Sulforaphane
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| Sulforaphane | |
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| IUPAC name | 1-isothiocyanato- 4-methylsulfinylbutane |
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| PubChem | |
| InChI | InChI=1/C6H11NOS2/c1-10 (8)5-3-2-4-7-6-9/h2- 5H2,1H3 |
| 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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Overview
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 [1] which, of the cruciferous vegetables, have the highest concentration of sulforaphane. Consumption of broccoli sprouts has shown to be effective at inhibiting Helicobacter pylori growth[1] with sulforaphane being at least one of the active agents[1].
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-detoxifying enzymes.[1]
Sulforaphane seems to protect skin against UV radiation damage, and thus potentially against cancer, when applied topically. [1]
| Image:Glucoraphanin.png glucoraphanin | → | Image:Sulforaphane.png (-)-(R)-sulforaphane |
Notes
| Major families of biochemicals | ||
| Peptides | Amino acids | Nucleic acids | Carbohydrates | Nucleotide sugars | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides | ||
| Analogues of nucleic acids: | Types of Glycosides | Analogues of nucleic acids: |
| Bond: | O-glycosidic bond | S-glycosidic bond | N-glycosidic bond | |
|---|---|---|
| Geometry: | α-Glycoside | β-Glycoside | 1,4-Glycoside | 1,6-Glycoside | |
| Glycone: | Glucoside | Fructoside | Glucuronide | |
| Aglycone: | Alcoholic glycoside | Anthraquinone glycoside | Coumarin glycoside | Cyanogenic glycoside | Flavonoid glycoside | Phenolic glycoside | Saponin | Cardiac glycoside | Steviol glycoside | Thioglycoside | Glycosylamine | Bufanolide | Cardenolide | |
de:Sulforaphan nl:Sulforafaan ja:スルフォラファン sl:Sulforafan
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
