Search Results (10)

Wheat (Triticum aestivum) is grown on more arable acreage than any other food crop and has been well documented to produce allelochemicals. Wheat allelochemicals include numerous benzoxazinoids and their microbially transformed metabolites that actively suppress growth of weed seedlings. Production and subsequent release of these metabolites by commercial wheat cultivars, however, has not yet been targeted by focussed breeding programmes seeking to develop more competitive crops. Recently, the Commonwealth Scientific and Industrial Organisation (CSIRO), through an extensive recurrent selection programme investment, released numerous early-vigour wheat genotypes for commercial use, but the physiological basis for their improved vigour is under investigation. In the current study, we evaluated several early-vigour genotypes alongside common commercial and heritage wheat cultivars to assess the impact of improved early vigour on the production and release of targeted benzoxazinoids by field-grown wheat roots over a two-year period. Using UPLC coupled with triple quadrupole mass spectrometry (LC-MS QQQ), we quantified common wheat benzoxazinoids and their microbially produced metabolites (aminophenoxazinones) in soil collected from the rhizosphere and rhizoplane of wheat plants over two growing seasons in the Riverina region of New South Wales, Australia. The benzoxazolinone MBOA and several aminophenoxazinones were readily detected in soil samples, but actual soil concentrations differed greatly between years and among genotypes. In contrast to 2019, the concentration of aminophenoxazinones in wheat rhizosphere soil was significantly elevated in 2020, a year receiving adequate rainfall for optimal wheat growth. Aminophenoxazinones were detected in the rhizosphere of early-vigour genotypes and also parental lines exhibiting weed suppression, suggesting that improved early vigour and subsequent weed competitiveness may be related to increased root exudation and production of microbial metabolites in addition to changes in canopy architecture or other root-related early-vigour traits. As previously reported, MBOA was detected frequently in both the rhizoplane and rhizosphere of wheat. Depending on the year and genotype, we also observed enhanced biotransformation of these metabolites to several microbially transformed aminophenoxazinones in the rhizosphere of many of the evaluated genotypes. We are now investigating the role of early-vigour traits, including early canopy closure and biomass accumulation upon improved competitive ability of wheat, which will eventually result in more cost-effective weed management. Full article

In the present study, new series of benzoxazolin-2-one linked to a variety of hydrazones and azoles were synthesized and assessed for their antibacterial properties against different bacterial microorganisms. All the synthesized target compounds were characterized by ¹H NMR, ¹³C NMR and IR spectroscopy, and elemental analysis as well. The antibacterial activity of the synthesized compounds was evaluated according to the bacteriostatic and bactericidal activity against the tested pathogen strains by determining the minimum inhibition (MIC) and minimum bactericidal (MBC) concentrations and MBC/MIC ratios. The MIC was evaluated by the broth dilution and the MBC was evaluated by plating methods. The in vitro analysis suggested that some compounds, namely, amide, 5-chlorobenzimidazole, hydrazones with a 3-chloro substitution on the additional phenyl ring, and hydrazones with 2-furyl and 5-nitro-2-furyl substituents, demonstrated wide antibacterial activity against Escherichia coli, Bacillus subtilis, Staphylococcus aureus, and Salmonella Enteritidis. The most sensitive strains appeared to be Gram-negative E. coli and Gram-positive B. subtilis, while S. aureus showed some resistance. The most resistant pathogen was found to be S. enteritidis. The remaining compounds demonstrated moderate to low antibacterial potential. The research results have shown that benzoxazolinone-based derivatives are suitable for the development of a library of compounds and can be used in the future development of antibacterial drugs against various Gram-positive and Gram-negative pathogens, which is of great importance in therapy practice. Full article

