Manipulation of sinapine, choline and betaine accumulation in Arabidopsis seed: Towards improving the nutritional value of the meal and enhancing the seedling performance under environmental stresses in oilseed crops

Huang, Jun; Rozwadowski, Kevin; Bhinu, V.-S.; Schäfer, Ulrike; Hannoufa, Abdelali

doi:10.1016/j.plaphy.2008.04.014

Cited by 31 publications

(31 citation statements)

References 57 publications

(80 reference statements)

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“…Because of the antinutritive properties of sinapoylcholine, engineering sinapate ester metabolism to reduce its biosynthesis in the seeds of B. napus could improve the nutritive quality of canola meal Milkowski and Strack, 2010). Two SCT genes (BnSCT1 and BnSCT2) have been identified in B. napus since the characterization of the Arabidopsis SCT, and metabolic engineering projects are currently underway to eliminate the biosynthesis of choline in B. napus seeds (Milkowski et al, 2004;Huang et al, 2008;Weier et al, 2008;Bhinu et al, 2009;Milkowski and Strack, 2010).…”

Section: Sinapoylglucose:choline Sinapoyltransferase (Sct)mentioning

confidence: 99%

The Phenylpropanoid Pathway in Arabidopsis

Fraser

Chapple

2011

The Arabidopsis Book

588

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: Sinapoylglucose:choline Sinapoyltransferase (Sct)mentioning

confidence: 99%

The Phenylpropanoid Pathway in Arabidopsis

Fraser

Chapple

2011

The Arabidopsis Book

588

489

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“…Choline occurs in plants as free choline, phosphocholine (PCho) 2 ; as a component of the integral membrane phospholipid, phosphatidylcholine (PtdCho); and as a precursor for the osmoprotectants choline-O-sulfate and glycine betaine (1)(2)(3).…”

mentioning

confidence: 99%

“…Evidence that choline content in plants is regulated and probably finite is offered by the results of research using Arabidopsis and tobacco, plants that do not naturally oxidize choline for glycine betaine accumulation (2,3,17). Nuccio et al (12) engineered transgenic tobacco that expressed the enzymes responsible for converting choline to glycine betaine, but these plants failed to accumulate glycine betaine to levels comparable in accumulating species.…”

mentioning

confidence: 99%

Identification of Phosphomethylethanolamine N-Methyltransferase from Arabidopsis and Its Role in Choline and Phospholipid Metabolism

BeGora¹,

MacLeod²,

McCarry

et al. 2010

Journal of Biological Chemistry

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Three sequential methylations of phosphoethanolamine (PEA) are required for the synthesis of phosphocholine (PCho) in plants. A cDNA encoding an N-methyltransferase that catalyzes the last two methylation steps was cloned from Arabidopsis by heterologous complementation of a Saccharomyces cerevisiae cho2, opi3 mutant. The cDNA encodes phosphomethylethanolamine N-methyltransferase (PMEAMT), a polypeptide of 475 amino acids that is organized as two tandem methyltransferase domains. PMEAMT shows 87% amino acid identity to a related enzyme, phosphoethanolamine N-methyltransferase, an enzyme in plants that catalyzes all three methylations of PEA to PCho. PMEAMT cannot use PEA as a substrate, but assays using phosphomethylethanolamine as a substrate result in both phosphodimethylethanolamine and PCho as products. PMEAMT is inhibited by the reaction products PCho and S-adenosyl-L-homocysteine, a property reported for phosphoethanolamine N-methyltransferase from various plants. An Arabidopsis mutant with a T-DNA insertion associated with locus At1g48600 showed no transcripts encoding PMEAMT. Shotgun lipidomic analyses of leaves of atpmeamt and wild-type plants generated phospholipid profiles showing the content of phosphatidylmethylethanolamine to be altered relative to wild type with the content of a 34:3 lipid molecular species 2-fold higher in mutant plants. In S. cerevisiae, an increase in PtdMEA in membranes is associated with reduced viability. This raises a question regarding the role of PMEAMT in plants and whether it serves to prevent the accumulation of PtdMEA to potentially deleterious levels.Choline occurs in plants as free choline, phosphocholine (PCho) 2

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“…On the other hand, it would be interesting to determine, whether the high amount of choline can be efficiently converted into betaine by the introduction of a gene encoding choline oxidase (Rozwadowski et al, 1991). So far, choline oxidase-mediated betaine production has been limited by low levels of free choline as a precursor, combined with choline homoeostasis in seeds (Nuccio et al, 1998;Huang et al, 2000Huang et al, , 2008. In future experiments, the hypothesis that the highcholine chemotype of seeds produced by BnSCE3 expression can overcome the substrate limitation in betaine production can be tested.…”

Section: Bnsce3 Expression Prevents the Accumulation Of Sinapine In Smentioning

confidence: 99%

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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Manipulation of sinapine, choline and betaine accumulation in Arabidopsis seed: Towards improving the nutritional value of the meal and enhancing the seedling performance under environmental stresses in oilseed crops

Cited by 31 publications

References 57 publications

The Phenylpropanoid Pathway in Arabidopsis

The Phenylpropanoid Pathway in Arabidopsis

Identification of Phosphomethylethanolamine N-Methyltransferase from Arabidopsis and Its Role in Choline and Phospholipid Metabolism

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

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