Sulforaphane

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Sulforaphane
Sulforaphane.png
Sulforaphane-3D-balls.png
Sulforaphane-3D-vdW.png
Names
IUPAC name
1-Isothiocyanato-4-methylsulfinylbutane
Identifiers
4478-93-7 YesY
ChEBI CHEBI:47807 N
ChEMBL ChEMBL48802 N
ChemSpider 5157 N
Jmol-3D images Image
PubChem 5350
Properties
C6H11NOS2
Molar mass 177.29 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Sulforaphane is a compound within the isothiocyanate group of organosulfur compounds. It is obtained from cruciferous vegetables such as broccoli, Brussels sprouts or cabbages. It is produced when the enzyme myrosinase transforms glucoraphanin, a glucosinolate, into sulforaphane upon damage to the plant (such as from chewing), which allows the two compounds to mix and react. Young sprouts of broccoli and cauliflower are particularly rich in glucoraphanin.

Glucoraphanin.png
glucoraphanin, glucosinolate precursor to sulforaphane

Occurrence and isolation[edit]

Sulforaphane was identified in broccoli sprouts, which, of the cruciferous vegetables, have the highest concentration of sulforaphane.[1] It is also found in Brussels sprouts, cabbage, cauliflower, bok choy, kale, collards, Chinese broccoli, broccoli raab, kohlrabi, mustard, turnip, radish, arugula, and watercress.

Research[edit]

Basic research on sulforaphane includes its potential effect on mechanisms of neurodegenerative disorders and cancer; however, results to date are contradictory.[2][3] Sulforaphane is under study for a potential neuroprotective effect on recovery from spinal cord injury[4] and as a possible factor in Helicobacter pylori-associated gastric diseases.[5][6]

See also[edit]

References[edit]

  1. ^ Zhang Y, Talalay P, Cho CG, Posner GH (March 1992). "A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure". Proc. Natl. Acad. Sci. U.S.A. 89 (6): 2399–2403. doi:10.1073/pnas.89.6.2399. PMC 48665. PMID 1549603. 
  2. ^ Tarozzi A, Angeloni C, Malaguti M, Morroni F, Hrelia S, Hrelia P (2013). "Sulforaphane as a potential protective phytochemical against neurodegenerative diseases". Oxid Med Cell Longev (Review) 2013: 415078. doi:10.1155/2013/415078. PMC 3745957. PMID 23983898. 
  3. ^ Grabacka MM, Gawin M, Pierzchalska M (2014). "Phytochemical modulators of mitochondria: the search for chemopreventive agents and supportive therapeutics". Pharmaceuticals (Basel) (Review) 7 (9): 913–42. doi:10.3390/ph7090913. PMC 4190497. PMID 25192192. 
  4. ^ Koushki D, Latifi S, Javidan AN, Matin M (June 2014). "Efficacy of some non-conventional herbal medications (sulforaphane, tanshinone IIA, and tetramethylpyrazine) in inducing neuroprotection in comparison with interleukin-10 after spinal cord injury: A meta-analysis". J Spinal Cord Med (Meta-analysis) 38: 13–22. doi:10.1179/2045772314Y.0000000215. PMID 24969510. 
  5. ^ Moon JK, Kim JR, Ahn YJ, Shibamoto T (2010). "Analysis and anti-Helicobacter activity of sulforaphane and related compounds present in broccoli ( Brassica oleracea L.) sprouts". J. Agric. Food Chem. 58 (11): 6672–7. doi:10.1021/jf1003573. PMID 20459098. 
  6. ^ Fahey JW, Haristoy X, Dolan PM, Kensler TW, Scholtus I, Stephenson KK, Talalay P, Lozniewski A (2002). "Sulforaphane inhibits extracellular, intracellular, and antibiotic-resistant strains of Helicobacter pylori and prevents benzo[a]pyrene-induced stomach tumors". Proc. Natl. Acad. Sci. U.S.A. 99 (11): 7610–5. doi:10.1073/pnas.112203099. PMC 124299. PMID 12032331.