DIMBOA-Glc
DIMBOA-Glc is a benzoxazinoid glucoside insecticide that exists in two epimeric forms. DIMBOA-Glc helps enhance the resistance of maize to lepidopteran larvae. When plant cells rupture, plant-derived (2R)-DIMBOA-Glc interacts with glucosidases and undergoes hydrolysis to produce toxic DIMBOA for defense against infestation. The accumulation process of DIMBOA-Glc is negatively regulated by ZmMPK6 and the ethylene signaling pathway. DIMBOA-Glc does not react with plant glucosidases and can act as a detoxification metabolite to help insects counter plant defenses.
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- CAS No.: 113565-32-5
- Formule: C15H19NO10
- Masse moléculaire:373.31
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Stockage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Activité biologique
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Chemical Information
- Pureté et documentation
- Références
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Help & FAQs
Activité biologique
Description
In Vitro
Supplementary ethylene suppresses the elevated levels of DIMBOA-Glc in ZmMPK6-silenced maize lines L1 and L2 treated with simulated herbivorous insect feeding, restoring them to the levels observed in the wild-type maize inbred line A188[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
DIMBOA-Glc (natural feeding; 8 h) is inert towards plant glucosidases as (2S)-DIMBOA-Glc, preventing hydrolysis back to the toxic DIMBOA aglucone in Spodoptera littoralis gut contents[2].
DIMBOA-Glc (natural feeding; 48 h) is produced and excreted in frass as part of a detoxification strategy in Spodoptera frugiperda, Spodoptera littoralis, and Spodoptera exigua[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 113565-32-5
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Masse moléculaire 373.31
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Formule C15H19NO10
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SMILES
ON1C2=CC=C(OC)C=C2O[C@@H](C1=O)O[C@@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)CO
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Structure Classification
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Initial Source
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Livraison
Room temperature in continental US; may vary elsewhere.
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Stockage
Please store the product under the recommended conditions in the Certificate of Analysis.
Pureté et documentation
Références
[1]. Zhang C, et al. ZmMPK6 and ethylene signalling negatively regulate the accumulation of anti-insect metabolites DIMBOA and DIMBOA-Glc in maize inbred line A188. New Phytol. 2021;229(4):2273-2287. [Content Brief]
[2]. Wouters FC, et al. Reglucosylation of the benzoxazinoid DIMBOA with inversion of stereochemical configuration is a detoxification strategy in lepidopteran herbivores. Angew Chem Int Ed Engl. 2014;53(42):11320-11324. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
DIMBOA-Glc Related Classifications
HY-W751266 Related Classifications
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