Bioscience, Biotechnology, and Biochemistry
Online ISSN : 1347-6947
Print ISSN : 0916-8451
Organic Chemistry Regular Papers
Species-Specific Glucosylation of DIMBOA in Larvae of the Rice Armyworm
Hiroaki SASAIMasahiro ISHIDAKenjiro MURAKAMINaoko TADOKOROAtsushi ISHIHARARitsuo NISHIDANaoki MORI
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2009 年 73 巻 6 号 p. 1333-1338

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DIMBOA [2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one] is a benzoxazinoid (Bx), part of the chemical defense system of graminaceous plants such as maize, wheat, and rye. When Bombyx mori larvae were fed artificial diets containing DIMBOA, they died in three days. In contrast, Mythimna separata larvae, a serious pest of rice, maize, sorghum, wheat etc., grew well on the same diets. Three kinds of glucosides [1-(2-hydroxy-4-methoxyphenylamino)-1-deoxy-β-glucopyranoside-1,2-carbamate (methoxy glucoside carbamate), 2-O-β-glucopyranosyl-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA-2-O-Glc), and 2-O-β-glucopyranosyl-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (HMBOA-2-O-Glc)] were identified by LC-MS and NMR analyses from the frass of M. separata that had been fed on a DIMBOA-containing diet. Furthermore, the incubation of DIMBOA with a midgut tissue suspension of M. separata in the presence of UDP-D-glucose generated DIMBOA-2-O-Glc. These findings strongly suggest that glucosylation by UDP-glucosyltransferase(s) was important for detoxification to circumvent the defenses of host plants against M. separata larvae.
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© 2009 by Japan Society for Bioscience, Biotechnology, and Agrochemistry
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