Quantification of Benzoxazinone Derivatives in Wheat (Triticum aestivum) Varieties Grown under Contrasting Conditions in Denmark

Abstract

Three varieties of winter wheat (Triticum aestivum) were grown in both conventional and organic farming systems. The contents of the benzoxazinone derivatives 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), 2-beta-d-glucopyranosyloxy-4-hydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA-Glc), 6-methoxybenzoxazolin-2-one (MBOA), 2-hydroxy-7-methoxy-1,4-benzoxazin-3-one (HMBOA), benzoxazolin-2-one (BOA), and 2-hydroxy-1,4-benzoxazin-3-one (HBOA) were analyzed at five growth stages (BBCH 9-10, 12, 21, 31, and 53). Major differences were found between the varieties, with Stakado exhibiting the highest contents. In contrast, only minor and erratic differences were found between the two farming systems, suggesting that the inherent differences in the content of benzoxazinone derivatives of the varieties were not significantly affected by the use of pesticides and synthetic fertilizers. The concentration of benzoxazinone derivatives in the foliage was considerably higher at the early growth stages than later in the growing season, with DIMBOA being the most abundant of the benzoxazinone derivatives. An increase in the concentration was observed in early spring compared to late autumn, suggesting that plants synthesized benzoxazinone derivatives at the commencement of growth in early spring. The concentrations in the roots were considerably lower than in the foliage at the early growth stages but remained relatively constant over time, resulting in a higher concentration than in the foliage at the late growth stages. The results are discussed in relation to previous findings that predominantly originate from experiments done under controlled conditions in either growth cabinets or greenhouses.

Phytotoxicity and Benzoxazinone Concentration in Field Grown Cereal Rye (Secale cerealeL.)

“…Thus, one might expect a similar reallocation or directed export of accumulated defense compounds and a resultant decrease in levels of these compounds in the senescing tissue. Interestingly, current data on secondary metabolites in senescing leaves in other plants indicate that the content of at least some of these compounds increases [43,46,47]. For example, higher levels of flavonoid and anthocyanin secondary metabolites and/or increased specific expression of their biosynthetic genes have been observed in senescing leaves of Arabidopsis and poplar [42,45].…”

“…However, it is well known that when cereal grasses and other plants shift from vegetative to reproductive growth, they begin a patterned reallocation of accumulated C and N products from older leaves to the flowering tissue. For instance, the programmed catabolism of chlorophyll and photosynthetic proteins and the remobilization of the recycled C and N to reproductive tissues are characteristic of this transition [43][44][45][46]. Thus, one might expect a similar reallocation or directed export of accumulated defense compounds and a resultant decrease in levels of these compounds in the senescing tissue.…”

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

“…Benzoxazinoids are known from maize and wheat (Sicker, Frey, Schulz, & Gierl, 2000), as well as rye. The occurrence of benzoxazinoids in cereals at several growth stages was recently investigated (Krogh et al, 2006;Mogensen, Krongaard, Mathiassen, & Kudsk, 2006;Rice, Park, Adam, Abdul-Baki, & Teasdale, 2005;Stochmal, Kus, Martyniuk, & Oleszek, 2006), as was their importance as alternative means of suppressing weeds and diseases (Etzerodt, Mortensen, & Fomsgaard, 2008;Fomsgaard, 2006;Krogh et al, 2006;Søltoft, Jørgensen, Svensmark, & Fomsgaard, 2008). Several studies have focused on a small complement of benzoxazinoid compounds (Copaja, Nicol, & Wratten, 1999;Copaja, Villarroel, Bravo, Pizarro, & Argandoña, 2006;Katina et al, 2007;Zúñiga, Argandoña, Niemeyer, & Corcuera, 1983), including just one report mentioning non-specific total benzoxazinoid content from mature cereal grains (Katina et al, 2007).…”

Determination of benzoxazinoids in Spring and Winter varieties of wheat using ultra-performance liquid chromatography coupled with mass spectrometry

“…Benzoxazinoid composition and concentration largely depend on a plant part, development stage, cultivar, and growing conditions [2,8,9]. Growing wheat varieties with high levels of particular hydroxamic acids could reduce the problems with diseases, pests, and weeds and thus limit the use of pesticides [1,10]. A possible use of allelochemicals as substitutes for pesticides in crop protection has created a need for their qualitative and quantitative analyses.…”