Dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) and 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA), two naturally occurring benzoxazinones contained in sprouts of Gramineae are potent aneugens in human-derived liver cells (HepG2)

Buchmann, Christoph; Nersesyan, Armen; Kopp, Brigitte; Schauberger, Doris; Darroudi, F.; Grummt, Tamara; Krupitza, Georg; Kundi, Michael; Schulte‐Hermann, Rolf; Knasmueller, Siegfried

doi:10.1016/j.canlet.2006.03.013

Cited by 29 publications

(24 citation statements)

References 44 publications

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“…If one or several of the beneficial health effects reported in vitro can be shown in vivo after the digestion of bread or HTP grains, it would constitute yet another reason, in addition to the acknowledged beneficial vitamin, mineral and fibre contents, for promoting the consumption of wholemeal bread or HTP grains. Caution regarding the potential risks stemming from in vitro studies that showed possible aneugenic and mutagenic effects of the agluconic hydroxamic acids DIBOA and DIMBOA (Buchmann et al, 2007;Hashimoto & Shudo, 1996) should be heeded, but the total hydroxamic acid content (glucosides and aglucones) in HTP rye bread was lower than in rye bread baked from conventional flour. Wholemeal rye bread has been a dietary staple of the Scandinavian countries for thousands of years.…”

Section: Resultsmentioning

confidence: 97%

Bread from common cereal cultivars contains an important array of neglected bioactive benzoxazinoids

et al. 2011

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Section: Resultsmentioning

confidence: 97%

Bread from common cereal cultivars contains an important array of neglected bioactive benzoxazinoids

et al. 2011

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“…Compound 90 and its methoxy derivative 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) 91 (Fig. 23), which is the dominant benzoxazinoid compound found in wheat, exerted mutagenic activity against human liver cell line HepG2 and 91 caused stronger effects than the parent compound 90 [149]. Moreover, the cytotoxic effects of DIBOA were also observed on different cancer cell lines, such as DU-145 (prostate cancer) and MCF-7 (breast cancer) cells [126].…”

Section: N-hydroxy-substituted Fused Six-membered Ring Systemsmentioning

confidence: 99%

Bioactive heterocycles containing endocyclic N-hydroxy groups

Rani

Granchi

2015

European Journal of Medicinal Chemistry

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Drug-likeness rules consider N-O single bonds as “structural alerts” which should not be present in a perspective drug candidate. In most cases this concern is correct, since it is known that N-hydroxy metabolites of branded drugs produce reactive species that cause serious side effects. However, this dangerous reactivity of the N-OH species generally takes place when the nitrogen atom is not comprised in a cyclic moiety. In fact, the same type of metabolic behavior should not be expected when the nitrogen atom is included in the ring of an aromatic heterocyclic scaffold. Nevertheless, heterocycles bearing endocyclic N-hydroxy portions have so far been poorly studied as chemical classes that may provide new therapeutic agents. This review provides an overview of N-OH-containing heterocycles with reported bioactivities that may be considered as therapeutically relevant and, therefore, may extend the chemical space available for the future development of novel pharmaceuticals. A systematic treatment of the various chemical classes belonging to this particular family of molecules is described along with a discussion of the biological activities associated to the most important examples.

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“…In planta benzoxazinoids exhibit strong bioactivity, such as allelopathic potency (10,11). Several in vitro studies were conducted to elucidate various bioactivities of benzoxazinoids, including antiproliferative, aneugenic, and anti-inflammatory effects (12)(13)(14)(15), but their potential impact as dietary compounds is so far not known.…”

Section: Introductionmentioning

confidence: 99%

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.

show abstract

Dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) and 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA), two naturally occurring benzoxazinones contained in sprouts of Gramineae are potent aneugens in human-derived liver cells (HepG2)

Cited by 29 publications

References 44 publications

Bread from common cereal cultivars contains an important array of neglected bioactive benzoxazinoids

Bread from common cereal cultivars contains an important array of neglected bioactive benzoxazinoids

Bioactive heterocycles containing endocyclic N-hydroxy groups

The Postprandial Plasma Rye Fingerprint Includes Benzoxazinoid-Derived Phenylacetamide Sulfates

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