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Chemical Compound Review

AC1LCV7Y     (2R,3S,4S,5R,6S)-3,4,5- trihydroxy-2...

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Disease relevance of (2S,3R,4S,5R,6R)-2-(C-allyl-N-sulfoxy-carbonimidoyl)thio-3,4,5-trihydroxy-6-methylol-tetrahydropyran


High impact information on (2S,3R,4S,5R,6R)-2-(C-allyl-N-sulfoxy-carbonimidoyl)thio-3,4,5-trihydroxy-6-methylol-tetrahydropyran


Biological context of (2S,3R,4S,5R,6R)-2-(C-allyl-N-sulfoxy-carbonimidoyl)thio-3,4,5-trihydroxy-6-methylol-tetrahydropyran


Anatomical context of (2S,3R,4S,5R,6R)-2-(C-allyl-N-sulfoxy-carbonimidoyl)thio-3,4,5-trihydroxy-6-methylol-tetrahydropyran

  • This may be due to increased apoptotic deletion of damaged stem cells in the crypts of animals fed sinigrin [8].
  • These results suggested that dietary sinigrin might reduce the incidence of NNK-induced hepatic tumors with no effect on NNK tumorigenesis of the lung and nasal cavity, whereas I3C might increase hepatic tumor incidence and reduce NNK tumorigenesis of the lung and nasal cavity [9].
  • Over a time course of 100 h, protein bodies within aleurone-like cells degraded, fused to form the cell vacuole and lost all myrosinase labelling but retained residual sinigrin labelling [13].
  • Aqueous extracts of cooked and autolysed Brussels sprouts and sinigrin decreased DNA strand breaks in human lymphocytes exposed to 100 microM H2O2 for 5 min on ice, although the level of EndoIII and FPG sensitive sites was not reduced [14].
  • In larval feces, only trace amounts of glucosinolates (sinalbin and sinigrin) could be detected [15].

Associations of (2S,3R,4S,5R,6R)-2-(C-allyl-N-sulfoxy-carbonimidoyl)thio-3,4,5-trihydroxy-6-methylol-tetrahydropyran with other chemical compounds


Gene context of (2S,3R,4S,5R,6R)-2-(C-allyl-N-sulfoxy-carbonimidoyl)thio-3,4,5-trihydroxy-6-methylol-tetrahydropyran

  • The stereochemistry of hydrolysis of sinigrin by Sinapis alba myrosinase was followed by 1H NMR and the enzyme was found to operate with a mechanism retaining the anomeric configuration at the cleavage point exactly like the related O-glycosidases found in family 1 [19].
  • Crude preparations of soluble proteins from leaf and flower extracts of wild-type Arabidopsis showed myrosinase activity when sinigrin was used as substrate [20].

Analytical, diagnostic and therapeutic context of (2S,3R,4S,5R,6R)-2-(C-allyl-N-sulfoxy-carbonimidoyl)thio-3,4,5-trihydroxy-6-methylol-tetrahydropyran

  • The bioassay results showed that dietary sinigrin had no effect on NNK tumorigenesis in these target tissues [9].
  • Reversed-phase ion-pair liquid chromatography has been investigated for directly analyzing sinigrin in mustard seed without desulfatation [21].
  • After extraction by phosphate buffer (pH 7.0) from the grind-pastes of inactivated-myrosinase mustard seeds, sinigrin was first isolated through deproteinization and centrifugation, followed by filtration and injection into the chromatographic system [21].
  • The glucosinolate content in membrane eluates is determined by HPLC using sinigrin standards [22].
  • We have studied the effect of preincubating human lymphocytes with aqueous extracts of raw, cooked and autolysed Brussels sprouts and the glucosinolate, sinigrin, on hydrogen peroxide-induced DNA damage, strand breaks and base oxidation, in vitro by means of the Comet assay [14].


