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{{chembox
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| ImageFile = Sulforaphane.png
| ImageFile = Sulforafane.png
| ImageSize = 200px
| ImageSize = 200px
| ImageFile1 = Sulforaphane-3D-balls.png
| ImageFile1 = Sulforafane-3D-balls.png
| ImageFile2 = Sulforaphane-3D-vdW.png
| ImageFile2 = Sulforafane-3D-vdW.png
| IUPACName = 1-Isothiocyanato-4-methylsulfinylbutane
| IUPACName = 1-Isothiocyanato-4-methylsulfinylbutane
| OtherNames =
| OtherNames =
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'''Sulforaphane''' is an [[organosulfur compound]] that exhibits anti[[cancer]], [[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.
'''Sulforafane''' is an [[organosulfur compound]] that exhibits anti[[cancer]], [[antidiabetic]], and [[antimicrobial]] properties. It is obtained from [[cruciferous vegetables]] such as [[broccoli]]. The [[enzyme]] [[myrosinase]] transforms [[glucorafanin]], a [[glucosinolate]], into sulforafane upon damage to the plant (such as from chewing). Young [[sprouts]] of broccoli and cauliflower are particularly rich in glucorafanin.
{| cellpadding="10"
{| cellpadding="10"
| align="center" | [[Image:Glucoraphanin.png]]<br>glucoraphanin
| align="center" | [[Image:Glucorafanin.png]]<br>glucorafanin
|}
|}


==Occurrence and isolation==
==Occurrence and isolation==
Sulforaphane was identified in broccoli sprouts, which, of the cruciferous vegetables, have the highest concentration of sulforaphane.<ref>{{cite journal |author=Zhang Y, Talalay P, Cho CG, Posner GH |title=A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=89 |issue=6 |pages=2399–403 |year=1992 |month=March |pmid=1549603 |pmc=48665 |doi= 10.1073/pnas.89.6.2399|url=http://www.pnas.org/cgi/pmidlookup?view=long&pmid=1549603}}</ref> It is also found in [[brussel sprouts]], [[cabbage]], [[cauliflower]], [[bok choy]], [[kale]], [[collards]], [[chinese broccoli]], [[broccoli raab]], [[kohlrabi]], [[Mustard plant|mustard]], [[turnip]], [[radish]], [[Eruca sativa|arugula]], and [[watercress]].
Sulforafane was identified in broccoli sprouts, which, of the cruciferous vegetables, have the highest concentration of sulforafane.<ref>{{cite journal |author=Zhang Y, Talalay P, Cho CG, Posner GH |title=A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=89 |issue=6 |pages=2399–403 |year=1992 |month=March |pmid=1549603 |pmc=48665 |doi= 10.1073/pnas.89.6.2399|url=http://www.pnas.org/cgi/pmidlookup?view=long&pmid=1549603}}</ref> It is also found in [[brussel sprouts]], [[cabbage]], [[cauliflower]], [[bok choy]], [[kale]], [[collards]], [[chinese broccoli]], [[broccoli raab]], [[kohlrabi]], [[Mustard plant|mustard]], [[turnip]], [[radish]], [[Eruca sativa|arugula]], and [[watercress]].


==Possible medicinal properties==
==Possible medicinal properties==
Consumption of broccoli sprouts has shown to be potentially effective at inhibiting ''[[Helicobacter pylori]]'' growth,<ref>{{ cite news | title = Baby broccoli 'controls gut bug' | work = [[BBC News Online]] | date = 6 April 2009 | accessdate = 6 April 2009 | url= http://news.bbc.co.uk/1/hi/health/7981095.stm }}</ref><ref>{{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}}</ref> with sulforaphane being at least one of the active agents.<ref>{{cite journal |author=Fahey JW, Haristoy X, Dolan PM, ''et al.'' |title=Sulforaphane inhibits extracellular, intracellular, and antibiotic-resistant strains of Helicobacter pylori and prevents benzo[a]pyrene-induced stomach tumors |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=99 |issue=11 |pages=7610–5 |year=2002 |month=May |pmid=12032331 |pmc=124299 |doi=10.1073/pnas.112203099 |url=}}</ref><ref>{{ cite journal | journal = Cancer Prev. Res. | volume = 2 | pages = 353–360 | issue = 4 | month = April | year = 2009 | author = A. Yanaka, J. W. Fahey, A. Fukumoto, M. Nakayama, S. Inoue, S. Zhang, M. Tauchi, H. Suzuki, I. Hyodo, M. Yamamoto | title = Dietary Sulforaphane-Rich Broccoli Sprouts Reduce Colonization and Attenuate Gastritis in ''Helicobacter pylori''–Infected Mice and Humans | doi = 10.1158/1940-6207.CAPR-08-0192 | pmid = 19349290 }}</ref>
Consumption of broccoli sprouts has shown to be potentially effective at inhibiting ''[[Helicobacter pylori]]'' growth,<ref>{{ cite news | title = Baby broccoli 'controls gut bug' | work = [[BBC News Online]] | date = 6 April 2009 | accessdate = 6 April 2009 | url= http://news.bbc.co.uk/1/hi/health/7981095.stm }}</ref><ref>{{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}}</ref> with sulforafane being at least one of the active agents.<ref>{{cite journal |author=Fahey JW, Haristoy X, Dolan PM, ''et al.'' |title=Sulforafane inhibits extracellular, intracellular, and antibiotic-resistant strains of Helicobacter pylori and prevents benzo[a]pyrene-induced stomach tumors |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=99 |issue=11 |pages=7610–5 |year=2002 |month=May |pmid=12032331 |pmc=124299 |doi=10.1073/pnas.112203099 |url=}}</ref><ref>{{ cite journal | journal = Cancer Prev. Res. | volume = 2 | pages = 353–360 | issue = 4 | month = April | year = 2009 | author = A. Yanaka, J. W. Fahey, A. Fukumoto, M. Nakayama, S. Inoue, S. Zhang, M. Tauchi, H. Suzuki, I. Hyodo, M. Yamamoto | title = Dietary Sulforafane-Rich Broccoli Sprouts Reduce Colonization and Attenuate Gastritis in ''Helicobacter pylori''–Infected Mice and Humans | doi = 10.1158/1940-6207.CAPR-08-0192 | pmid = 19349290 }}</ref>


