Non-injured maize contains several 1,4-benzoxazin-3-one related compounds but only as glucoconjugates
(1999) Phytochemical Analysis — Vol. 10, n° 3, p. 119-126 (1999)
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- Abstract
- DIMBOA (2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one) and its derivatives are known to participate in the resistance of the Poaceae to several pests. A more efficient analytical method for the determination of these compounds is reported, employing high performance liquid chromatography coupled with UV and atmospheric pressure chemical ionisation-tandem mass spectrometric detection. The results showed that in non-injured 5 or 15-day-old plants only the glucosylated forms of DIMBOA and related compounds were present: aglycones were only detected when enzymatic deglucosylation occurred during sample work-up. Maize plants contain seven glucosides related to DIMBOA belonging to three classes: hydroxamates, lactams and N-O-methylated hydroxamate derivatives. Rarely reported dimethoxylated compounds and 8-methoxy-N-O-methylated DIMBOA are now reported in the Poaceae, the latter for the first time. Their presence and relative concentrations in 5 and 15-day-old maize roots and aerial parts are discussed. The non-hydroxamic N-O-methylated DIMBOA is present in the plant in significant quantities which exceed all others in 15-day-old maize roots. After enzymatic degradation, deglucosylation products from hydroxamates and lactams are observed. The N-O-methylated deglucosylated compounds are not observed as they are chemically degraded, most probably to benzoxazolinone derivatives. The results reported here provide a new view on the DIMBOA-related compounds present in maize plants, and the implications of these findings are discussed. Copyright (C) 1999 John Whey & Sons, Ltd.
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Cambier, V., Hance, T., & de Hoffmann, E. (1999). Non-injured maize contains several 1,4-benzoxazin-3-one related compounds but only as glucoconjugates. Phytochemical Analysis, 10(3), 119-126. https://doi.org/10.1002/(SICI)1099-1565(199905/06)10:3<119::AID-PCA450>3.0.CO;2-3 (Original work published 1999)