Thymoquinone

Thymoquinone
Names
IUPAC name
2-Isopropyl-5-methylbenzo-1,4-quinone
Other names
Thymoquinone
Identifiers
490-91-5 N
ChEMBL ChEMBL1672002 N
ChemSpider 9861 YesY
Jmol 3D model Interactive image
PubChem 10281
Properties
C10H12O2
Molar mass 164.20 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Thymoquinone is a phytochemical compound found in the plant Nigella sativa. It is also found in select cultivated Monarda fistulosa plants grown and steam distilled in the USA producing an essential oil.

Clinical study

In 2010, an Iranian pilot study was done where thymoquinone was administered to children with epilepsy. Thymoquinone may have anti-convulsant action in pediatric epilepsy.[1] Thymoquinone and other components of N. sativa may be neuroprotective.[2]

As of November 2013 there were no clinical trials for thymoquinone registered by the U.S government.[3]

Research in animals

It has antioxidant effects and has been shown to protect against heart, liver and kidney damage in animal studies[4][5] as well as having possible anti-cancer effects.[6][7][8][9][10][11][12]

It also has analgesic[13] and anticonvulsant effects in animal models.[14] It is an angiogenesis inhibitor.

In 2008 in-vitro tests showed it was an HDAC inhibitor, affecting genes such p53, Bax, bcl-2 and p21.[15]

Thymoquinone has been studied for its potential effects on colon cancer cells. It reduces mouse colon tumor cell invasion and inhibits tumor growth in animal models of colon cancer. The stress response sensor CHEK1 may contribute to the anti-colon cancer effects of thymoquinone.[16] Thymoquinone may affect immune function by influencing dendritic cell functions such as maturation, cell pH (by affecting Na+/H+ activity), oxidative burst, migration and cytokine release. Dendritic cell volume may also be affected by thymoquinone.[17]

Thymoquinone has been shown to induce apoptosis in thrombocytes, an effect largely dependent on PI3K signaling.[18] In colorectal cancer, however, thymoquinone's apoptotic effects arise from inhibition of the MEK1/2 pathway instead of PI3K. In this case, cell-specific apoptosis in tumors is induced through the former pathway. This is associated with a reduction in GSK-3β phosphorylation (increased activation) and subsequent translocation of β-catentin to the cellular membrane where the stabilized protein would fail to induce proliferation.[19] It is reported that in a mouse model of breast cancer model and in cancer cell lines in vitro, thymoquinone downregulates TWIST1 transcription factor to reduce epithelial to mesenchymal transition and thus inhibits metastasis.[20]

