Thymoquinone

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Nom de la substance

Thymoquinone et Thymohydroquinone

Famille moléculaire

Benzoquinone

Source végétale

Propriétés

  • Considéré comme une molécule thérapeutique émergente [1], [2] en raison de ses propriétés immunomodulantes, hépatoprotectrices, anti-inflammatoires, antioxydantes, cytotoxiques et anti-cancer [3], [4]
  • Hépatoprotecteur [5]
  • Immunomodulant, module l'inflammation et les réponses immunitaires adaptatives cellulaires et humorales ainsi que la balance Th1/Th2 [6]
  • Anti-inflammatoire par inhibition des fonctions du neutrophile humain [7], la thymoquinone diminue l’arthrite expérimentale chez le rat [8], antioxydant, inhibiteur de la peroxydation lipidique [9]
  • Antitumoral [10], activité anticancéreuse vis-à-vis des cancers du côlon et de la prostate, et du cancer du pancréas [3], [4], potentialise les effets de la chimiothérapie [11], inducteur d'apoptose sur les cellules de cancer du col utérin [12]
  • Analgésique [13]
  • Anticonvulsivant [14], même sur des épilepsies résistantes [15], [16]
  • Propriétés anticholinestérase (surtout thymohydroquinone) [17]
  • Propriétés anticancéreuses [18], augmente l'activité cytotoxique des cellules NK contre les cellules cancéreuses [6]
  • Protection vis-à-vis de la transformation hépatocarcinomateuse [19], et de la carcinogenèse gastrique induite par le benzopyrène [20]
  • Anti-angiogénique [21], [22]
  • Protection vis-à-vis de la toxicité myocardique de la doxorubicine [23], vis-à-vis de la néphrotoxicité du cisplatine [24], [25]
  • Antimicrobiennne
  • Neuroprotection [26], [27], [28], protection des neurones dopaminergiques vis-à-vis de certains toxiques (roténone) [29], protection vis-à-vis de l'auto-oxydation de la l-dopa [30], effet protecteur vis-à-vis de la peroxydation lipidique induite par le processus d'ischémie-reperfusion dans l'hippocampe de rat [31]
  • Améliore la qualité du sperme et des spermatozoïdes [32]

Effet thérapeutique

  • Allergie, autoimmunité, cancer [6], polyarthrite
  • Protection hépatique et chimioprotection avec les traitements anticancéreux (?)
  • Cancers (?)
  • Alzheimer (?)
  • Parkinson (?)

