Occurrence of 2-(2-Hydroxy-4,7-dimethoxy-2H-1,4-benzoxazin-3-one)- β-ᴅ-glucopyranoside in Triticum aestivum Leaves and Its Conversion into 6-Methoxy-benzoxazolinone

Grambow, Hans J.; Lückge, Johanna; Klausener, Alexander; Müller, E.

doi:10.1515/znc-1986-7-804

Cited by 46 publications

(31 citation statements)

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“…As compared to DIMBOA levels in young leaves, the low levels in stems likely fail to afford sufficient protection. We demonstrate that ECB and the concurrent application of JA and ACC induces HDMBOA-Glc in stems, but far less is known regarding the activity of this compound, in part because benzoxazinoids such as HDMBOA are highly unstable (Woodward et al 1978;Grambow et al 1986). There are studies suggesting that HDMBOA can have anti-insect activity (Hedin et al 1993;Cambier et al 2001), but the effect of HDMBOA on ECB has not yet been investigated.…”

Section: Discussionmentioning

confidence: 88%

Rapidly Induced Chemical Defenses in Maize Stems and Their Effects on Short-term Growth of Ostrinia nubilalis

et al. 2011

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Plants damaged by insect herbivory often respond by inducing a suite of defenses that can negatively affect an insect's growth and fecundity. Ostrinia nubilalis (European corn borer, ECB) is one of the most devastating insect pests of maize, and in the current study, we examined the early biochemical changes that occur in maize stems in response to ECB herbivory and how these rapidly induced defenses influence the growth of ECB. We measured the quantities of known maize defense compounds, benzoxazinoids and the kauralexin class of diterpenoid phytoalexins. ECB herbivory resulted in decreased levels of the benzoxazinoid, 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one)-β-D-glucopyranose (DIMBOA-Glc), and a corresponding increase in 2-(2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one)-β-D-glucopyranose (HDMBOA-Glc). Total quantities of benzoxazinoids and kauralexins were increased as early as 24 h after the initiation of ECB feeding. The plant hormones, jasmonic acid (JA) and ethylene (ET), and the transcripts encoding their key biosynthetic enzymes also accumulated in response to ECB herbivory, consistent with a role in defense regulation. The combined pharmacological application of JA and the ET precursor, 1-aminocyclopropane-1-carboxylic acid to stem internode tissue likewise resulted in changes in benzoxazinoids similar to that observed with ECB damage. Despite the fact that maize actively mounts a defense response to ECB stem feeding, no differences in percent weight gain were observed between ECB larvae that fed upon non-wounded control tissues compared to tissues obtained from plants previously subjected to 24 h ECB stem herbivory. These rapid defense responses in maize stems do not appear to negatively impact ECB growth, thus suggesting that ECB have adapted to these induced biochemical changes.

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Section: Discussionmentioning

confidence: 88%

Rapidly Induced Chemical Defenses in Maize Stems and Their Effects on Short-term Growth of Ostrinia nubilalis

et al. 2011

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“…Tissue maceration by chewing herbivores results in the release of active aglucones by the action of endogenous b-glucosidases (Figure 1). The nonenzymatic breakdown of the major aglucone DIMBOA results in the formation of 6-methoxybenzoxalin-3-one, which is insect deterrent (Grambow et al, 1986). Insect feeding also induces enzymatic conversion of DIMBOA-Glc to HDMBOA-Glc (Oikawa et al, 2004;Dafoe et al, 2011;Glauser et al, 2011).…”

Section: Introductionmentioning

confidence: 99%

Natural Variation in Maize Aphid Resistance Is Associated with 2,4-Dihydroxy-7-Methoxy-1,4-Benzoxazin-3-One Glucoside Methyltransferase Activity

et al. 2013

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Plants differ greatly in their susceptibility to insect herbivory, suggesting both local adaptation and resistance tradeoffs. We used maize (Zea mays) recombinant inbred lines to map a quantitative trait locus (QTL) for the maize leaf aphid (Rhopalosiphum maidis) susceptibility to maize Chromosome 1. Phytochemical analysis revealed that the same locus was also associated with high levels of 2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one glucoside (HDMBOA-Glc) and low levels of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one glucoside (DIMBOA-Glc). In vitro enzyme assays with candidate genes from the region of the QTL identified three O-methyltransferases (Bx10a-c) that convert DIMBOA-Glc to HDMBOA-Glc. Variation in HDMBOA-Glc production was attributed to a natural CACTA family transposon insertion that inactivates Bx10c in maize lines with low HDMBOA-Glc accumulation. When tested with a population of 26 diverse maize inbred lines, R. maidis produced more progeny on those with high HDMBOA-Glc and low DIMBOA-Glc. Although HDMBOA-Glc was more toxic to R. maidis than DIMBOA-Glc in vitro, BX10c activity and the resulting decline of DIMBOA-Glc upon methylation to HDMBOA-Glc were associated with reduced callose deposition as an aphid defense response in vivo. Thus, a natural transposon insertion appears to mediate an ecologically relevant trade-off between the direct toxicity and defense-inducing properties of maize benzoxazinoids.

