Reglucosylation of the Benzoxazinoid DIMBOA with Inversion of Stereochemical Configuration is a Detoxification Strategy in Lepidopteran Herbivores

Wouters, Felipe C.; Reichelt, Michael; Glauser, Gaétan; Bauer, Eugen; Erb, Matthias; Gershenzon, Jonathan; Vassão, Daniel G. (2014). Reglucosylation of the Benzoxazinoid DIMBOA with Inversion of Stereochemical Configuration is a Detoxification Strategy in Lepidopteran Herbivores. Angewandte Chemie (International ed.), 53(42), pp. 11320-11324. Wiley-VCH 10.1002/anie.201406643

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Benzoxazinoids are chemical defenses against herbivores and are produced by many members of the grass family. These compounds are stored as stable glucosides in plant cells and require the activity of glucosidases to release the corresponding toxic aglucones. In maize leaves, the most abundant benzoxazinoid is (2R)-DIMBOA-Glc, which is converted into the toxic DIMBOA upon herbivory. The ways in which three Spodoptera species metabolize this toxin were investigated. (2S)-DIMBOA-Glc, an epimer of the initial plant compound, was observed in the insect frass, and the associated glucosyltransferase activity was detected in the insect gut tissue. The epimeric glucoside produced by the insect was found to be no longer reactive towards plant glucosidases and thus cannot be converted into a toxin. Stereoselective reglucosylation thus represents a detoxification strategy in Spodoptera species that might help to explain their success as agricultural pests on benzoxazinoid-containing crops.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Department of Biology > Institute of Plant Sciences (IPS) > Biotic Interactions
08 Faculty of Science > Department of Biology > Institute of Plant Sciences (IPS)

UniBE Contributor:

Erb, Matthias

Subjects:

500 Science > 580 Plants (Botany)

ISSN:

1433-7851

Publisher:

Wiley-VCH

Language:

English

Submitter:

Peter Alfred von Ballmoos-Haas

Date Deposited:

10 Jul 2015 13:35

Last Modified:

10 Jul 2015 13:35

Publisher DOI:

10.1002/anie.201406643

PubMed ID:

25196135

Uncontrolled Keywords:

detoxification; diastereoselectivity; glycosylation; insect biochemistry; plant defenses

BORIS DOI:

10.7892/boris.70152

URI:

https://boris.unibe.ch/id/eprint/70152

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