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Chemical Compound Review

AC1O3DD9     (2R,3R,4S,5R,6S)-3,4,5- trihydroxy-2...

Synonyms:
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Disease relevance of Glucoraphanin

 

High impact information on Glucoraphanin

  • This compound has previously been described as a product of myrosinase-mediated breakdown of glucoraphanin, the predominant glucosinolate in Arabidopsis leaves [4].
  • Induction of cytochrome P450, generation of oxidative stress and in vitro cell-transforming and DNA-damaging activities by glucoraphanin, the bioprecursor of the chemopreventive agent sulforaphane found in broccoli [5].
  • These findings indicate that sulforaphane but not the native GL GRA can exert both protective and toxic effects inhibiting leukemic cell growth [6].
  • A formal phase I study of safety, tolerance, and pharmacokinetics appeared justified because these sprouts are being used as vehicles for the delivery of the glucosinolate glucoraphanin and its cognate isothiocyanate sulforaphane [1-isothiocyanato-(4R)-(methylsulfinyl)butane] in clinical trials [7].
  • The effects of feeding rats purified SF (5 mmol/kg of diet), broccoli containing SF formed in situ during laboratory hydrolysis (broccoli-HP; 20% freeze-dried broccoli diet, 0.16 mmol of SF/kg of diet), and broccoli containing intact glucosinolates (broccoli-GS; 20% freeze-dried broccoli diet, 2.2 mmol of glucoraphanin/kg of diet) were compared [8].
 

Gene context of Glucoraphanin

  • Broccoli-GS and SF diets increased QR to the same extent, even though the broccoli-GS diet contained far less SF (as the unhydrolyzed glucosinolate, glucoraphanin) than the purified SF diet [8].
 

Analytical, diagnostic and therapeutic context of Glucoraphanin

  • The isolation and purification of glucoraphanin from broccoli seeds by solid phase extraction and preparative high performance liquid chromatography [9].
  • A novel preparative scale HPLC method with simple compound recovery has been developed to meet the need for a glucoraphanin standard [9].
  • In the present study, the best method for preserving glucoraphanin concentration in broccoli heads after harvest was storage of broccoli in MAP and refrigeration at 4 degrees C. This condition maintained the glucoraphanin concentration for at least 10 days and also maintained the visual quality of the broccoli heads [10].

References

  1. Sulforaphane inhibits human MCF-7 mammary cancer cell mitotic progression and tubulin polymerization. Jackson, S.J., Singletary, K.W. J. Nutr. (2004) [Pubmed]
  2. Selective cytostatic and cytotoxic effects of glucosinolates hydrolysis products on human colon cancer cells in vitro. Gamet-Payrastre, L., Lumeau, S., Gasc, N., Cassar, G., Rollin, P., Tulliez, J. Anticancer Drugs (1998) [Pubmed]
  3. Dietary approaches to positively influence fetal determinants of adult health. Noyan-Ashraf, M.H., Wu, L., Wang, R., Juurlink, B.H. FASEB J. (2006) [Pubmed]
  4. Study of the role of antimicrobial glucosinolate-derived isothiocyanates in resistance of Arabidopsis to microbial pathogens. Tierens, K.F., Thomma, B.P., Brouwer, M., Schmidt, J., Kistner, K., Porzel, A., Mauch-Mani, B., Cammue, B.P., Broekaert, W.F. Plant Physiol. (2001) [Pubmed]
  5. Induction of cytochrome P450, generation of oxidative stress and in vitro cell-transforming and DNA-damaging activities by glucoraphanin, the bioprecursor of the chemopreventive agent sulforaphane found in broccoli. Paolini, M., Perocco, P., Canistro, D., Valgimigli, L., Pedulli, G.F., Iori, R., Croce, C.D., Cantelli-Forti, G., Legator, M.S., Abdel-Rahman, S.Z. Carcinogenesis (2004) [Pubmed]
  6. Growth inhibition, cell-cycle arrest and apoptosis in human T-cell leukemia by the isothiocyanate sulforaphane. Fimognari, C., Nüsse, M., Cesari, R., Iori, R., Cantelli-Forti, G., Hrelia, P. Carcinogenesis (2002) [Pubmed]
  7. Safety, tolerance, and metabolism of broccoli sprout glucosinolates and isothiocyanates: a clinical phase I study. Shapiro, T.A., Fahey, J.W., Dinkova-Kostova, A.T., Holtzclaw, W.D., Stephenson, K.K., Wade, K.L., Ye, L., Talalay, P. Nutrition and cancer. (2006) [Pubmed]
  8. Food matrix effects on bioactivity of broccoli-derived sulforaphane in liver and colon of F344 rats. Keck, A.S., Qiao, Q., Jeffery, E.H. J. Agric. Food Chem. (2003) [Pubmed]
  9. The isolation and purification of glucoraphanin from broccoli seeds by solid phase extraction and preparative high performance liquid chromatography. Rochfort, S., Caridi, D., Stinton, M., Trenerry, V.C., Jones, R. Journal of chromatography. A. (2006) [Pubmed]
  10. The effect of post-harvest and packaging treatments on glucoraphanin concentration in broccoli (Brassica oleracea var. italica). Rangkadilok, N., Tomkins, B., Nicolas, M.E., Premier, R.R., Bennett, R.N., Eagling, D.R., Taylor, P.W. J. Agric. Food Chem. (2002) [Pubmed]
 
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