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Thursday, 31 October 2013

Phytochemicals in Foods - 10 Health Benefits of Sinigrin

Sinigrin is a phytochemical glucosinolate, belongs to the family of glucosides found abundantly in Brussels sprouts, broccoli, the seeds of black mustard, etc.

Health Benefits
1. Bladder cancer
In the design of testing the hypothesis of AITC-containing cruciferous vegetables also inhibit bladder cancer development, indicated that Comparison between hydrated MSP-1 and pure sinigrin with added myrosinase suggested that the anticancer effect of MSP-1 was derived principally, if not entirely, from the AITC generated from sinigrin. In an orthotopic rat bladder cancer model, oral MSP-1 at 71.5 mg/kg (sinigrin dose of 9 μmol/kg) inhibited bladder cancer growth by 34.5% (P < 0.05) and blocked muscle invasion by 100%, according to "Allyl isothiocyanate-rich mustard seed powder inhibits bladder cancer growth and muscle invasion" by Bhattacharya A, Li Y, Wade KL, Paonessa JD, Fahey JW, Zhang Y.(1)

2. Multidirectional time-dependent effect
In a research of nutritional significance of parent glucosinolate sinigrin 50 μmol/kg b. w./day and its degradation product allyl isothiocyanate 25 μmol/kg b. w./day and 50 μmol/kg b. w./day was studied by the evaluation of their influence on some parameters of carbohydrate and lipid metabolism in an animal rat model in vivo after their single (4 h) and 2 weeks oral administration, showed that the effect of SIN and AITC is multidirectional, indicating its impact on many organs like liver as well as pancreas, intestine in vivo action and rat adipocytes in vitro. Whilst consumption of cruciferous vegetables at levels currently considered "normal" seems to be beneficial to human health, this data suggest that any large increase in intake could conceivably lead to undesirable effect, according to "Multidirectional time-dependent effect of sinigrin and allyl isothiocyanate on metabolic parameters in rats" by Okulicz M.(2)

3. Postprandial hypertriglyceridemia
In the examination of the bioactivity of Yamato-mana (Brassica rapa L. Oleifera Group) constituent glucosinolates with 3-butenyl glucosinolate (gluconapin) decreased the plasma triglyceride gain induced by corn oil administration to mice, indicated that phenethyl glucosinolate (gluconasturtiin) had little effect. 2-Propenyl glucosinolate (sinigrin) also reduced the plasma triglyceride level, which suggests that alkenyl glucosinolates might be promising agents to prevent postprandial hypertriglyceridemia, according to "Suppressive effect of Yamato-mana (Brassica rapa L. Oleifera Group) constituent 3-butenyl glucosinolate (gluconapin) on postprandial hypertriglyceridemia in mice" by Washida K, Miyata M, Koyama T, Yazawa K, Nomoto K.(3)

4. Antimicrobial effects
In the investigation of Allyl isothiocyanate (AIT) derived from the glucosinolate sinigrin found in plants of the family Brassicaceae and its antimicrobial agent against a variety of organisms, including foodborne pathogens such as Escherichia coli O157:H7, found that it can be postulated that: 1) AIT is a more effective antimicrobial at low pH values and its degradation reduces this activity; 2) decomposition products in water might not participate in the antimicrobial action of AIT; and 3) AIT seems to have a multi-targeted mechanism of action, perhaps inhibiting several metabolic pathways and damaging cellular structures, according to "Enzymatic inhibition by allyl isothiocyanate and factors affecting its antimicrobial action against Escherichia coli O157:H7" by Luciano FB, Holley RA.(4)

5. Liver cancer
In the determination of the inhibitory effects of AITC and its NAC conjugate on cell proliferation, the expression of matrix metalloproteinases (MMPs), adhesion, invasion, and migration in SK-Hep 1 human hepatoma cells, found that AITC and NAC-AITC suppress SK-Hep 1 cell proliferation in a dose-dependent manner; by 25% and 30% for 10 microM AITC and 10 microM NAC-AITC, respectively. The influence of AITC and NAC-AITC on the gene expression of MMPs and tissue inhibitors of metalloproteinase (TIMPs). Gelatin zymography also revealed a significant downregulation of MMP-2/-9 expression in SK-Hep1 cells treated with 0.1-5 microM AITC and NAC-AITC compared with controls. Reverse transcriptase polymerase chain reaction revealed dose-dependent decreases in MMP-2/-9 messenger RNA levels in both AITC-treated and NAC-AITC-treated cells, according to "Allyl isothiocyanate and its N-acetylcysteine conjugate suppress metastasis via inhibition of invasion, migration, and matrix metalloproteinase-2/-9 activities in SK-Hep 1 human hepatoma cells" by Hwang ES, Lee HJ.(5)

6. Detoxication enzymes
In the examination of the ability of allyl nitrile, a hydrolysis product of the glucosinolate sinigrin, to increase tissue levels of the phase 2 detoxication enzymes glutathione S-transferase and quinone reductase and GSH in a variety of mouse tissues, found that show that allyl nitrile displays its maximum potency in the stomach and lungs, which is of interest in light of epidemiological studies demonstrating an inverse association between crucifer intake and the incidence of stomach and lung cancers, according to "Induction of detoxication enzymes in mice by naturally occurring allyl nitrile" by Tanii H, Higashi T, Nishimura F, Higuchi Y, Saijoh K.(6)

