Sulforaphane

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

Sulforaphane is a molecule 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, glucosinolate precursor to sulforaphane

Occurrence and isolation

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

Sulforaphane has attracted recent research attention for its antioxidant properties, which may persist for hours after ingestion.[2]

Basic research on sulforaphane indicates potential for effects on mechanisms of human disease, including neurodegenerative disorders and cancer; however, results to date are contradictory, requiring clarification by future studies.[3][4] In animal models sulforaphane appears to have a protective effect against diabetes-related kidney damage.[2]

Sulforaphane may have a neuroprotective effect that can aid recovery from spinal cord injury, though the effect is not as strong as that of interleukin-10.[5]

See also

References

  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. ↑ 2.0 2.1 Dadras F, Khoshjou F (September 2013). "NF-E2-related factor 2 and its role in diabetic nephropathy". Iran J Kidney Dis (Review) 7 (5): 346–51. PMID 24072144.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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.