or HIGH BX diet, and analysed for 12 BXs and 4 phenoxazinone derivatives.

Results: We found that the plasma BX level peaked approximately 3 h after food intake, whereas BXs in urine were present even at 36 h after consuming a meal. No phenoxazinone derivatives could be detected in either plasma or urine. The dominant BX metabolite in both plasma and urine was 2-β-D-glucopyranosyloxy-1,4-benzoxazin-3-one (HBOA-Glc), even though 2-β-D-glucopyranosyloxy-4-hydroxy-1,4-benzoxazin-3-one (DIBOA-Glc) was the major component in the diet.

Conclusion: The dietary BX treatment correlated well with the plasma and urine levels, illustrating strong dose-dependent BX absorption, which also had a rapid washout, especially from the plasma compartment.

Citing Articles

Effects of 6-methoxybenzoxazolinone (6-MBOA) on animals: state of knowledge and open questions.

Shi J, Gu K, Yang S, Wei W, Dai X Naturwissenschaften. 2024; 111(5):45.

PMID: 39141101 DOI: 10.1007/s00114-024-01930-8.

Identification and Quantification of Selected Benzoxazinoids and Phenolics in Germinated Spelt ().

Zivkovic A, Godevac D, Cigic B, Polak T, Pozrl T Foods. 2023; 12(9).

PMID: 37174307 PMC: 10178788. DOI: 10.3390/foods12091769.

An inverse association between plasma benzoxazinoid metabolites and PSA after rye intake in men with prostate cancer revealed with a new method.

Nordin E, Steffensen S, Laursen B, Andersson S, Johansson J, Aman P Sci Rep. 2022; 12(1):5260.

PMID: 35347164 PMC: 8960836. DOI: 10.1038/s41598-022-08856-z.

Pharmacological Activities of Aminophenoxazinones.

Zorrilla J, Rial C, Cabrera D, Molinillo J, Varela R, Macias F Molecules. 2021; 26(11).

PMID: 34200139 PMC: 8201375. DOI: 10.3390/molecules26113453.

Toxicity and Anti-promastigote Activity of Benzoxazinoid Analogs Against and .

de Sousa G, Lima W, Dos Santos F, Macias F, Molinillo J, Teixeira-Neto R Adv Pharm Bull. 2020; 10(1):119-124.

PMID: 32002370 PMC: 6983991. DOI: 10.15171/apb.2020.015.

References

Duda-Chodak A, Tarko T, Satora P, Sroka P . Interaction of dietary compounds, especially polyphenols, with the intestinal microbiota: a review. Eur J Nutr. 2015; 54(3):325-41. PMC: 4365176. DOI: 10.1007/s00394-015-0852-y. View

Carlsen S, Kudsk P, Laursen B, Mathiassen S, Mortensen A, Fomsgaard I . Allelochemicals in rye (Secale cereale L.): cultivar and tissue differences in the production of benzoxazinoids and phenolic acids. Nat Prod Commun. 2009; 4(2):199-208. View

Gents M, Nielsen S, Mortensen A, Christophersen C, Fomsgaard I . Transformation products of 2-benzoxazolinone (BOA) in soil. Chemosphere. 2005; 61(1):74-84. DOI: 10.1016/j.chemosphere.2005.03.068. View

Adhikari K, Laursen B, Laerke H, Fomsgaard I . Bioactive benzoxazinoids in rye bread are absorbed and metabolized in pigs. J Agric Food Chem. 2012; 60(10):2497-506. DOI: 10.1021/jf2048492. View

Epstein W, Rowsemitt C, Berger P, Negus N . Dynamics of 6-methoxybenzoxazolinone in winter wheat : Effects of photoperiod and temperature. J Chem Ecol. 2013; 12(10):2011-20. DOI: 10.1007/BF01041950. View

Fomsgaard I, Mortensen A, Carlsen S . Microbial transformation products of benzoxazolinone and benzoxazinone allelochemicals--a review. Chemosphere. 2003; 54(8):1025-38. DOI: 10.1016/j.chemosphere.2003.09.044. View

Understrup A, Ravnskov S, Hansen H, Fomsgaard I . Biotransformation of 2-benzoxazolinone to 2-amino-(3H)-phenoxazin-3-one and 2-acetylamino-(3H)-phenoxazin-3-one in soil. J Chem Ecol. 2005; 31(5):1205-22. DOI: 10.1007/s10886-005-4257-x. View

