<i>Pantoea ananatis</i> Converts MBOA to 6-Methoxy-4-nitro-benzoxazolin-2(3<i>H</i>)-one (NMBOA) for Cooperative Degradation with its Native Root Colonizing Microbial Consortium

Schulz, Margot; Hofmann, Diana; Sicker, Dieter; Hennig, Lothar; Schütz, Vadim; Preusche, Matthias; Thiele, Björn

doi:10.1177/1934578x1801301010

Cited by 7 publications

(13 citation statements)

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“…MBOA is another substrate for bacterial nitration, which lead to 6-methoxy-4-nitro-benzoxazolin-2(3H)-one (NMBOA,18). Nitration of MBOA also occurs spontaneously, as found for the generation of NBOA-6-OH, but at a much slower rate (Schulz et al, 2018). Therefore, the nitration of MBOA is a rate limiting step.…”

Section: Nitration Of Benzoxazolinones By Bacteriamentioning

confidence: 84%

“…The compound can be attached to cellular surfaces, as found with the yeast Papiliotrema baii. NBOA-6-OH and NMBOA are degraded by P. ananatis and the A. elegans consortium (Schulz et al, 2017b(Schulz et al, , 2018. Hydroxylation of BOA prevents its degradation to AP and subsequent formation of APO or AAPO (19).…”

Section: Nitration Of Benzoxazolinones By Bacteriamentioning

confidence: 99%

“…The growth of the microorganisms was monitored by OD 600 determination over a period of 72 h if not otherwise noted. Next, 200µL aliquots were obtained at t 0 and every 24 h for HPLC/DAD (Shimadzu) analyses using the method described by Schulz et al (2018). At the end of the incubation period, the cultures including the microorganisms were extracted with ethyl acetate and the organic and aqueous phases evaporated.…”

Section: Incubations With Microorganismsmentioning

confidence: 99%

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Conversions of Benzoxazinoids and Downstream Metabolites by Soil Microorganisms

et al. 2019

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Benzoxazinoids, secondary metabolites of several Poaceae, and some benzoxazinoid downstream metabolites are bioactive compounds that act as allelochemicals and natural pesticides. Since a short lifetime of the substances is crucial to avoid long-term environmental effects, total degradation by microorganisms is of exceptional importance. We performed a screening with cultivable microorganisms (Species names and strain numbers: Mycobacterium fortuitum, 7; Bacillus aryabhattai, 34; Bacillus cereus, 59; Bacillus megaterium, 21, 48; Bacillus methylotrophicus, 58; Lysinibacillus xylanilyticus, 56; Paenibacillus polymyxa, 51; Aminobacter aminovorans, 49; the fungi Papulaspora sepedonioides, 12 and Trichoderma viride, 47) isolated from soil previously used for wheat and Persian clover mixed-culture systems to assess their behavior in the presence of the compounds. The microorganisms were exposed to glucosylated benzoxazinones, the benzoxazinones HBOA, DIBOA, and DIMBOA, the benzoxazolinones BOA, BOA-6-OH, and MBOA, and to several downstream products (AP, AAP, oHPMA, glucoside carbamate) in liquid culture to avoid interferences with soil minerals and other organisms. The microorganisms differed strongly in their metabolic activities in terms of growth, compound modification, and degradation. We observed degradation with DIBOA and GDIMBOA but rarely with DIMBOA, whereas BOA and MBOA showed almost no degradation when directly applied. Hydroxylation of BOA and demethylation of MBOA by the plant, resulting in BOA-6-OH, activated the benzoxazolinones for bacterial nitration. The resulting NBOA-6-OH was short-lived but could function temporarily as an allelochemical by inhibiting photosynthesis, e.g., in young seedlings of cress and kohlrabi. The BOA downstream products AP and oHPMA were converted to AAP, which can be nitrated to N-(2-OH-5-nitrophenyl)-acetamide and then degraded by A. aminovorans (49) and P. polymyxa (51). Only P. sepedonioides (12) and P. polymyxa (51) failed in the conversion of HBOA into AAP. While DIBOA, DIMBOA, MBOA, NBOA-6-OH, AP, AAP, and oHPMA reduced the growth of most microorganisms, glucoside carbamate promoted their growth. GDIMBOA had a stimulatory effect toward the fungi and three bacterial species. These findings lead to the hypothesis that in a natural habitat, such as the root surface, microorganisms may cooperate, perhaps by involving the plant, for the successful elimination of benzoxazinoids and their downstream metabolites.

