Benzoxazinoids–cyclic hydroxamic acids, lactams and their corresponding glucosides in the genus Aphelandra (Acanthaceae)

Baumeler, Andreas; Hesse, Manfred; Werner, Christa

doi:10.1016/s0031-9422(99)00508-7

Cited by 67 publications

(47 citation statements)

References 24 publications

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“…All spectral data corresponded well with those of authentic 2-O--D-glucopyranosyl-7-methoxy-2H-1,4-benzoxazin-3(4H)-one. 21) The amounts of methoxy glucoside carbamate, DIMBOA, DIMBOA-2-O-Glc, HMBOA-2-O-Glc and MBOA in the frass of M. separata larvae that had been fed on DIMBOA were determined to be 125:1 AE 6:0, 5:8 AE 0:5, 321:9 AE 33:3, 111:4 AE 12:5, and 4:2 AE 0:5 mg/larva, respectively (mean AE SEM, n ¼ 6, Fig. 4).…”

Section: Resultsmentioning

confidence: 99%

Species-Specific Glucosylation of DIMBOA in Larvae of the Rice Armyworm

Sasai

Ishida

Murakami

et al. 2009

Bioscience, Biotechnology, and Biochemistry

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DIMBOA[2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one] is a benzoxazinoid (Bx), part of the chemical defense system of graminaceous plants such as maize, wheat, and rye. When Bombyx mori larvae were fed artificial diets containing DIMBOA, they died in three days. In contrast, Mythimna separata larvae, a serious pest of rice, maize, sorghum, wheat etc., grew well on the same diets. Three kinds of glucosides [1-(2-hydroxy-4-methoxyphenylamino)-1-deoxy--glucopyranoside-1,2-carbamate (methoxy glucoside carbamate), 2-O--glucopyranosyl-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA-2-O-Glc), and 2-O--glucopyranosyl-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (HMBOA-2-O-Glc)] were identified by LC-MS and NMR analyses from the frass of M. separata that had been fed on a DIMBOA-containing diet. Furthermore, the incubation of DIMBOA with a midgut tissue suspension of M. separata in the presence of UDP-D-glucose generated DIMBOA-2-O-Glc. These findings strongly suggest that glucosylation by UDP-glucosyltransferase(s) was important for detoxification to circumvent the defenses of host plants against M. separata larvae.

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Section: Resultsmentioning

confidence: 99%

Species-Specific Glucosylation of DIMBOA in Larvae of the Rice Armyworm

Sasai

Ishida

Murakami

et al. 2009

Bioscience, Biotechnology, and Biochemistry

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“…The method used here was adapted from Baumeler et al (2000). An ACE C-18 column (dimension l ˚ 250 9 4.6 mm, particle size 5 m, pore size 100 A) was used in a DGU-20A5 Prominence Degasser (Shimadzu) and the mobile phase involved deionized water plus 0.…”

Section: High Pressure Liquid Chromatography (Hplc)mentioning

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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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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“…plants, the lactams 2-hydroxy-1,4-benzoxazin-3(2H)-one (HBOA) and 2-hydroxy-7-methoxy-1,4-benzoxazin-3(2H)-one (HMBOA), the hydroxamic acids 2,4-dihydroxy-1,4-benzoxazin-3(4H)-one (DIBOA) and 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3(4H)-one (DIMBOA) (Fig. 1), and the corresponding glucosides are accumulated (2). As soon as the integrity of the cells is ruptured, rapid deglucosylation leads to the aglucons.…”

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confidence: 99%

Biotransformation of 2-Benzoxazolinone and 2-Hydroxy-1,4-Benzoxazin-3-one by Endophytic Fungi Isolated from Aphelandra tetragona

Zikmundová

Drandarov

Bigler

et al. 2002

Appl Environ Microbiol

136

116

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The biotransformation of the phytoanticipins 2-benzoxazolinone (BOA) and 2-hydroxy-1,4-benzoxazin-3-one (HBOA) by four endophytic fungi isolated from Aphelandra tetragona was studied. Using high-performance liquid chromatography-mass spectrometry, several new products of acylation, oxidation, reduction, hydrolysis, and nitration were identified. Fusarium sambucinum detoxified BOA and HBOA to N-(2-hydroxyphenyl)malonamic acid. Plectosporium tabacinum, Gliocladium cibotii, and Chaetosphaeria sp. transformed HBOA to 2-hydroxy-N-(2-hydroxyphenyl)acetamide, N-(2-hydroxyphenyl)acetamide, N-(2-hydroxy-5-nitrophenyl)acetamide, N-(2-hydroxy-3-nitrophenyl)acetamide, 2-amino-3H-phenoxazin-3-one, 2-acetylamino-3H-phenoxazin-3-one, and 2-(N-hydroxy)acetylamino-3H-phenoxazin-3-one. BOA was not degraded by these three fungal isolates. Using 2-hydroxy-N-(2-hydroxyphenyl)[ 13 C 2 ]acetamide, it was shown that the metabolic pathway for HBOA and BOA degradation leads to o-aminophenol as a key intermediate.

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Benzoxazinoids–cyclic hydroxamic acids, lactams and their corresponding glucosides in the genus Aphelandra (Acanthaceae)

Cited by 67 publications

References 24 publications

Species-Specific Glucosylation of DIMBOA in Larvae of the Rice Armyworm

Species-Specific Glucosylation of DIMBOA in Larvae of the Rice Armyworm

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

Biotransformation of 2-Benzoxazolinone and 2-Hydroxy-1,4-Benzoxazin-3-one by Endophytic Fungi Isolated from Aphelandra tetragona

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