Non‐injured maize contains several 1,4‐benzoxazin‐3‐one related compounds but only as glucoconjugates

Cambier, Vincent; Hance, Thierry; Hoffmann, Edmond de

doi:10.1002/(sici)1099-1565(199905/06)10:3<119::aid-pca450>3.3.co;2-v

Cited by 8 publications

(18 citation statements)

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“…DIBOA-Glc, DIBOA, BOA, APO, and AAPO, together with 2-aminophenol (APH) constitute a complete degradation series carried out by soil microbes, as well as by other organisms (31). DIBOA-Glc is produced by the plant and liberated as the aglucon DIBOA, which participates in the different degradation processes (7,9,10). Thus, it is interesting to compare bioactivity values for the complete series since all these compounds are together in soil while the degradation process takes place.…”

Section: Resultsmentioning

confidence: 99%

“…Interesting bioactivity was observed for both compounds, some of their degradation products, and also some synthetic analogues, being antimicrobial (3), antifeedant, insecticide (4), and phytotoxic behaviors (5, 6) widely described. The DIBOA natural glycoside (2-O--D-glucopyranosyl-4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one (DIBOA-Glc) (Table 1, A) is the form in which DIBOA is preserved inside the plant prior to its release (7). Benzoxazolin-2-one (BOA) and 6-methoxybenzoxazolin-2-one (MBOA) ( Table 2, A) are the first chemicals in the DIBOA and DIMBOA degradation series, respectively (8)(9)(10).…”

Section: Introductionmentioning

confidence: 99%

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Structure−Activity Relationships (SAR) Studies of Benzoxazinones, Their Degradation Products and Analogues. Phytotoxicity on Standard Target Species (STS)

Macías

Marı́n

Oliveros‐Bastidas

et al. 2005

J. Agric. Food Chem.

106

140

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Benzoxazinones 2,4-dihydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one (DIMBOA) and 2,4-dihydroxy-(2H)-1,4-benzoxazin-3(4H)-one (DIBOA) have been considered key compounds for understanding allelopathic phenomena in Gramineae crop plants such as corn (Zea mays L.), wheat (Triticum aestivum L.), and rye (Secale cereale L.). The degradation processes in the environment observed for these compounds, in which soil microbes are directly involved, could affect potential allelopathic activity of these plants. We present in this work a complete structure-activity relationships study based on the phytotoxic effects observed for DIMBOA, DIBOA, and their main degradation products, in addition to several synthetic analogues of them. Their effects were evaluated on standard target species (STS), which include Triticum aestivum L. . They showed high inhibitory activity over almost all species growth. The fact that APO is a degradation product from DIBOA with high phytotoxicity and stability makes it possible to assign an important ecological role regarding plant defense mechanisms. 2-Deoxy derivatives of natural benzoxazinones display a wide range of activities that allow proposing them as new leads for natural herbicide models with a 1,4-benzoxazine skeleton.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structure−Activity Relationships (SAR) Studies of Benzoxazinones, Their Degradation Products and Analogues. Phytotoxicity on Standard Target Species (STS)

Macías

Marı́n

Oliveros‐Bastidas

et al. 2005

J. Agric. Food Chem.

106

140

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“…Besides DIMBOA-Glc and HDMBOA-Glc, many maize lines produce significant amounts of other benzoxazinoid derivatives such as the 8-O-methylated compounds, 2-(2,4-dihydroxy-7,8-dimethoxy-1,4-benzoxazin-3-one)-b-D-glucopyranose (DIM 2 BOA-Glc) and 2-(2-hydroxy-4,7,8-trimethoxy-1,4-benzoxazin-3-one)-b-D-glucopyranose (HDM 2 BOA-Glc) (Cambier et al, 1999;Glauser et al, 2011). DIM 2 BOA-Glc is most likely formed through the addition of a methoxy group to DIMBOA-Glc.…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of 8-O-methylated benzoxazinoid defense compounds in maize

