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Friday, 4 January 2013

Sulforaphane, a natural product present in cruciferous vegetables like broccoli, reduces childhood leukemia progression


Sulforaphane
1-Isothiocyanato-4-methylsulfinylbutane
Sulforaphane is a molecule, ref1 within the isothiocyanate group of organosulfur compounds. It exhibits anti-cancer and antimicrobial properties in experimental models. It is obtained from cruciferous vegetables such as broccoliBrussels sprouts or cabbages. It is produced when the enzyme myrosinase transforms glucoraphanin, a glucosinolate, into sulforaphane upon damage to the plant (such as from chewing) which allows the two compounds to mix and react. Young sprouts of broccoli and cauliflower are particularly rich in glucoraphanin.
Glucoraphanin.png
glucoraphanin, glucosinolate precursor to sulforaphane
Sulforaphane, discovered by accident in 1995 by a group of scientists researching the anticancer compounds in broccoli, is a phytochemical compound that can be obtained by eating cruciferous vegetables such as arugula, watercress, Brussels sprouts, broccoli, broccoli sprouts, cabbage, cauliflower, bok choy, kale, collards, kohlrabi, mustard, turnip, radish and rutabaga.  Sulforaphane is particularly abundant in watercress and broccoli sprouts.

Sulforaphane, a natural product present in cruciferous vegetables like broccoli, reduces childhood leukemia progression

article
Sulforaphane Induces Cell Cycle Arrest and Apoptosis in Acute Lymphoblastic Leukemia Cells,
K. Suppipat, C. Shik Park, Y. Shen, X. Zhu, H. D. Lacorazza, 
PLOS ONE 2012.
DOI: 10.1371/journal.pone.0051251


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Sulforaphane is a phytochemical belonging to the family of isothiocyanates, which means it contains the typical NCS group.
Sulforaphane was identified in broccoli sprouts, which, of the cruciferous vegetables, have the highest concentration of sulforaphane. It is also found in Brussels sproutscabbage,cauliflowerbok choykalecollardsChinese broccolibroccoli raabkohlrabimustard,turnipradisharugula, and watercress
The optimal level of intake is not known, but some doctors recommend 200 to 400 mcg of sulforaphane daily from broccoli-sprout extracts.
Acute lymphoblastic leukemia is the most common form of blood cancer affecting children. Although the current treatments cure 8 % of the patients, in the remaining cases the disease recurs and it can be fatal. Thus, novel drugs effective against relapses are needed.

To this regard, Koramit Suppipat, Texas Children’s Hospital, USA, and colleagues investigated the anti leukemic properties of sulforaphane, a dietary isothiocyanate abundant in cruciferous vegetables, such as broccoli. This compound blocked the proliferation of pediatric leukemic cells and selectively promoted their death, mostly by inhibiting Akt and mTOR, two serine/threonine kinases necessary for the survival of these malignant cells. When administered orally to mice affected by leukemia, moreover, sulforaphane reduced the progression of the tumor.
This compound may thus be beneficial for acute lymphoblastic leukemia patients at high risk of relapse.
We know that stress accelerates aging and disease.  When you are under stress, your immune system is also compromised, weakening your ability to ward off invading organisms.  Chronic stress raises the level of the excitatory hormones, including norepinephrine and cortisol, which can wear your body down and lead to disease.  Sulforaphane inhibits the norepinephrine-mediated increase in the interleukin-6 levels in the cells, which is a very good thing.  Interleukin-6 is responsible for the shift from acute inflammation to chronic inflammation, the root of so many diseases.  Finding a safe and effective substance that can inhibit the overproduction of norepinephrine, like sulforaphane,  is a significant accomplishment.

Consumption of broccoli sprouts has shown to be potentially effective at inhibitingHelicobacter pylori growth,[2][3] with sulforaphane being at least one of the active agents.[4][2]
Sulforaphane and dietary consumption of cruciferous vegetables are known to affect the action of drug-metabolizing enzymes in vitroand in preliminary human studies.[5] 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.
The possible anticancer activity of sulforaphane may 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.[6]
Sulforaphane and diindolylmethane (another compound from Brassica vegetables) inhibit cancer growth in vitro and in experimental animals.[7] Sulforaphane downregulated the Wnt/beta-catenin self-renewal pathway in breast cancer stem cells.[7]


Sulforaphane

Sulforaphane

MW: 177
Formula: C6H11NOS2

Linkslinks

  1. 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): 2399–2403. doi:10.1073/pnas.89.6.2399PMC 48665.PMID 1549603.
  2. Yanaka A, Fahey JW, Fukumoto A, Nakayama M, Inoue S, Zhang S, Tauchi M, Suzuki H, Hyodo I, Yamamoto M (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:10.1158/1940-6207.CAPR-08-0192PMID 19349290Lay summary.
  3. 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): 1088–1090. doi:10.1023/B:DDAS.0000037792.04787.8aPMID 15387326.
  4. Fahey JW, Haristoy X, Dolan PM et al. (May 2002). "Sulforaphane inhibits extracellular, intracellular, and antibiotic-resistant strains of Helicobacter pylori and prevents benzo[a]pyrene-induced stomach tumors"Proc. Natl. Acad. Sci. U.S.A. 99 (11): 7610–7615.doi:10.1073/pnas.112203099PMC 124299PMID 12032331.
  5. Kall MA, Vang O, Clausen J (March 1997). "Effects of dietary broccoli on human drug metabolising activity". Cancer Lett. 114 (1–2): 169–170. doi:10.1016/S0304-3835(97)04652-1PMID 9103281.
  6. Hayes, JD; Kelleher, MO; Eggleston, IM (2008). "The cancer chemopreventive actions of phytochemicals derived from glucosinolates".European Journal of Nutrition 47 Suppl 2: 73–88. doi:10.1007/s00394-008-2009-8PMID 18458837.
  7. Li et al. (May 2010). "Sulforaphane, a dietary component of broccoli/broccoli sprouts, inhibits breast cancer stem cells"Clinical Cancer Research 16 (9): 2580–2590. doi:10.1158/1078-0432.CCR-09-2937PMC 2862133PMID 20388854.



read about synthesis
[PDF] 

A Facile and Green Synthesis of Sulforaphane

imm.ac.cn/journal/ccl/1709/170905-1152-c060185-p3.pdf
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by D Tong Jian - 2006 - Cited by 3 - Related articles
A Facile and Green Synthesis of Sulforaphane. Tong Jian DING, Ling ZHOU, Xiao Ping CAO*. Sate Key Laboratory of Applied Organic Chemistry and College of ...


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