Sulforaphane

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Nom de la substance

Sulforaphane

Famille moléculaire

Isothiocyanate (dérivé de glucosinolate), produit par l'hydrolyse de la glucoraphanine

Source végétale

Propriétés

  • Anti-inflammatoire, inhibe la prolifération des tumeurs et déclenche l’apoptose, effet antidiabétique par amélioration de la tolérance au glucose, effet anti-obésité en réduisant l’accumulation de graisse, neuroprotecteur (adjuvant dans Alzheimer, Parkinson, sclérose en plaques) [1], active le Nrf2, un facteur de transcription régulant le stress oxydatif et l'inflammation, protecteur contre les composés toxiques [2]
  • Détoxifiant par inhibition des enzymes de phase 1 et augmentation des enzymes de phase 2 [3], [4], [5], [6], [7]
    • Inhibiteur de cytochromes P-450 et inducteur des glutathion transférases [8]
  • Antioxydant [9], [10]
  • Prévention des complications vasculaires du diabète [11]
  • Prévention nutritionnelle de cancers [12], prévention du développement de certains cancers [13], induction de l‘apoptose, suppression de la progression tumorale, inhibition de l’angiogenèse et activité anti-inflammatoire [14], [15], inhibe la progression du taux de PSA dans le cancer de la prostate [16], limite l’élévation du PSA ("récidive biologique") après prostatectomie radicale [17], diminue la cancérogénicité de l'estradiol [18], inhibition de la croissance de cellules de cancer de vessie [19], comme l'érucine
  • Propriétés chimiopréventives, le sulforaphane cible la voie de signalisation Keap1-Nrf2 impliquée dans la réponse cellulaire au stress [20]
  • Neuroprotecteur [21], protecteur des cellules dopaminergiques [22], [23], protège de la neurotoxine endogène 5-S-cystéinyl-dopamine [24]
  • Anti-Helicobacter pylori [25], [26], [27], [28], [29]
  • Après prise alimentaire de brocolis, riches en sulforaphane, on retrouve des thiocyanates dans l'articulation, avec induction de modifications histologiques du cartilage [30]
  • Potentialités dans les accidents vasculaires cérébraux ischémiques : en cas d’AVC ischémique, l’efficacité de l'activateur tissulaire du plasminogène (qui réduit la taille du caillot) passe de 20 % à 60 % lorsque le médicament est co-administré avec le sulforaphane [31]

Effet thérapeutique

  • Cancers [32], surtout de la prostate, intérêt chez des patients atteints de cancer de la prostate localisé en récidive biologique après prostatectomie [1]
  • Maladie de Parkinson (?) [33]
  • Accidents vasculaires cérébraux ischémiques [31]

Effets indésirables

  • Très bonne tolérance
  • Inhibiteur des cytochromes P-450 CYP2B et CYP3A2
  • La surgélation et la cuisson à haute température détruiraient le sulforaphane [34], [35]

