Allelochemicals of the phenoxazinone class act at physiologically relevant concentrations

Venturelli, Sascha; Petersen, Sebastian; Langenecker, Tobias; Weigel, Detlef; Lauer, Ulrich M.; Becker, Claude

doi:10.1080/15592324.2016.1176818

Cited by 10 publications

(13 citation statements)

References 8 publications

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“…In addition to its antifungal properties, APO has been shown to selectively inhibit anaerobic growth of cellulolytic bacteria [42] and was initially described as the antibiotic Questiomycin A [43]. Although little is known about the mode of action of its precursors DI(M)BOA and (M)BOA, APO is an intercalating agent that inhibits growth of A. thaliana seedlings at concentrations detected in root leachates of rye and wheat plants [3,[44][45][46][47]. Although it has recently been shown that APO acts as an inhibitor of plant and animal histone deacetylases, its mode of action in prokaryotes remains to be identified.…”

Section: Bx Compounds In Plant-microbe Interactionsmentioning

confidence: 99%

“…It is now clear that what is commonly observed as BX-mediated allelopathy is the combined activity of various compounds derived from the plant-released BXs that influence organisms from diverse branches of the tree of life [24,42,44,45,47]. However, although BXs constitute one of the biochemically best-characterised allelochemicals, understanding the extent and the (molecular) mechanisms by which the release of BXs into the rhizosphere influences the root, rhizosphere, and/or soil microbiota requires further investigation.…”

Section: Root and Soil Microbiota As Modulators And Targets Of Allelomentioning

confidence: 99%

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Allelopathic Plants: Models for Studying Plant–Interkingdom Interactions

Schandry

Becker

2020

Trends in Plant Science

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116

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Allelopathy is a biochemical interaction between plants in which a donor plant releases secondary metabolites, allelochemicals, that are detrimental to the growth of its neighbours. Traditionally considered as bilateral interactions between two plants, allelopathy has recently emerged as a cross-kingdom process that can influence and be modulated by the other organisms in the plant's environment. Here, we review the current knowledge on plant-interkingdom interactions, with a particular focus on benzoxazinoids. We highlight how allelochemical-producing plants influence not only their plant neighbours but also insects, fungi, and bacteria that live on or around them. We discuss challenges that need to be overcome to study chemical plantinterkingdom interactions, and we propose experimental approaches to address how biotic and chemical processes impact plant health.

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Section: Bx Compounds In Plant-microbe Interactionsmentioning

confidence: 99%

Section: Root and Soil Microbiota As Modulators And Targets Of Allelomentioning

confidence: 99%

Allelopathic Plants: Models for Studying Plant–Interkingdom Interactions

Schandry

Becker

2020

Trends in Plant Science

Self Cite

116

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“…Treatment with these compounds has led to a number of effects, including reduced activity of other enzymes such as papain, α ‐chymotrypsin and GSTs 86 . The mode of action has not been conclusively identified for DIMBOA or DIBOA, or their respective degradation products, 87 and has been elucidated only in APO and AMPO 88 . These compounds bind to and inhibit the action of highly‐conserved histone deacetylase (HDAC) enzymes, which are necessary for amino acid transcription and therefore cell development 88 .…”

Section: Examples Of Allelochemical Multi‐kingdom Functionalitymentioning

confidence: 99%

“…These compounds bind to and inhibit the action of highly‐conserved histone deacetylase (HDAC) enzymes, which are necessary for amino acid transcription and therefore cell development 88 . Such effects occur at concentrations as low as 3.25 μ m , sufficient for physiological relevance 87 . This explains the notable allelopathic potency of APO in particular, being a much more potent phytoallelochemical than DIMBOA or DIBOA 81 …”

Section: Examples Of Allelochemical Multi‐kingdom Functionalitymentioning

confidence: 99%

Review: Allelochemicals as multi‐kingdom plant defence compounds: towards an integrated approach

