Thymoquinone

==﻿Nom de la substance==
Thymoquinone et Thymohydroquinone
==Famille moléculaire==
Benzoquinone
==Source végétale==
* Nigelle aromatique (cumin noir), huile essentielle d'ayapana, monarde
==Propriétés==
* Considéré comme une molécule thérapeutique émergente 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, Gupta, B., Ghosh, K. K., & Gupta, R. C. (2016). Thymoquinone. In Nutraceuticals (pp. 541-550). Academic Press. en raison de ses propriétés immunomodulantes, hépatoprotectrices, anti-inflammatoires, antioxydantes, cytotoxiques et anti-cancer 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, 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
* Hépatoprotecteur 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
* Immunomodulant, module l'inflammation et les réponses immunitaires adaptatives cellulaires et humorales ainsi que la balance Th1/Th2 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
* Anti-inflammatoire par inhibition des fonctions du neutrophile humain 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. , la thymoquinone diminue l’arthrite expérimentale chez le rat 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, antioxydant, inhibiteur de la peroxydation lipidique 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
* Antitumoral 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, activité anticancéreuse vis-à-vis des cancers du côlon et de la prostate, et du cancer du pancréas , , potentialise les effets de la chimiothérapie 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, inducteur d'apoptose sur les cellules de cancer du col utérin 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
* Analgésique 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
* Anticonvulsivant 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, même sur des épilepsies résistantes 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, 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
* Propriétés anticholinestérase (surtout thymohydroquinone) 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
* Propriétés anticancéreuses 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., augmente l'activité cytotoxique des cellules NK contre les cellules cancéreuses 
* Protection vis-à-vis de la transformation hépatocarcinomateuse 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, et de la carcinogenèse gastrique induite par le benzopyrène 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
* Anti-angiogénique 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 : , 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
* Protection vis-à-vis de la toxicité myocardique de la doxorubicine 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, vis-à-vis de la néphrotoxicité du cisplatine 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, 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
* Antimicrobiennne, antivirale, l'huile essentielle d'Ayapana triplinervis et son composant principal la thymohydroquinone-diméthyl-éther inhibent le virus Zika Haddad, J. G., Picard, M., Bénard, S., Desvignes, C., Desprès, P., Diotel, N., & El Kalamouni, C. (2019). Ayapana triplinervisEssential Oil and Its Main Component Thymohydroquinone Dimethyl Ether Inhibit Zika Virus at Doses Devoid of Toxicity in Zebrafish. Molecules (Basel, Switzerland), 24(19), 3447. https://doi.org/10.3390/molecules24193447. PMID 31547527
* Neuroprotection 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, 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, 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, protection des neurones dopaminergiques vis-à-vis de certains toxiques (roténone) 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, protection vis-à-vis de l'auto-oxydation de la l-dopa 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, effet protecteur vis-à-vis de la peroxydation lipidique induite par le processus d'ischémie-reperfusion dans l'hippocampe de rat 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
* Améliore la qualité du sperme et des spermatozoïdes 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
* Des dérivés pourraient provenir de la métabolisation du thymol Takada, M., Agata, I., Sakamoto, M., Yagi, N., & Hayashi, N. (1979). On the metabolic detoxication of thymol in rabbit and man. The Journal of toxicological sciences, 4(4), 341–350. https://doi.org/10.2131/jts.4.341. PMID 548583
==Effet thérapeutique==
* Allergie, autoimmunité, cancer , polyarthrite
* Protection hépatique et chimioprotection avec les traitements anticancéreux (?)
* Cancers (?)
* Alzheimer (?)
* Parkinson (?)
==Effets indésirables==
* Risque allergique faible
* La thymoquinone est métabolisée par le CYP 2C9 Ahmed A. Albassam, Abdul Ahad, Abdullah Alsultan, Fahad I. Al-Jenoobi. Inhibition of cytochrome P450 enzymes by thymoquinone in human liver microsomes. Saudi Pharmaceutical Journal, Volume 26, Issue 5, 2018, Pages 673-677, https://doi.org/10.1016/j.jsps.2018.02.024.
==Bibliographie==
* 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
Catégorie:Principes actifs