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^[1][2][3].

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.

DIMBOA-Glc (natural feeding; 4 days) undergoes stereoselective conversion of (2R)-DIMBOA-Glc to (2S)-DIMBOA-Glc in Spodoptera frugiperda during digestion, with (2S)-DIMBOA-Glc being the only epimer excreted in frass^[2].
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.

373.31

C₁₅H₁₉NO₁₀

113565-32-5

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

Room temperature in continental US; may vary elsewhere.

Please store the product under the recommended conditions in the Certificate of Analysis.

• [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]