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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/10/02 23:05:18」(JST)

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Sulforaphane is a molecule 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 broccoli, Brussels 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, glucosinolate precursor to sulforaphane

Occurrence and isolation[edit]

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

Possible medicinal properties[edit]

Consumption of broccoli sprouts has shown to be potentially effective at inhibiting Helicobacter 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 vitro and 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]

When applied topically, sulforaphane may protect skin against UV radiation damage, and thus potentially against cancer.^[8] Sulforaphane may inhibit histone deacetylase (HDAC) activity.^[9]^[10]^{[unreliable medical source?]}

Preliminary experiments indicate sulforaphane may protect the heart from vascular inflammation and atherosclerosis.^[11]^{[unreliable medical source?]}

In vitro studies[edit]

In vitro studies have shown that sulforaphane can inactivate Histone deacetylase 6 (HDAC6), and so interfere with the expression of androgen receptor genes in prostate cancer cells.^[12]

Clinical trials[edit]

Sulforaphane (as broccoli sprout extracts) is in numerous clinical trials^[13] including a phase II trial for prostate cancer.^[14]

References[edit]

^ 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.89.6.2399. PMC 48665. PMID 1549603.
^ ^a ^b 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-08-0192. PMID 19349290. Lay summary.
^ 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.0000037792.04787.8a. PMID 15387326.
^ 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.112203099. PMC 124299. PMID 12032331.
^ 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)04652-1. PMID 9103281.
^ 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/s00394-008-2009-8. PMID 18458837.
^ ^a ^b 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-09-2937. PMC 2862133. PMID 20388854.
^ 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): 17500–17505. doi:10.1073/pnas.0708710104. PMC 2077285. PMID 17956979.
^ Dashwood RH, Ho E (October 2007). "Dietary histone deacetylase inhibitors: from cells to mice to man". Semin. Cancer Biol. 17 (5): 363–369. doi:10.1016/j.semcancer.2007.04.001. PMC 2737738. PMID 17555985.
^ "Synergistic activity of sulforaphane (Broccozym) and parthenolide (Butterzym) abolishes cancer stem cell characteristics.". 8 Nov 2010.
^ "Research reveals a broccoli boost for arteries". 4 Sep 2009.
^ Gibbs A, Schwartzman J, Deng V, Alumkal J (2009 Sep 29). "Sulforaphane destabilizes the androgen receptor in prostate cancer cells by inactivating histone deacetylase 6". PNAS 106 (39): 16663–8. doi:10.1073/pnas.0908908106. PMC 2757849. PMID 19805354.
^ http://clinicaltrials.gov/ct2/results?term=Sulforaphane
^ "The effects of sulforaphane in patients with biochemical recurrence of prostate cancer".

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1. 小児および思春期における自閉症スペクトラム障害：補完代替療法 autism spectrum disorder in children and adolescents complementary and alternative therapies

English Journal

Sulforaphane produces antidepressant- and anxiolytic-like effects in adult mice.

Wu S1, Gao Q2, Zhao P3, Gao Y4, Xi Y5, Wang X5, Liang Y5, Shi H6, Ma Y7.
Behavioural brain research.Behav Brain Res.2016 Mar 15;301:55-62. doi: 10.1016/j.bbr.2015.12.030. Epub 2015 Dec 22.
Increasing evidence suggests that depression is accompanied by dysregulation of neuroimmune system. Sulforaphane (SFN) is a natural compound with antioxidative, anti-inflammatory and neuroprotective activities. The present study aims to investigate the effects of SFN on depressive- and anxiety-like
PMID 26721468

S-allyl-L-cysteine and isoliquiritigenin improve mitochondrial function in cellular models of oxidative and nitrosative stress.

Denzer I1, Münch G2, Pischetsrieder M3, Friedland K4.
Food chemistry.Food Chem.2016 Mar 1;194:843-8. doi: 10.1016/j.foodchem.2015.08.052. Epub 2015 Aug 18.
Oxidative and nitrosative stress resulting in mitochondrial dysfunction are an early event in the pathogenesis of Alzheimer's disease (AD). Nuclear factor erythroid-2-related factor 2 (Nrf2) is a key transcription factor and regulator of the cellular response to oxidative stress. Thus known Nrf2 act
PMID 26471626

Sulforaphane-induced apoptosis in human leukemia HL-60 cells through extrinsic and intrinsic signal pathways and altering associated genes expression assayed by cDNA microarray.

