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Chemical Compound Review

Sinapine     2-[(E)-3-(4-hydroxy-3,5- dimethoxy...

Synonyms: AC1NQWZ5, SureCN424529, AG-E-36088, CHEBI:16353, MEGxp0_001763, ...
 
 
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Disease relevance of Sinapine bisulphate

  • Transgenic B. napus with cauliflower mosaic virus 35S-antisense BNF5H contained up to 40% less sinapine, from 9.0 +/- 0.3 mg in the controls to 5.3 +/- 0.3 mg g(-1) seed [1].
  • During the first 8 days, the dry matter intake and live weight gain of the rats were significantly reduced by the intake of sinapine and other phenolic compounds [2].
 

High impact information on Sinapine bisulphate

  • Characterization of the ref2 mutants showed that they contained reduced levels of a number of phenylpropanoid pathway-derived products: sinapoylmalate in leaves, sinapoylcholine in seeds, and syringyl lignin in stems [3].
  • Members of the Brassicaceae family accumulate specific sinapate esters, i.e. sinapoylcholine (sinapine), which is considered as a major antinutritive compound in seeds of important crop plants like Brassica napus, and sinapoylmalate, which is implicated in UV-B tolerance in leaves [4].
  • Together with sinapine esterase (SCE) and sinapoylglucose:malate sinapoyltransferase (SMT), activities of BnSGT1 and BnSCT show a close correlation with the accumulation kinetics of the corresponding metabolites [4].
  • Homozygous sng2 seeds accumulate sinapoylglucose instead of sinapoylcholine, and have increased levels of choline and decreased activity of the enzyme sinapoylglucose:choline sinapoyltransferase (SCT) [5].
  • Identification of a CYP84 family of cytochrome P450-dependent mono-oxygenase genes in Brassica napus and perturbation of their expression for engineering sinapine reduction in the seeds [1].
 

Biological context of Sinapine bisulphate

 

Associations of Sinapine bisulphate with other chemical compounds

 

Gene context of Sinapine bisulphate

  • In contrast, the positive regulatory function of the downstream region is not required for F5H transcript or sinapoylcholine accumulation in embryos [8].

References

  1. Identification of a CYP84 family of cytochrome P450-dependent mono-oxygenase genes in Brassica napus and perturbation of their expression for engineering sinapine reduction in the seeds. Nair, R.B., Joy, R.W., Kurylo, E., Shi, X., Schnaider, J., Datla, R.S., Keller, W.A., Selvaraj, G. Plant Physiol. (2000) [Pubmed]
  2. Valorization of rapeseed meal. 5. Effects of sinapine and other phenolic compounds on food intake and nutrient utilization in growing rats. Vermorel, M., Hocquemiller, R., Evrard, J. Reproduction, nutrition, development. (1987) [Pubmed]
  3. The Arabidopsis ref2 mutant is defective in the gene encoding CYP83A1 and shows both phenylpropanoid and glucosinolate phenotypes. Hemm, M.R., Ruegger, M.O., Chapple, C. Plant Cell (2003) [Pubmed]
  4. 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. Milkowski, C., Baumert, A., Schmidt, D., Nehlin, L., Strack, D. Plant J. (2004) [Pubmed]
  5. The sng2 mutant of Arabidopsis is defective in the gene encoding the serine carboxypeptidase-like protein sinapoylglucose:choline sinapoyltransferase. Shirley, A.M., McMichael, C.M., Chapple, C. Plant J. (2001) [Pubmed]
  6. Purification and characterization of sinapine synthase from seeds of Brassica napus. Vogt, T., Aebershold, R., Ellis, B. Arch. Biochem. Biophys. (1993) [Pubmed]
  7. The voluntary food intake by growing pigs of diets containing 'treated' rapeseed meals or extracts of rapeseed meal. Lee, P.A., Pittam, S., Hill, R. Br. J. Nutr. (1984) [Pubmed]
  8. Regulation of ferulate-5-hydroxylase expression in Arabidopsis in the context of sinapate ester biosynthesis. Ruegger, M., Meyer, K., Cusumano, J.C., Chapple, C. Plant Physiol. (1999) [Pubmed]
 
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