Transformation of Benzoxazinones and Derivatives and Microbial Activity in the Test Environment of Soil Ecotoxicological Tests on <i>Poecilus cupreus </i>and <i>Folsomia candida</i>

Fomsgaard, Inge S.; Mortensen, Alan; Idinger, Jacqueline; Čoja, Tamara; Blümel, S.

doi:10.1021/jf050914a

Cited by 43 publications

(42 citation statements)

References 19 publications

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“…For example, recent experiments with cultivated fine fescue, sorghum species, and wheat have identified putative allelochemicals released from plant root exudates or residues, followed their degradation over time in soil settings, addressed their respective modes of action on higher plant growth, and identified bioactive allelochemicals or their metabolites at levels that could account for significant allelopathic interference in field settings (Nimbal et al 1996a, b;Bertin et al 2003;Dayan 2006;Macias et al 2006;Bertin et al 2007). Fomsgaard et al (2006) provide an excellent example of rigorous and well-documented method validation (i.e. reporting the inclusion of blanks, a standard curve, and recovery efficiencies from soil).…”

Section: Discussionmentioning

confidence: 99%

The importance of analytical techniques in allelopathy studies with the reported allelochemical catechin as an example

Blair

Weston²,

Nissen

et al. 2008

Biol Invasions

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Allelopathy can be challenging to demonstrate. Developing rigorous analytical techniques to detect and quantify compound(s) of interest from soil or liquid media lays the foundation for designing ecologically relevant experiments that incorporate candidate allelochemicals. In this paper, fundamental components of analytical techniques, including method development, validation, and appropriate controls are discussed. Research on the candidate allelochemical from spotted knapweed, catechin, is used as an example to demonstrate the importance of including these components both during data collection and in subsequent publications. This example shows how contrasting results between research groups can be difficult to interpret when information on controls and method validation are not included in publications. Recent research suggests that catechin is not likely driving spotted knapweed's invasion, and thus future research on this system should focus on alternate candidate toxins from spotted knapweed. By employing appropriate analytical techniques, such as those outlined here, a strong foundation can be laid for ecologically oriented experiments that examine the role of allelochemicals in structuring communities.

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Section: Discussionmentioning

confidence: 99%

The importance of analytical techniques in allelopathy studies with the reported allelochemical catechin as an example

Blair

Weston²,

Nissen

et al. 2008

Biol Invasions

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“…Many cereals produce the hydroxamic acids 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3(4 H)-one (DIM-BOA) and 2,4-dihydroxy-1,4-benzoxazin-3(4 H)-one (DIBOA) (Niemeyer, 1988;Baumeler et al, 2000). The benzoxazolinones 6-methoxy-2-benzoxazolinone (MBOA) and 2-benzoxazolinone (BOA), interestingly enough, are the degradation products of DIMBOA and DIBOA, respectively (Fomsgaard et al, 2006). 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).…”

Section: Increases In Allelochemical Toxicity Through Microbialmentioning

confidence: 99%

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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“…A highly toxic quinone responsible for walnut allelopathy is juglone (5,hydroxyl-1,4-naphthoquinone), which is also used in pharmacological studies (Gries, 1942;Kamei et al, 1998;Inbaraj and Chignell, 2004). Fomsgaard et al (2006) reported that cereals contain biologically active secondary metabolites such as the benzoxazinones [2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) and 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA)] and the benzoxazolinones [6-methoxy-2-benzoxazolinone (MBOA) and 2-benzoxazolinone (BOA)]. The benzoxazolinones are found as degradation products of DIMBOA and DIBOA both in plants and in soil, respectively.…”

Section: Biochemical Naturementioning

confidence: 99%

“…During ecotoxicological tests, Fomsgaard et al (2006) found that DIMBOA was degraded and partly transformed to MBOA. Testing of MBOA on Poecilus cupreus media showed that at the initial concentrations of 2 and 10 mg kg -1 no MBOA was left after 45 days, but AMPO was formed, and on both Folsomia candida and Poecilus cupreus test media BOA was transformed to a biologically more active compound APO.…”

Section: Fate In Soilmentioning

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 of Benzoxazinones and Derivatives and Microbial Activity in the Test Environment of Soil Ecotoxicological Tests on Poecilus cupreus and Folsomia candida

Cited by 43 publications

References 19 publications

The importance of analytical techniques in allelopathy studies with the reported allelochemical catechin as an example

The importance of analytical techniques in allelopathy studies with the reported allelochemical catechin as an example

Microbes as Targets and Mediators of Allelopathy in Plants

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

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