Sinigrin

1 Brassica sp. 2 Caparis sp. 3 Crambe sp. 4 Lepidium sp. 5 Raphanus sp. 6 Wasabi sp.

Sinigrin is a glucosinolate that belongs to the family of glucosides found in some plants of the family Brassicaceae such as Brussels sprouts, broccoli, and the seeds of black mustard (Brassica nigra). Whenever sinigrin-containing plant tissue is crushed or otherwise damaged, the enzyme myrosinase degrades sinigrin to a mustard oil (allyl isothiocyanate), which is responsible for the pungent taste of mustard and horseradish. Seeds of white mustard, Sinapis alba, will give a much less pungent mustard because this species contains a different glucosinolate, sinalbin. The chemical name of sinigrin is allylglucosinolate or 2-propenylglucosinolate. Sinigrin stereochemical configuration on the C=N double bond was for a time uncertain, and has been resolved by X-ray crystallography in 1963 to be the Z (or syn) isomer.Singrin is also known to be allelopathic.

The effect of processing on the glucosinolate profile in mustard seed.[Pubmed:29478552]

Food Chem. 2018 Jun 30;252:343-348.

Brassica juncea mustard seed are used to make mustard paste or condiment. Mustard seed contains glucosinolates which are converted to isothiocyanates following cell disruption by the enzyme, myrosinase. Isothiocyanates are sulphur-containing compounds which give a pungent flavour to the mustard condiment. Three mustard seed cultivars from two seasons were processed into Dijon- and wholegrain-style mustard and glucosinolates and isothiocyanates analysed. Canadian cv. Centennial tended to contain higher glucosinolates compared with the French cv. AZ147 and Ukrainian cv. Chorniava. Conversion of the mustard seed into a wholegrain condiment had a lesser effect on total isothiocyanates and Sinigrin content compared with the Dijon-style preparation. The Canadian mustard cultivars produced wholegrain-style mustard with higher total isothyocyantes and Sinigrin compared with the French and Ukrainian cultivars. In summary, results herein suggest that Canadian mustard seed cvs. Centennial and Forge, and wholegrain processing may result in a condiment with greater bioactive composition.

Inhibitory effect of sinigrin on adipocyte differentiation in 3T3-L1 cells: Involvement of AMPK and MAPK pathways.[Pubmed:29604586]

Biomed Pharmacother. 2018 Jun;102:670-680.

Adipocyte differentiation is a critical adaptive response to nutritional overload and affects the metabolic outcome of obesity. Sinigrin (2-propenyl glucosinolate) is a glucosinolate belong to the glucoside contained in broccoli, brussels sprouts, and black mustard seeds. We investigated the effects of Sinigrin on adipogenesis in 3T3-L1 preadipocytes and its underlying mechanisms. Sinigrin remarkably inhibited the accumulation of lipid droplets and adipogenesis by downregulating the expression of CCAAT-enhancer-binding protein alpha (C/EBPalpha), peroxisome proliferator-activated receptor gamma (PPARgamma), leptin and aP2. Sinigrin arrested cells in the G0/G1 phase of the cell cycle and increased the expression of p21 and p27. CDK2 expression was suppressed by sinigirn in MDI-induced adipocytes. Sinigrin increased the phosphorylation of adenosine monophosphate-activated protein kinase (AMPK), mitogen-activated protein kinase (MAPK) and acetyl-CoA carboxylase (ACC) in the early stage of adipocyte differentiation, suggesting that Sinigrin has anti-adipogenic effects through AMPK, MAPK and ACC activation. Sinigrin also inhibited the production of pro-inflammatory cytokines including tumor necrosis factor -alpha (TNF-alpha) and interleukin (IL)-6, IL-1beta and IL-18. Taken together, these data suggest that Sinigrin inhibits early-stage adipogenesis of 3T3-L1 adipocytes through the AMPK and MAPK signaling pathways.

