2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, an Inhibitor from Zea mays with Differential Activity against Soft Rotting Erwinia Species

Corcuera, Luís J.; Woodward, Michael D.; Helgeson, John P.; Kelman, A.; Upper, Christen D.

doi:10.1104/pp.61.5.791

Cited by 88 publications

(37 citation statements)

References 11 publications

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“…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).…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2007

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The benzoxazolinones, specifically benzoxazolin-2(3H)-one (BOA), are important transformation products of the benzoxazinones that can serve as allelochemicals providing resistance to maize from pathogenic bacteria, fungi, and insects. However, maize pathogens such as Fusarium verticillioides are capable of detoxifying the benzoxazolinones to 2-aminophenol (AP), which is converted to the less toxic N-(2-hydroxyphenyl) malonamic acid (HPMA) and 2-acetamidophenol (HPAA). As biocontrol strategies that utilize a species of endophytic bacterium, Bacillus mojavensis, are considered efficacious as a control of this Fusarium species, the in vitro transformation and effects of BOA on growth of this bacterium was examined relative to its interaction with strains of F. verticillioides. The results showed that a red pigment was produced and accumulated only on BOA-amended media when wild type and the progeny of genetic crosses of F. verticillioides are cultured in the presence of the bacterium. The pigment was identified as 2-amino-3H-phenoxazin-3-one (APO), which is a stable product. The results indicate that the bacterium interacts with the fungus preventing the usual transformation of AP to the nontoxic HPMA, resulting in the accumulation of higher amounts of APO than when the fungus is cultured alone. APO is highly toxic to F. verticillioides and other organisms. Thus, an enhanced biocontrol is suggested by this in vitro study.

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Section: Introductionmentioning

confidence: 99%

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

et al. 2007

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“…1) (27). DIMBOA has been implicated in resistance to several diseases (3,16) and insects (17) in maize although many of these relationships have not been substantiated. By far the most extensively characterized biological function proposed for DIMBOA in the developing maize plant is its resistance effect on the first brood of the European corn borer, Ostrinia nubilalis (Hbn.)…”

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confidence: 99%

“…By far the most extensively characterized biological function proposed for DIMBOA in the developing maize plant is its resistance effect on the first brood of the European corn borer, Ostrinia nubilalis (Hbn.) (1 [1][2][3][4][5][6][7][8][9][10][11][12][13]21). The concentration of DIMBOA in young maize plants can be closely correlated with resistance to the European corn borer.…”

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Hydroxamic Acid Glucosyltransferases from Maize Seedlings

Bailey¹,

Larson²

1989

Plant Physiol.

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Hydroxamic acids occur in several forms in maize (Zea mays L.) with 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA) being the predominant form and others including 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA) being found at lower concentrations. Two enzymes capable of glucosylating hydroxamic acids were identified in maize protein extracts and partially purified and characterized. The total enzyme activity per seedling increased during the first 4 days of germination and was concurrent with the accumulation of DIMBOA. Purification of the enzymes by ammonium sulfate precipitation followed by Sephadex G-200 and Q-Sepharose gel chromatography resulted in a 13-fold increase in specific activity. The enzymes are initially separated into two peaks (peak 1 and peak 2) of activity by 0-Sepharose gel chromatography. The peak 1 glucosyltransferase had 3.6% of the DIMBOA glucosylating activity when DIBOA was used as substrate, whereas this percentage increased to 57% for the peak 2 enzyme. The enzyme in peak 2 has a Km of 174 micromolar for DIMBOA and a Km of 638 micromolar for DIBOA; the enzyme in peak I has a Km of 217 micromolar for DIMBOA and its activity on DIBOA was too low to determine a Km. The identification of two glucosyltransferases capable of glucosylating hydroxamic acids in vitro serves as an initial step in the characterization of the enzymes involved in production of hydroxamic acids in maize. which differs from DIMBOA by a methoxyl group, is present at a lesser concentration (Fig.