See also

References

  1. ↑ Akhondian, Javad; Kianifar, Hamidreza; Raoofziaee, Mohammad; Moayedpour, Amir; Toosi, Mehran Beiraghi; Khajedaluee, Mohammad (2011). "The effect of thymoquinone on intractable pediatric seizures (pilot study)". Epilepsy Research 93 (1): 39–43. doi:10.1016/j.eplepsyres.2010.10.010. PMID 21112742.
  2. ↑ Khazdair, Mohammad Reza (2015-01-01). "The Protective Effects of Nigella sativa and Its Constituents on Induced Neurotoxicity". Journal of Toxicology 2015: 841823. doi:10.1155/2015/841823. ISSN 1687-8191. PMC 4641935. PMID 26604923.
  3. ↑ http://clinicaltrials.gov/ct2/results?term=Thymoquinone
  4. ↑ 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. doi:10.1139/y97-169. PMID 9534946.
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ Badary, OA; Al-Shabanah, OA; Nagi, MN; Al-Rikabi, AC; Elmazar, MM (1999). "Inhibition of benzo(a)pyrene-induced forestomach carcinogenesis in mice by thymoquinone". European Journal of Cancer Prevention 8 (5): 435–40. doi:10.1097/00008469-199910000-00009. PMID 10548399.
  8. ↑ 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.
  9. ↑ Gali-Muhtasib, H; Roessner, A; Schneider-Stock, R (2006). "Thymoquinone: a promising anti-cancer drug from natural sources". The international journal of biochemistry & cell biology 38 (8): 1249–53. doi:10.1016/j.biocel.2005.10.009. PMID 16314136.
  10. ↑ Al-Majed, AA; Al-Omar, FA; Nagi, MN (2006). "Neuroprotective effects of thymoquinone against transient forebrain ischemia in the rat hippocampus". European Journal of Pharmacology 543 (1–3): 40–7. doi:10.1016/j.ejphar.2006.05.046. PMID 16828080.
  11. ↑ Gali-Muhtasib, H; Roessner, A; Schneider-Stock, R (2006). "Thymoquinone: a promising anti-cancer drug from natural sources". The international journal of biochemistry & cell biology 38 (8): 1249–53. doi:10.1016/j.biocel.2005.10.009. PMID 16314136.
  12. ↑ Effenberger-Neidnicht, K; Breyer, S; Mahal, K; Diestel, R; Sasse, F; Schobert, R (May 16, 2011). "Cellular localisation of antitumoral 6-alkyl thymoquinones revealed by an alkyne-azide click reaction and the streptavidin-biotin system". Chembiochem : a European journal of chemical biology 12 (8): 1237–41. doi:10.1002/cbic.201000762. PMID 21500333.
  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. doi:10.1016/S0014-2999(00)00340-X. 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. doi:10.1078/0944-7113-00376. PMID 14971722.
  15. ↑ "Traditional herbal medicine kills pancreatic cancer cells, researchers report.". May 19, 2008.
  16. ↑ Gali-Muhtasib, H; Kuester, D; Mawrin, C; Bajbouj, K; Diestel, A; Ocker, M; Habold, C; Foltzer-Jourdainne, C; Schoenfeld, P; Peters, B; Diab-Assaf, M; Pommrich, U; Itani, W; Lippert, H; Roessner, A; Schneider-Stock, R (Jul 15, 2008). "Thymoquinone triggers inactivation of the stress response pathway sensor CHEK1 and contributes to apoptosis in colorectal cancer cells". Cancer Research 68 (14): 5609–18. doi:10.1158/0008-5472.CAN-08-0884. PMID 18632613. Cite uses deprecated parameter |coauthors= (help)
  17. ↑ Yang, W; Bhandaru, M; Pasham, V; Bobbala, D; Zelenak, C; Jilani, K; Rotte, A; Lang, F (2012). "Effect of thymoquinone on cytosolic pH and Na+/H+ exchanger activity in mouse dendritic cells". Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 29 (1–2): 21–30. doi:10.1159/000337583. PMID 22415071.
  18. ↑ Towhid, Syeda Tasneem; Schmidt, Eva-Maria; Schmid, Evi; Münzer, Patrick; Qadri, Syed M.; Borst, Oliver; Lang, Florian (November 2011). "Thymoquinone-induced platelet apoptosis". J. Cell. Biochem. 112 (11): 3112–21. doi:10.1002/jcb.23237. PMID 21688304.
  19. ↑ Lang, Michaela; Borgmann, Melanie; Oberhuber, Georg; Evstatiev, Rayko; Jimenez, Kristine; Dammann, Kyle W; Jambrich, Manuela; Khare, Vineeta; Campregher, Christoph; Ristl, Robin; Gasche, Christoph (2013). "Thymoquinone attenuates tumor growth in ApcMin mice by interference with Wnt-signaling". Molecular Cancer 12 (1): 41. doi:10.1186/1476-4598-12-41. Cite uses deprecated parameter |coauthors= (help)
  20. ↑ Khan MA, Tania M, Wei C, Mei Z, Fu S, Cheng J, Xu J, Fu J (2015). "Thymoquinone inhibits cancer metastasis by downregulating TWIST1 expression to reduce epithelial to mesenchymal transition". Oncotarget 6: 19580–91. doi:10.18632/oncotarget.3973. PMID 26023736.
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