Effect of different proportion of sulphur treatments on the contents of glucosinolate in kale (Brassica oleracea var. acephala) commonly consumed in Republic of Korea.[Pubmed:29472789]

Saudi J Biol Sci. 2018 Feb;25(2):349-353.

Kale (Brassica oleracea L. Acephala Group) is the rich source of medicinal value sulphur compounds, glucosinolates (GLSs). The aim of this study was to investigate the effect of different proportion of sulphur (S) supplementation levels on the accumulation of GLSs in the leaves of the kale cultivar ('TBC'). High performance liquid chromatography (HPLC) separation method guided to identify and quantify six GSLs including three aliphatic (progoitrin, Sinigrin and gluconapin) and three indolyl (glucobrassicin, 4-methoxyglucobrassicin and neoglucobrasscin) respectively. Analysis of these distinct levels of S supplementation revealed that the accumulation of individual and total GLSs was directly proportional to the S concentration. The maximum levels of total GLSs (26.8 micromol/g DW) and glucobrassicin (9.98 micromol/g DW) were found in lower and upper parts of the leaves supplemented with 1 mM and 2 mM S, respectively. Interestingly, aliphatic GSLs were noted predominant in all the parts (50.1, 59.3 and 56% of total GSLs). Among the aliphatic and indolyl GSLs, Sinigrin and glucobrassicin account 35.3 and 30.88% of the total GSLs. From this study, it is concluded that supply of S enhance the GSLs accumulation in kale.

Allyl isothiocyanate reduces liver fibrosis by regulating Kupffer cell activation in rats.[Pubmed:29669958]

J Vet Med Sci. 2018 Jun 6;80(6):893-897.

Allyl isothiocyanate (AITC), a metabolite of the glucosinolate Sinigrin, protects the liver of rats injured by carbon tetrachloride (CCl4). This study evaluated whether AITC reduces hepatic fibrosis in rats repetitively exposed to CCl4. Serum chemistry showed that AITC (doses of 5 and 50 mg) administered to rats exposed to CCl4 significantly reduced the levels of alanine aminotransferase and aspartate aminotransferase activity that were elevated in CCl4-intoxicated rats. The connective tissue in AITC-treated rats was significantly reduced based on Sirius staining. In addition, Kupffer cell activation was significantly reduced in the AITC and CCl4 co-treated groups. Collectively, this study suggests that AITC mitigates hepatic fibrosis in rats repetitively exposed to CCl4 with concurrent regulation of Kupffer cell and monocyte activation.

Exposure of kale root to NaCl and Na2SeO3 increases isothiocyanate levels and Nrf2 signalling without reducing plant root growth.[Pubmed:29507323]

Sci Rep. 2018 Mar 5;8(1):3999.

A plant factory is a closed cultivation system that provides a consistent and modified environment for plant growth. We speculated that treatment of kale (Brassica oleracea) grown in a plant factory with NaCl, Na2SeO3, or both would increase the bioactive phytochemical levels including glucosinolates (GLSs) and isothiocyanates (ITCs), the key molecules in cancer prevention. The kale was harvested and analysed after treatment with NaCl and Na2SeO3 alone or in combination for 1 or 2 weeks. Exposure to NaCl alone but not Na2SeO3 increased plant root growth. Levels of Sinigrin were increased by a 2-week exposure to Na2SeO3 alone or in combination with NaCl, whereas no changes were observed in glucoraphanin and gluconasturtiin gluconasturtiin levels. Importantly, the ITC concentration was affected by 2-week treatment with both compounds. To evaluate the bioactivity of kale, HepG2 human hepatoma cells were treated with plant extract for 6 h. Only the extract of kale roots exposed to a combination NaCl and Na2SeO3 for 2 weeks showed an increased expression of nuclear factor erythroid 2-related factor (Nrf2), which regulates genes encoding antioxidant proteins. These data suggest that co-treatment with NaCl and Na2SeO3 increased the ITC content and chemopreventive effects of kale root.

Sinigrin is a major glucosinolate present in plants of the Brassicaceae family, with anti-adipogenic effects.

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