Effets indésirables

  • Risque allergique faible

Bibliographie

  1. Khader M, Eckl PM. Thymoquinone: an emerging natural drug with a wide range of medical applications. Iran J Basic Med Sci. 2014 Dec;17(12):950-7. PMID 25859298
  2. Gupta, B., Ghosh, K. K., & Gupta, R. C. (2016). Thymoquinone. In Nutraceuticals (pp. 541-550). Academic Press.
  3. Randhawa MA, Alghamdi MS. Anticancer activity of Nigella sativa (black seed) - a review. Am J Chin Med. 2011;39(6):1075-91. Review. PMID 22083982
  4. Gholamnezhad Z, Havakhah S, Boskabady MH. Preclinical and clinical effects of Nigella sativa and its constituent, thymoquinone: A review. J Ethnopharmacol. 2016 Aug 22;190:372-86. doi: 10.1016/j.jep.2016.06.061. PMID 27364039
  5. Fahrettin Yildiz, Sacit Coban, Alpaslan Terzi, Mustafa Ates, Nurten Aksoy, Hale Cakir, Ali Riza Ocak, and Muharrem Bitiren. Nigella sativa relieves the deleterious effects of ischemia reperfusion injury on liver. World J Gastroenterol. 2008 September 7; 14(33): 5204–5209. PMCID: PMC2744011
  6. 6,0 6,1 et 6,2 Majdalawieh AF, Fayyad MW. Immunomodulatory and anti-inflammatory action of Nigella sativa and thymoquinone: A comprehensive review. Int Immunopharmacol. 2015 Sep;28(1):295-304. doi: 10.1016/j.intimp.2015.06.023. PMID 26117430
  7. BOUDIAF, Kaouthar. Etude des propriétés anti-inflammatoires de la thymoquinone et de ses mécanismes d’inhibition des fonctions du neutrophile humain. Thèse de doctorat en sciences. Université Ferhat Abbas Sétif 1. Algérie. 2018. [1]
  8. Tekeoglu I, Dogan A, Ediz L, Budancamanak M, Demirel A. Effects of thymoquinone (volatile oil of black cumin) on rheumatoid arthritis in rat models. Phytother Res. 2007 Sep;21(9):895-7. PMID 17562570
  9. Houghton, PJ; Zarka, R; De Las Heras, B; Hoult, JR (1995). Fixed oil of Nigella sativa and derived thymoquinone inhibit eicosanoid generation in leukocytes and membrane lipid peroxidation. Planta medica 61 (1): 33–6. doi:10.1055/s-2006-957994. PMID 7700988
  10. Lesgards JF, Baldovini N, Vidal N, Pietri S. Anticancer activities of essential oils constituents and synergy with conventional therapies: a review. Phytother Res. 2014 Oct;28(10):1423-46. doi: 10.1002/ptr.5165. PMID 24831562
  11. Banerjee S, Kaseb AO, Wang Z, Kong D, Mohammad M, Padhye S, Sarkar FH, Mohammad RM. Antitumor activity of gemcitabine and oxaliplatin is augmented by thymoquinone in pancreatic cancer. Cancer Res. 2009 Jul 1;69(13):5575-83. PMID 19549912
  12. Ichwan SJ, Al-Ani IM, Bilal HG, Suriyah WH, Taher M, Ikeda MA. Apoptotic activities of thymoquinone, an active ingredient of black seed (Nigella sativa), in cervical cancer cell lines. Chin J Physiol. 2014 Oct 31;57(5):249-55. doi: 10.4077/CJP.2014.BAB190. PMID 25241984
  13. Abdel-Fattah, AM; Matsumoto, K; Watanabe, H (2000). Antinociceptive effects of Nigella sativa oil and its major component, thymoquinone, in mice. European journal of pharmacology 400 (1): 89–97. PMID 10913589
  14. Hosseinzadeh, H; Parvardeh, S (2004). Anticonvulsant effects of thymoquinone, the major constituent of Nigella sativa seeds, in mice. Phytomedicine : international journal of phytotherapy and phytopharmacology 11 (1): 56–64. PMID 14971722
  15. Akhondian J, Kianifar H, Raoofziaee M, Moayedpour A, Toosi MB, Khajedaluee M. The effect of thymoquinone on intractable pediatric seizures (pilot study). Epilepsy Res. 2011 Jan;93(1):39-43. doi: 10.1016/j.eplepsyres.2010.10.010. PMID 21112742
  16. Akhondian J, Parsa A, Rakhshande H. The effect of Nigella sativa L. (black cumin seed) on intractable pediatric seizures. Med Sci Monit. 2007 Dec;13(12):CR555-9. PMID 18049435
  17. Jukic M, Politeo O, Maksimovic M, Milos M, Milos M. In vitro acetylcholinesterase inhibitory properties of thymol, carvacrol and their derivatives thymoquinone and thymohydroquinone. Phytother Res. 2007 Mar;21(3):259-61. PMID 17186491
  18. Schneider-Stock, R., Fakhoury, I. H., Zaki, A. M., El-Baba, C. O., & Gali-Muhtasib, H. U. (2014). Thymoquinone: fifty years of success in the battle against cancer models. Drug discovery today, 19(1), 18-30.