Shang HS1, Shih YL2,3,4, Lee CH5, Hsueh SC6, Liu JY6, Liao NC6, Chen YL7, Huang YP8, Lu HF6,9, Chung JG10,11.
Environmental toxicology.Environ Toxicol.2016 Feb 2. doi: 10.1002/tox.22237. [Epub ahead of print]
Sulforaphane (SFN), one of the isothiocyanates, is a biologically active compound extracted from cruciferous vegetables, and has been shown to induce cytotoxic effects on many human cancer cells including human leukemia cells. However, the exact molecular mechanism and altered gene expression associ
PMID 26833863

Japanese Journal

膵癌幹細胞 (特集がん幹細胞 : 新しい医療を求めて) -- (臨床研究動向)

濱田晋,正宗淳,下瀬川徹
日本臨床 73(5), 844-849, 2015-05
NAID 40020445345

Sulforaphane down-regulates SKP2 to stabilize p27[KIP]¹ for inducing antiproliferation in human colon adenocarcinoma cells

Chung Yuan-Kai,Chi-Hung Or Richard,Lu Chien-Hsing [他]
Journal of bioscience and bioengineering 119(1), 35-42, 2015-01
NAID 40020349818

Sulforaphane down-regulates SKP2 to stabilize p27^<KIP1> for inducing antiproliferation in human colon adenocarcinoma cells(GENETICS, MOLECULAR BIOLOGY, AND GENE ENGINEERING)

Chung Yuan-Kai,Or Richard Chi-Hung,Lu Chien-Hsing,Ouyang Wei-Ting,Yang Shu-Yi,Change Chia-Che
Journal of bioscience and bioengineering 119(1), 35-42, 2015-01
… Sulforaphane is a cruciferous vegetable-derived isothiocyanate with promising chemopreventive and therapeutic activities. … Induction of proliferation arrest and apoptosis principally contribute to sulforaphane's anticancer activity, but the precise molecular mechanisms remain elusive. … axis in sulforaphane-induced antiproliferation in various human colon adenocarcinoma cell lines. …
NAID 110009892230

Related Pictures

Sulforaphane Benefits Foods Sources and Sulforaphane Sulforaphane File:Sulforaphane.png - Wikimedia Commons Sulforaphane may also trigger production File:Sulforaphane-3D-vdW.png - Wikimedia Sulforaphane, a Brocolli Extract, down Sulforaphane Sulforaphane Extra Strength

★リンクテーブル★

リンク元	「スルホラファン」「スルフォラファン」

「スルホラファン」

Sulforaphane
	IUPAC name 1-Isothiocyanato-4-methylsulfinylbutane
Identifiers
CAS number	4478-93-7
PubChem	5350
ChEMBL	CHEMBL48802
Jmol-3D images	Image 1
	SMILES CS(=O)CCCCN=C=S ;
	InChI InChI=1/C6H11NOS2/c1-10; (8)5-3-2-4-7-6-9/h2-; 5H2,1H3 ;
Properties
Molecular formula	C6H11NOS2
Molar mass	177.29 g/mol
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

英: sulforaphane
関: スルフォラファン

「スルフォラファン」

　　[★]

英: sulforaphane
関: スルホラファン

[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.89.6.2399. PMC 48665. PMID 1549603.

[pmid19349290-2] 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-08-0192. PMID 19349290. Lay 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.0000037792.04787.8a. 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[a]pyrene-induced stomach tumors". Proc. Natl. Acad. Sci. U.S.A. 99 (11): 7610–7615. doi:10.1073/pnas.112203099. PMC 124299. PMID 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)04652-1. PMID 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/s00394-008-2009-8. PMID 18458837.

[pmid20388854-7] 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-09-2937. PMC 2862133. PMID 20388854.

[8] 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): 17500–17505. doi:10.1073/pnas.0708710104. PMC 2077285. PMID 17956979.

[9] Dashwood RH, Ho E (October 2007). "Dietary histone deacetylase inhibitors: from cells to mice to man". Semin. Cancer Biol. 17 (5): 363–369. doi:10.1016/j.semcancer.2007.04.001. PMC 2737738. PMID 17555985.

[10] "Synergistic activity of sulforaphane (Broccozym) and parthenolide (Butterzym) abolishes cancer stem cell characteristics.". 8 Nov 2010.

[11] "Research reveals a broccoli boost for arteries". 4 Sep 2009.

[12] Gibbs A, Schwartzman J, Deng V, Alumkal J (2009 Sep 29). "Sulforaphane destabilizes the androgen receptor in prostate cancer cells by inactivating histone deacetylase 6". PNAS 106 (39): 16663–8. doi:10.1073/pnas.0908908106. PMC 2757849. PMID 19805354.

[13] ttp://clinicaltrials.gov/ct2/results?term=Sulforaphane

[14] "The effects of sulforaphane in patients with biochemical recurrence of prostate cancer".

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sulforaphane