Hickman

Rasmussen

Ritz

et al. 2020

Pest Management Science

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The capability of synthetic pesticides to manage weeds, insect pests and pathogens in crops has diminished due to evolved resistance. Sustainable management is thus becoming more challenging. Novel solutions are needed and, given the ubiquity of biologically active secondary metabolites in nature, such compounds require further exploration as leads for novel crop protection chemistry. Despite improving understanding of allelochemicals, particularly in terms of their potential for use in weed control, their interactions with multiple biotic kingdoms have to date largely been examined in individual compounds and not as a recurrent phenomenon. Here, multi‐kingdom effects in allelochemicals are introduced by defining effects on various organisms, before exploring current understanding of the inducibility and possible ecological roles of these compounds with regard to the evolutionary arms race and dose–response relationships. Allelochemicals with functional benefits in multiple aspects of plant defence are described. Gathering these isolated areas of science under the unified umbrella of multi‐kingdom allelopathy encourages the development of naturally‐derived chemistries conferring defence to multiple discrete biotic stresses simultaneously, maximizing benefits in weed, insect and pathogen control, while potentially circumventing resistance. © 2020 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

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“…The compound possesses phytotoxic properties; however, regarding the molecular targets, the mode of action is not well understood. The compound was recently described as a histone deacetylase inhibitor (Venturelli et al, 2015(Venturelli et al, , 2016.…”

Section: Degradation and Detoxification Of Benzoxazolinones By Fungi mentioning

confidence: 99%

Conversions of Benzoxazinoids and Downstream Metabolites by Soil Microorganisms

et al. 2019

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Benzoxazinoids, secondary metabolites of several Poaceae, and some benzoxazinoid downstream metabolites are bioactive compounds that act as allelochemicals and natural pesticides. Since a short lifetime of the substances is crucial to avoid long-term environmental effects, total degradation by microorganisms is of exceptional importance. We performed a screening with cultivable microorganisms (Species names and strain numbers: Mycobacterium fortuitum, 7; Bacillus aryabhattai, 34; Bacillus cereus, 59; Bacillus megaterium, 21, 48; Bacillus methylotrophicus, 58; Lysinibacillus xylanilyticus, 56; Paenibacillus polymyxa, 51; Aminobacter aminovorans, 49; the fungi Papulaspora sepedonioides, 12 and Trichoderma viride, 47) isolated from soil previously used for wheat and Persian clover mixed-culture systems to assess their behavior in the presence of the compounds. The microorganisms were exposed to glucosylated benzoxazinones, the benzoxazinones HBOA, DIBOA, and DIMBOA, the benzoxazolinones BOA, BOA-6-OH, and MBOA, and to several downstream products (AP, AAP, oHPMA, glucoside carbamate) in liquid culture to avoid interferences with soil minerals and other organisms. The microorganisms differed strongly in their metabolic activities in terms of growth, compound modification, and degradation. We observed degradation with DIBOA and GDIMBOA but rarely with DIMBOA, whereas BOA and MBOA showed almost no degradation when directly applied. Hydroxylation of BOA and demethylation of MBOA by the plant, resulting in BOA-6-OH, activated the benzoxazolinones for bacterial nitration. The resulting NBOA-6-OH was short-lived but could function temporarily as an allelochemical by inhibiting photosynthesis, e.g., in young seedlings of cress and kohlrabi. The BOA downstream products AP and oHPMA were converted to AAP, which can be nitrated to N-(2-OH-5-nitrophenyl)-acetamide and then degraded by A. aminovorans (49) and P. polymyxa (51). Only P. sepedonioides (12) and P. polymyxa (51) failed in the conversion of HBOA into AAP. While DIBOA, DIMBOA, MBOA, NBOA-6-OH, AP, AAP, and oHPMA reduced the growth of most microorganisms, glucoside carbamate promoted their growth. GDIMBOA had a stimulatory effect toward the fungi and three bacterial species. These findings lead to the hypothesis that in a natural habitat, such as the root surface, microorganisms may cooperate, perhaps by involving the plant, for the successful elimination of benzoxazinoids and their downstream metabolites.

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Allelochemicals of the phenoxazinone class act at physiologically relevant concentrations

Cited by 10 publications

References 8 publications

Allelopathic Plants: Models for Studying Plant–Interkingdom Interactions

Allelopathic Plants: Models for Studying Plant–Interkingdom Interactions

Review: Allelochemicals as multi‐kingdom plant defence compounds: towards an integrated approach

Conversions of Benzoxazinoids and Downstream Metabolites by Soil Microorganisms

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