Bibliographie

  1. ↑ Schepici G, Bramanti P, Mazzon E. Efficacy of Sulforaphane in Neurodegenerative Diseases. Int J Mol Sci. 2020 Nov 16;21(22):8637. doi: 10.3390/ijms21228637. PMID 33207780; PMCID: PMC7698208.
  2. ↑ Baralić K, Živanović J, Marić Đ, Bozic D, Grahovac L, Antonijević Miljaković E, Ćurčić M, Buha Djordjevic A, Bulat Z, Antonijević B, Đukić-Ćosić D. Sulforaphane-A Compound with Potential Health Benefits for Disease Prevention and Treatment: Insights from Pharmacological and Toxicological Experimental Studies. Antioxidants (Basel). 2024 Jan 25;13(2):147. doi: 10.3390/antiox13020147. PMID 38397745; PMCID: PMC10886109.
  3. ↑ Abel EL, Boulware S, Fields T, McIvor E, Powell KL, DiGiovanni J, Vasquez KM, MacLeod MC. Sulforaphane induces phase II detoxication enzymes in mouse skin and prevents mutagenesis induced by a mustard gas analog. Toxicol Appl Pharmacol. 2013 Feb 1;266(3):439-42. doi: 10.1016/j.taap.2012.11.020. PMID 23201461
  4. ↑ Boddupalli S, Mein JR, Lakkanna S, James DR. Induction of phase 2 antioxidant enzymes by broccoli sulforaphane: perspectives in maintaining the antioxidant activity of vitamins A, C, and E. Front Genet. 2012 Jan 24;3:7. doi: 10.3389/fgene.2012.00007. eCollection 2012. PMID 22303412
  5. ↑ James D, Devaraj S, Bellur P, Lakkanna S, Vicini J, Boddupalli S. Novel concepts of broccoli sulforaphanes and disease: induction of phase II antioxidant and detoxification enzymes by enhanced-glucoraphanin broccoli. Nutr Rev. 2012 Nov;70(11):654-65. doi: 10.1111/j.1753-4887.2012.00532.x. PMID 23110644
  6. ↑ Fahey JW, Talalay P. Antioxidant functions of sulforaphane: a potent inducer of Phase II detoxication enzymes. Food Chem Toxicol. 1999 Sep-Oct;37(9-10):973-9. PMID 10541453
  7. ↑ Trinh K, Moore K, Wes PD, Muchowski PJ, Dey J, Andrews L, Pallanck LJ. Induction of the phase II detoxification pathway suppresses neuron loss in Drosophila models of Parkinson's disease. J Neurosci. 2008 Jan 9;28(2):465-72. doi: 10.1523/JNEUROSCI.4778-07.2008. PMID 18184789
  8. ↑ Maheo K, Guillouzo A. Effets de deux agents chimioprotecteurs, l'oltipraz et le sulforaphane, sur l'expression des cytochromes p-450 et des glutathion transférases hépatiques en situation normale et inflammatoire. Thèse Université de Rennes 1, 1998. 178 p. http://cat.inist.fr/?aModele=afficheN&cpsidt=188662
  9. ↑ de Figueiredo SM, Filho SA, Nogueira-Machado JA, Caligiorne RB. The anti-oxidant properties of isothiocyanates: a review. Recent Pat Endocr Metab Immune Drug Discov. 2013 Sep;7(3):213-25. Review. PMID 23978168
  10. ↑ de Figueiredo SM, Binda NS, Nogueira-Machado JA, Vieira-Filho SA, Caligiorne RB. The antioxidant properties of organosulfur compounds (sulforaphane). Recent Pat Endocr Metab Immune Drug Discov. 2015;9(1):24-39. doi: 10.2174/1872214809666150505164138. PMID 25944116.
  11. ↑ Yamagishi S, Matsui T. Protective role of sulphoraphane against vascular complications in diabetes. Pharm Biol. 2016 Oct;54(10):2329-39. doi: 10.3109/13880209.2016.1138314. PMID 26841240.
  12. ↑ Kaiser AE, Baniasadi M, Giansiracusa D, Giansiracusa M, Garcia M, Fryda Z, Wong TL, Bishayee A. Sulforaphane: A Broccoli Bioactive Phytocompound with Cancer Preventive Potential. Cancers (Basel). 2021 Sep 25;13(19):4796. doi: 10.3390/cancers13194796. PMID 34638282; PMCID: PMC8508555.
  13. ↑ Bayat Mokhtari, R., Baluch, N., Homayouni, T. S., Morgatskaya, E., Kumar, S., Kazemi, P., & Yeger, H. (2018). The role of Sulforaphane in cancer chemoprevention and health benefits: a mini-review. Journal of cell communication and signaling, 12(1), 91–101. https://doi.org/10.1007/s12079-017-0401-y PMID 28735362
