Sinapine

The seeds of Raphanus sativus L.

Overexpression of sinapine esterase BnSCE3 in oilseed rape seeds triggers global changes in seed metabolism.[Pubmed:21248075]

Plant Physiol. 2011 Mar;155(3):1127-45.

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-beta-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.

Sinapine detection in radish taproot using surface desorption atmospheric pressure chemical ionization mass spectrometry.[Pubmed:21332204]

J Agric Food Chem. 2011 Mar 23;59(6):2148-56.

Plant research and natural product detection are of sustainable interests. Benefited by direct detection with no sample preparation, Sinapine, a bioactive chemical usually found in various seeds of Brassica plants, has been unambiguously detected in radish taproot (Raphanus sativus) tissue using a liquid-assisted surface desorption atmospheric pressure chemical ionization mass spectrometry (DAPCI-MS). A methanol aqueous solution (1:1) was nebulized by a nitrogen sheath gas toward the corona discharge, resulting in charged ambient small droplets, which affected the radish tissue for desorption/ionization of analytes on the tissue surface. Thus, Sinapine was directly detected and identified by tandem DAPCI-MS experiments without sample pretreatment. The typical relative standard deviation (RSD) of this method for Sinapine detection was 5-8% for six measurements (S/N=3). The dynamic response range was 10(-12)-10(-7) g/cm2 for Sinapine on the radish skin surface. The discovery of Sinapine in radish taproot was validated by using HPLC-UV methods. The data demonstrated that DAPCI assisted by solvent enhanced the overall efficiency of the desorption/ionization process, enabling sensitive detection of bioactive compounds in plant tissue.

Sinapine as an active compound for inhibiting the proliferation of Caco-2 cells via downregulation of P-glycoprotein.[Pubmed:24607798]

Food Chem Toxicol. 2014 May;67:187-92.

Sinapine, an alkaloid from seeds of the cruciferous species, shows favorable biological activities such as antioxidant and radio-protective activities. However, the inhibitory effect of Sinapine on tumors, and the molecular mechanisms have not been completely understood thus far. In this study, we determined anti-proliferative effects of Sinapine. We examined the anti-tumor effects of the combination of Sinapine and doxorubicin. The results of the MTT assay and apoptosis showed that Sinapine increased the sensitivity of Caco-2 cells to doxorubicin in a dose-dependent manner, whereas no or less effect was observed in the cells treated with doxorubicin alone. The combination of Sinapine and doxorubicin had a synergistic effect and increased the cytotoxicity of doxorubicin against Caco-2 cells. Doxorubicin accumulation assay showed that Sinapine increased the intracellular accumulation of doxorubicin in dose-dependent manner. Immunoblotting and QT-PCR analysis showed that Sinapine suppressed P-glycoprotein (P-gp) expression via ubiquitination. A significant correlation was observed between the expression of p-ERK1/2 and P-gp. These results indicated that Sinapine played an important role in the down-regulation of P-gp expression through suppression of FGFR4-FRS2alpha-ERK1/2 signaling pathway. To our knowledge, this is the first study to show that Sinapine can be used as an effective natural compound for chemo-resistance.

Characterization of the factors that influence sinapine concentration in rapeseed meal during fermentation.[Pubmed:25606856]

PLoS One. 2015 Jan 21;10(1):e0116470.

We analyzed and compared the difference in Sinapine concentration in rapeseed meal between the filamentous fungus, Trametes sp 48424, and the yeast, Saccharomyces cerevisiae, in both liquid and solid-state fermentation. During liquid and solid-state fermentation by Trametes sp 48424, the Sinapine concentration decreased significantly. In contrast, the liquid and solid-state fermentation process by Saccharomyces cerevisiae just slightly decreased the Sinapine concentration (P Sinapine in rapeseed meal decreased significantly in Saccharomyces cerevisiae. Based on the measurement of laccase activity, we observed that laccase induced the decrease in the concentration of Sinapine during fermentation with Trametes sp 48424. In order to eliminate the influence of microorganisms and the metabolites produced during fermentation, high moisture rapeseed meal and the original rapeseed meal were dried at 90 degrees C and 105 degrees C, respectively. During drying, the concentration of Sinapine in high moisture rapeseed meal decreased rapidly and we obtained a high correlation coefficient between the concentration of Sinapine and loss of moisture. Our results suggest that drying and enzymes, especially laccase that is produced during the solid-state fermentation process, may be the main factors that affect the concentration of Sinapine in rapeseed meal.

[Radiation protection effects of sinapine on Drosophila melanogaster in a sex-linked recessive lethal test system].[Pubmed:8191802]

Shi Yan Sheng Wu Xue Bao. 1993 Sep;26(3):269-74.

It has been shown that the radiation resistance of some cruciferous plants is related to some natural radiation protection substances in these plants. Sinapine, which has shown radiation protection effects on barley, wheat and mouse, is one of such substances distributed in cruciferous plants. In this paper, the radiation protection effects of Sinapine on Drosophila melanogaster in a sex-linked recessive lethal (SLRL) test system were observed. The Sinapine solution could be fed to the D. melanogaster (Oregon K). 40 Gy X-irradiation induced SLRL mutation rate of 8.96%. However, if 10 mg/ml Sinapine which was found to have no physiological toxicity or harmful effects on its reproductive function, was fed before 40 Gy X-irradiation, the SLRL mutation rate could be reduced to 0.40%, which was within the range of spontaneous SLRL mutation rate of Oregon K Drosophila, i.e. 0-0.4%. The potential of the using of the very strong radiation protection effects of Sinapine in anticarcinogenesis was also discussed.

Sinapine is an alkaloid from seeds of the cruciferous species which shows favorable biological activities such as antioxidant and radio-protective activities.

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