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“…The proportional composition of benzoxazolinones may be influenced by the vacuolar environment, as production of DIMBOA-Glc can be affected by pH (Hashimoto & Shudo, 1996). The conversion of DIMBOA-Glc to HDMBOA-Glc, in maize (Klun et al, 1970) and wheat shoots (Wu et al, 1999), has been proposed to be a duplication of MBOA production, as both precursors lead eventually to MBOA (Grambow et al, 1986), and may accelerate formation of MBOA in response to pathogen attack (Oikawa et al, 2004). As biotic stress induces higher HDMBOA (a di-methoxylated BOA) accumulation, Glauser et al (2011) proposed that from an evolutionary perspective that DIBOA to DIMBOA to HDMBOA is a developmental progression of benzoxazinones.…”

Section: Production Of Benzoxazinoids In Cerealsmentioning

confidence: 99%

“…Upon cellular rupture and/or pathogen attack the glycosylation is removed via beta-glucosidase (Glu1 or Glu2) (Wahlroos & Virtanen, 1959) to produce the unstable intermediates: 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA), 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA), and 2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-o ne (HDMBOA) (Oikawa et al, 2004). The deglycosylated hydroxamic acids spontaneously degrade from DIBOA to benzoxazolin-2-one (BOA); and 2,4-dihydroxy-7-methoxy-2H-1 ,4-benzoxazin-3(4H)-one (DIMBOA) and 2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-o ne (HDMBOA) (Grambow et al, 1986) to 6-methoxy-benzoxazolin-2-one (MBOA). Additionally, the lactams, 2-hydroxy-1,4-benzoxazin-3(2H)-one (HBOA) and 2-hydroxy-7-methoxy-1 ,4-benzoxazin-3-one (HMBOA), are produced within this pathway.…”

Section: Production Of Benzoxazinoids In Cerealsmentioning

confidence: 99%

Degradation of the benzoxazolinone class of phytoalexins by Fusarium pseudograminearum, a pathogenic fungus of wheat

Kettle¹

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The benzoxazolinone class of phytoalexins are released by wheat, maize and rye upon pathogen attack. Benzoxazolinones have antimicrobial activity, but certain fungi have evolved mechanisms to actively detoxify these compounds, which may contribute to the virulence of these pathogens. In many Fusarium spp. a cluster of genes is thought to be involved in the detoxification of benzoxazolinones. However, only one enzyme, Fusarium Detoxification of Benzoxazolinone 2 (Fdb2), encoded in the cluster has been unequi vocally assigned a role in this process. The FDB2 gene encodes a N-malonyltransferase and was identified in the maize pathogen F. verticillioides. In this thesis, through comparative genome analysis of several Fusarium species, a conserved genomic region has been identified around FDB2. Expression analyses demonstrated that a cluster of nine genes were responsive to exogenous benzoxazolinone in the important wheat pathogen Fusarium pseudograminearum.

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Occurrence of 2-(2-Hydroxy-4,7-dimethoxy-2H-1,4-benzoxazin-3-one)- β-ᴅ-glucopyranoside in Triticum aestivum Leaves and Its Conversion into 6-Methoxy-benzoxazolinone

Cited by 46 publications

References 0 publications

Rapidly Induced Chemical Defenses in Maize Stems and Their Effects on Short-term Growth of Ostrinia nubilalis

Rapidly Induced Chemical Defenses in Maize Stems and Their Effects on Short-term Growth of Ostrinia nubilalis

Natural Variation in Maize Aphid Resistance Is Associated with 2,4-Dihydroxy-7-Methoxy-1,4-Benzoxazin-3-One Glucoside Methyltransferase Activity

Degradation of the benzoxazolinone class of phytoalexins by Fusarium pseudograminearum, a pathogenic fungus of wheat

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