Sulforaphane

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ImageFile = Sulforaphane.png ImageSize = 200px
ImageFile1 = Sulforaphane-3D-balls.png ImageFile2 = Sulforaphane-3D-vdW.png IUPACName = 1-Isothiocyanato-4-methylsulfinylbutane
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Section1 = Chembox Identifiers
CASNo = 4478-93-7
PubChem = 5350
SMILES = CS(=O)CCCCN=C=S
InChI=1/C6H11NOS2/c1-10 (8)5-3-2-4-7-6-9/h2- 5H2,1H3
Section2 = Chembox Properties
Formula = C₆H₁₁NOS₂
MolarMass = 177.29 g/mol
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Section3 = Chembox Hazards
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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, 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.Fact|date=February 2007

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. [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] Consumption of broccoli sprouts has shown to be effective at inhibiting "Helicobacter pylori" growth [cite journal|author=Galan MV, Kishan AA, Silverman AL|title=Oral broccoli sprouts for the treatment of "Helicobacter pylori" infection: a preliminary report|journal=Dig Dis Sci.|month=August | year = 2004|volume=49|issue=7–8|pages=1088–90|pmid=15387326|doi=10.1023/B:DDAS.0000037792.04787.8a] with sulforaphane being at least one of the active agents. [cite journal|author=Fahey JW, Haristoy X, Dolan PM, Kensler TW, Scholtus I, Stephenson KK, Talalay P, Lozniewski A|title=Sulforaphane inhibits extracellular, intracellular, and antibiotic-resistant strains of Helicobacter pylori and prevents benzo [a] pyrene-induced stomach tumors.|year=2002|month=May|pmid=12032331]

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 mcg of sulforaphane daily from broccoli-sprout extracts. Sulforaphane and dietary consumption of cruciferous vegetables are known to affect the action of drug-metabolizing enzymes. [Kall MA, Vang O, Clausen J. Effects of dietary broccoli on human drug metabolising activity. "Cancer Lett" 1997;114:169–70.] 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. [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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