Changes in hydroxamic acid levels of wheat plants induced by aphid feeding

Niemeyer, Hermann M.; Pesel, Erika; Copaja, Sylvia V.; Bravo, Héctor R.; Franke, Stephan; Francke, Wittko

doi:10.1016/0031-9422(89)80029-9

Cited by 90 publications

(47 citation statements)

References 32 publications

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“…Higher DIMBOA concentration in flag leaves in comparison to ears at anthesis was consistent with the higher MRGR of S. avenae in ears than in flag leaves (Nicol and Wratten 1997). Besides that, the susceptibility of three grass species to Metopolophium dirhodum is related to the presence or absence of those Table 1 where the means and LSD (5%) for statistical comparison are displayed acids (Argandon˜a et al 1980), DIMBOA was shown to deter feeding by R. padi and to reduce BYDV transmission to wheat (Givovich and Niemeyer 1991) and effects of hydroxamic acids in aphid performance was also reported by others (Niemeyer et al 1989;Bravo and Copaja 2002). When consid-ering only BRS Timbau´va and BRS Guabiju, two of the wheat genotypes evaluated here, it is clear that an association exist between the DIMBOA and the plant resistance against S. avenae and R. padi.…”

Section: Discussionsupporting

confidence: 85%

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: Discussionsupporting

confidence: 85%

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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“…Given that previous work showed 48 hr of continuous aphid infestation as sufficient to generate IR of Hx in wheat (Niemeyer et al, 1989;, we evaluated whether 16 hr of infestation could trigger IR as well. In order to determine whether a hypothetical lack of IR at the end of the 16-hr infestation could be due to either an insufficient stimulus or to a temporal constraint to the expression of the response, a treatment was included consisting of 16 hr of infestation and Hx analysis 32 hr later (to complete 48 hr from the onset of infestation until chemical analysis).…”

Section: Methodsmentioning

confidence: 99%

“…Hydroxamic acids (Hx) are defensive metabolites typical of Gramineae (Niemeyer and Perez, 1995). Hx are induced in wheat by aphid feeding, and this induction is affected by plant genotype (Niemeyer et al, 1989), aphid genotype , and environmental conditions . In addition, constitutive accumulation of Hx reduced aphid infestation in the field but did not impose a cost in grain yield to wheat cultivars .…”

Section: Introductionmentioning

confidence: 99%

Characteristics of Hydroxamic Acid Induction in Wheat Triggered by Aphid Infestation

Gianoli

Niemeyer

1997

J Chem Ecol

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Abstract-Hydroxamic acids (Hx) are natural products of Gramineae that are associated with cereal resistance to pests. We aimed at characterizing the induction of Hx accumulation in seedlings of wheat, Triticum aestivum, by short-term infestation of the cereal aphid, Rhopalosiphum padi. A load of 25 aphids increased significantly the Hx levels in the infested primary leaf in comparison with control levels. Lower loads did not increase Hx concentration. Aphid infestation lasting 16 hr did not elicit induction of Hx, even after a time-lag of 32 hr to allow the expression of any induced response. Fortyeight hours was the minimum duration of aphid infestation required to trigger Hx induction. The age of the infested tissue (the primary leaf) did not affect induction. Similar increases of Hx were found in unfolding, expanding, and totally expanded primary leaves. It was determined that the regime of nutrient supply (N-intensive nutritive solutions at low and high concentration) to wheat seedlings had no effect on the magnitude of the aphid-induced Hx (N-based secondary metabolites). Results obtained are discussed in the framework of general theories of plant defense allocation.

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“…As plantas produzem metabólitos secundários, chamados substâncias alelopáticas ou aleloquímicos, que atuam na sua defesa contra herbívoros, patógenos ou mesmo contra plantas competidoras 1 . Estudos têm demonstrado que ácidos hidroxâmicos (Hx) cíclicos do tipo 4-hidróxi-1,4-benzoxazin-3-onas (benzoxazinóides), presentes em cereais na forma de 2-β-O-D-glicosídeos, atuam sobre insetos, fungos e bactérias [2][3][4][5] . Os glicosídeos são biologicamente inativos, mas a ruptura das células vegetais libera β-glicosidases que degradam os glicosídeos enzimaticamente, liberando as agliconas tóxicas 6 .…”