et al. 2016

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Benzoxazinoids are important defense compounds in grasses. Here, we investigated the biosynthesis and biological roles of the 8-O-methylated benzoxazinoids, DIM 2 BOA-Glc and HDM 2 BOA-Glc. Using quantitative trait locus mapping and heterologous expression, we identified a 2-oxoglutarate-dependent dioxygenase (BX13) that catalyzes the conversion of DIMBOA-Glc into a new benzoxazinoid intermediate (TRIMBOA-Glc) by an uncommon reaction involving a hydroxylation and a likely ortho-rearrangement of a methoxy group. TRIMBOA-Glc is then converted to DIM 2 BOA-Glc by a previously described O-methyltransferase BX7. Furthermore, we identified an O-methyltransferase (BX14) that converts DIM 2 BOA-Glc to HDM 2 BOA-Glc. The role of these enzymes in vivo was demonstrated by characterizing recombinant inbred lines, including Oh43, which has a point mutation in the start codon of Bx13 and lacks both DIM 2 BOA-Glc and HDM 2 BOA-Glc, and Il14H, which has an inactive Bx14 allele and lacks HDM 2 BOA-Glc in leaves. Experiments with near-isogenic maize lines derived from crosses between B73 and Oh43 revealed that the absence of DIM 2 BOA-Glc and HDM 2 BOA-Glc does not alter the constitutive accumulation or deglucosylation of other benzoxazinoids. The growth of various chewing herbivores was not significantly affected by the absence of BX13-dependent metabolites, while aphid performance increased, suggesting that DIM 2 BOA-Glc and/or HDM 2 BOA-Glc provide specific protection against phloem feeding insects.

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“…Many of the Poaceae contain hydroxamic acids (Hx), the main group of secondary metabolites involved in resistance against a wide variety of herbivores (Niemeyer and Perez, 1995;Sicker and Schultz, 2002). Hx are present in the intact plant as glucosides, which are hydrolyzed by β-glucosidases released upon tissue injury (Hofman and Hofmanova, 1969;Cambier et al, 1999). Hx produce behavioural, ecological and metabolic effects on S. avenae, including feeding deterrence (Niemeyer et al, 1989), decrease in performance (individual growth rates as well as intrinsic rates of population increase) (Thackray et al, 1990;Figueroa et al, 2004) and the induction of various detoxification systems (Leszczynski and Dixon, 1992;Leszczynski et al, 1994;Figueroa et al, 1999).…”

Section: Introductionmentioning

confidence: 99%

Energetic costs of detoxification systems in herbivores feeding on chemically defended host plants: a correlational study in the grain aphid,Sitobion avenae

Castañeda

Figueroa

Contreras

et al. 2009

Journal of Experimental Biology

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SUMMARYHerbivorous insects have developed mechanisms to cope with plant barriers, including enzymatic systems to detoxify plant allelochemicals. Detoxification systems may be induced when insects are feeding on plants with increasing levels of allelochemicals. Increases in enzymatic activity have been related to energetic costs, and therefore less energy may be allocated to fitness-related traits. In this study, we explored the induction and energetic costs of detoxifying hydroxamic acids (Hx; a wheat allelochemical) in the grain aphid, Sitobion avenae. Aphids were reared on three wheat cultivars with different levels of Hx (0.26±0.08, 2.09±0.6 and 5.91±1.18 mmol kg -1 fresh mass). We performed a nested ANOVA to test the effect of Hx (main factor) and intrahost variation (nested factor) on body mass, standard metabolic rate (SMR) and the enzymatic activity of cytochrome P450s monooxygenases (P450s), glutathione S-transferases (GSTs) and esterases (ESTs). We found non-significant effects of Hx levels (P>0.5 for all tests), but there was significant intrahost variation (P<0.05 for all tests). In addition, we found a negative correlation between SMR and ESTs (P=0.003) and no correlation between SMR and GSTs or P450s (P=n.s after a Bonferroni correction).Multiple regression between SMR (dependent variable) and enzymatic activities (predictor variables) was significant (P=0.007), but detoxification enzymes only explained about 5% of the variation of SMR. Finally, we found a non-significant path coefficient between 'metabolism' and 'detoxifying capacity' (P>0.05). These results suggest that increased enzymatic activities do not entail increased metabolic rate. Therefore, low energetic costs in aphids would facilitate the use of different hosts and promote a wider ecological niche.

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Non‐injured maize contains several 1,4‐benzoxazin‐3‐one related compounds but only as glucoconjugates

Cited by 8 publications

References 0 publications

Structure−Activity Relationships (SAR) Studies of Benzoxazinones, Their Degradation Products and Analogues. Phytotoxicity on Standard Target Species (STS)

Structure−Activity Relationships (SAR) Studies of Benzoxazinones, Their Degradation Products and Analogues. Phytotoxicity on Standard Target Species (STS)

Biosynthesis of 8-O-methylated benzoxazinoid defense compounds in maize

Energetic costs of detoxification systems in herbivores feeding on chemically defended host plants: a correlational study in the grain aphid,Sitobion avenae

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