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Sulforaphane
Sulforaphane.png
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IUPAC name
Identifiers
CAS number 4478-93-7
PubChem 5350
SMILES
InChI
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 references

Sulforaphane is an organosulfur compound that exhibits anticancer, antidiabetic, and antimicrobial properties. It is obtained from cruciferous vegetables such as broccoli. The enzyme myrosinase transforms glucoraphanin, a glucosinolate, into sulforaphane upon damage to the plant (such as from chewing). Young sprouts of broccoli and cauliflower are particularly rich in glucoraphanin.

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glucoraphanin

Contents

Occurrence and isolation

Sulforaphane was identified in broccoli sprouts which, of the cruciferous vegetables, have the highest concentration of sulforaphane.[1] It is also found in brussel sprouts, cabbage, cauliflower, bok choy, kale, collards, chinese broccoli, broccoli raab, kohlrabi, mustard, turnip, radish, arugula, and watercress.

Medicinal properties

Consumption of broccoli sprouts has shown to be effective at inhibiting Helicobacter pylori growth,[2][3] with sulforaphane being at least one of the active agents.[4][5]

Optimal dosage has not yet been determined, but some doctors recommend 200-400 μg of sulforaphane daily from broccoli-sprout extracts. Sulforaphane and dietary consumption of cruciferous vegetables are known to affect the action of drug-metabolizing enzymes.[6] 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 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, possibly via inhibitory effects on histone deacetylase.

Sulforaphane and diindolylmethane (another compound from Brassica vegetables) inhibit cancer growth.

When applied topically, sulforaphane is proposed to protect skin against UV radiation damage, and thus potentially against cancer, .[7] Sulforaphane may inhibit histone deacetylase (HDAC) activity.[8]

Preclinical research

Sulforaphane may protect the heart from inflammation that can lead to atherosclerosis.[9]

See also

References

  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): 2399–403. doi:10.1073/pnas.89.6.2399. PMID 1549603. PMC 48665. http://www.pnas.org/cgi/pmidlookup?view=long&pmid=1549603.  
  2. ^ "Baby broccoli 'controls gut bug'". BBC News Online. 6 April 2009. http://news.bbc.co.uk/1/hi/health/7981095.stm. Retrieved 6 April 2009.  
  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): 1088–90. doi:10.1023/B:DDAS.0000037792.04787.8a. PMID 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[apyrene-induced stomach tumors"]. Proc. Natl. Acad. Sci. U.S.A. 99 (11): 7610–5. doi:10.1073/pnas.112203099. PMID 12032331.  
  5. ^ A. Yanaka, J. W. Fahey, A. Fukumoto, M. Nakayama, S. Inoue, S. Zhang, M. Tauchi, H. Suzuki, I. Hyodo, M. Yamamoto (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-08-0192.  
  6. ^ Kall MA, Vang O, Clausen J (March 1997). "Effects of dietary broccoli on human drug metabolising activity". Cancer Lett. 114 (1-2): 169–70. doi:10.1016/S0304-3835(97)04652-1. PMID 9103281.  
  7. ^ Talalay P, Fahey JW, Healy ZR, et al. (October 2007). "Sulforaphane mobilizes cellular defenses that protect skin against damage by UV radiation". Proc. Natl. Acad. Sci. U.S.A. 104 (44): 17500–5. doi:10.1073/pnas.0708710104. PMID 17956979.  
  8. ^ Dashwood RH, Ho E (October 2007). "Dietary histone deacetylase inhibitors: from cells to mice to man.". Semin. Cancer Biol. 17 (5): 363–9. doi:10.1016/j.semcancer.2007.04.001. PMID 17555985.  
  9. ^ http://www3.imperial.ac.uk/newsandeventspggrp/imperialcollege/newssummary/news_4-9-2009-15-8-42
Glycosides
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Geometry:
Glycone:
Aglycone:
Major families of biochemicals
Saccharides/Carbohydrates/Glycosides · Amino acids/Peptides/Proteins/Glycoproteins · Lipids/Terpenes/Steroids/Carotenoids · Alkaloids/Nucleobases/Nucleic acids · Cofactors/Phenylpropanoids/Polyketides/Tetrapyrroles







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