Section: Introductionunclassified

“…Em solução aquosa, 1 está em equilíbrio com a forma aldólica 2 (Figura 1) 7 . A participação desse Hx na defesa do trigo contra insetos é sugerida pelo aumento de seus níveis na planta após infestação por afídios 3,5 e pelo seu efeito anti-alimentar em insetos alimentados com dietas artificiais contendo 1 8 . Existem várias indicações quanto aos possíveis sítios bioquímicos de ação dos áci-dos hidroxâmicos.…”

Section: Introductionunclassified

Estudo semi-empírico de ácidos hidroxâmicos: ácido formoidroxâmico e derivados do aleloquímico dimboa

Sant’Anna

Souza

2001

Quím. Nova

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Recebido em 22/3/00; aceito em 5/2/01 A SEMIEMPIRICAL STUDY ON HYDROXAMIC ACIDS: FORMOHYDROXAMIC ACID AND DERIVATIVES OF THE ALLELOCHEMICAL DIMBOA. Open chain hydroxamic acid (Hx) can exist as Z and E diastereomers of two tautomers, hydroxamic acid and hydroximic acid. The conformational stability of the formohydroxamic acid isomers evaluated by PM3 compared better to ab initio results from the literature than AM1 results. Structural data of the cyclic Hx 2,4-dihydroxy-7-metoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA) obtained by both semiempirical methods compared well to ab initio results. pK a data from the literature for derivatives of the aldolic isomer of DIMBOA were compared to the stability of the anions resulting from the loss of protons of their phenol and hydroxamic acid groups, determined as the difference in heat of formation between anionic and neutral forms, calculated by AM1 and PM3 methods. Good correlations between theoretical and experimental data were obtained for both semiempirical methods.Keywords: semiempirical; hydroxamic acids; acidity. Quim. Nova, Vol. 24, No. 5, 583-587, 2001. Artigo INTRODUÇÃOTodos os anos a produção mundial de grãos sofre grandes perdas, tanto em quantidade quanto em qualidade, devido à infestação por pragas, principalmente insetos. Além do custo elevado, o uso em larga escala de inseticidas sintéticos para o controle dos insetos tem resultado na perda de eficiência devido ao desenvolvimento de resistência pelos insetos e em efeitos danosos sobre o meio ambiente. A investigação dos mecanismos naturais de defesa das plantas contra organismos agressores é uma possível fonte de alternativas para o desenvolvimento de novas classes de inseticidas. As plantas produzem metabólitos secundários, chamados substâncias alelopáticas ou aleloquímicos, que atuam na sua defesa contra herbívoros, patógenos ou mesmo contra plantas competidoras 1 . Estudos têm demonstrado que ácidos hidroxâmicos (Hx) cíclicos do tipo 4-hidróxi-1,4-benzoxazin-3-onas (benzoxazinóides), presentes em cereais na forma de 2-β-O-D-glicosídeos, atuam sobre insetos, fungos e bactérias 2-5 . Os glicosídeos são biologicamente inativos, mas a ruptura das células vegetais libera β-glicosidases que degradam os glicosídeos enzimaticamente, liberando as agliconas tóxicas 6 . O Hx predominante no trigo e no milho é a 2,4-diidroxi-7-metoxi-1,4-benzoxazin-3-ona (DIMBOA, 1, Figura 1), isolada sob a forma do glicosídeo (2R)-2-β-glicopiranosiloxi-4-hidroxi-7-metoxi-2H-1,4-benzoxazin-3-ona 6 . Em solução aquosa, 1 está em equilíbrio com a forma aldólica 2 (Figura 1) 7 . A participação desse Hx na defesa do trigo contra insetos é sugerida pelo aumento de seus níveis na planta após infestação por afídios 3,5 e pelo seu efeito anti-alimentar em insetos alimentados com dietas artificiais contendo 1 8 . Existem várias indicações quanto aos possíveis sítios bioquímicos de ação dos áci-dos hidroxâmicos. Foi demonstrado que 1 inibe enzimas envolvidas na síntese de ATP 9 , a acilcolinaesterase (acilcolina hidrolase) 10 , a enzima destoxi...

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Changes in hydroxamic acid levels of wheat plants induced by aphid feeding

Cited by 90 publications

References 32 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

Characteristics of Hydroxamic Acid Induction in Wheat Triggered by Aphid Infestation

Estudo semi-empírico de ácidos hidroxâmicos: ácido formoidroxâmico e derivados do aleloquímico dimboa

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