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Non-injured maize contains several 1,4-benzoxazin-3-one related compounds but only as glucoconjugates

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Cambier, V Hance, Thierry [UCL] de Hoffmann, Edmond [UCL]

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.

Document type Article de périodique (Journal article) – Article de recherche
Publication date 1999
Language Anglais
Journal information "Phytochemical Analysis" - Vol. 10, no. 3, p. 119-126 (1999)
Peer reviewed yes
Publisher John Wiley & Sons Ltd (W Sussex)
issn 0958-0344
e-issn 1099-1565
Publication status Publié
Affiliation UCL - SC/BIOL - Département de biologie
Keywords mass spectrometry ; maize ; hydroxamic acids ; benzoxazinones ; DIMBOA ; plant resistance
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Bibliographic reference Cambier, V ; Hance, Thierry ; de Hoffmann, Edmond. Non-injured maize contains several 1,4-benzoxazin-3-one related compounds but only as glucoconjugates. In: Phytochemical Analysis, Vol. 10, no. 3, p. 119-126 (1999)
Permanent URL http://hdl.handle.net/2078.1/44437