Sulforaphane

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Sulforaphane
Sulforaphane.png
Sulforaphane-3D-balls.png
Sulforaphane-3D-vdW.png
Identifiers
CAS number 4478-93-7 YesY
PubChem 5350
ChemSpider 5157 N
ChEBI CHEBI:47807 N
ChEMBL CHEMBL48802 N
Jmol-3D images Image 1
Properties
Molecular formula C6H11NOS2
Molar mass 177.29 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Sulforaphane is a molecule within the isothiocyanate group of organosulfur compounds. It exhibits anticancer and antimicrobial properties in experimental models. 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.

Possible medicinal properties[edit]

Consumption of broccoli sprouts has shown to be potentially effective at inhibiting Helicobacter pylori growth,[2][3] with sulforaphane being at least one of the active agents.[2][4]

Consumption of raw broccoli has been shown to "result in faster absorption, higher bioavailability, and higher peak plasma amounts of sulforaphane, compared to cooked broccoli".[5]

Sulforaphane and dietary consumption of cruciferous vegetables are known to affect the action of drug-metabolizing enzymes in vitro and in preliminary human studies.[6] Although no side-effects or direct drug interactions have been reported as of 2008, people taking prescription drugs are advised to consult a doctor before taking sulforaphane or broccoli-sprout extracts.

The possible anticancer activity of sulforaphane may be related to the induction of phase-II enzymes of xenobiotic transformation (such as quinone reductase and glutathione S-transferase), and enhancing the transcription of tumor suppressor proteins, possibly via inhibitory effects on histone deacetylase.[7]

Sulforaphane and diindolylmethane (another compound from Brassica vegetables) inhibit cancer growth in vitro and in experimental animals.[8] Sulforaphane downregulated the Wnt/beta-catenin self-renewal pathway in breast cancer stem cells.[8]

When applied topically, sulforaphane may protect skin against UV radiation damage, and thus potentially against cancer.[9] Sulforaphane may inhibit histone deacetylase (HDAC) activity.[10] Preliminary experiments indicate that sulforaphane may protect the heart from vascular inflammation and atherosclerosis.[11][12]


In vitro studies[edit]

In vitro studies have shown that sulforaphane can inactivate histone deacetylase 6 (HDAC6), and so interfere with the expression of androgen receptor genes in prostate cancer cells.[13]

Clinical trials[edit]

Sulforaphane (as broccoli sprout extracts) is in numerous clinical trials[14] including a phase II trial for prostate cancer.[15]

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. ^ a b Yanaka A, Fahey JW, Fukumoto A, Nakayama M, Inoue S, Zhang S, Tauchi M, Suzuki H, Hyodo I, Yamamoto M (April 2009). "Dietary sulforaphane-rich broccoli sprouts reduce colonization and attenuate gastritis in Helicobacter pylori–infected mice and humans". Cancer Prev. Res. 2 (4): 353–360. doi:10.1158/1940-6207.CAPR-08-0192. PMID 19349290. Lay summary. 
  3. ^ Galan MV, Kishan AA, Silverman AL (August 2004). "Oral broccoli sprouts for the treatment of Helicobacter pylori infection: a preliminary report". Dig Dis Sci. 49 (7–8): 1088–1090. doi:10.1023/B:DDAS.0000037792.04787.8a. PMID 15387326. 
  4. ^ Fahey JW, Haristoy X, Dolan PM et al. (May 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): 7610–7615. doi:10.1073/pnas.112203099. PMC 124299. PMID 12032331. 
  5. ^ Vermeulen, M; Klöpping-Ketelaars, IW; van den Berg, R; Vaes, WH (November 2008). "Bioavailability and kinetics of sulforaphane in humans after consumption of cooked versus raw broccoli". J Agric Food Chem. 56 (22): 10505–10509. doi:10.1021/jf801989e. PMID 18950181. 
  6. ^ Kall MA, Vang O, Clausen J (March 1997). "Effects of dietary broccoli on human drug metabolising activity". Cancer Lett. 114 (1–2): 169–170. doi:10.1016/S0304-3835(97)04652-1. PMID 9103281. 
  7. ^ Hayes, JD; Kelleher, MO; Eggleston, IM (2008). "The cancer chemopreventive actions of phytochemicals derived from glucosinolates". European Journal of Nutrition. 47 Suppl 2: 73–88. doi:10.1007/s00394-008-2009-8. PMID 18458837. 
  8. ^ a b Li et al. (May 2010). "Sulforaphane, a dietary component of broccoli/broccoli sprouts, inhibits breast cancer stem cells". Clinical Cancer Research 16 (9): 2580–2590. doi:10.1158/1078-0432.CCR-09-2937. PMC 2862133. PMID 20388854. 
  9. ^ Talalay P, Fahey JW, Healy ZR et al. (October 2007). "Sulforaphane mobilizes cellular defenses that protect skin against damage by UV radiation". Proc. Natl. Acad. Sci. U.S.A. 104 (44): 17500–17505. doi:10.1073/pnas.0708710104. PMC 2077285. PMID 17956979. 
  10. ^ Dashwood RH, Ho E (October 2007). "Dietary histone deacetylase inhibitors: from cells to mice to man". Semin. Cancer Biol. 17 (5): 363–369. doi:10.1016/j.semcancer.2007.04.001. PMC 2737738. PMID 17555985. 
  11. ^ "Research reveals a broccoli boost for arteries". 4 Sep 2009. 
  12. ^ http://www.bg.ic.ac.uk/research/r.krams/paper2.pdf
  13. ^ Gibbs A, Schwartzman J, Deng V, Alumkal J (Sep 29, 2009). "Sulforaphane destabilizes the androgen receptor in prostate cancer cells by inactivating histone deacetylase 6". PNAS 106 (39): 16663–8. doi:10.1073/pnas.0908908106. PMC 2757849. PMID 19805354. 
  14. ^ http://clinicaltrials.gov/ct2/results?term=Sulforaphane
  15. ^ "The effects of sulforaphane in patients with biochemical recurrence of prostate cancer".