Sulforaphane and dietary consumption of cruciferous vegetables are known to affect the action of drug-metabolizing enzymes [[in vitro]] and in preliminary human studies.<ref>{{cite journal |author=Kall MA, Vang O, Clausen J |title=Effects of dietary broccoli on human drug metabolising activity |journal=Cancer Lett. |volume=114 |issue=1-2 |pages=169–70 |year=1997 |month=March |pmid=9103281 |doi=10.1016/S0304-3835(97)04652-1 |url=}}</ref> 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.
Sulforafane and dietary consumption of cruciferous vegetables are known to affect the action of drug-metabolizing enzymes [[in vitro]] and in preliminary human studies.<ref>{{cite journal |author=Kall MA, Vang O, Clausen J |title=Effects of dietary broccoli on human drug metabolising activity |journal=Cancer Lett. |volume=114 |issue=1-2 |pages=169–70 |year=1997 |month=March |pmid=9103281 |doi=10.1016/S0304-3835(97)04652-1 |url=}}</ref> 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 sulforafane or broccoli-sprout extracts.


The possible anticancer activity of sulforaphane may be related to the [[Enzyme induction and inhibition|induction]] of phase-II enzymes of [[xenobiotic]] transformation (such as [[quinone reductase]] and [[Glutathione S-transferase|glutathione ''S''-transferase]]), and enhancing the transcription of tumor suppressor proteins, possibly via inhibitory effects on histone deacetylase.{{citation needed|date=February 2007}}
The possible anticancer activity of sulforafane may be related to the [[Enzyme induction and inhibition|induction]] of fase-II enzymes of [[xenobiotic]] transformation (such as [[quinone reductase]] and [[Glutathione S-transferase|glutathione ''S''-transferase]]), and enhancing the transcription of tumor suppressor proteins, possibly via inhibitory effects on histone deacetylase.{{citation needed|date=February 2007}}


Sulforaphane and [[diindolylmethane]] (another compound from ''Brassica'' vegetables) inhibit cancer growth in vitro and in experimental animals.{{citation needed|date=June 2010}}
Sulforafane and [[diindolylmethane]] (another compound from ''Brassica'' vegetables) inhibit cancer growth in vitro and in experimental animals.{{citation needed|date=June 2010}}