  19. Iddamaldeniya SS, Wickramasinghe N, Thabrew I, Ratnatunge N, Thammitiyagodage MG. Protection against diethylnitrosoamine-induced hepatocarcinogenesis by an indigenous medicine comprised of Nigella sativa, Hemidesmus indicus and Smilax glabra: a preliminary study. J Carcinog. 2003 Oct 18;2(1):6. PMID 14613573
  20. Badary OA, Al-Shabanah OA, Nagi MN, Al-Rikabi AC, Elmazar MM. Inhibition of benzo(a)pyrene-induced forestomach carcinogenesis in mice by thymoquinone. European journal of cancer prevention : the official journal of the European Cancer Prevention Organisation (ECP) 8 (5): 435–40. PMID 10548399
  21. Tingfang Yi, Sung-Gook Cho, Zhengfang Yi, Xiufeng Pang, Melissa Rodriguez, Ying Wang, Gautam Sethi, Bharat B. Aggarwal, and Mingyao Liu. Thymoquinone inhibits tumor angiogenesis and tumor growth through suppressing AKT and ERK signaling pathways. Mol Cancer Ther. Texte intégral : [2]
  22. Yi T, Cho SG, Yi Z, Pang X, Rodriguez M, Wang Y, Sethi G, Aggarwal BB, Liu M. Thymoquinone inhibits tumor angiogenesis and tumor growth through suppressing AKT and extracellular signal-regulated kinase signaling pathways. Mol Cancer Ther. 2008 Jul;7(7):1789-96. PMID 18644991
  23. Al-Shabanah, OA; Badary, OA; Nagi, MN; Al-Gharably, NM; Al-Rikabi, AC; Al-Bekairi, AM (1998). Thymoquinone protects against doxorubicin-induced cardiotoxicity without compromising its antitumor activity. Journal of experimental & clinical cancer research : CR 17 (2): 193–8. PMID 9700580
  24. Badary, OA; Nagi, MN; Al-Shabanah, OA; Al-Sawaf, HA; Al-Sohaibani, MO; Al-Bekairi, AM (1997). Thymoquinone ameliorates the nephrotoxicity induced by cisplatin in rodents and potentiates its antitumor activity. Canadian journal of physiology and pharmacology 75 (12): 1356–61. PMID 9534946
  25. Al-Malki AL, Sayed A. Thymoquinone attenuates cisplatin-induced hepatotoxicity via nuclear factor kappa-ß. BMC Complementary and Alternative Medicine 2014, 14:282 (3 August 2014) Abstract texte intégral
  26. Sedaghat R, Roghani M, Khalili M. Neuroprotective effect of thymoquinone, the nigella sativa bioactive compound, in 6-hydroxydopamine-induced hemi-parkinsonian rat model. Iran J Pharm Res. 2014 Winter;13(1):227-34. PMID 24734075
  27. Beheshteh Babazadeh, Hamid Reza Sadeghnia, Elham Safarpour Kapurchal, Heydar Parsaee, Sima Nasri, Zahra Tayarani-Najaran. Protective effect of Nigella sativa and thymoquinone on serum/glucose deprivation-induced DNA damage in PC12 cells. Avicenna J Phytomed. 2012 Summer; 2(3): 125–132. PMCID: PMC4075672. Abstract texte intégral
  28. Makini K Cobourne-Duval, Equar Taka, Patricia Mendonca, Karam F A Soliman. Thymoquinone Increases the Expression of Neuroprotective Proteins While Decreasing the Expression of Pro-Inflammatory Cytokines and the Gene Expression NFκB Pathway Signaling Targets in LPS/IFNγ -Activated BV-2 Microglia Cells. J Neuroimmunol, 320, 87-97, 2018 Jul 15. PMID 29759145 DOI:10.1016/j.jneuroim.2018.04.018
  29. Radad K, Moldzio R, Taha M, Rausch WD. Thymoquinone protects dopaminergic neurons against MPP+ and rotenone. Phytother Res. 2009 May;23(5):696-700. doi: 10.1002/ptr.2708. PMID 19089849
  30. Martin TM, Benghuzzi H, Tucci M. The effect of conventional and sustained delivery of thymoquinone and levodopa on SH-SY5Y human neuroblastoma cells. Biomed Sci Instrum. 2006;42:332-7. PMID 16817630
  31. Hosseinzadeh H, Parvardeh S, Asl MN, Sadeghnia HR, Ziaee T. Effect of thymoquinone and Nigella sativa seeds oil on lipid peroxidation level during global cerebral ischemia-reperfusion injury in rat hippocampus. Phytomedicine. 2007 Sep;14(9):621-7. PMID 17291733
  32. Salahshoor MR, Haghjoo M, Roshankhah S, Makalani F, Jalili C. Effect of Thymoquinone on Reproductive Parameter in Morphine-treated Male Mice. Adv Biomed Res. 2018 Jan 30;7:18. doi: 10.4103/abr.abr_69_17. PMID 29456989
  • Ali, BH; Blunden, G (2003). Pharmacological and toxicological properties of Nigella sativa. Phytotherapy research : PTR 17 (4): 299–305. doi:10.1002/ptr.1309. PMID 12722128