Transformation products of 2-benzoxazolinone (BOA) in soil

Gents, Mia B.; Nielsen, Susan T.; Mortensen, Alan; Christophersen, Carsten; Fomsgaard, Inge S.

doi:10.1016/j.chemosphere.2005.03.068

Cited by 39 publications

(46 citation statements)

References 28 publications

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“…Gents et al (2005) were able to demonstrate that the degradation of BOA to APO was concentration-dependent with low soil concentrations (400 μg kg −1 ) yielding only one unidentified transformation product, while higher soil concentrations (400 mg kg −1 ) yielded eight distinct transformation products, one of which was confirmed as APO in accordance with Gagliardo and Chilton (1992). APO has been shown to be more biologically active than BOA (Gagliardo and Chilton, 1992) including higher phytotoxicity and increased toxicity towards beneficial soil organisms and fungi (Gents et al, 2005). Gents et al (2005) suggest that BOA is only toxic to microorganisms at higher concentrations and, therefore, microbes may convert BOA into APO and several other products thus ameliorating toxic conditions, thereby increasing phytotoxicity.…”

Section: Increases In Allelochemical Toxicity Through Microbialmentioning

confidence: 97%

“…MBOA and BOA have been shown to be further transformed into 2-amino-7-methoxy-3 H-phenoxazin-3-one (AMPO) and 2-amino-3 H-phenoxazin-3-one (APO), respectively (Understrup et al, 2005). Gents et al (2005) were able to demonstrate that the degradation of BOA to APO was concentration-dependent with low soil concentrations (400 μg kg −1 ) yielding only one unidentified transformation product, while higher soil concentrations (400 mg kg −1 ) yielded eight distinct transformation products, one of which was confirmed as APO in accordance with Gagliardo and Chilton (1992). APO has been shown to be more biologically active than BOA (Gagliardo and Chilton, 1992) including higher phytotoxicity and increased toxicity towards beneficial soil organisms and fungi (Gents et al, 2005).…”

Section: Increases In Allelochemical Toxicity Through Microbialmentioning

confidence: 99%

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Microbes as Targets and Mediators of Allelopathy in Plants

2012

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Studies of allelopathy in terrestrial systems have experienced tremendous growth as interest has risen in describing biochemical mechanisms responsible for structuring plant communities, determining agricultural and forest productivity, and explaining invasive behaviors in introduced organisms. While early criticisms of allelopathy involved issues with allelochemical production, stability, and degradation in soils, an understanding of the chemical ecology of soils and its microbial inhabitants has been increasingly incorporated in studies of allelopathy, and recognized as an essential predictor of the outcome of allelopathic interactions between plants. Microbes can mediate interactions in a number of ways with both positive and negative outcomes for surrounding plants and plant communities. In this review, we examine cases where soil microbes are the target of allelopathic plants leading to indirect effects on competing plants, provide examples where microbes play either a protective effect on plants against allelopathic competitors or enhance allelopathic effects, and we provide examples where soil microbial communities have changed through time in response to allelopathic plants with known or potential effects on plant communities. We focus primarily on interactions involving wild plants in natural systems, using case studies of some of the world's most notorious invasive plants, but we also provide selected examples from agriculturally managed systems. Allelopathic interactions between plants cannot be fully understood without considering microbial participants, and we conclude with suggestions for future research. Allelopathy and Soil MicrobesAllelopathy, generally, is considered as a form of negative chemical communication between organisms, whereby one participant (the donor) in an interaction produces a compound(s) that is released in the environment in ecologically relevant quantities that negatively impacts the fitness of other participants (the receivers); the effect presumably benefits fitness of the donor. While the concept of allelopathy extends back to at least Theophrastus in the third century B.C., who invoked this phenomenon as an explanatory mechanism of plant growth, abundance, or community structure in natural systems, the concept has fluctuated in popularity over time (see Willis, 2007 for review). Allelopathy often has been subjected to criticisms of ecological relevance that other phenomena, such as resource competition, have not, thus explaining why it has fallen out of favor during certain time periods. However, studies of allelopathy in terrestrial systems have experienced a tremendous "rebirth" in the last 20 years as interest has risen in describing biochemical mechanisms responsible for structuring plant communities, determining agricultural and forest productivity, and explaining invasive behaviors in introduced organisms. More rigorous observational and experimental approaches, along with better analytical techniques, have

