113565-32-5
Chemical Structure
DIMBOA-Glc
- CAS No.: 113565-32-5
- Formula:C15H19NO10
- Molecular Weight:373.31
IUPAC Name: (R)-4-hydroxy-7-methoxy-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2H-benzo[b][1,4]oxazin-3(4H)-one
InChIKey: WTGXAWKVZMQEDA-XFWGRBSCSA-N
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
Biological Activity: 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[1][2][3].
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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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References
- [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]
