Hydroxamic acid content of perennial triticeae

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

“…The majority of the total benzoxazinoid content, including both hydroxamic acids and their derived benzoxazolinones, consisted of non-methoxylated compounds (DIBOA and derivatives) in rye, whereas it consisted of methoxylated compounds (DIMBOA and derivatives) in wheat. (Copaja et al, 1991(Copaja et al, , 1999(Copaja et al, , 2006Nakagawa et al, 1995;Rice et al, 2005;Wilkes et al, 1999). Our results differed slightly, showing a majority of non-methoxylated benzoxazinoids in both wheat and rye, although the concentration of methoxylated compounds was over 40% in wheat, i.e., over four times higher than in rye.…”

“…A broad range of studies on young cereal plants grown in soil or hydroponics showed that the most abundant agluconic hydroxamic acid in Triticum sp. seedlings was DIMBOA (Copaja et al, 1999;Nakagawa et al, 1995;Wilkes, Marshall, & Copeland, 1999), and the most abundant agluconic hydroxamic acid in S. cereale seedlings was DIBOA (Copaja, Barria, & Niemeyer, 1991;Copaja et al, 2006;Rice et al, 2005). The majority of the total benzoxazinoid content, including both hydroxamic acids and their derived benzoxazolinones, consisted of non-methoxylated compounds (DIBOA and derivatives) in rye, whereas it consisted of methoxylated compounds (DIMBOA and derivatives) in wheat.…”

Potential of Hydroxamic Acids in the Control of Cereal Pests, Diseases, and Weeds

“…In wheat, Hx are absent from the seed, increase upon germination (peaking at the young seedling stage) and decrease thereafter (17). In mature plants, the youngest tissue still retains a high concentration of Hx (9)(10)(11)(17)(18)(19)(20). Hx are present in all organs of the plant (17).…”

“…In addition, Hx have also been associated with detoxification of triazine herbicides (3-5) and with iron acquisition by plant roots (6-8). Hx are known to occur not only in maize, rye and wheat, but also in triticale and in several wild Gramineae (2,[9][10][11][12][13][14], and to be absent from barley, oats and rice (2). Hx occcur in the plant as 2-B-O-D-glucopyranosides which are hydrolyzed by endo-B-glucosidases when the plant is injured 0097-6156/95/0582-0260$08.00/0…”

Interactions of Bacillus mojavensis and Fusarium verticillioides with a Benzoxazolinone (BOA) and its Transformation Product, APO

“…Because of their wide spectrum of biological activity, they offer promise for natural controls of pests. The main benzoxazinones produced by maize are 2,4-dihydroxy-7-mcthoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA), and its dimethoxy derivative 2,4-dihydroxy-6,7-dimethoxy-1,4-benzoxazin-3(4H)-one (DIM 2 BOA), with the former occurring in greater concentrations (Whitney and Mortimore 1959;Klun and Robinson 1969;Corcuera et al 1978;Copaja et al 1991;Hedin et al 1993;Frey et al 1997;Cambier et al 2000). These benzoxazinones are present in maize mainly as glycosides, but upon injury from insects or pathogens they are degraded to their unstable and highly toxic agluconic forms, which spontaneously decompose to the corresponding benzoxazolinones, such as MBOA (6-methoxy-2-benzoxazolinone) and BOA (benzoxazolin-2-one) (Niemeyer 1988).…”