Glycosyltransferases from Oat (Avena) Implicated in the Acylation of Avenacins

Owatworakit, Amorn; Townsend, Belinda; Louveau, Thomas; Jenner, Helen; Rejzek, Martin; Hughes, Richard K.; Saalbach, Gerhard; Qi, Xiaoquan; Bakht, Saleha; Roy, Abhijeet Deb; Mugford, Sam T.; Goss, Rebecca J. M.; Field, Robert A.; Osbourn, Anne

doi:10.1074/jbc.m112.426155

Cited by 36 publications

(41 citation statements)

References 43 publications

(58 reference statements)

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“…Thus, As-MT1 catalyzes the first committed step in the synthesis of the N-methyl anthraniloyl acyl donor that is used by the As-SCPL1 acyltransferase, namely, methylation of the primary shikimate pathway intermediate anthranilate. This is consistent with the proposed pathway in Figure 4B and with the catalytic properties of As-UGT74H5, which has a strong affinity for N-methyl anthranilate compared with anthranilate (Owatworakit et al, 2012).…”

Section: Mt1supporting

confidence: 77%

“…Three Genes Encoding a Methyltransferase, Glucosyltransferase, and an Acyltransferase Are Adjacent within the Avenacin Gene Cluster Previously, we identified and sequenced a BAC contig spanning four genes within the avenacin gene cluster: Sad1, 2, 7, and 10 ( Qi et al, 2006;Mugford et al, 2009;Owatworakit et al, 2012). Further extension of this BAC contig identified a gene predicted to encode an S-adenosyl-methionine-dependent methyltransferase (MT1), which lies 45 kb from the UGT74H5 (Sad10) gene ( Figure 2A).…”

Section: Resultsmentioning

confidence: 99%

“…The glucosyltransferase UGT74H5 glucosylates N-methyl anthranilate to give the activated acyl donor substrate N-methyl anthraniloyl-O-Glc (NMA-Glc). UGT74H5 has a clear preference for N-methyl anthranilate but also has weak activity toward anthranilate to give anthraniloyl-O-Glc (Anth-Glc) (Owatworakit et al, 2012). In wild-type A. strigosa, the SCPL1 acyltransferase uses NMA-Glc as the acyl donor to give avenacin A-1 (A1).…”

Section: Mt1mentioning

confidence: 99%

“…These avenacin-deficient mutants were found to have increased susceptibility to infection by soil-borne pathogens (Papadopoulou et al, 1999). This mutant collection has proved to be a valuable resource for investigating triterpenoid biosynthesis, and we cloned genes encoding several steps of the avenacin biosynthetic pathway (Haralampidis et al, 2001;Qi et al, 2004Qi et al, , 2006Mugford et al, 2009;Owatworakit et al, 2012). An important discovery has been that the loci for the synthesis of avenacins are clustered.…”

Section: Introductionmentioning

confidence: 99%

“…We recently identified a family 1 glycosyltransferase (UGT74H5) in A. strigosa that catalyzes the glucosylation of N-methyl anthranilate to N-methyl anthranilate-O-Glc, the acyl donor substrate for SCPL1. UGT74H5 is encoded by the A. strigosa Sad10 gene, which lies within the avenacin gene cluster, adjacent to the Sad7 (SCPL1) gene (Owatworakit et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

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Modularity of Plant Metabolic Gene Clusters: A Trio of Linked Genes That Are Collectively Required for Acylation of Triterpenes in Oat

et al. 2013

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Operon-like gene clusters are an emerging phenomenon in the field of plant natural products. The genes encoding some of the best-characterized plant secondary metabolite biosynthetic pathways are scattered across plant genomes. However, an increasing number of gene clusters encoding the synthesis of diverse natural products have recently been reported in plant genomes. These clusters have arisen through the neo-functionalization and relocation of existing genes within the genome, and not by horizontal gene transfer from microbes. The reasons for clustering are not yet clear, although this form of gene organization is likely to facilitate co-inheritance and co-regulation. Oats (Avena spp) synthesize antimicrobial triterpenoids (avenacins) that provide protection against disease. The synthesis of these compounds is encoded by a gene cluster. Here we show that a module of three adjacent genes within the wider biosynthetic gene cluster is required for avenacin acylation. Through the characterization of these genes and their encoded proteins we present a model of the subcellular organization of triterpenoid biosynthesis.

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Section: Mt1supporting

confidence: 77%

Section: Resultsmentioning

confidence: 99%

Section: Mt1mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Modularity of Plant Metabolic Gene Clusters: A Trio of Linked Genes That Are Collectively Required for Acylation of Triterpenes in Oat

et al. 2013

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Plant terpenes that mediate below‐ground interactions: prospects for bioengineering terpenoids for plant protection

Huang

Osbourn

2019

Pest Management Science

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Plants are sessile organisms that have evolved various mechanisms to adapt to complex and changing environments. One important feature of plant adaption is the production of specialised metabolites. Terpenes are the largest class of specialised metabolites, with over 80 000 structures reported so far, and they have important ecological functions in plant adaptation. Here, we review the current knowledge on plant terpenes that mediate below‐ground interactions between plants and other organisms, including microbes, herbivores and other plants. The discovery, functions and biosynthesis of these terpenes are discussed, and prospects for bioengineering terpenoids for plant protection are considered. © 2019 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

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