The role of UDP-glucose:hydroxycinnamate glucosyltransferases in phenylpropanoid metabolism and the response to UV-B radiation in Arabidopsis thaliana

Meissner, Dirk; Albert, Andreas; Böttcher, Christoph; Strack, Dieter; Milkowski, Carsten

doi:10.1007/s00425-008-0768-3

Cited by 62 publications

(50 citation statements)

References 53 publications

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“…Consistent with the role of the enzyme in sinapate ester synthesis, brt1 leaves accumulate less sinapoylmalate Meißner et al, 2008), and brt1 seeds accumulate less sinapoylcholine and sinapoylglucose. Interestingly, the trichomes of the brt1 mutant fluoresce with a distinctive intensity not seen in wild type (Fig.…”

Section: Sinapate:udp-glucose Glucosyltransferase (Sgt)supporting

confidence: 58%

“…SGT is a member of a family of UDP-glucosyltransferases (UGTs) in Arabidopsis, which contains 107 members divided into 12 major groups on the basis of sequence similarity . Many Arabidopsis UGTs exhibit activity towards secondary metabolites , including the phenylpropanoids (Milkowski et al, 2000;Lim et al, 2001;Lim et al, 2005;Lanot et al, 2006;Sinlapadech et al, 2007;Lanot et al, 2008;Meißner et al, 2008), synthesizing both glucosides and glucose esters. Initially, a single member of this UGT superfamily was identified as the likely Arabidopsis SGT: UGT84A2 (At3g21560; Lim et al, 2001).…”

Section: Sinapate:udp-glucose Glucosyltransferase (Sgt)mentioning

confidence: 99%

“…Kinetic analyses showed that UGT84A2 exhibits a much greater affinity for sinapic acid than any other UGT in Arabidopsis. Nonetheless, UGT84A2 is one of four UGTs (UGT84A1, UG-T84A2, UGT84A3 and UGT84A4) with affinities for the hydroxycinnamic acids (Milkowski et al, 2000;Lim et al, 2001), and there appears to be some functional overlap between the four enzymes (Milkowski et al, 2000;Lim et al, 2001;Sinlapadech et al, 2007;Meißner et al, 2008). The close proximity of of UGT84A1, UG-T84A3, and UGT84A4 in the Arabidopsis genome has prevented the generation of multiple mutants that would help to elucidate the biochemical roles of each individual protein and reveal any potential genetic redundancy (Meißner et al, 2008).…”

Section: Sinapate:udp-glucose Glucosyltransferase (Sgt)mentioning

confidence: 99%

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The Phenylpropanoid Pathway in Arabidopsis

Fraser

Chapple

2011

The Arabidopsis Book

624

489

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The phenylpropanoid pathway serves as a rich source of metabolites in plants, being required for the biosynthesis of lignin, and serving as a starting point for the production of many other important compounds, such as the flavonoids, coumarins, and lignans. In spite of the fact that the phenylpropanoids and their derivatives are sometimes classified as secondary metabolites, their relevance to plant survival has been made clear via the study of Arabidopsis and other plant species. As a model system, Arabidopsis has helped to elucidate many details of the phenylpropanoid pathway, its enzymes and intermediates, and the interconnectedness of the pathway with plant metabolism as a whole. These advances in our understanding have been made possible in large part by the relative ease with which mutations can be generated, identified, and studied in Arabidopsis. Herein, we provide an overview of the research progress that has been made in recent years, emphasizing both the genes (and gene families) associated with the phenylpropanoid pathway in Arabidopsis, and the end products that have contributed to the identification of many mutants deficient in the phenylpropanoid metabolism: the sinapate esters.

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Section: Sinapate:udp-glucose Glucosyltransferase (Sgt)supporting

confidence: 58%

Section: Sinapate:udp-glucose Glucosyltransferase (Sgt)mentioning

confidence: 99%

Section: Sinapate:udp-glucose Glucosyltransferase (Sgt)mentioning

confidence: 99%

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The Phenylpropanoid Pathway in Arabidopsis

Fraser

Chapple

2011

The Arabidopsis Book

624

489

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“…The biosynthesis of hydroxycinnamate shikimate and quinate esters has been established in Nicotiana tabacum and Nicotiana benthamiana starting from their respective CoA thioesters via an HCT (Hoffmann et al, 2004). Glycosylation by UDP-glycosyltransferases of hydroxycinnamic acids has been described previously (Meissner et al, 2008).…”

Section: Profiling Of Methanol-soluble Phenolicsmentioning

confidence: 99%

Different Routes for Conifer- and Sinapaldehyde and Higher Saccharification upon Deficiency in the Dehydrogenase CAD1