  14. ↑ Juge N, Mithen RF, Traka M. Molecular basis for chemoprevention by sulforaphane: a comprehensive review. Cell Mol Life Sci. 2007 May;64(9):1105-27. PMID 17396224
  15. ↑ Parul Gupta, Bonglee Kim, Sung-Hoon Kim, Sanjay K. Srivastava. Molecular targets of isothiocyanates in cancer: Recent advances. Molecular Nutrition & Food Research, Volume 58, Issue 8, pages 1685–1707, August 2014. DOI: 10.1002/mnfr.201300684 texte intégral
  16. ↑ Bernard G Cipolla, Eric Mandron, Jean Marc Lefort, Yves Coadou, Emmanuel Della Negra, Luc Corbel, Romuald Le Scodan, Nicolas Mottet. First double-blind placebo-controlled, multicenter, randomized trial of stabilized natural sulforaphane in men with rising PSA following radical prostatectomy. 2014 ASCO Annual Meeting, Poster Highlights Session, Genitourinary (Prostate) Cancer, Abstract Number: 5032. J Clin Oncol 32:5s, 2014 (suppl; abstr 5032)
  17. ↑ Cipolla BG, Mandron E, Lefort J, Coadou Y, Della Negra E, Corbel L, Le Scodan R, Azzouzi AR, Mottet N. Effect of Sulforaphane in Men with Biochemical Recurrence after Radical Prostatectomy. Cancer Prev Res (Phila). 2015 Aug;8(8):712-9. doi: 10.1158/1940-6207.CAPR-14-0459. PMID 25968598
  18. ↑ Yager JD. Mechanisms of estrogen carcinogenesis: The role of E2/E1-quinone metabolites suggests new approaches to preventive intervention - A review. Steroids. 2014 Aug 24. pii: S0039-128X(14)00199-8. doi: 10.1016/j.steroids.2014.08.006. PMID 25159108
  19. ↑ Abbaoui B, Riedl KM, Ralston RA, Thomas-Ahner JM, Schwartz SJ, Clinton SK, Mortazavi A. Inhibition of bladder cancer by broccoli isothiocyanates sulforaphane and erucin: characterization, metabolism, and interconversion. Mol Nutr Food Res. 2012 Nov;56(11):1675-87. doi: 10.1002/mnfr.201200276. PMID 23038615
  20. ↑ Kensler TW, Egner PA, Agyeman AS, Visvanathan K, Groopman JD, Chen JG, Chen TY, Fahey JW, Talalay P. Keap1-nrf2 signaling: a target for cancer prevention by sulforaphane. Top Curr Chem. 2013;329:163-77. doi: 10.1007/128_2012_339. PMID 22752583; PMCID: PMC3553557.
  21. ↑ Morroni F, Tarozzi A, Sita G, Bolondi C, Zolezzi Moraga JM, Cantelli-Forti G, Hrelia P. Neuroprotective effect of sulforaphane in 6-hydroxydopamine-lesioned mouse model of Parkinson's disease. Neurotoxicology. 2013 May;36:63-71. doi: 10.1016/j.neuro.2013.03.004. PMID 23518299
  22. ↑ Tarozzi A, Morroni F, Merlicco A, Hrelia S, Angeloni C, Cantelli-Forti G, Hrelia P. Sulforaphane as an inducer of glutathione prevents oxidative stress-induced cell death in a dopaminergic-like neuroblastoma cell line. J Neurochem. 2009 Dec;111(5):1161-71. doi: 10.1111/j.1471-4159.2009.06394.x. PMID 19780897
  23. ↑ Han JM, Lee YJ, Lee SY, Kim EM, Moon Y, Kim HW, Hwang O. Protective effect of sulforaphane against dopaminergic cell death. J Pharmacol Exp Ther. 2007 Apr;321(1):249-56. PMID 17259450
  24. ↑ Vauzour D, Buonfiglio M, Corona G, Chirafisi J, Vafeiadou K, Angeloni C, Hrelia S, Hrelia P, Spencer JP. Sulforaphane protects cortical neurons against 5-S-cysteinyl-dopamine-induced toxicity through the activation of ERK1/2, Nrf-2 and the upregulation of detoxification enzymes. Mol Nutr Food Res. 2010 Apr;54(4):532-42. doi: 10.1002/mnfr.200900197. PMID 20166144
  25. ↑ Yanaka A, Fahey JW, Fukumoto A, Nakayama M, Inoue S, Zhang S, Tauchi M, Suzuki H, Hyodo I, Yamamoto M. Dietary sulforaphane-rich broccoli sprouts reduce colonization and attenuate gastritis in Helicobacter pylori-infected mice and humans. Cancer Prev Res (Phila). 2009 Apr;2(4):353-60. doi: 10.1158/1940-6207.CAPR-08-0192. PMID 19349290
