Sulforaphane

Sulforaphane
Names
IUPAC name
1-Isothiocyanato-4-methylsulfinylbutane
Identifiers
4478-93-7 YesY
ChEBI CHEBI:47807 N
ChEMBL ChEMBL48802 N
ChemSpider 5157 N
Jmol 3D model Interactive 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).
N verify (what is YesYN ?)
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, 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

Basic research on sulforaphane includes how it may affect neurodegenerative disorders, cancer, spinal cord injury or gastric diseases,[2][3][4][5] and preliminary human research on autism.[6]

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. ↑ 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. ↑ Singh, Kanwaljit; Connors, Susan L.; Macklin, Eric A.; Smith, Kirby D.; Fahey, Jed W.; Talalay, Paul; Zimmerman, Andrew W. (2014-10-28). "Sulforaphane treatment of autism spectrum disorder (ASD)". Proceedings of the National Academy of Sciences 111 (43): 15550–15555. doi:10.1073/pnas.1416940111. ISSN 0027-8424. PMC 4217462. PMID 25313065.
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