Benzoxazolinone Detoxification and Degradation – A Molecule ́s Journey

Schulz, Margot; Sicker, Dieter; Baluška, Frantǐsek; Sablofski, Tina; Scherer, Heinrich W.; Ritter, Felix Martin

doi:10.5772/32624

Cited by 2 publications

(6 citation statements)

References 93 publications

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“…Lipid metabolism is disrupted, enzymes such as PMH + -ATPase or α-amylase, are inhibited (Friebe et al, 1997;Burgos et al, 2004;Kato-Noguchi et al, 2010). Cellular transport and the actin cytoskeleton are disturbed (Schulz et al, 2012a). BOA treatment results in the decrease of the densities of ribosomes, dictyosomes, and mitochondria (Burgos et al, 2004).…”

Section: Efffects Of Benzoxazinoids In Target Plants and Weed Suppresmentioning

confidence: 99%

“…Due to an increased peroxidase activity and H 2 O 2 production in BX-treated plants, lignin accumulation and cell wall rigidity are enhanced, which contribute to the growth inhibition (González and Rojas, 1999). Nuclei show shifts in their typical central to lateral and/or axial positions (Schulz et al, 2012a). Benzoxazolinones, known as anti-auxin, can block lateral root formation (Hoshi-Sakoda et al, 1994;Anai et al, 1996;Burgos et al, 2004).…”

Section: Efffects Of Benzoxazinoids In Target Plants and Weed Suppresmentioning

confidence: 99%

“…All plant detoxification products exuded by the roots can be converted to phenoxazinone(s), by fungal and bacterial activities, which most likely localize to the rhizosphere. In maize, phenoxazinone in concentrations of less than 0.3 mM have a stimulatory effect on root growth, but higher concentrations are inhibitory although the compound is obviously not absorbed (Knop et al, 2007;Schulz et al, 2012a). The relatively stable glucoside carbamate is subject to ring opening at the lactone group, which yields glucosylated carbamic acid as Table 5 Representative dicot.…”

Section: Degradation Of Plant Detoxification Productsmentioning

confidence: 99%

“…Abutilon theophrasti 1 mg/2 ml Burgos and Talbert, 2000 Ambrosia artemisiifolia RR Amaranthus retroflexus RR 40 ml/gFW 5 mM Schulz et al, 2012a, b;Tabaglio et al, 2008 Amranthus palmeri 0.3 mg/3 ml 0.6 mg/2 ml Burgos and Talbert, 2000 Arabidopsis thaliana Col-0 1 mM 20-40 ml/gFW, 2 mM von Rad et al, 2001;Baerson et al, 2005 Chenopodium album RR 20-40 ml/gFW 5 mM Schulz and Wieland, 1999;Schulz et al, 2012a (Schulz et al, 2008;2012a). Because of the instability of free carbamic acid, subsequent deglucosylation causes either a rearrangement back to BOA, or the aglycone is decarboxylated to 2-aminophenol, the precursor for phenoxazinone production.…”

Section: Dicotyledonous Weeds Referencementioning

confidence: 99%

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Benzoxazinoids in Rye Allelopathy - From Discovery to Application in Sustainable Weed Control and Organic Farming

et al. 2013

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The allelopathic potency of rye (Secale cereale L.) is due mainly to the presence of phytotoxic benzoxazinones-compounds whose biosynthesis is developmentally regulated, with the highest accumulation in young tissue and a dependency on cultivar and environmental influences. Benzoxazinones can be released from residues of greenhouse-grown rye at levels between 12 and 20 kg/ha, with lower amounts exuded by living plants. In soil, benzoxazinones are subject to a cascade of transformation reactions, and levels in the range 0.5-5 kg/ha have been reported. Starting with the accumulation of less toxic benzoxazolinones, the transformation reactions in soil primarily lead to the production of phenoxazinones, acetamides, and malonamic acids. These reactions are associated with microbial activity in the soil. In addition to benzoxazinones, benzoxazolin-2(3H)-one (BOA) has been investigated for phytotoxic effects in weeds and crops. Exposure to BOA affects transcriptome, proteome, and metabolome patterns of the seedlings, inhibits germination and growth, and can induce death of sensitive species. Differences in the sensitivity of cultivars and ecotypes are due to different species-dependent strategies that have evolved to cope with BOA. These strategies include the rapid activation of detoxification reactions and extrusion of detoxified compounds. In contrast to sensitive ecotypes, tolerant ecotypes are less affected by exposure to BOA. Like the original compounds BOA and MBOA, all exuded detoxification products are converted to phenoxazinones, which can be degraded by several specialized fungi via the Fenton reaction. Because of their selectivity, specific activity, and presumably limited persistence in the soil, benzoxazinoids or rye residues are suitable means for weed control. In fact, rye is one of the best cool season cover crops and widely used because of its excellent weed suppressive potential. Breeding of benzoxazinoid resistant crops and of rye with high benzoxazinoid contents, as well as a better understanding of the soil persistence of phenoxazinones, of the weed resistance against benzoxazinoids, and of how allelopathic interactions are influenced by cultural practices, would provide the means to include allelopathic rye varieties in organic cropping systems for weed control.

