Glucoraphanin

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, Sulforaphane glucosinolate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C12H23NO10S3/c1-25(18)5-3-2-4-8(13-23-26(19,20)21)24-12-11(17)10(16)9(15)7(6-14)22-12/h7,9-12,14-17H,2-6H2,1H3,(H,19,20,21)/p-1/t7-,9-,10+,11-,12+,25?/m1/s1
    Key: GMMLNKINDDUDCF-SISVVIKZSA-M
  • InChI=1/C12H23NO10S3/c1-25(18)5-3-2-4-8(13-23-26(19,20)21)24-12-11(17)10(16)9(15)7(6-14)22-12/h7,9-12,14-17H,2-6H2,1H3,(H,19,20,21)/p-1/t7-,9-,10+,11-,12+,25?/m1/s1
    Key: GMMLNKINDDUDCF-XQSZSTCOBC
  • [O-]S(=O)(=O)ON=C(S[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)CCCCS(=O)C
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).

Glucoraphanin is a glucosinolate found in broccoli,[1][2] mustard and other cruciferous vegetables.[3][4]

Glucoraphanin is converted to sulforaphane by the enzyme myrosinase.[5] In plants, sulforaphane deters insect predators and acts as a selective antibiotic.[6]

  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. ^ Cite error: The named reference lpi was invoked but never defined (see the help page).
  4. ^ 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.
  5. ^ Cuomo, Valentina; Luciano, Fernando B.; Meca, Giuseppe; Ritieni, Alberto; Mañes, Jordi (26 November 2014). "Bioaccessibility of glucoraphanin from broccoli using an gastrointestinal digestion model". CyTA - Journal of Food. 13 (3): 361–365. doi:10.1080/19476337.2014.984337. S2CID 96578211.
  6. ^ Fahey, Jed W.; Holtzclaw, W. David; Wehage, Scott L.; Wade, Kristina L.; Stephenson, Katherine K.; Talalay, Paul; Mukhopadhyay, Partha (2 November 2015). "Sulforaphane Bioavailability from Glucoraphanin-Rich Broccoli: Control by Active Endogenous Myrosinase". PLOS ONE. 10 (11): e0140963. Bibcode:2015PLoSO..1040963F. doi:10.1371/journal.pone.0140963. PMC 4629881. PMID 26524341.