Macias F, Oliveros-Bastidas A, Marin D, Castellano D, Simonet A, Molinillo J . Degradation studies on benzoxazinoids. Soil degradation dynamics of (2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-(2H)- 1,4-benzoxazin-3(4H)-one (DIBOA-Glc) and its degradation products, phytotoxic allelochemicals from Gramineae. J Agric Food Chem. 2005; 53(3):554-61. DOI: 10.1021/jf048702l. View

Beckmann M, Lloyd A, Haldar S, Seal C, Brandt K, Draper J . Hydroxylated phenylacetamides derived from bioactive benzoxazinoids are bioavailable in humans after habitual consumption of whole grain sourdough rye bread. Mol Nutr Food Res. 2013; 57(10):1859-73. DOI: 10.1002/mnfr.201200777. View

10.

Etzerodt T, Mortensen A, Fomsgaard I . Transformation kinetics of 6-methoxybenzoxazolin-2-one in soil. J Environ Sci Health B. 2007; 43(1):1-7. DOI: 10.1080/03601230701734774. View

11.

Krogh S, Mensz S, Nielsen S, Mortensen A, Christophersen C, Fomsgaard I . Fate of benzoxazinone allelochemicals in soil after incorporation of wheat and rye sprouts. J Agric Food Chem. 2006; 54(4):1064-74. DOI: 10.1021/jf051147i. View

12.

Tanwir F, Fredholm M, Gregersen P, Fomsgaard I . Comparison of the levels of bioactive benzoxazinoids in different wheat and rye fractions and the transformation of these compounds in homemade foods. Food Chem. 2013; 141(1):444-50. DOI: 10.1016/j.foodchem.2013.02.109. View

13.

Baba S, Osakabe N, Natsume M, Yasuda A, Muto Y, Hiyoshi K . Absorption, metabolism, degradation and urinary excretion of rosmarinic acid after intake of Perilla frutescens extract in humans. Eur J Nutr. 2004; 44(1):1-9. DOI: 10.1007/s00394-004-0482-2. View

14.

Ampatzoglou A, Williams C, Atwal K, Maidens C, Ross A, Thielecke F . Effects of increased wholegrain consumption on immune and inflammatory markers in healthy low habitual wholegrain consumers. Eur J Nutr. 2015; 55(1):183-95. DOI: 10.1007/s00394-015-0836-y. View

15.

Adhikari K, Laerke H, Mortensen A, Fomsgaard I . Plasma and urine concentrations of bioactive dietary benzoxazinoids and their glucuronidated conjugates in rats fed a rye bread-based diet. J Agric Food Chem. 2012; 60(46):11518-24. DOI: 10.1021/jf301737n. View

16.

Etzerodt T, Nielsen S, Mortensen A, Christophersen C, Fomsgaard I . Elucidating the transformation pattern of the cereal allelochemical 6-methoxy-2-benzoxazolinone (MBOA) and the trideuteriomethoxy analogue [D3]-MBOA in soil. J Agric Food Chem. 2006; 54(4):1075-85. DOI: 10.1021/jf0509052. View

17.

Okarter N, Liu R . Health benefits of whole grain phytochemicals. Crit Rev Food Sci Nutr. 2010; 50(3):193-208. DOI: 10.1080/10408390802248734. View

18.

Georgoulis M, Kontogianni M, Tileli N, Margariti A, Fragopoulou E, Tiniakos D . The impact of cereal grain consumption on the development and severity of non-alcoholic fatty liver disease. Eur J Nutr. 2014; 53(8):1727-35. DOI: 10.1007/s00394-014-0679-y. View

19.

Hanhineva K, Rogachev I, Aura A, Aharoni A, Poutanen K, Mykkanen H . Qualitative characterization of benzoxazinoid derivatives in whole grain rye and wheat by LC-MS metabolite profiling. J Agric Food Chem. 2011; 59(3):921-7. DOI: 10.1021/jf103612u. View

20.

Adhikari K, Laursen B, Gregersen P, Schnoor H, Witten M, Poulsen L . Absorption and metabolic fate of bioactive dietary benzoxazinoids in humans. Mol Nutr Food Res. 2013; 57(10):1847-58. DOI: 10.1002/mnfr.201300107. View