Sulforaphane
From Wikipedia, the free encyclopedia
| Sulforaphane | |
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| IUPAC name | 1-Isothiocyanato-4-methylsulfinylbutane |
| Identifiers | |
| CAS number | [4478-93-7] |
| PubChem | |
| SMILES | CS(=O)CCCCN=C=S |
| InChI | 1/C6H11NOS2/c1-10 (8)5-3-2-4-7-6-9/h2- 5H2,1H3 |
| 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 disclaimer and references |
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Sulforaphane is an anticancer 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, rocket, 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.
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.[citation needed]
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] with sulforaphane being at least one of the active agents.[3]
Sulforaphane and diindolylmethane (another compound from Brassica vegetables) have recently been shown to synergize together in the inhibition of cancer growth.
In terms of dosage, optimal levels have not yet been determined but some doctors recommend 200 - 400 mcg of sulforaphane daily from broccoli-sprout extracts. Despite that no side effects or drug interactions have been reported yet, people taking prescription drugs are still advised to consult a doctor before taking sulforaphane or broccoli-sprout extracts. Sulforaphane and dietary consumption of cruciferous vegetables are known to affect the action of drug-metabolizing enzymes.[4]
Sulforaphane seems to protect skin against UV radiation damage, and thus potentially against cancer, when applied topically.[5]
 glucoraphanin |
→ |  (-)-(R)-sulforaphane |
[edit] References
- ^ Zhang Y, Talalay P, Cho CG, Posner GH. A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure. Proc Natl Acad Sci 1992;89:2399–403
- ^ 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, Kensler TW, Scholtus I, Stephenson KK, Talalay P, Lozniewski A (May 2002). "Sulforaphane inhibits extracellular, intracellular, and antibiotic-resistant strains of Helicobacter pylori and prevents benzo[a]pyrene-induced stomach tumors.". PMID 12032331.
- ^ Kall MA, Vang O, Clausen J. Effects of dietary broccoli on human drug metabolising activity. Cancer Lett 1997;114:169–70.
- ^ Talalay P, Fahey JW, Healy ZR, Wehage SL, Benedict AL, Min C, Dinkova-Kostova AT. Sulforaphane mobilizes cellular defenses that protect skin against damage by UV radiation. Proc Natl Acad Sci U S A. 2007 Oct 23; [Epub ahead of print].
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