Molecular regulation of sinapate ester metabolism in <i>Brassica napus</i>: expression of genes, properties of the encoded proteins and correlation of enzyme activities with metabolite accumulation

Milkowski, Carsten; Baumert, A.; Schmidt, Diana; Nehlin, Lilian; Strack, Dieter

doi:10.1111/j.1365-313x.2004.02036.x

Cited by 94 publications

(87 citation statements)

References 48 publications

(59 reference statements)

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“…Phenolic choline esters are characteristic and may contribute to the bitter taste and astringency of seed products. Sinapine, the choline ester of sinapic acid, is the most abundant one in seeds of the Brassicaceae family, being considered a major anti-nutritive com-pound [2,21]. The results obtained with B. oleracea seed extract showed that phenolics and organic acids in seeds were important as antioxidants [20].…”

Section: Introductionmentioning

confidence: 88%

“…The decrease of sinapoylcholine (7) in sprouts from 1.7 g/kg on day 2 to 0.3 g/kg on day 12 is a positive feature of the germination process once this compound is considered anti-nutritive [21]. This decrease in sinapoylcholine content can be ascribed to the fact that during the germination of seedlings, sinapoylcholine is hydrolysed to choline, an important substrate in the methylation cycle, and sinapic acid.…”

Section: Changes In Phenolic Compounds During Sproutingmentioning

confidence: 99%

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Screening of Antioxidant Compounds During Sprouting of Brassica oleracea L. var. costata DC

Sousa¹,

Lopes²,

Pereira³

et al. 2007

CCHTS

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Abstract:The changes in antioxidant compounds of Brassica oleracea L. var. costata DC seeds were monitored during the first twelve days of seedling development. Sprouts were screened at time intervals of two days for phenolic compounds and organic acids. The identified phenolic compounds included esters of sinapic acid with glucose, gentiobiose and kaempferol, as well as sinapoylcholine. The organic acids were oxalic, aconitic, citric, pyruvic, malic, shikimic, and fumaric acids. During germination, a depletion of phenolic compounds was observed, although no qualitative changes were seen. Among individual compounds, kaempferol, choline and glucose esters of sinapic acid showed a marked decrease between days two and six, whereas the changes in gentiobiose esters of sinapic acid were smaller. The total organic acids content increased rapidly during the first four days, with less significant variations thereafter. Malic acid, the major organic acid found in sprouts, greatly contributed to this result though oxalic, pyruvic, and fumaric acids also increased in the same manner. In contrast, aconitic, citric and shikimic acids showed decreases between days two and twelve of germination.

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Section: Introductionmentioning

confidence: 88%

Section: Changes In Phenolic Compounds During Sproutingmentioning

confidence: 99%

Screening of Antioxidant Compounds During Sprouting of Brassica oleracea L. var. costata DC

Sousa¹,

Lopes²,

Pereira³

et al. 2007

CCHTS

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“…2 and Table 1). Sinapoylmalate and sinapoylglucose serve as UV protectants and constitute the major sinapate esters in A. thaliana leaves (27). Several mutants with impaired sinapoylmalate levels, designated reduced epidermal fluorescence (ref ) mutants have been characterized (28).…”

Section: Discussionmentioning

confidence: 99%

Metabolic engineering of dhurrin in transgenic Arabidopsis plants with marginal inadvertent effects on the metabolome and transcriptome

Kristensen

Morant

Olsen

et al. 2005

Proc. Natl. Acad. Sci. U.S.A.