  1. Degradation of sinigrin by Lactobacillus agilis strain R16. Llanos Palop, M., Smiths, J.P., Brink, B.T. Int. J. Food Microbiol. (1995) [Pubmed]
  2. Thioglucosidase activity from Sphingobacterium sp. strain OTG1. Meulenbeld, G.H., Hartmans, S. Appl. Microbiol. Biotechnol. (2001) [Pubmed]
  3. Formation of allyl isothiocyanate from sinigrin in the digestive tract of rats monoassociated with a human colonic strain of Bacteroides thetaiotaomicron. Elfoul, L., Rabot, S., Khelifa, N., Quinsac, A., Duguay, A., Rimbault, A. FEMS Microbiol. Lett. (2001) [Pubmed]
  4. In vitro digestion of sinigrin and glucotropaeolin by single strains of Bifidobacterium and identification of the digestive products. Cheng, D.L., Hashimoto, K., Uda, Y. Food Chem. Toxicol. (2004) [Pubmed]
  5. Effects of Brussels sprout juice on the cell cycle and adhesion of human colorectal carcinoma cells (HT29) in vitro. Smith, T.K., Lund, E.K., Clarke, R.G., Bennett, R.N., Johnson, I.T. J. Agric. Food Chem. (2005) [Pubmed]
  6. Metabolism of sinigrin (2-propenyl glucosinolate) by the human colonic microflora in a dynamic in vitro large-intestinal model. Krul, C., Humblot, C., Philippe, C., Vermeulen, M., van Nuenen, M., Havenaar, R., Rabot, S. Carcinogenesis (2002) [Pubmed]
  7. An unusual case of 'uncompetitive activation' by ascorbic acid: purification and kinetic properties of a myrosinase from Raphanus sativus seedlings. Shikita, M., Fahey, J.W., Golden, T.R., Holtzclaw, W.D., Talalay, P. Biochem. J. (1999) [Pubmed]
  8. Inhibition of dimethylhydrazine-induced aberrant crypt foci and induction of apoptosis in rat colon following oral administration of the glucosinolate sinigrin. Smith, T.K., Lund, E.K., Johnson, I.T. Carcinogenesis (1998) [Pubmed]
  9. Effects of dietary sinigrin or indole-3-carbinol on O6-methylguanine-DNA-transmethylase activity and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced DNA methylation and tumorigenicity in F344 rats. Morse, M.A., Wang, C.X., Amin, S.G., Hecht, S.S., Chung, F.L. Carcinogenesis (1988) [Pubmed]
  10. Colon cancer proliferating desulfosinigrin in wasabi (Wasabia japonica). Weil, M.J., Zhang, Y., Nair, M.G. Nutrition and cancer. (2004) [Pubmed]
  11. Identification of new derivatives of sinigrin and glucotropaeolin produced by the human digestive microflora using 1H NMR spectroscopy analysis of in vitro incubations. Combourieu, B., Elfoul, L., Delort, A.M., Rabot, S. Drug Metab. Dispos. (2001) [Pubmed]
  12. Uptake and distribution of sinigrin in microspore derived embryos of Brassica napus L. Iqbal, M.C., Möllers, C. J. Plant Physiol. (2003) [Pubmed]
  13. Sub-cellular immunolocalization of the glucosinolate sinigrin in seedlings of Brassica juncea. Kelly, P.J., Bones, A., Rossiter, J.T. Planta (1998) [Pubmed]
  14. Effects of Brussels sprouts extracts on hydrogen peroxide-induced DNA strand breaks in human lymphocytes. Zhu, C.Y., Loft, S. Food Chem. Toxicol. (2001) [Pubmed]
  15. Sequestration of host plant glucosinolates in the defensive hemolymph of the sawfly Athalia rosae. Müller, C., Agerbirk, N., Olsen, C.E., Boevé, J.L., Schaffner, U., Brakefield, P.M. J. Chem. Ecol. (2001) [Pubmed]
  16. Selective induction of phase II enzymes in the urinary bladder of rats by allyl isothiocyanate, a compound derived from Brassica vegetables. Munday, R., Munday, C.M. Nutrition and cancer. (2002) [Pubmed]
  17. Anti-SARS coronavirus 3C-like protease effects of Isatis indigotica root and plant-derived phenolic compounds. Lin, C.W., Tsai, F.J., Tsai, C.H., Lai, C.C., Wan, L., Ho, T.Y., Hsieh, C.C., Chao, P.D. Antiviral Res. (2005) [Pubmed]
  18. Induction of detoxication enzymes in mice by naturally occurring allyl nitrile. Tanii, H., Higashi, T., Nishimura, F., Higuchi, Y., Saijoh, K. J. Agric. Food Chem. (2005) [Pubmed]
  19. Mechanism-based inhibition and stereochemistry of glucosinolate hydrolysis by myrosinase. Cottaz, S., Henrissat, B., Driguez, H. Biochemistry (1996) [Pubmed]
  20. COI1 affects myrosinase activity and controls the expression of two flower-specific myrosinase-binding protein homologues in Arabidopsis. Capella, A.N., Menossi, M., Arruda, P., Benedetti, C.E. Planta (2001) [Pubmed]
  21. Direct determination of sinigrin in mustard seed without desulfatation by reversed-phase ion-pair liquid chromatography. Jen, J.F., Lin, T.H., Huang, J.W., Chung, W.C. Journal of chromatography. A. (2001) [Pubmed]
  22. Determination of glucosinolates in canola seeds using anion exchange membrane extraction combined with the high-pressure liquid chromatography detection. Szmigielska, A.M., Schoenau, J.J., Levers, V. J. Agric. Food Chem. (2000) [Pubmed]
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