Sulforaphane
From Wikipedia, the free encyclopedia
| Sulforaphane | |
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| CAS number | [] |
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| 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, 100 kPa) Infobox references |
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Sulforaphane is an anticancer, antidiabetic, and antimicrobial compound that can be obtained by eating cruciferous vegetables such as brussel sprouts, broccoli, cabbage, cauliflower, bok choy, kale, collards, broccoli sprouts, chinese broccoli, broccoli raab, kohlrabi, mustard, turnip, radish, arugula, and watercress. The enzyme myrosinase transforms glucoraphanin (a glucosinolate) into sulforaphane upon damage to the plant (such as from chewing). The young sprouts of broccoli and cauliflower are particularly rich in glucoraphanin.
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[edit] Health benefits
The anticancer activity of sulforaphane is thought to 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.[citation needed]
[edit] Research
Researchers at the Johns Hopkins University School of Medicine in Baltimore MD first identified sulforaphane in broccoli sprouts which, of the cruciferous vegetables, have the highest concentration of sulforaphane.[1] Consumption of broccoli sprouts has shown to be effective at inhibiting Helicobacter pylori growth[2][3] with sulforaphane being at least one of the active agents.[4][5]
Sulforaphane and diindolylmethane (another compound from Brassica vegetables) have recently been shown to synergize together in the inhibition of cancer growth.
Optimal dosage has not yet been determined, but some doctors recommend 200-400 μg of sulforaphane daily from broccoli-sprout extracts. Sulforaphane and dietary consumption of cruciferous vegetables are known to affect the action of drug-metabolizing enzymes.[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.
Sulforaphane seems to protect skin against UV radiation damage, and thus potentially against cancer, when applied topically.[7] There is evidence for sulforaphane inhibiting histone deacetylase (HDAC) activity.[8]
 glucoraphanin |
→ | (-)-(R)-sulforaphane |
[edit] See also
[edit] References
- ^ 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): 2399–403. doi:. PMID 1549603. PMC: 48665. http://www.pnas.org/cgi/pmidlookup?view=long&pmid=1549603.
- ^ "Baby broccoli 'controls gut bug'". BBC News Online. 6 April 2009. http://news.bbc.co.uk/1/hi/health/7981095.stm. Retrieved on 6 April 2009.
- ^ 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): 1088–90. doi:. PMID 15387326.
- ^ Fahey JW, Haristoy X, Dolan PM, et al. (May 2002). "Sulforaphane inhibits extracellular, intracellular, and antibiotic-resistant strains of Helicobacter pylori and prevents benzo[apyrene-induced stomach tumors]". Proc. Natl. Acad. Sci. U.S.A. 99 (11): 7610–5. doi:. PMID 12032331.
- ^ A. Yanaka, J. W. Fahey, A. Fukumoto, M. Nakayama, S. Inoue, S. Zhang, M. Tauchi, H. Suzuki, I. Hyodo, M. Yamamoto (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:.
- ^ Kall MA, Vang O, Clausen J (March 1997). "Effects of dietary broccoli on human drug metabolising activity". Cancer Lett. 114 (1-2): 169–70. doi:. PMID 9103281.
- ^ 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): 17500–5. doi:. PMID 17956979.
- ^ Dashwood RH, Ho E (October 2007). "Dietary histone deacetylase inhibitors: from cells to mice to man.". Semin. Cancer Biol. 17 (5): 363–9. doi:. PMID 17555985.
