Thymoquinone

Thymoquinone

Names
IUPAC name 2-Isopropyl-5-methylbenzo-1,4-quinone
Other names Thymoquinone
Identifiers
CAS Number	490-91-5 N
3D model (JSmol)	Interactive image
ChemSpider	9861 Y
ECHA InfoCard	100.007.020
PubChem CID	10281
InChI InChI=1S/C10H12O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6H,1-3H3 Y Key: KEQHJBNSCLWCAE-UHFFFAOYSA-N Y
SMILES CC1=CC(=O)C(=CC1=O)C(C)C
Properties
Chemical formula	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 YN ?)
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, brain, liver and kidney damage in animal studies ^[4][5][6] as well as having possible anti-cancer effects.^{[7][8][9][10][11][12][13]}

It also has analgesic^[14] and anticonvulsant effects in animal models.^[15] 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.^[16]

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.^[17] 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.^[18]

Thymoquinone has been shown to induce apoptosis in thrombocytes, an effect largely dependent on PI3K signaling.^[19] 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.^[20] 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.^[21]

See also

• Dithymoquinone, a dimer of thymoquinone
• 2,5-Dimethoxy-p-cymene

References