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Absorption and metabolic fate of bioactive dietary benzoxazinoids in humans

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Adhikari, Khem B ; Laursen, Bente Birgitte ; Gregersen, Per L. ; Schnoor, Heidi J ; Witten, Marianne ; Poulsen, Lars K ; Jensen, Bettina M ; Fomsgaard, Inge S. / Absorption and metabolic fate of bioactive dietary benzoxazinoids in humans. In: Molecular Nutrition & Food Research (Online). 2013 ; Vol. 57, No. 10. pp. 1847-1858.

Bibtex

@article{9c73bdebbff344439ba27acb3a0c4610,
title = "Absorption and metabolic fate of bioactive dietary benzoxazinoids in humans",
abstract = "SCOPE: Benzoxazinoids, which are natural compounds recently identified in mature whole grain cereals and bakery products, have been suggested to have a range of pharmacological properties and health-protecting effects. There are no published reports concerned with the absorption and metabolism of bioactive benzoxazinoids in humans. METHODS AND RESULTS: The absorption, metabolism, and excretion of ten different dietary benzoxazinoids were examined by LC-MS/MS by analyzing plasma and urine from 20 healthy human volunteers after daily intake of 143 μmol of total benzoxazinoids from rye bread and rye buns. The results showed that 2-β-d-glucopyranosyloxy-1,4-benzoxazin-3-one (HBOA-Glc) and its oxidized analog, 2-β-d-glucopyranosyloxy-4-hydroxy-1,4-benzoxazin-3-one (DIBOA-Glc), were the major circulating benzoxazinoids. After consuming a benzoxazinoid diet for 1 week, morning urine contained eight benzoxazinoids with abundant HBOA-Glc (219 nmol × μmol(-1) of creatinine). The sulfate and glucuronide conjugates of 2-hydroxy-1,4-benzoxazin-3-one (HBOA) and 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA) were detected in plasma and urine, indicating substantial phase II metabolism. Direct absorption of lactam glycosides, the reduction of hydroxamic acid glycosides, glucuronidation, and sulfation were the main mechanisms of the absorption and metabolism of benzoxazinoids. CONCLUSION: 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.",
author = "Adhikari, {Khem B} and Laursen, {Bente Birgitte} and Gregersen, {Per L.} and Schnoor, {Heidi J} and Marianne Witten and Poulsen, {Lars K} and Jensen, {Bettina M} and Fomsgaard, {Inge S.}",
note = "{\textcopyright} 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",
year = "2013",
month = may,
day = "3",
doi = "10.1002/mnfr.201300107",
language = "English",
volume = "57",
pages = "1847--1858",
journal = "Molecular Nutrition & Food Research (Online)",
issn = "1613-4133",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "10",

}

RIS

TY - JOUR

T1 - Absorption and metabolic fate of bioactive dietary benzoxazinoids in humans

AU - Adhikari, Khem B

AU - Laursen, Bente Birgitte

AU - Gregersen, Per L.

AU - Schnoor, Heidi J

AU - Witten, Marianne

AU - Poulsen, Lars K

AU - Jensen, Bettina M

AU - Fomsgaard, Inge S.

N1 - © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

PY - 2013/5/3

Y1 - 2013/5/3

N2 - SCOPE: Benzoxazinoids, which are natural compounds recently identified in mature whole grain cereals and bakery products, have been suggested to have a range of pharmacological properties and health-protecting effects. There are no published reports concerned with the absorption and metabolism of bioactive benzoxazinoids in humans. METHODS AND RESULTS: The absorption, metabolism, and excretion of ten different dietary benzoxazinoids were examined by LC-MS/MS by analyzing plasma and urine from 20 healthy human volunteers after daily intake of 143 μmol of total benzoxazinoids from rye bread and rye buns. The results showed that 2-β-d-glucopyranosyloxy-1,4-benzoxazin-3-one (HBOA-Glc) and its oxidized analog, 2-β-d-glucopyranosyloxy-4-hydroxy-1,4-benzoxazin-3-one (DIBOA-Glc), were the major circulating benzoxazinoids. After consuming a benzoxazinoid diet for 1 week, morning urine contained eight benzoxazinoids with abundant HBOA-Glc (219 nmol × μmol(-1) of creatinine). The sulfate and glucuronide conjugates of 2-hydroxy-1,4-benzoxazin-3-one (HBOA) and 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA) were detected in plasma and urine, indicating substantial phase II metabolism. Direct absorption of lactam glycosides, the reduction of hydroxamic acid glycosides, glucuronidation, and sulfation were the main mechanisms of the absorption and metabolism of benzoxazinoids. CONCLUSION: 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.

AB - SCOPE: Benzoxazinoids, which are natural compounds recently identified in mature whole grain cereals and bakery products, have been suggested to have a range of pharmacological properties and health-protecting effects. There are no published reports concerned with the absorption and metabolism of bioactive benzoxazinoids in humans. METHODS AND RESULTS: The absorption, metabolism, and excretion of ten different dietary benzoxazinoids were examined by LC-MS/MS by analyzing plasma and urine from 20 healthy human volunteers after daily intake of 143 μmol of total benzoxazinoids from rye bread and rye buns. The results showed that 2-β-d-glucopyranosyloxy-1,4-benzoxazin-3-one (HBOA-Glc) and its oxidized analog, 2-β-d-glucopyranosyloxy-4-hydroxy-1,4-benzoxazin-3-one (DIBOA-Glc), were the major circulating benzoxazinoids. After consuming a benzoxazinoid diet for 1 week, morning urine contained eight benzoxazinoids with abundant HBOA-Glc (219 nmol × μmol(-1) of creatinine). The sulfate and glucuronide conjugates of 2-hydroxy-1,4-benzoxazin-3-one (HBOA) and 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA) were detected in plasma and urine, indicating substantial phase II metabolism. Direct absorption of lactam glycosides, the reduction of hydroxamic acid glycosides, glucuronidation, and sulfation were the main mechanisms of the absorption and metabolism of benzoxazinoids. CONCLUSION: 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.

U2 - 10.1002/mnfr.201300107

DO - 10.1002/mnfr.201300107

M3 - Journal article

C2 - 23650214

VL - 57

SP - 1847

EP - 1858

JO - Molecular Nutrition & Food Research (Online)

JF - Molecular Nutrition & Food Research (Online)

SN - 1613-4133

IS - 10

ER -

ID: 39039244