Glucoraphanin

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Glucoraphanin
Glucoraphanin.png
Potassium salt of glucoraphanin
Names
IUPAC name
1-S-[(1E)-5-(methylsulfinyl)-N-(sulfonatooxy)pentanimidoyl]-1-thio-β-D-glucopyranose
Other names
Glucorafanin; 4-Methylsulfinylbutyl glucosinolate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
Properties
C12H23NO10S3
Molar mass 437.49 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Glucoraphanin is a glucosinolate found in broccoli,[1] cauliflower,[2] and mustard[3] in particular in the young sprouts. When these foods are consumed, the enzyme myrosinase transforms glucoraphanin into raphanin, which is an antibiotic, and into sulforaphane, which exhibits anti-cancer and antimicrobial properties in experimental models.[citation needed] Preliminary research also suggests that glucoraphanin may slow and prevent arthritis,[4] and 'retune' mitochondrial metabolism.[5] A variety of broccoli has been bred to reliably contain 2-3 times more glucoraphanin than standard broccoli.[6][7] Consumption of large amounts of glucoraphanin may produce negative effects due to increased creation of reactive oxygen species.[8] However, this is based on studies on rats fed pure glucoraphanin at a dose equivalent to a human consuming approximately 250 portions of broccoli per day. Other studies have shown glucoraphanin to be safe, even at doses far higher than would be obtained through eating broccoli.[9]

References[edit]

  1. ^ James, D.; Devaraj, S.; Bellur, P.; Lakkanna, S.; Vicini, J.; Boddupalli, S. (2012). "Novel concepts of broccoli sulforaphanes and disease: Induction of phase II antioxidant and detoxification enzymes by enhanced-glucoraphanin broccoli". Nutrition Reviews. 70 (11): 654–65. doi:10.1111/j.1753-4887.2012.00532.x. PMID 23110644. 
  2. ^ Jeffery, E. H.; Brown, A. F.; Kurilich, A. C.; Keck, A. S.; Matusheski, N.; Klein, B. P.; Juvik, J. A. (2003). "Variation in content of bioactive components in broccoli". Journal of Food Composition and Analysis. 16 (3): 323–330. doi:10.1016/S0889-1575(03)00045-0. 
  3. ^ Oh, K.; SangOk, K.; Rak, C. (2015). "Sinigrin content of different parts of Dolsan leaf mustard". Korean Journal of Food Preservation. 22 (4): 553–558. doi:10.11002/kjfp.2015.22.4.553. 
  4. ^ Roberts, Michelle (27 August 2013). "Broccoli slows arthritis, researchers think". BBC News. Retrieved 28 August 2013. 
  5. ^ Armah, CN; Traka, MH; Dainty, JR; Defernez, M; Janssens, A; Leung, W; Doleman, JF; Potter, JF; Mithen, RF (Sep 2013). "A diet rich in high-glucoraphanin broccoli interacts with genotype to reduce discordance in plasma metabolite profiles by modulating mitochondrial function". The American Journal of Clinical Nutrition. 98 (3): 712–22. doi:10.3945/ajcn.113.065235. PMC 3743733Freely accessible. PMID 23964055. Retrieved 3 June 2014. 
  6. ^ Cheng, Maria (October 26, 2011). "UK scientists grow super broccoli". Associated Press. Retrieved 10 November 2011. 
  7. ^ "Beneforte, Super Broccoli". Institute of Food Research, Norwich Research Park, Colney, Norwich, UK. 2014. Retrieved 29 September 2014. 
  8. ^ Perocco P, Bronzetti G, Canistro D, Valgimigli L, Sapone A, Affatato A, Pedulli GF, Pozzetti L, Broccoli M, Iori R, Barillari J, Sblendorio V, Legator MS, Paolini M, Abdel-Rahman SZ.; Bronzetti; Canistro; Valgimigli; Sapone; Affatato; Pedulli; Pozzetti; Broccoli; Iori; Barillari; Sblendorio; Legator; Paolini; Abdel-Rahman (2006). "Glucoraphanin, the bioprecursor of the widely extolled chemopreventive agent sulforaphane found in broccoli, induces phase-I xenobiotic metabolizing enzymes and increases free radical generation in rat liver". Mutation Research. 595 (1–2): 125–136. doi:10.1016/j.mrfmmm.2005.11.007. PMID 16442570. 
  9. ^ Lai, RH; Keck, AS; Wallig, MA; West, LG; Jeffery, EH (Jan 2008). "Evaluation of the safety and bioactivity of purified and semi-purified glucoraphanin". Food and Chemical Toxicology. 46 (1): 195–202. doi:10.1016/j.fct.2007.07.015. PMID 17804139. Retrieved 3 June 2014.