Cuscuta campestris is a parasitic weed species with noxious effects in broadleaf crops worldwide. The control of Cuscuta in the majority of crops affected is limited or non-existing. We tested, for the first time, the effect of eighteen metabolites in in vitro-grown Cuscuta seedlings. We found that 2-benzoxazolinone, hydrocinnamic acid and pisatin caused the strongest inhibition of seedling growth. In addition to seedling growth, pisatin caused necrosis of the Cuscuta seedling, occurring mostly at the seedling shoot. Scopoletin and sesamol treatments caused toxicity, observed as a black staining, only at the Cuscuta root apices, while caffeic acid, ferulic acid and vanillic acid caused toxicity, observed as brown staining, in the root apices. The structure–activity relationships in four structural derivatives of 2-benzoxazolinone, and five structural derivatives of hydrocinnamic acid, were also studied. The identification of new herbicidal modes of action against Cuscuta is the first step in creating new alternatives to sustainable chemical control of parasitic weeds. Full article

Incubation of Aminobacter aminovorans, Paenibacillus polymyxa, and Arthrobacter MPI764 with the microbial 2-benzoxazolinone (BOA)-degradation-product 2-acetamido-phenol, produced from 2-aminophenol, led to the recently identified N-(2-hydroxy-5-nitrophenyl) acetamide, to the hitherto unknown N-(2-hydroxy-5-nitrosophenyl)acetamide, and to N-(2-hydroxy-3-nitrophenyl)acetamide. As an alternative to the formation of phenoxazinone derived from aminophenol, dimers- and trimers-transformation products have been found. Identification of the compounds was carried out by LC/HRMS and MS/MS and, for the new structure N-(2-hydroxy-5-nitrosophenyl)acetamide, additionally by 1D- and 2D-NMR. Incubation of microorganisms, such as the soil bacteria Pseudomonas laurentiana, Arthrobacter MPI763, the yeast Papiliotrema baii and Pantoea ananatis, and the plants Brassica oleracea var. gongylodes L. (kohlrabi) and Arabidopsis thaliana Col-0, with N-(2-hydroxy-5-nitrophenyl) acetamide, led to its glucoside derivative as a prominent detoxification product; in the case of Pantoea ananatis, this was together with the corresponding glucoside succinic acid ester. In contrast, Actinomucor elegans consortium synthesized 2-acetamido-4-nitrophenyl sulfate. 1 mM bioactive N-(2-hydroxy-5-nitrophenyl) acetamide elicits alterations in the Arabidopsis thaliana expression profile of several genes. The most responsive upregulated gene was pathogen-inducible terpene synthase TPS04. The bioactivity of the compound is rapidly annihilated by glucosylation. Full article

The determination of the reliable thermodynamic properties of 2-benzoxazolinone derivatives is the main goal of this work. Some correlations are established between the energetic properties determined and the structural characteristics of the title compounds, and the reactivity of this class of compounds is also evaluated. Static-bomb combustion calorimetry and high-temperature Calvet microcalorimetry were used to determine, respectively, the standard molar enthalpies of formation in the solid state and the standard molar enthalpies of sublimation, both at T = 298.15 K. Using the results obtained for each compound, the respective gas-phase standard molar enthalpy of formation was derived. High-level quantum chemical calculations were performed to estimate the same property and the results evidence good accordance. Moreover, the gas-phase relative thermodynamic stability of 2-benzoxazolinone derivatives was also evaluated using the respective gas-phase standard molar Gibbs energy of formation. In addition, the relationship between the energetic and structural characteristics of the benzoxazolinones is presented, evidencing the enthalpic increments associated with the presence of a methyl and a nitro groups in the molecule, and this effect is compared with similar ones in other structurally related compounds. Full article

According to current opinion, the first step of benzoxazinoids (BXs) synthesis, that is, the conversion of indole-3-glycerol phosphate to indole, occurs exclusively in the photosynthesising parts of plants. However, the results of our previous work and some other studies suggest that this process may also occur in the roots. In this study, we provide evidence that the first step of BXs synthesis does indeed occur in the roots of rye seedlings. We detected ScBx1 transcripts, BX1 enzyme, and six BXs (2-hydroxy-1,4-benzoxazin-3-one, 2,4-dihydroxy-1,4-benzoxazin-3-one, (2R)-2-O-β-d-glucopyranosyl-4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one glucoside, 2,4-dihydroxy- 7-methoxy-1,4-benzoxazin-3-one, 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one glucoside, and 6-methoxy-2-benzoxazolinone) in the roots developed from seeds deprived of the coleoptile at 2 days after sowing (i.e., roots without contact with aerial parts). In roots regenerated in vitro, both ScBx1 transcripts and BX1 enzyme were detected at a low but still measurable levels. Thus, BXs are able to be synthesised in both the roots and above-ground parts of rye plants. Full article