195

149

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Focused and nontargeted approaches were used to assess the impact associated with introduction of new high-flux pathways in Arabidopsis thaliana by genetic engineering. Transgenic A. thaliana plants expressing the entire biosynthetic pathway for the tyrosine-derived cyanogenic glucoside dhurrin as accomplished by insertion of CYP79A1, CYP71E1, and UGT85B1 from Sorghum bicolor were shown to accumulate 4% dry-weight dhurrin with marginal inadvertent effects on plant morphology, free amino acid pools, transcriptome, and metabolome. In a similar manner, plants expressing only CYP79A1 accumulated 3% dry weight of the tyrosine-derived glucosinolate, p-hydroxybenzylglucosinolate with no morphological pleitropic effects. In contrast, insertion of CYP79A1 plus CYP71E1 resulted in stunted plants, transcriptome alterations, accumulation of numerous glucosides derived from detoxification of intermediates in the dhurrin pathway, and in loss of the brassicaceae-specific UV protectants sinapoyl glucose and sinapoyl malate and kaempferol glucosides. The accumulation of glucosides in the plants expressing CYP79A1 and CYP71E1 was not accompanied by induction of glycosyltransferases, demonstrating that plants are constantly prepared to detoxify xenobiotics. The pleiotrophic effects observed in plants expressing sorghum CYP79A1 and CYP71E1 were complemented by retransformation with S. bicolor UGT85B. These results demonstrate that insertion of high-flux pathways directing synthesis and intracellular storage of high amounts of a cyanogenic glucoside or a glucosinolate is achievable in transgenic A. thaliana plants with marginal inadvertent effects on the transcriptome and metabolome.DNA microarrays ͉ metabolic engineering ͉ metabolite profiling ͉ channeling ͉ substantial equivalence M etabolic engineering offers the possibility to design plants that produce desired compounds (1-3). Knowledge of the impact of insertion of metabolic pathways on preexisting metabolic pathways is typically scarce, and is assessed by targeted approaches, but not by more global and unbiased approaches. We have previously reported transfer of the entire pathway for synthesis of the tyrosine-derived cyanogenic glucoside dhurrin from Sorghum bicolor to Arabidopsis thaliana by coexpression of three S. bicolor cDNAs: two multifunctional cytochromes P450, CYP79A1 and CYP71E1, and a family 1 glucosyltransferase, UGT85B1 (Fig. 1). The transgenic A. thaliana plants accumulated up 4% of plant dry matter of dhurrin (4). Transgenic A. thaliana plants in which only CYP79A1 was introduced accumulated up to 3% dry matter of the tyrosine derived p-hydroxybenzylglucosinolate, a glucosinolate that does not occur naturally in A. thaliana (5). The accumulation of tyrosine derived p-hydroxybenzylglucosinolate in A. thaliana is the result of metabolic crosstalk, where the p-hydroxyphenylacetaldoxime produced by CYP79A1 is efficiently used by the post-oximemetabolizing enzymes CYP83B1 or CYP83A1 in the endogenous glucosinolate biosynthetic pathway (5, 6) (Fig. 1).In this study,...

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“…Flavonoids and sinapinic acid esters, compounds derived from the phenylpropanoid pathway, fulfill important functions of the plant in development and interactions with the environment (Milkowski et al, 2004;Taylor and Grotewold, 2005). Flavonoids have crucial roles in cellular protection against UV light irradiation, as well as in maintaining cellular redox balance (Laundry et al, 1995;Pietta, 2000).…”

Section: Comparison Of Metabolite Profiles Obtained With Lc-msmentioning

confidence: 99%

“…Flavonoids also serve as phytoalexins to protect against damage caused by pathogen attack (Van Etten et al, 1994). Sinapoyl glucose (101) and sinapoyl malate (102) serve as UV protectants and constitute the major sinapate esters in Arabidopsis thaliana leaves (Milkowski et al, 2004). Because each glucosinolate contains a b-D-glucopyranose residue, the uptake of exogenous sinalbin (1) is expected to have a significant effect on the levels of the secondary metabolites, especially flavonol glycosides.…”

Section: Comparison Of Metabolite Profiles Obtained With Lc-msmentioning

confidence: 99%

Metabolite profiling of Arabidopsis seedlings in response to exogenous sinalbin and sulfur deficiency

et al. 2011

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Molecular regulation of sinapate ester metabolism in Brassica napus: expression of genes, properties of the encoded proteins and correlation of enzyme activities with metabolite accumulation

Cited by 94 publications

References 48 publications

Screening of Antioxidant Compounds During Sprouting of Brassica oleracea L. var. costata DC

Screening of Antioxidant Compounds During Sprouting of Brassica oleracea L. var. costata DC

Metabolic engineering of dhurrin in transgenic Arabidopsis plants with marginal inadvertent effects on the metabolome and transcriptome

Metabolite profiling of Arabidopsis seedlings in response to exogenous sinalbin and sulfur deficiency

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