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Sulforaphane - What is it

 

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SULFORAPHANE - what is it?


Extract from PDRHealth

Description
Sulforaphane is the aglycone breakdown product of the glucosinolate glucoraphanin, also known as sulforaphane glucosinolate (SGS). Glucosinolates are beta-thioglucoside-N-hydroxysulfates and are primarily found in cruciferous vegetables (cabbage, broccoli, broccoli sprouts, brussels sprouts, cauliflower, cauliflower sprouts, bok choy, kale, collards, arugula, kohlrabi, mustard, turnip, red radish and watercress). Young broccoli sprouts and young cauliflower sprouts are especially rich in glucoraphanin.

Sulforaphane may have cancer chemopreventive activity. However, glucosinolates themselves typically have low anticancer activity. Sulforaphane is produced from sulforaphane glucosinolate via the action of the enzyme myrosinase (thioglucoside glucohydrolase), an enzyme present in cruciferous vegetables that is activated upon maceration of the vegetables.

Sulforaphane is also classified as an isothiocyanate. Its molecular formula is C6H11NOS2, and its molecular weight is 177.29 daltons. It is also known as 4-methylsulfinylbutyl isothiocyanate and (-)-1-isothiocyanato-4(R)-(methylsulfinyl) butane. Sulforaphane glucosinolate (glucoraphanin) is also known as 4-methylsufinylbutyl glucosinolate. The structural formula is:


Sulforaphane (chemical structure)


Actions
Sulforaphane may have anticarcinogenic activity.


Mechanism of Action
Sulforaphane's possible anticarcinogenic activity is accounted for by its ability to induce phase II detoxication enzymes, such as glutathione S-transferase and quinone reductase [NAD(P)H: (quinone-acceptor) oxidoreductase]. These enzymes may afford protection against certain carcinogens and other toxic electrophiles, including reactive oxygen species.


Pharmocology
Little is presently known about the pharmacokinetics of sulforaphane in humans. Some preliminary studies indicate that sulforaphane is absorbed and that it is metabolized by first undergoing conjugation with reduced glutathione to form a dithiocarbamate. The dithiocarbamate is then converted sequentially to conjugates with cysteinylglycine, cysteine and N-acetylcysteine.


Indications and Usage
Experimental data suggest that sulforaphane may have anticarcinogenic effects.


Research Summary
Sulforaphane has significantly reduced the incidence, multiplicity and rate of development of chemically induced mammary tumors in rats. It has demonstrated an ability to detoxify a number of carcinogens and thus might have the ability to protect against a variety of cancers. It has been shown that dietary supplementation with sulforaphane enhances glutathione S-transferase (GST) enzyme activity, which is known to detoxify many carcinogens.

One group of researchers has reported that three-day-old sprouts of certain broccoli and cauliflower cultivars contain 10 to 100 times higher levels of glucoraphanin, the glucosinolate of sulforaphane, than do mature broccoli and cauliflower sprouts. Thus they have concluded that "small quantities of crucifer sprouts may protect against the risk of cancer as effectively as much larger quantities of mature vegetables of the same variety." Additionally they have noted that the indole glucosinates that are prevalent in mature broccoli, for example, are present in only small quantities in the sprouts. One report suggested that the degradation products (e.g., indole-3-carbinol) of these glucosinates might themselves promote tumorigenesis, but several other investigators have not confirmed this.


Contraindications
Sulforaphane is contraindicated in those who are hypersensitive to any component of a sulforaphane-containing product.


Precautions
Pregnant women and nursing mothers should avoid sulforaphane supplementation pending long-term safety data.


Adverse Reactions
No adverse reactions reported.


Dosage and Administration
Sulforaphane is available in a few different formulations, usually in combination with other dietary phytochemicals. There are no typical doses.

Sulforaphane, in the form of its glucosinolate glucoraphanin, is abundant in three-day old broccoli sprouts, which are available in the marketplace. The levels of glucoraphanin in three-day old broccoli sprouts are from 10 to 100 times greater than in mature broccoli.


References
Fahey JW, Talalay P. Antioxidant functions of sulforaphane: a potent inducer of Phase II detoxification enzymes. Food Chem Toxicol. 1999; 37:973-979.
Fahey JW, Zhang Y, Talalay P. Broccoli sprouts: an exceptionally rich source of inducers of enzymes that protect against chemical carcinogens. Proc Natl Acad Sci USA. 1997; 94:10367-10372.
Faulkner K, Mithen R, Williamson G. Selective increase of the potential anticarcinogen 4-methylsulphinylbutyl glucosinolate in broccoli. Carcinogenesis. 1998; 19:605-609.
Singletary K, MacDonald C. Inhibition of benzo[a]pyrene- and 1, 6-dinitropyrene-DNA adduct formation in human mammary epithelial cells by dibenzoylmethane and sulforaphane. Cancer Letters. 2000; 155:47-54.
Zeligs MA. Diet and estrogen status: the cruciferous connection. J Med Food. 1998; 1:67-82.
Zhang Y. Role of glutathione in the accumulation of anticarcinogenic isothiocyanates and their glutathione conjugates by murine hepatoma cells. Carcinogenesis. 2000; 21:1175-1182.
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 USA. 1992; 89:2399-2403.


Sulforaphane is effective in fighting Helicobacter pylori



See below for a sample of the Fortified Flax Jar




Each jar contains 180gm of natural organic
flax hulls with 3-day old broccoli sprouts







The above information is provided for general educational purposes only. It is not intended to replace competent health care advice received from a knowledgeable healthcare professional. You are urged to seek healthcare advice for the treatment of any illness or disease.
Health Canada and the FDA (USA) have not evaluated these statements. This product is not intended to diagnose, treat, cure, or prevent any disease.


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