6-Methoxy-2-benzoxazolinone (MBOA) is an allelochemical that is found in Poaceae and is generally associated with monocotyledon species. This compound is formed from the glycosylated form of 2,4-dihydroxy-(2H)-1,4-benzoxazin-3(4H)-one (Gly-DIMBOA) by a two-stage degradation process. The MBOA detoxification capacity of two weed species, namely Echinochloa crus-galli and Lolium rigidum, and a resistant biotype of Lolium rigidum (SLR31) was studied both qualitatively and quantitatively. The product of metabolism is similar for both weed species. This finding indicates that these weeds probably metabolize xenobiotics by an identical route, since the product detected was the same in both cases. Kinetic studies on the absorption and translocation to the shoot showed differences in these processes depending on the species. The analysis of treated plants, which were subsequently transplanted to a growth medium without xenobiotic compound, showed that the weeds studied are capable of transmitting the previously absorbed compound to the medium by root exudation. The results show that this process is another defense mechanism of plants facing external threats. Full article

Chemosensory perception in insects involves a broad set of chemosensory proteins (CSPs) that identify the bouquet of chemical compounds present in the external environment and regulate specific behaviors. The current study is focused on the Spodoptera litura (Fabricius) chemosensory-related protein, SlitCSP3, a midgut-expressed CSP, which demonstrates differential gene expression upon different diet intake. There is an intriguing possibility that SlitCSP3 can perceive food-derived chemical signals and modulate insect feeding behavior. We predicted the three-dimensional structure of SlitCSP3 and subsequently performed an accelerated molecular dynamics (aMD) simulation of the best-modeled structure. SlitCSP3 structure has six α-helices arranged as a prism and a hydrophobic binding pocket predominated by leucine and isoleucine. We analyzed the interaction of selected host plant metabolites with the modeled structure of SlitCSP3. Out of two predicted binding pockets in SlitCSP3, the plant-derived defensive metabolites 2-b-D-glucopyranosyloxy-4-hydroxy-7-methoxy-1, 4-benzoxazin-3-one (DIMBOA), 6-Methoxy-2–benzoxazolinone (MBOA), and nicotine were found to interact preferably to the hydrophobic site 1, compared to site 2. The current study provides the potential role of CSPs in recognizing food-derived chemical signals, host-plant specialization, and adaptation to the varied ecosystem. Our work opens new perspectives in designing novel pest-management strategies. It can be further used in the development of CSP-based advanced biosensors. Full article

Many cereals accumulate hydroxamic acids involved in defense of plant against various fungi, bacteria, and insects. 2,4-dihydroxy-7-methoxy-1,4-benzoxazine-3-one, commonly known as DIMBOA, is one of the principal cyclic hydroxamic acids in aqueous extracts of maize. The aim of this study was to evaluate the antibacterial activity of the isolated DIMBOA and its derivatives 2-benzoxazolinone (BOA), 6-chloro-2-benzoxazolinone (CDHB), and 2-mercaptobenzothiazole (MBT) against Ralstonia solanacearum. MBT showed the strongest antibacterial activity, followed by CDHB and DIMBOA, with minimum inhibitory concentrations (MICs) of 50, 100 and 200 mg/L, respectively, better than the BOA with 300 mg/L. These compounds also significantly affect bacterial growth, reduce biofilm formation, and inhibit swarming motility within 24 h. This paper is the first to report the anti-R. solanacearum activity of DIMBOA from Z. mays. The bioassay and pot experiment results suggested that DIMBOA and its derivatives exhibit potential as a new matrix structure of designing target bactericide or elicitor for controlling tobacco bacterial wilt. Further studies must evaluate the efficacy of DIMBOA and its derivatives in controlling bacterial wilt under natural field conditions where low inoculum concentrations exist. Full article