Plasma and urine concentrations of bioactive dietary benzoxazinoids and their glucuronidated conjugates in rats fed a rye bread-based diet.

Thorough knowledge of the absorption and metabolism of dietary benzoxazinoids is needed to understand their health-promoting effects. In this study, the fates of these bioactive compounds were examined by LC-MS/MS in plasma, urine, and feces after ingesting a daily dose of 4780 ± 68 nmol benzoxazinoids from rye bread using Wistar rats as a model. HBOA-glc (2-β-D-glucopyranosyloxy-1,4-benzoxazin-3-one) was the predominant benzoxazinoid in the plasma (74 ± 27 nmol/L), followed by DIBOA-glc (2-β-D-glucopyranosyloxy-4-hydroxy-1,4-benzoxazin-3-one) and HBOA.

Phytotoxic effect, uptake, and transformation of biochanin A in selected weed species.

Certain isoflavones are plant growth inhibitors, and biochanin A is a major isoflavone in clover species used for weed management. The effect of biochanin A on the monocot weed species Echinochloa crus-galli L. and Lolium perenne L.

Variation of polyphenols and betaines in aerial parts of young, field-grown Amaranthus genotypes.

Amaranthus hybridus and Amaranthus mantegazzianus are commonly cultivated and the entire young fresh plants consumed as vegetables in regions of Africa and Asia. A. hybridus and A.

Synthesis and quantitation of six phenolic amides in Amaranthus spp.

Cinnamoylphenethylamines are phenolic amides in which cinnamic acid provides the acid moiety and phenethylamine the amine moiety. Single ion monitoring (SIM) in LC-MS was performed on amaranth leaf extracts. Masses corresponding to sets of regioisomers, including previously reported compounds, were examined.

Phenolic compounds in different barley varieties: identification by tandem mass spectrometry (QStar) and NMR; quantification by liquid chromatography triple quadrupole-linear ion trap mass spectrometry (Q-Trap).

Barley (Hordeum vulgare) is an important cereal that has many applications; as a human food, in malt products and as livestock feed. The content of soluble health-promoting fibers, beta-glucans, varies substantially among barley varieties. In the present study, the content of secondary metabolites with potential positive health effects in different high- and low-beta-glucan barley varieties was studied.

Allelochemicals in rye (Secale cereale L.): cultivar and tissue differences in the production of benzoxazinoids and phenolic acids.

In the present study, a range of benzoxazinoid compounds and phenolic acids, all known to be allelochemicals of rye, were identified and quantified in 13 rye cultivars grown at three different localities. Plant samples were collected in the spring at the time when an autumn-sown rye cover crop would be incorporated into the soil. Significant variations in content among shoots and roots were seen for all of the secondary metabolites, with non-methoxy-substituted benzoxazinoids (BX) dominating the shoots, whereas comparable levels were found in the concentrations of BX and methoxy-substituted benzoxazinoids (MBX) in the roots.

Transformation kinetics of 6-methoxybenzoxazolin-2-one in soil.

Wheat (Triticum aestivum L.) and other cereals produce allelochemicals as natural defense compounds against weeds, fungi, insects and soil-borne diseases. The main benzoxazinoid allelochemical of wheat is 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), bound as beta-glucoside and released upon plant injury.

Transformation of benzoxazinones and derivatives and microbial activity in the test environment of soil ecotoxicological tests on Poecilus cupreus and Folsomia candida.

Benzoxazinones, such as 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) and 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA), and benzoxazolinones, such as 6-methoxy-2-benzoxazolinone (MBOA) and 2-benzoxazolinone (BOA), are biologically active secondary metabolites found in cereals. Because these compounds could be exploited as part of a strategy for reducing the use of synthetic pesticides, ecotoxicological tests were performed recently. In this paper, the transformation of the compounds in the test environment of the ecotoxicological tests was studied.

Elucidating the transformation pattern of the cereal allelochemical 6-methoxy-2-benzoxazolinone (MBOA) and the trideuteriomethoxy analogue [D3]-MBOA in soil.

To deduce the structure of the large array of compounds arising from the transformation pathway of 6-methoxybenzoxazolin-2-one (MBOA), the combination of isotopic substitution and liquid chromatography analysis with mass spectrometry detection was used as a powerful tool. MBOA is formed in soil when the cereal allelochemical 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) is exuded from plant material to soil. Degradation experiments were performed in concentrations of 400 microg of benzoxazolinone/g of soil for MBOA and its isotopomer 6-trideuteriomethoxybenzoxazolin-2-one ([D3]-MBOA).

Fate of benzoxazinone allelochemicals in soil after incorporation of wheat and rye sprouts.

Growing cereals (especially rye), which are incorporated into the soil to increase soil fertility or organic matter content, is a common practice in crop rotation. The additional sanitizing effect of this incorporation has often been appreciated and is said to be due to leaching of benzoxazinones and subsequent formation of benzoxazolinones. In this study wheat (Stakado) and rye (Hacada) sprouts were incorporated into soil in amounts that simulated agricultural practice.

Transformation products of 2-benzoxazolinone (BOA) in soil.

Three degradation experiments were performed to examine the formation of transformation products from 2-benzoxazolinone (BOA) in different soil types and concentrations. In two experiments using BOA in low concentration (400 microgkg(-1)) only one unidentified transformation product was found, whereas in the degradation experiment in high concentration (400 mgkg(-1)) several metabolites occurred. Two of these metabolites, 2-amino-(3H)-phenoxazin-3-one (APO); and 2-acetylamino-(3H)-phenoxazin-3-one (AAPO) were synthesized to prove their identity.

Microbial transformation products of benzoxazolinone and benzoxazinone allelochemicals--a review.

Cyclic hydroxamic acids and lactams are allelochemicals present in the common agricultural crops wheat, rye, and maize. The hydroxamic acids are mainly present in the plants as glucosides. Upon injury or insect attack or when exuded to the soil environment, the hydroxamic acids occur in their unstable agluconic form.