Glucoraphanin
 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 | |
21414-41-5  | |
| ChEBI | CHEBI:79311 |
| ChemSpider | 570930 |
| Jmol interactive 3D | Image |
| PubChem | 656556 |
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| |
| Properties | |
| C12H22NO10S3 | |
| Molar mass | 436.49 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] and cauliflower,[2] 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. Preliminary research also suggests that glucoraphanin may slow and prevent arthritis,[3] and 'retune' mitochondrial metabolism.[4] A variety of broccoli has been bred to reliably contain 2-3 times more glucoraphanin than standard broccoli.[5][6] Consumption of large amounts of glucoraphanin may produce negative effects due to increased creation of reactive oxygen species.[7] 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.[8]
References
- ↑ 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.
- ↑ 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.
- ↑ Roberts, Michelle (27 August 2013). "Broccoli slows arthritis, researchers think". BBC News. Retrieved 28 August 2013.
- ↑ 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 3743733. PMID 23964055. Retrieved 3 June 2014.
- ↑ Cheng, Maria (October 26, 2011). "UK scientists grow super broccoli". Associated Press. Retrieved 10 November 2011.
- ↑ "Beneforte, Super Broccoli". Institute of Food Research, Norwich Research Park, Colney, Norwich, UK. 2014. Retrieved 29 September 2014.
- ↑ 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.
- ↑ 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.