Déjardin²,

et al. 2017

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In the search for renewable energy sources, genetic engineering is a promising strategy to improve plant cell wall composition for biofuel and bioproducts generation. Lignin is a major factor determining saccharification efficiency and, therefore, is a prime target to engineer. Here, lignin content and composition were modified in poplar (Populus tremula 3 Populus alba) by specifically down-regulating CINNAMYL ALCOHOL DEHYDROGENASE1 (CAD1) by a hairpin-RNA-mediated silencing approach, which resulted in only 5% residual CAD1 transcript abundance. These transgenic lines showed no biomass penalty despite a 10% reduction in Klason lignin content and severe shifts in lignin composition. Nuclear magnetic resonance spectroscopy and thioacidolysis revealed a strong increase (up to 20-fold) in sinapaldehyde incorporation into lignin, whereas coniferaldehyde was not increased markedly. Accordingly, ultra-high-performance liquid chromatography-mass spectrometry-based phenolic profiling revealed a more than 24,000-fold accumulation of a newly identified compound made from 8-8 coupling of two sinapaldehyde radicals. However, no additional cinnamaldehyde coupling products could be detected in the CAD1-deficient poplars. Instead, the transgenic lines accumulated a range of hydroxycinnamate-derived metabolites, of which the most prominent accumulation (over 8,500-fold) was observed for a compound that was identified by purification and nuclear magnetic resonance as syringyl lactic acid hexoside. Our data suggest that, upon down-regulation of CAD1, coniferaldehyde is converted into ferulic acid and derivatives, whereas sinapaldehyde is either oxidatively coupled into S9(8-8)S9 and lignin or converted to sinapic acid and derivatives. The most prominent sink of the increased flux to hydroxycinnamates is syringyl lactic acid hexoside. Furthermore, low-extent saccharification assays, under different pretreatment conditions, showed strongly increased glucose (up to +81%) and xylose (up to +153%) release, suggesting that down-regulating CAD1 is a promising strategy for improving lignocellulosic biomass for the sugar platform industry.

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“…Likewise, the accumulation of phenolic glucosides was observed in transgenic poplar (Populus spp.) plants designed to produce modified lignin (Meyermans et al, 2000;Suzuki et al, 2010) as well as in Arabidopsis ugt84A2 mutants defective in the enzyme UDP-Glc:sinapate glucosyltransferase (Meissner et al, 2008). On the other hand, the appearance of glycosylated sinapoylcholine in OE1 and OE2 suggests that the BnSCE3 enzymatic activity was not able to act on the whole sinapine pool in the seeds of the transgenic oilseed rape lines described in this study.…”

Section: Bnsce3 Expression Affects Seed Metabolismmentioning

confidence: 79%

Overexpression of Sinapine Esterase BnSCE3 in Oilseed Rape Seeds Triggers Global Changes in Seed Metabolism

et al. 2011

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Sinapine (O-sinapoylcholine) is the predominant phenolic compound in a complex group of sinapate esters in seeds of oilseed rape (Brassica napus). Sinapine has antinutritive activity and prevents the use of seed protein for food and feed. A strategy was developed to lower its content in seeds by expressing an enzyme that hydrolyzes sinapine in developing rape seeds. During early stages of seedling development, a sinapine esterase (BnSCE3) hydrolyzes sinapine, releasing choline and sinapate. A portion of choline enters the phospholipid metabolism, and sinapate is routed via 1-O-sinapoyl-b-glucose into sinapoylmalate. Transgenic oilseed rape lines were generated expressing BnSCE3 under the control of a seed-specific promoter. Two distinct single-copy transgene insertion lines were isolated and propagated to generate homozygous lines, which were subjected to comprehensive phenotyping. Sinapine levels of transgenic seeds were less than 5% of wild-type levels, whereas choline levels were increased. Weight, size, and water content of transgenic seeds were significantly higher than those of wild-type seeds. Seed quality parameters, such as fiber and glucosinolate levels, and agronomically important traits, such as oil and protein contents, differed only slightly, except that amounts of hemicellulose and cellulose were about 30% higher in transgenic compared with wild-type seeds. Electron microscopic examination revealed that a fraction of the transgenic seeds had morphological alterations, characterized by large cavities near the embryonic tissue. Transgenic seedlings were larger than wild-type seedlings, and young seedlings exhibited longer hypocotyls. Examination of metabolic profiles of transgenic seeds indicated that besides suppression of sinapine accumulation, there were other dramatic differences in primary and secondary metabolism. Mapping of these changes onto metabolic pathways revealed global effects of the transgenic BnSCE3 expression on seed metabolism.Brassicaceous plants, such as oilseed rape (Brassica napus) and Arabidopsis (Arabidopsis thaliana), are characterized by the pronounced formation of soluble sinapate esters (Bouchereau et al., 1992). Seeds of this plant family accumulate sinapine, the choline ester of sinapate (O-sinapoylcholine; Henry and Garot, 1825; Gadamer, 1897), as the major component of complex patterns of sinapate esters, including various sinapoylated Glcs, gentiobioses, and kaempferol glycosides (Baumert et al., 2005;Wolfram et al., 2010). When oilseed rape seeds are processed, a high-quality vegetable oil is produced, and most of the sinapine is found in the residual protein meal. However, this compound is unpalatable and antinutritive (Ismail et al., 1981), making the meal unsuitable for human or animal consumption. Oilseed rape could be a valuable source of protein as well as oil if sinapine and related sinapate esters were reduced or eliminated from the seeds.The enzymes involved in the brassicaceous sinapate ester metabolism include UDP-Glc:sinapate glucosyltransferase (EC 2.4...

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The role of UDP-glucose:hydroxycinnamate glucosyltransferases in phenylpropanoid metabolism and the response to UV-B radiation in Arabidopsis thaliana

Cited by 62 publications

References 53 publications

The Phenylpropanoid Pathway in Arabidopsis

The Phenylpropanoid Pathway in Arabidopsis

Different Routes for Conifer- and Sinapaldehyde and Higher Saccharification upon Deficiency in the Dehydrogenase CAD1

Overexpression of Sinapine Esterase BnSCE3 in Oilseed Rape Seeds Triggers Global Changes in Seed Metabolism

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