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Section: Increases In Allelochemical Toxicity Through Microbialmentioning

confidence: 97%

Section: Increases In Allelochemical Toxicity Through Microbialmentioning

confidence: 99%

Microbes as Targets and Mediators of Allelopathy in Plants

2012

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“…Maybe the best estimate for naturally occurring APO concentrations can be gained from studies of exudation of the APO precursor DIBOA from roots: In hydroponic cultures, DIBOA released from rye (Secale cereale) and durum (Triticum durum) roots accumulated to concentrations of 300 and 30 µM, respectively (Belz and Hurle, 2005;Macías et al, 2014). Given the equimolar conversion of DIBOA to BOA, and a conversion rate of 10:1 of BOA into APO (Gents et al, 2005;Understrup et al, 2005), this would result in APO concentrations of 30 and 3 µM, respectively. These concentrations are in the range determined to be effective in our assays, which supports HDAC inhibition by APO as a realistic model for allelopathy.…”

Section: Discussionmentioning

confidence: 99%

Plants Release Precursors of Histone Deacetylase Inhibitors to Suppress Growth of Competitors

et al. 2015

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To secure their access to water, light, and nutrients, many plant species have developed allelopathic strategies to suppress competitors. To this end, they release into the rhizosphere phytotoxic substances that inhibit the germination and growth of neighbors. Despite the importance of allelopathy in shaping natural plant communities and for agricultural production, the underlying molecular mechanisms are largely unknown. Here, we report that allelochemicals derived from the common class of cyclic hydroxamic acid root exudates directly affect the chromatin-modifying machinery in Arabidopsis thaliana. These allelochemicals inhibit histone deacetylases both in vitro and in vivo and exert their activity through locus-specific alterations of histone acetylation and associated gene expression. Our multilevel analysis collectively shows how plant-plant interactions interfere with a fundamental cellular process, histone acetylation, by targeting an evolutionarily highly conserved class of enzymes.

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“…The hydroxamic acids are bound as glucosides in plant vacuoles and released by -glucosidases upon disruption of cellular integrity (Yue et al, 1998). Further degradation products have Name of allelochemical Acronym Source Benzoxazolin-2-one BOA DIBOA 6-methoxybenzoxazolin-2-one MBOA DIMBOA 2,4-dihydroxy-1,4-(2H)-benzoxazin-3-one DIBOA 2,4-dihydroxy-7-methoxy-1,4-(2H)-benzoxazin-3-one DIMBOA 2-amino-3H-phenoxazin-3-one APO BOA 2-amino-7-methoxy-3H-phenoxazin-3-one AMPO DIMBOA, MBOA 2-acetylamino-7-methoxyphenoxazin-3-one AAMPO MBOA N-(2-hydroxyphenyl) malonamic acid HPMA been identified as 2-amino-3H-phenoxazin-3-one (APO) and 2-amino-7-methoxy-3H-phenoxazin-3-one (AMPO) from BOA and MBOA, respectively (Kumar et al, 1993;Fomsgaard et al, 2004;Macías et al, 2004;Gents et al, 2005;Understrup et al, 2005). Formation of APO from BOA has been found to occur through the intermediate 2-aminophenol, both as a chemical process and as a microbial process (Gagliardo and Chilton, 1992).…”

Section: Chemical Formsmentioning

confidence: 99%

Allelochemicals: sources, toxicity and microbial transformation in soil —a review

et al. 2008

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Soil microorganisms interact with plants in diversified manner ranging from mobilising nutrients and enhancing their growth, to inducing diseases. They also produce allelochemicals directly or indirectly through conversion from other compounds. In order to hamper plant growth, allelochemicals must accumulate and persist at phytotoxic levels in the rhizosphere soil. However, after their entry into environment, persistence, availability and biological activities of allelochemicals are influenced by microorganisms. Transformation of allelochemicals by soil microbes may result into the compounds with modified biological properties. Such bio-transformations affect the overall allelopathic capability of the producer plant in a direct manner. Several reports describe the allelopathic significance of microbial metabolism products. For instance, a bacterium Actinetobacter calcoaceticus, can convert 2(3H)-benzoxazolinone (BOA) to 2,2´-oxo-l,l´-azobenzene (AZOB) which is more inhibitory to some plants. On the contrary, bacterium Pseudomonas putida catabolises juglone in soils beneath walnut trees; otherwise, juglone accumulates at phytotoxic levels. This review article describes the nature of microbially produced allelochemicals, and the ways to mediate microbial degradation of putative allelochemicals. The given information develops an understanding of persistence, fate and phytotoxicity of allelochemicals in the natural environment, and also points out the possible solution of the problems due to microbial interventions in the soil.

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Transformation products of 2-benzoxazolinone (BOA) in soil

Cited by 39 publications

References 28 publications

Microbes as Targets and Mediators of Allelopathy in Plants

Microbes as Targets and Mediators of Allelopathy in Plants

Plants Release Precursors of Histone Deacetylase Inhibitors to Suppress Growth of Competitors

Allelochemicals: sources, toxicity and microbial transformation in soil —a review

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