Sulforaphane

Sulforaphane
Names
IUPAC name
1-Isothiocyanato-4-methylsulfinylbutane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
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 (sulphoraphane in British English) is a compound within the isothiocyanate group of organosulfur compounds. It is obtained from cruciferous vegetables such as broccoli, Brussels sprouts, and 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 sprout, cabbage, cauliflower, bok choy, kale, collards, Chinese broccoli, broccoli raab, kohlrabi, mustard, turnip, radish, arugula, and watercress.

Research

Although there is basic research on how sulforaphane may affect mechanisms in vivo,[2][3] there is limited evidence to date for its effects on human diseases.[4][5] While investigations support the effect of sulforaphane on Nrf2 activity, it has far less effect than synthetic triterpenoid analogues.[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. PMC 48665 Freely accessible. PMID 1549603. doi:10.1073/pnas.89.6.2399.
  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. PMC 3745957 Freely accessible. PMID 23983898. doi:10.1155/2013/415078.
  3. ↑ 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. PMID 20459098. doi:10.1021/jf1003573.
  4. ↑ van Die, MD; Bone, KM; Emery, J; Williams, SG; Pirotta, MV; Paller, CJ (April 2016). "Phytotherapeutic interventions in the management of biochemically recurrent prostate cancer: a systematic review of randomised trials". BJU Int. 117 (S4): 17–34. PMID 26898239. doi:10.1111/bju.13361.
  5. ↑ Yang L, Palliyaguru DL, Kensler TW (February 2016). "Frugal chemoprevention: targeting Nrf2 with foods rich in sulforaphane". Semin Oncol. 43 (1): 146–53. PMC 4789124 Freely accessible. PMID 26970133. doi:10.1053/j.seminoncol.2015.09.013.
  6. ↑ Mi-Kyoung Kwak; Thomas W. Kensler (1 April 2010). "Targeting NRF2 signaling for cancer chemoprevention". Toxicol Appl Pharmacol. 244 (1): 66–76. PMC 3584341 Freely accessible. PMID 19732782. doi:10.1016/j.taap.2009.08.028.


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