Detoxification pathways of the phytoalexins brassilexin and sinalexin in Leptosphaeria maculans: isolation and synthesis of the elusive intermediate 3-formylindolyl-2-sulfonic acid
Bibliographic record
Abstract
Brassilexin and sinalexin are among the most potent antifungal phytoalexins produced by crucifer plants. Nonetheless, the crucifer pathogen Leptosphaeria maculans(Desm.) Ces. et de Not. (asexual stage Phoma lingam(Tode ex Fr.) Desm.) is able to detoxify these phytoalexins. To understand and control these reactions, the elusive brassilexin and sinalexin detoxification pathways in L. maculans were investigated and compared to those of the synthetic derivatives 8-methylbrassilexin and 8-acetylbrassilexin. The chemical structures, syntheses and antifungal activities of the metabolic intermediates, including the most polar metabolite identified thus far, 3-formylindolyl-2-sulfonic acid, were established. Our overall findings suggest that the first detoxification step of brassilexin involves its reductive bioconversion to 3-aminomethyleneindole-2-thione, followed by hydrolysis and oxidation to the water soluble metabolite 3-formylindolyl-2-sulfonic acid.
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How this classification was reachedexpand
Full frame distilled prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one teacher head, not a consensus.
How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".