When applied topically, sulforaphane may protect skin against [[UV radiation]] damage, and thus potentially against [[skin cancer|cancer]].<ref>{{cite journal |author=Talalay P, Fahey JW, Healy ZR, ''et al.'' |title=Sulforaphane mobilizes cellular defenses that protect skin against damage by UV radiation |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=104 |issue=44 |pages=17500–5 |year=2007 |month=October |pmid=17956979 |pmc=2077285 |doi=10.1073/pnas.0708710104 |url=}}</ref> Sulforaphane may inhibit [[histone deacetylase]] (HDAC) activity.<ref>{{cite journal |author=Dashwood RH, Ho E |title=Dietary histone deacetylase inhibitors: from cells to mice to man.|journal=Semin. Cancer Biol. |volume=17 |issue=5 |pages=363–9 |year=2007 |month=October |pmid=17555985 |doi=10.1016/j.semcancer.2007.04.001 |pmc=2737738 }}</ref>
When applied topically, sulforafane may protect skin against [[UV radiation]] damage, and thus potentially against [[skin cancer|cancer]].<ref>{{cite journal |author=Talalay P, Fahey JW, Healy ZR, ''et al.'' |title=Sulforafane mobilizes cellular defenses that protect skin against damage by UV radiation |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=104 |issue=44 |pages=17500–5 |year=2007 |month=October |pmid=17956979 |pmc=2077285 |doi=10.1073/pnas.0708710104 |url=}}</ref> Sulforafane may inhibit [[histone deacetylase]] (HDAC) activity.<ref>{{cite journal |author=Dashwood RH, Ho E |title=Dietary histone deacetylase inhibitors: from cells to mice to man.|journal=Semin. Cancer Biol. |volume=17 |issue=5 |pages=363–9 |year=2007 |month=October |pmid=17555985 |doi=10.1016/j.semcancer.2007.04.001 |pmc=2737738 }}</ref>


Sulforaphane may protect the heart from inflammation that can lead to atherosclerosis.<ref>http://www3.imperial.ac.uk/newsandeventspggrp/imperialcollege/newssummary/news_4-9-2009-15-8-42 </ref>
Sulforafane may protect the heart from inflammation that can lead to atherosclerosis.<ref>http://www3.imperial.ac.uk/newsandeventspggrp/imperialcollege/newssummary/news_4-9-2009-15-8-42 </ref>


== See also ==
== See also ==
* [[Herbalism]]
* [[Herbalism]]
* [[Nutrition]]
* [[Nutrition]]
* [[Phytonutrients]]
* [[fytonutrients]]
* [[Broccoli sprouts]]
* [[Broccoli sprouts]]


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[[Category:Isothiocyanates]]
[[Category:Isothiocyanates]]


[[de:Sulforaphan]]
[[de:Sulforafan]]
[[lt:Sulforafanas]]
[[lt:Sulforafanas]]
[[nl:Sulforafaan]]
[[nl:Sulforafaan]]

Revision as of 09:33, 30 October 2010

Sulforaphane
File:Sulforafane.png
File:Sulforafane-3D-balls.png
File:Sulforafane-3D-vdW.png
Names
IUPAC name
1-Isothiocyanato-4-methylsulfinylbutane
Identifiers
3D model (JSmol)
  • InChI=1/C6H11NOS2/c1-10
    (8)5-3-2-4-7-6-9/h2-
    5H2,1H3
  • CS(=O)CCCCN=C=S
Properties
C6H11NOS2
Molar mass 177.29 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

File:Glucorafanin.png
glucorafanin

Occurrence and isolation

Sulforafane was identified in broccoli sprouts, which, of the cruciferous vegetables, have the highest concentration of sulforafane.[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.

Possible medicinal properties

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

Sulforafane and dietary consumption of cruciferous vegetables are known to affect the action of drug-metabolizing enzymes in vitro and in preliminary human studies.[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 sulforafane or broccoli-sprout extracts.

The possible anticancer activity of sulforafane may be related to the induction of fase-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.[citation needed]

Sulforafane and diindolylmethane (another compound from Brassica vegetables) inhibit cancer growth in vitro and in experimental animals.[citation needed]

When applied topically, sulforafane may protect skin against UV radiation damage, and thus potentially against cancer.[7] Sulforafane may inhibit histone deacetylase (HDAC) activity.[8]

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

See also

References

  1. ^ Zhang Y, Talalay P, Cho CG, Posner GH (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. PMC 48665. PMID 1549603. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  2. ^ "Baby broccoli 'controls gut bug'". BBC News Online. 6 April 2009. Retrieved 6 April 2009.
  3. ^ Galan MV, Kishan AA, Silverman AL (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  4. ^ Fahey JW, Haristoy X, Dolan PM; et al. (2002). "Sulforafane 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): 7610–5. doi:10.1073/pnas.112203099. PMC 124299. PMID 12032331. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  5. ^ A. Yanaka, J. W. Fahey, A. Fukumoto, M. Nakayama, S. Inoue, S. Zhang, M. Tauchi, H. Suzuki, I. Hyodo, M. Yamamoto (2009). "Dietary Sulforafane-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. PMID 19349290. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  6. ^ Kall MA, Vang O, Clausen J (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  7. ^ Talalay P, Fahey JW, Healy ZR; et al. (2007). "Sulforafane 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. PMC 2077285. PMID 17956979. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  8. ^ Dashwood RH, Ho E (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. PMC 2737738. PMID 17555985. {{cite journal}}: Unknown parameter |month= ignored (help)
  9. ^ http://www3.imperial.ac.uk/newsandeventspggrp/imperialcollege/newssummary/news_4-9-2009-15-8-42
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