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Section: Efffects Of Benzoxazinoids In Target Plants and Weed Suppresmentioning

confidence: 99%

Section: Efffects Of Benzoxazinoids In Target Plants and Weed Suppresmentioning

confidence: 99%

Section: Degradation Of Plant Detoxification Productsmentioning

confidence: 99%

Section: Dicotyledonous Weeds Referencementioning

confidence: 99%

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Benzoxazinoids in Rye Allelopathy - From Discovery to Application in Sustainable Weed Control and Organic Farming

et al. 2013

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“…The endophyte Fusarium verticillioides could mobilize the allelochemical via glucosylated carbamic acid. 50 The fungus is able to hydrolyse glucose from this compound and can rearrange carbamic acid to BOA, if no decarboxylation to 2-aminophenol occurs. The depot also remained in dead root material, but can be mobilized by fungi.…”

Section: Discussionmentioning

confidence: 99%

Benzoxazolinone detoxification byN-Glucosylation: The multi-compartment-network ofZea maysL.

Schulz¹,

Filary²,

Kühn³

et al. 2016

Plant Signaling & Behavior

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The major detoxification product in maize roots after 24 h benzoxazolin-2(3H)-one (BOA) exposure was identified as glucoside carbamate resulting from rearrangement of BOA-N-glucoside, but the pathway of N-glucosylation, enzymes involved and the site of synthesis were previously unknown. Assaying whole cell proteins revealed the necessity of H2O2 and Fe(2+) ions for glucoside carbamate production. Peroxidase produced BOA radicals are apparently formed within the extraplastic space of the young maize root. Radicals seem to be the preferred substrate for N-glucosylation, either by direct reaction with glucose or, more likely, the N-glucoside is released by glucanase/glucosidase catalyzed hydrolysis from cell wall components harboring fixed BOA. The processes are accompanied by alterations of cell wall polymers. Glucoside carbamate accumulation could be suppressed by the oxireductase inhibitor 2-bromo-4´-nitroacetophenone and by peroxidase inhibitor 2,3-butanedione. Alternatively, activated BOA molecules with an open heterocycle may be produced by microorganisms (e.g., endophyte Fusarium verticillioides) and channeled for enzymatic N-glucosylation. Experiments with transgenic Arabidopsis lines indicate a role of maize glucosyltransferase BX9 in BOA-N-glycosylation. Western blots with BX9 antibody demonstrate the presence of BX9 in the extraplastic space. Proteomic analyses verified a high BOA responsiveness of multiple peroxidases in the apoplast/cell wall. BOA incubations led to shifting, altered abundances and identities of the apoplast and cell wall located peroxidases, glucanases, glucosidases and glutathione transferases (GSTs). GSTs could function as glucoside carbamate transporters. The highly complex, compartment spanning and redox-regulated glucoside carbamate pathway seems to be mainly realized in Poaceae. In maize, carbamate production is independent from benzoxazinone synthesis.

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Benzoxazolinone Detoxification and Degradation – A Molecule ́s Journey

Cited by 2 publications

References 93 publications

Benzoxazinoids in Rye Allelopathy - From Discovery to Application in Sustainable Weed Control and Organic Farming

Benzoxazinoids in Rye Allelopathy - From Discovery to Application in Sustainable Weed Control and Organic Farming

Benzoxazolinone detoxification byN-Glucosylation: The multi-compartment-network ofZea maysL.

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