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“…The nature of the inhibition of bacterial growth caused by DIM-BOA5 is a prolongation of lag phase, with no substantial effect on log phase growth rate (1). DIMBOA is unstable in our bioassay medium and decomposes to 6-methoxy-2-benzoxazolinone (MBOA) and other uncharacterized compounds (6).…”

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confidence: 99%

“…The cyclic hydroxamate, 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, is the principal component in extracts of corn (Zea mays L.) tissue that is inhibitory to soft rotting Erwinia (1). The nature of the inhibition of bacterial growth caused by DIM-BOA5 is a prolongation of lag phase, with no substantial effect on log phase growth rate (1).…”

mentioning

confidence: 99%

Factors That Influence the Activity of 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one on Erwinia Species in Growth Assays

Woodward

Corcuera²,

Helgeson³

et al. 1978

Plant Physiol.

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Factors affecting the inhibitory activity of 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA) against Erwimia carotovors, a nonpathogen of Zen mays L., and against a maize pathovar of Erwinia chrysanthemi (ECZ) were examined. Most experiments were performed with DIMBOA dissolved in a bacterial growth medium containing 10 g/liter of sucrose, inorganic salts, and 1 g/liter of casamino acids at pH 6.75. When temperature and pH were held constant, inhibition of E. carotovora varied linearly with the logarithm of the initial cel population. By altering temperatures, assays with constant pH and initial cell populations were performed under conditions of varying DIMBOA stability. When E. carotovors was grown at 24, 28, 32, and 36 C in the presence of 0.1 to 0.5 mM DIMBOA, the inhibition of bacterial growth was maintained long after DIMBOA had decomposed in the medium to levels which, if added initially, would not have been inhibitory. When assays were performed at pH 5.5, the pH of aqueous maize extracts, E. carotovors was more inhibited than at pH 6.75; however, ECZ was substantially less inhibited at the lower pH.The cyclic hydroxamate, 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, is the principal component in extracts of corn (Zea mays L.) tissue that is inhibitory to soft rotting Erwinia (1). The nature of the inhibition of bacterial growth caused by DIM-BOA5 is a prolongation of lag phase, with no substantial effect on log phase growth rate (1). DIMBOA is unstable in our bioassay medium and decomposes to 6-methoxy-2-benzoxazolinone (MBOA) and other uncharacterized compounds (6). The half-life of DIMBOA (5.3 hr at 28 C, pH 6.75) is substantially less than the duration of inhibition at initial DIMBOA concentrations greater than 0.2 to 0.3 mM (1, 6). Similarly, when DIMBOA was incubated in our bacterial growth medium before addition of bacterial cells, inhibitory activity also was lost with a half-life of about 5 hr (6). MBOA and the other decomposition products were not sufficiently active to account for the observed inhibition (6). Furthermore, other measurements of the biological effects of DIMBOA have extended over periods as long as 21 days (1-5). Clearly then, the relationship between the stability of DIMBOA and its biological activity needs to be examined. In this paper, we present results of tests with variation in pH, incubation temperature, and cell populations. MATERIALS AND METHODSBacterial isolates used in this study were Erwinia carotovora (EC, SR-53) and Erwinia chrysanthemi pathovar zeae (ECZ, SR-120) (see Table I in ref. 1). The former is nonpathogenic on corn, whereas the latter causes a bacterial stalk rot of corn. The bacterial growth assay medium and activity assays were as previously described (1) and inhibition was measured as A lag or relative inhibition (RI) as illustrated in Figure 2 of that reference.DIMBOA (prepared as in ref. 6) was dissolved in the medium by shaking at room temperature for a few min. Solutions were then fiter-sterilized (pore size 0.2 ,um, Syb...

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2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, an Inhibitor from Zea mays with Differential Activity against Soft Rotting Erwinia Species

Cited by 88 publications

References 11 publications

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

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

Hydroxamic Acid Glucosyltransferases from Maize Seedlings

Factors That Influence the Activity of 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one on Erwinia Species in Growth Assays

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