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Section: Nitration Of Benzoxazolinones By Bacteriamentioning

confidence: 84%

Section: Nitration Of Benzoxazolinones By Bacteriamentioning

confidence: 99%

Section: Incubations With Microorganismsmentioning

confidence: 99%

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Conversions of Benzoxazinoids and Downstream Metabolites by Soil Microorganisms

et al. 2019

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“…AP, MBOA, BOA-6-OH, and picolinic acid were purchased from Sigma-Merck, Germany. Nitrated BOA-6-OH and MBOA were synthesized (Schulz et al 2017a(Schulz et al , b, 2018. Growth was monitored every 24 h for a total of 72 h by measuring the OD 600 of culture aliquots.…”

Section: Growth Of Trichoderma Viride F-00612 In Liquid Culture Supplmentioning

confidence: 99%

“…This substitution allows for subsequent microbial degradation. Several soil bacteria isolates, two fungal species (Papulaspora sepedonioides and Trichoderma viride), and an Actinomucor elegans microbial consortium isolated from the Abutilon theophrasti root surface quickly degrade the nitro compound (Schulz et al 2017a(Schulz et al , b, 2018Schütz et al 2019).…”

Section: Introductionmentioning

confidence: 99%

The Trichoderma viride F-00612 consortium tolerates 2-amino-3H-phenoxazin-3-one and degrades nitrated benzo[d]oxazol-2(3H)-one

et al. 2020

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Numerous allelopathic plant secondary metabolites impact plant-microorganism interactions by injuring plant-associated beneficial bacteria and fungi. Fungi belonging to the genus Trichoderma positively influence crops, including benzoxazinonecontaining maize. However, benzoxazinones and their downstream metabolites such as benzoxazolinone and phenoxazinones are often fungitoxic. Specimen Trichoderma viride F-00612 was found to be insensitive to 100-µM phenoxazinone and 500-µM benzoxazolinone. Screening of 46 additional specimens of ascomycetes revealed insensitivity to phenoxazinones among fungi that cause disease in benzoxazinone-producing cereal crops, whereas many other ascomycetes were highly sensitive. In contrast, most of the screened fungi were insensitive to benzoxazolinone. T. viride F-00612 was associated with bacteria and, thus, existed as a consortium. By contrast, Enterobacter species and Acinetobacter calcoaceticus were prominent in the original specimen, and Bacillus species predominated after antibiotic application. Prolonged cultivation of T. viride F-00612 in liquid medium and on Czapek agar in the presence of < 100 µM phenoxazinone and < 500 µM benzoxazolinone resulted in a massive loss of bacteria accompanied by impacted fungal growth in the presence of phenoxazinone. The original consortium was actively involved in implementing metabolic sequences for the degradation and detoxification of nitrated benzoxazolinone derivatives. The 2-aminophenol was rapidly converted into acetamidophenol, but benzoxazolinone, methoxylated benzoxazolinone, and picolinic acid remained unchanged. Excluding phenoxazinone, none of the tested compounds markedly impaired fungal growth in liquid culture. In conclusion, members of the T. viride F-00612 consortium may contribute to the ability to manage benzoxazinone downstream products and facilitate BOA-6-OH degradation via nitration.

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Genomics-based annotations help unveil the molecular composition of edible plants

Ofaim

Menichetti

Sebek

et al. 2022

Preprint

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Given the important role food plays in health and wellbeing, the past decades have seen considerable experimental efforts dedicated to mapping the chemical composition of food ingredients. As the composition of raw food is genetically predetermined, here we ask, to what degree can we rely on genomics to predict the chemical composition of natural ingredients. We therefore developed tools to unveil the chemical composition of 75 edible plants genomes, finding that genome-based annotations increase the number of compounds linked to specific plants by 42 to 100%. We rely on Gibbs free energy to identify compounds that accumulate in plants, i.e., those that are more likely to be detected experimentally. To quantify the accuracy of our predictions, we performed untargeted metabolomics on 13 plants, allowing us to experimentally confirm the detectability of the predicted compounds. For example, we find 59 novel compounds in corn, predicted by genomics annotations and supported by our experiments, but previously not assigned to the plant. Our study shows that genome-based annotations can lead to an integrated metabologenomics platform capable of unveiling the chemical composition of edible plants, and the biochemical pathways responsible for the observed compounds.

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Pantoea ananatis Converts MBOA to 6-Methoxy-4-nitro-benzoxazolin-2(3H)-one (NMBOA) for Cooperative Degradation with its Native Root Colonizing Microbial Consortium

Cited by 7 publications

References 11 publications

Conversions of Benzoxazinoids and Downstream Metabolites by Soil Microorganisms

Conversions of Benzoxazinoids and Downstream Metabolites by Soil Microorganisms

The Trichoderma viride F-00612 consortium tolerates 2-amino-3H-phenoxazin-3-one and degrades nitrated benzo[d]oxazol-2(3H)-one

Genomics-based annotations help unveil the molecular composition of edible plants

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