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)

Cancer Letters
Christoph A BuchmannSiegfried Knasmueller

Abstract

Benzoxazinoids (BAs) are toxic constituents of sprouts of Gramineae such as wheat, maize and rye and are part of the plant defence system against pests. In the last years, sprouts have been increasingly consumed as health foods and are also used for the production of dietary supplements. In the present study we investigated the mutagenic activities of the two most abundant BAs, namely 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) and 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA) in the Salmonella/microsome assay and additionally, in micronucleus (MN) assay and single cell gel electrophoresis (SCGE) assay in a human-derived liver cell line (HepG2). DIBOA caused significant induction of his(+) revertants in all three strains in the range between 0.02 and 0.50 mg/plate; the highest activity was observed in TA100 (fivefold increase over the background at the highest dose level). The effect in YG1024 (a derivative of TA98 with increased acetyltransferase activity) was only slightly higher than the effect in the parental strain indicating that acetylation plays no crucial role in the activation of this BA. DIMBOA was in general less active and a positive result was only seen in the base substitution strain (TA100). Addition of r...Continue Reading

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Citations

Dec 4, 2014·European Journal of Medicinal Chemistry·Reshma Rani, Carlotta Granchi
Jan 21, 2015·Molecular Nutrition & Food Research·Khem B AdhikariInge S Fomsgaard
Jun 5, 2015·Journal of Agricultural and Food Chemistry·Otto SavolainenKati Hanhineva
Jul 20, 2016·Journal of Agricultural and Food Chemistry·Wouter J C de BruijnHarry Gruppen
Oct 25, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Bing GuoWei Ding
May 9, 2014·The Journal of Nutrition·Kati HanhinevaKaisa Poutanen
Feb 10, 2009·Journal of Agricultural and Food Chemistry·Hermann M Niemeyer
Jan 11, 2011·Journal of Agricultural and Food Chemistry·Kati HanhinevaHannu Mykkänen

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