Decomposition of 2,4-Dihydroxy-7-methoxy-2<i>H</i>-1,4-benzoxazin-3(4<i>H</i>)-one in Aqueous Solutions

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

doi:10.1104/pp.61.5.796

Cited by 140 publications

(101 citation statements)

References 26 publications

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“…The high persistence in soil shown by APO, much higher than its precursors, in addition to its high phytotoxicity, leads us to assign a critical role regarding chemicals defense in DIBOA producer plants, other than DIBOA or BOA, that have been proposed as the main responsibles for several plant-plant interaction phenomena (6,34,35). The occurrence of degradation in buffered aqueous solution (8,10) also enforces a careful revision of the bioassay methodologies employed in the phytotoxicity evaluation of 2,4-dihydroxybenzoxazinones and benzoxazolinones since the activities observed could be due to degradation products instead of the original materials dosed.…”

Section: Resultsmentioning

confidence: 99%

“…In general terms, natural 2,4-dihydroxybenzoxazin-3-ones (DIMBOA, DIBOA) ( In addition to this bioactivity research, the low stability of DIMBOA, DIBOA, and their related benzoxazolinones in several conditions, such as biotransformation by fungi (15), and degradation in crop soil (16,17) and in aqueous solution (8)(9)(10), has been investigated. We have recently developed a complete degradation study of these allelochemicals in wheat crop soil in which we observed and characterized the conversion dynamics of these compounds into several molecules carried out by soil microbial population (9,10).…”

Section: Introductionmentioning

confidence: 99%

“…The DIBOA natural glycoside (2-O--D-glucopyranosyl-4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one (DIBOA-Glc) (Table 1, A) is the form in which DIBOA is preserved inside the plant prior to its release (7). Benzoxazolin-2-one (BOA) and 6-methoxybenzoxazolin-2-one (MBOA) ( Table 2, A) are the first chemicals in the DIBOA and DIMBOA degradation series, respectively (8)(9)(10). There are interesting precedents regarding their bioactivity on different systems.…”

Section: Introductionmentioning

confidence: 99%

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Structure−Activity Relationships (SAR) Studies of Benzoxazinones, Their Degradation Products and Analogues. Phytotoxicity on Standard Target Species (STS)

Macías

Marı́n

Oliveros‐Bastidas

et al. 2005

J. Agric. Food Chem.

106

140

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Benzoxazinones 2,4-dihydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one (DIMBOA) and 2,4-dihydroxy-(2H)-1,4-benzoxazin-3(4H)-one (DIBOA) have been considered key compounds for understanding allelopathic phenomena in Gramineae crop plants such as corn (Zea mays L.), wheat (Triticum aestivum L.), and rye (Secale cereale L.). The degradation processes in the environment observed for these compounds, in which soil microbes are directly involved, could affect potential allelopathic activity of these plants. We present in this work a complete structure-activity relationships study based on the phytotoxic effects observed for DIMBOA, DIBOA, and their main degradation products, in addition to several synthetic analogues of them. Their effects were evaluated on standard target species (STS), which include Triticum aestivum L. . They showed high inhibitory activity over almost all species growth. The fact that APO is a degradation product from DIBOA with high phytotoxicity and stability makes it possible to assign an important ecological role regarding plant defense mechanisms. 2-Deoxy derivatives of natural benzoxazinones display a wide range of activities that allow proposing them as new leads for natural herbicide models with a 1,4-benzoxazine skeleton.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Structure−Activity Relationships (SAR) Studies of Benzoxazinones, Their Degradation Products and Analogues. Phytotoxicity on Standard Target Species (STS)

Macías

Marı́n

Oliveros‐Bastidas

et al. 2005

J. Agric. Food Chem.

106

140

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“…The principal hydroxamic acid in aqueous extracts of corn is 2,4-dihydroxy-7-methoxy-2H-l,4-benzoxazin-3(4H)-one (DIMBOA), which decomposes to 6-methoxy-2-benzoxazolinone (MBOA) in aqueous solutions (19,23). DIMBOA and MBOA ( Fig.…”

mentioning

confidence: 99%

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

Corcuera¹,

Woodward²,

Helgeson³

et al. 1978

Plant Physiol.

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12,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H) (11) reported that a lyophilized water extract from corn was only slightly inhibitory to most isolates of ECZ; however, it was strongly inhibitory to most other soft rot bacteria. The observed effect was an extension of the duration of the lag phase of growth. No significant effect on growth rate was detected after the lag phase. It was suggested that the differential inhibitor(s) to soft rotting Erwinia species present in the extract could be involved in the resistance of corn to these bacteria.-'Research cooperative with the College of Agricultural and Life Sciences,

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“…Aglycone concentrations were determined using established extinction coefficients of E254 = 8500 for DIBOA and E262 = 10,000 for DIMBOA (9,26). DIBOA glucoside concentrations were determined using an extinction coefficientof E255 = 8500 (9).…”

mentioning

confidence: 99%

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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Decomposition of 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one in Aqueous Solutions

Cited by 140 publications

References 26 publications

Structure−Activity Relationships (SAR) Studies of Benzoxazinones, Their Degradation Products and Analogues. Phytotoxicity on Standard Target Species (STS)

Structure−Activity Relationships (SAR) Studies of Benzoxazinones, Their Degradation Products and Analogues. Phytotoxicity on Standard Target Species (STS)

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

Hydroxamic Acid Glucosyltransferases from Maize Seedlings

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