Benzoxazinoid biosynthesis, a model for evolution of secondary metabolic pathways in plants

Frey, Monika; Schullehner, Katrin; Dick, Regina; Fiesselmann, Andreas; Gierl, Alfons

doi:10.1016/j.phytochem.2009.05.012

Cited by 320 publications

(371 citation statements)

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“…5A and 6A), a class of specialized metabolites in grasses that provide defense against insect herbivory (Frey et al, 2009;Ahmad et al, 2011). Ten enzymes (Bx1-Bx9 and Igl1) catalyze the formation of DIMBOA-Glc from indole-3-glycerol phosphate (Frey et al, 2009;Niemeyer, 2009; This is followed by methylation into HDMBOA-Glc through the activity of three Bx10 enzymes Mijares et al, 2013). Transcripts of Bx1 (GRMZM2G085381), Bx2 (GRMZM2G085661), Bx6 (GRMZM6G617209), and Bx7 (GRMZM2G441753) were significantly induced at early time points as well as at 96 h after aphid attack.…”

Section: Benzoxazinoid Biosynthesis Is Involved In Herbivore Defense mentioning

confidence: 99%

“…The predominant benzoxazinoids in maize foliar tissue are 4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one glucoside (DIMBOA-Glc) and 2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one glucoside (HDMBOA-Glc; Frey et al, 1997Frey et al, , 2009). These compounds inhibit the growth of fungi, arrest insect herbivore growth, and cause allelopathic effects (Niemeyer, 2009;Ahmad et al, 2011).…”

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confidence: 99%

“…These compounds inhibit the growth of fungi, arrest insect herbivore growth, and cause allelopathic effects (Niemeyer, 2009;Ahmad et al, 2011). Benzoxazinoids are stored in a glucoside form that has reduced toxicity compared with the aglycones, which are produced upon cell disruption during pathogen or herbivore attack (Frey et al, 2009). Aphid feeding does not increase overall DIMBOA-Glc or HDMBOA-Glc accumulation in tested maize cultivars (Cambier et al, 2001;Meihls et al, 2013).…”

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Dynamic maize responses to aphid feeding are revealed by a time series of transcriptomic and metabolomic assays

et al. 2015

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(A.H.); 0000-0002-9675-934X (G.J.).As a response to insect attack, maize (Zea mays) has inducible defenses that involve large changes in gene expression and metabolism. Piercing/sucking insects such as corn leaf aphid (Rhopalosiphum maidis) cause direct damage by acquiring phloem nutrients as well as indirect damage through the transmission of plant viruses. To elucidate the metabolic processes and gene expression changes involved in maize responses to aphid attack, leaves of inbred line B73 were infested with corn leaf aphids for 2 to 96 h. Analysis of infested maize leaves showed two distinct response phases, with the most significant transcriptional and metabolic changes occurring in the first few hours after the initiation of aphid feeding. After 4 d, both gene expression and metabolite profiles of aphid-infested maize reverted to being more similar to those of control plants. Although there was a predominant effect of salicylic acid regulation, gene expression changes also indicated prolonged induction of oxylipins, although not necessarily jasmonic acid, in aphid-infested maize. The role of specific metabolic pathways was confirmed using Dissociator transposon insertions in maize inbred line W22. Mutations in three benzoxazinoid biosynthesis genes, Bx1, Bx2, and Bx6, increased aphid reproduction. In contrast, progeny production was greatly decreased by a transposon insertion in the single W22 homolog of the previously uncharacterized B73 terpene synthases TPS2 and TPS3. Together, these results show that maize leaves shift to implementation of physical and chemical defenses within hours after the initiation of aphid feeding and that the production of specific metabolites can have major effects in maize-aphid interactions.

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Section: Benzoxazinoid Biosynthesis Is Involved In Herbivore Defense mentioning

confidence: 99%

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confidence: 99%

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Dynamic maize responses to aphid feeding are revealed by a time series of transcriptomic and metabolomic assays

et al. 2015

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“…In maize the four P450 genes are known as BX2 (CYP71C1) to BX5 (CYP71C4). The availability of other Poaceae genomes has revealed that the pathway has evolved monophyletically in the grasses ( [104] and references therein). An evolutionary sequence leading to benzoxazinoids was suggested based on phylogenetic relationship of the P450s involved and by the specific reaction catalysed by each.…”

Section: Evolution and Elongation Of Pathways By Tandem Gene Duplicatmentioning

confidence: 99%

“…The 'founding event' of the pathway was suggested to be the clustering of duplicated tryptophan synthase a-subunit (TSA) and an ancestral CYP71C gene, followed by neofunctionalization of both into Bx1 and Bx2, respectively, and yielding biosynthetic access to indole and the oxidized indolin-2-one, derived from the primary metabolite indole-3-glyceraldehyde. The elongation of this cluster through duplication of Bx2 (CYP71C1) giving rise to Bx3 (CYP71C2) was followed by two subsequent duplications of Bx3 resulting in Bx4 (CYP71C3) and Bx5 (CYP71C4), and generated the material that, after neofunctionalization, resulted in a series of successive oxidations from indolin-2-one via 3-hydroxy indolin-2-one and 2-hydroxy-1,4(2H)-benzoxazin-3(4H)-one (HBOA) to 2,4-dihydroxy-2H-1,4-benzoxazin-3 (4H)-one (DIBOA) [104,105]. Both HBOA and DIBOA are subsequently glycosylated by Bx8/Bx9, further hydroxylated by Bx6 (a 2-oxogluterate-dependent dioxygenase) to 2,4,7-trihydroxy-2H-1,4-benzoxazin-3(4H)-one (TRIBOA)-glc and methoxylated by Bx7 to 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA)-glc ( [104] and references therein).…”

Section: Evolution and Elongation Of Pathways By Tandem Gene Duplicatmentioning

confidence: 99%

Plant P450s as versatile drivers for evolution of species-specific chemical diversity

Hamberger

Bak

2013

Phil. Trans. R. Soc. B

268

231

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The irreversible nature of reactions catalysed by P450s makes these enzymes landmarks in the evolution of plant metabolic pathways. Founding members of P450 families are often associated with general (i.e. primary) metabolic pathways, restricted to single copy or very few representatives, indicative of purifying selection. Recruitment of those and subsequent blooms into multi-member gene families generates genetic raw material for functional diversification, which is an inherent characteristic of specialized (i.e. secondary) metabolism. However, a growing number of highly specialized P450s from not only the CYP71 clan indicate substantial contribution of convergent and divergent evolution to the observed general and specialized metabolite diversity. We will discuss examples of how the genetic and functional diversification of plant P450s drives chemical diversity in light of plant evolution. Even though it is difficult to predict the function or substrate of a P450 based on sequence similarity, grouping with a family or subfamily in phylogenetic trees can indicate association with metabolism of particular classes of compounds. Examples will be given that focus on multi-member gene families of P450s involved in the metabolic routes of four classes of specialized metabolites: cyanogenic glucosides, glucosinolates, mono-to triterpenoids and phenylpropanoids.

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The Role of Phytochemicals in Relationships of Plants with Other Organisms

Bednarek¹

2014

Natural Products

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Benzoxazinoid biosynthesis, a model for evolution of secondary metabolic pathways in plants

Cited by 320 publications

References 52 publications

Dynamic maize responses to aphid feeding are revealed by a time series of transcriptomic and metabolomic assays

Dynamic maize responses to aphid feeding are revealed by a time series of transcriptomic and metabolomic assays

Plant P450s as versatile drivers for evolution of species-specific chemical diversity

The Role of Phytochemicals in Relationships of Plants with Other Organisms

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