3-β-d-Glucopyranosyl-6-methoxy-2-benzoxazolinone (MBOA-N-Glc) is an insect detoxification product of maize 1,4-benzoxazin-3-ones

Maag, Daniel; Dalvit, Claudio; Thévenet, Damien; Köhler, Angela; Wouters, Felipe C.; Vassão, Daniel Giddings; Gershenzon, Jonathan; Wolfender, Jean‐Luc; Turlings, Ted C. J.; Erb, Matthias; Glauser, Gaëtan

doi:10.1016/j.phytochem.2014.03.018

Cited by 78 publications

(76 citation statements)

References 31 publications

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“…Besides that, increase in enzymatic activity has been detected in aphids grow-ing in wheat containing different amounts of hydrox-amic acids. These enzymes could act on the hydroxamic acids leading to compounds more readily excretable by aphids, meaning that some aphids are able to detoxify the harmful compounds and thus gain an advantage over competitors (Loayza-Muro et al 2000;Maag et al 2014). This would mean that small increments in the concentration of hydroxamic acids in wheat would not be beneficial.…”

Section: Discussionmentioning

confidence: 99%

“…Different types of hydroxamic acids (HDMBOA, HMBOA, MBOA, MBOA-N-Glc, BOA and TRIMBOA-Glc) can be found in plants (Niemeyer 2009) and different levels of toxicity are reported for these molecules (Meihls et al 2013). In wheat, DIMBOA (2,4-dihydroxy-7-methoxy-1,4-benzox-azin-3-one) is the main hydroxamic acid isolated (Meihls et al 2013;Maag et al 2014;Makowska et al 2015;Handrick et al 2016;Wouters et al 2016). DIMBOA has been shown to have a toxic effect against aphids when applied in artificial diets (Elek et al 2013a) and it has also been shown to induce callose deposition as a plant defense response (Ahmad et al 2011;Meihls et al 2013).…”

Section: Introductionmentioning

confidence: 99%

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DIMBOA levels in hexaploid Brazilian wheat are not associated with antibiosis against the cereal aphids Rhopalosiphum padi and Sitobion avenae

Pereira

Sarria

Powers

et al. 2017

Theor. Exp. Plant Physiol.

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UK variety used as reference. Bioassays were conducted to evaluate the development and fecundity of both aphids when grown on the wheat genotypes. Although BRS Guabiju and BRS Timbau´va were among the genotypes showing the highest susceptibility and resistance, respectively, against both aphid species, no correlation could be found between DIMBOA levels and antibiosis effects. The cultivar BRS 327 was among the genotypes showing lower intrinsic rate of population increase for the two aphid species. Elucidating the role of secondary metabolites in plant resistance to aphids and the characterization of the genotypes that allowed reduced development of R. padi and S. avenae are important steps to achieve a better natural resistance in hexaploid Brazilian wheat.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

DIMBOA levels in hexaploid Brazilian wheat are not associated with antibiosis against the cereal aphids Rhopalosiphum padi and Sitobion avenae

Pereira

Sarria

Powers

et al. 2017

Theor. Exp. Plant Physiol.

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“…UDP-glucosyltransferase(s) are employed to overcome a benzoxazolinone defence for the cereal pest moth, Mythimna separata larvae (Sasai et al, 2009) and the cereal aphid, Sitobion avenae (Leszczynski et al, 1992). The glycosylation product of MBOA, MBOA-N-Glc, by agricultural pests, Spodoptera littoralis (Maag et al, 2014), prevents hydrolysis of the glycosyl groups due to the nitrogen glycosylation. Interestingly, MBOA root exudation in soil functions as a chemo-attractant for western corn rootworm larvae to locate specific benzoxazolinones producing hosts (Bjostad & Hibbard, 1992).…”

Section: Pest Insect Benzoxazolinone Detoxification Mechanismsmentioning

confidence: 99%

“…Autocatalysis, liberating formic acid (Niemeyer, 1988), produces the active benzoxazolinones, which contain a nitrogenous hetero-pentacyclic ring (Maag et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

“…Detoxification of benzoxazolinones can be achieved by at least two distinct mechanisms. Plants and insects appear to utilise conjugative detoxi fication mechanisms, which include O-and N-glycosylation of the hetero-pentacyclic ring (Schulz & Wieland, 1999), and conjugation to glutathione (Maag et al, 2014;Schulz et al, 2012;Wieland et al, 1998). In contrast, fungi and bacteria use degradative detoxification mechanisms whereby the hetero-pentacyclic ring is opened and the product is either partially or completely catabolised (Chase et al, 1991;Friebe et al, 1998;Macias et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

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Degradation of the benzoxazolinone class of phytoalexins by Fusarium pseudograminearum, a pathogenic fungus of wheat

Kettle¹

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The benzoxazolinone class of phytoalexins are released by wheat, maize and rye upon pathogen attack. Benzoxazolinones have antimicrobial activity, but certain fungi have evolved mechanisms to actively detoxify these compounds, which may contribute to the virulence of these pathogens. In many Fusarium spp. a cluster of genes is thought to be involved in the detoxification of benzoxazolinones. However, only one enzyme, Fusarium Detoxification of Benzoxazolinone 2 (Fdb2), encoded in the cluster has been unequi vocally assigned a role in this process. The FDB2 gene encodes a N-malonyltransferase and was identified in the maize pathogen F. verticillioides. In this thesis, through comparative genome analysis of several Fusarium species, a conserved genomic region has been identified around FDB2. Expression analyses demonstrated that a cluster of nine genes were responsive to exogenous benzoxazolinone in the important wheat pathogen Fusarium pseudograminearum.

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Catalytic Oxidative Carbonylation of Amino Moieties to Ureas, Oxamides, 2‐Oxazolidinones, and Benzoxazolones

et al. 2015

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The direct syntheses of ureas, oxamides, 2-oxazolidinones, and benzoxazolones by the oxidative carbonylation of amines, β-amino alcohols, and 2-aminophenols allows us to obtain high value added molecules, which have a large number of important applications in several fields, from very simple building blocks. We have found that it is possible to perform these transformations using the PdI2 /KI catalytic system in an ionic liquid, such as 1-butyl-3-methylimidazolium tetrafluoroborate, as the solvent, the solvent/catalyst system can be recycled several times with only a slight loss of activity, and the product can be recovered easily by crystallization.

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3-β-d-Glucopyranosyl-6-methoxy-2-benzoxazolinone (MBOA-N-Glc) is an insect detoxification product of maize 1,4-benzoxazin-3-ones

Cited by 78 publications

References 31 publications

DIMBOA levels in hexaploid Brazilian wheat are not associated with antibiosis against the cereal aphids Rhopalosiphum padi and Sitobion avenae

DIMBOA levels in hexaploid Brazilian wheat are not associated with antibiosis against the cereal aphids Rhopalosiphum padi and Sitobion avenae

Degradation of the benzoxazolinone class of phytoalexins by Fusarium pseudograminearum, a pathogenic fungus of wheat

Catalytic Oxidative Carbonylation of Amino Moieties to Ureas, Oxamides, 2‐Oxazolidinones, and Benzoxazolones

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