  26. ↑ Fahey JW, Haristoy X, Dolan PM, Kensler TW, Scholtus I, Stephenson KK, Talalay P, Lozniewski A. 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. 2002 May 28;99(11):7610-5. PMID 12032331
  27. ↑ Galan, M. V., Kishan, A. A., & Silverman, A. L. (2004). Oral broccoli sprouts for the treatment of Helicobacter pylori infection: a preliminary report. Digestive diseases and sciences, 49(7-8), 1088–1090. https://doi.org/10.1023/b:ddas.0000037792.04787.8a PMID 15387326
  28. ↑ Yanaka A. (2017). Role of Sulforaphane in Protection of Gastrointestinal Tract Against H. pylori and NSAID-Induced Oxidative Stress. Current pharmaceutical design, 23(27), 4066–4075. https://doi.org/10.2174/1381612823666170207103943 PMID 28176666
  29. ↑ Haristoy, X., Angioi-Duprez, K., Duprez, A., & Lozniewski, A. (2003). Efficacy of sulforaphane in eradicating Helicobacter pylori in human gastric xenografts implanted in nude mice. Antimicrobial agents and chemotherapy, 47(12), 3982–3984. https://doi.org/10.1128/aac.47.12.3982-3984.2003 PMID 14638516
  30. ↑ Davidson R, Gardner S, Jupp O, Bullough A, Butters S, Watts L, Donell S, Traka M, Saha S, Mithen R, Peffers M, Clegg P, Bao Y, Cassidy A, Clark I. Isothiocyanates are detected in human synovial fluid following broccoli consumption and can affect the tissues of the knee joint. Sci Rep. 2017 Jun 13;7(1):3398. doi: 10.1038/s41598-017-03629-5. PMID 28611391; PMCID: PMC5469854.
  31. ↑ 31,0 et 31,1 Guan IA, Liu JST, Sawyer RC, Li X, Jiao W, Jiramongkol Y, White MD, Hagimola L, Passam FH, Tran DP, Liu X, Schoenwaelder SM, Jackson SP, Payne RJ, Liu X. Integrating Phenotypic and Chemoproteomic Approaches to Identify Covalent Targets of Dietary Electrophiles in Platelets. ACS Cent Sci. 2024 Jan 29;10(2):344-357. doi: 10.1021/acscentsci.3c00822. PMID 38435523 PMCID: PMC10906253.
  32. ↑ Fimognari C, Hrelia P. Sulforaphane as a promising molecule for fighting cancer. Mutat Res. 2007 May-Jun;635(2-3):90-104. PMID 17134937
  33. ↑ Beal MF. Therapeutic approaches to mitochondrial dysfunction in Parkinson's disease. Parkinsonism Relat Disord. 2009 Dec;15 Suppl 3:S189-94. doi: 10.1016/S1353-8020(09)70812-0. PMID 20082988
  34. ↑ Dosz EB, Jeffery EH. Modifying the processing and handling of frozen broccoli for increased sulforaphane formation. J Food Sci. 2013 Sep;78(9):H1459-63. doi: 10.1111/1750-3841.12221. PMID 23915112
  35. ↑ Edward B. Dosz, Elizabeth H. Jeffery, Commercially produced frozen broccoli lacks the ability to form sulforaphane. Journal of Functional Foods, Volume 5, Issue 2, April 2013, Pages 987–990. DOI: 10.1016/j.jff.2013.01.033
  • Yeh CT, Yen GC. Effect of sulforaphane on metallothionein expression and induction of apoptosis in human hepatoma HepG2 cells. Carcinogenesis. 2005 Dec;26(12):2138-48. PMID 16033772
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  • Niso-Santano M, González-Polo RA, Bravo-San Pedro JM, Gómez-Sánchez R, Lastres-Becker I, Ortiz-Ortiz MA, Soler G, Morán JM, Cuadrado A, Fuentes JM; Centro de Investigación Biomédica en Red sobre Enfermedades Neurodegenerativas (CIBERNED). Activation of apoptosis signal-regulating kinase 1 is a key factor in paraquat-induced cell death: modulation by the Nrf2/Trx axis. Free Radic Biol Med. 2010 May 15;48(10):1370-81. doi: 10.1016/j.freeradbiomed.2010.02.024. PMID 20202476
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