7. Anti-SARS coronavirus 3C-like protease effects
In the study, Isatis indigotica root extract, five major compounds of I. indigotica root, and seven plant-derived phenolic compounds were tested for anti-SARS-CoV 3CLpro effects using cell-free and cell-based cleavage assays, found that Cleavage assays with the 3CLpro demonstrated that IC50 values were in micromolar ranges for I. indigotica root extract, indigo, sinigrin, aloe emodin and hesperetin. Sinigrin (IC50: 217 microM) was more efficient in blocking the cleavage processing of the 3CLpro than indigo (IC50: 752 microM) and beta-sitosterol (IC50: 1210 microM) in the cell-based assay. Only two phenolic compounds aloe emodin and hesperetin dose-dependently inhibited cleavage activity of the 3CLpro, in which the IC50 was 366 microM for aloe emodin and 8.3 microM for hesperetin in the cell-based assay, according to "Anti-SARS coronavirus 3C-like protease effects of Isatis indigotica root and plant-derived phenolic compounds" by Lin CW, Tsai FJ, Tsai CH, Lai CC, Wan L, Ho TY, Hsieh CC, Chao PD.(7)

8. Colorectal cancer
In the investigation of raw juice extracted from Brussels sprouts rich in the glucosinolate sinigrin to explore the effect of naturally occurring glucosinolate breakdown products on cell cycle progression and apoptosis in human colorectal carcinoma cells (HT29), found that the main glucosinolate breakdown products were as follows: the sinigrin breakdown product, 1-cyano-2,3-epithiopropane (ca. 38 mM); the gluconapin hydrolysis product, 3-butenyl isothiocyanate (ca. 2.2.mM); the glucobrassicin metabolite, ascorbigen (ca. 8 mM); and low concentrations of other indole glucosinolate-derived hydrolysis products such as neoascorbigen and 3,3'-diindolylmethane. A variety of biologically active glucosinolate breakdown products are released by mechanical disruption of raw Brussels sprout tissue, but contrary to previous assumptions, allyl isothiocyanate is not the main compound responsible for the inhibition of cell proliferation, according to "Effects of Brussels sprout juice on the cell cycle and adhesion of human colorectal carcinoma cells (HT29) in vitro" by Smith TK, Lund EK, Clarke RG, Bennett RN, Johnson IT.(8)

9. Tumor cell proliferation and cyclooxygenase inhibitory
In the investigation of Cyclooxygenase and human tumor cell growth inhibitory from 5 compounds, namely plastoquinone-9 (1), 6-O-acyl-beta-d-glucosyl-beta-sitosterol (2), 1,2-dilinolenoyl-3-galactosylglycerol (3), linolenoyloleoyl-3-beta-galactosylglycerol (4), and 1,2-dipalmitoyl-3-beta-galactosylglycerol (5). 3-Acyl-sitosterols, sinigrin, gluconasturtiin, and phosphatidylcholines isolated from horseradish and alpha-tocopherol and ubiquinone-10 from wasabi rhizomes, showed that Compounds 3, 4, and 5 gave 75, 42, and 47% inhibition of COX-1 enzyme, respectively, at a concentration of 250 microg/mL. In a dose response study, compound 3 inhibited the proliferation of colon cancer cells (HCT-116) by 21.9, 42.9, 51.2, and 68.4% and lung cancer cells (NCI-H460) by 30, 39, 44, and 71% at concentrations of 7.5, 15, 30, and 60 microg/mL, respectively. At a concentration of 60 microg/mL, compound 4 inhibited the growth of colon, lung, and stomach cancer cells by 28, 17, and 44%, according to "Tumor cell proliferation and cyclooxygenase inhibitory constituents in horseradish (Armoracia rusticana) and Wasabi (Wasabia japonica)" by Weil MJ, Zhang Y, Nair MG.(9)

10. Antioxidants
In the examination of the effect of an aqueous extract of cooked Brussels sprouts on formation of 7-hydro-8-oxo-2'-deoxyguanosine (8-oxodG) in calf thymus DNA in vitro, found that Sinigrin, a glucosinolate abundant in Brussels sprouts, co-eluted with the most effective fraction and had DNA protective effects. In comparison with other antioxidants the patterns of effect of the extract in the five damage systems were more similar to that of sodium azide than to those of dimethylsulfoxide and vitamin C, according to "Inhibition of oxidative DNA damage in vitro by extracts of brussels sprouts" by Zhu C, Poulsen HE, Loft S.(10)

11. Etc.
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Sources
(1) http://www.ncbi.nlm.nih.gov/pubmed/20889681
(2) http://www.ncbi.nlm.nih.gov/pubmed/20809411
(3) http://www.ncbi.nlm.nih.gov/pubmed/20530888
(4) http://www.ncbi.nlm.nih.gov/pubmed/19346022
(5) http://www.ncbi.nlm.nih.gov/pubmed/16565438
(6) http://www.ncbi.nlm.nih.gov/pubmed/16277393
(7) http://www.ncbi.nlm.nih.gov/pubmed/16115693
(8) http://www.ncbi.nlm.nih.gov/pubmed/15884814
(9) http://www.ncbi.nlm.nih.gov/pubmed/15740020
(10) http://www.ncbi.nlm.nih.gov/pubmed/10885626