User:Ahjinyoo0804

Ahjinyoo0804
Names
	Preferred IUPAC name 2-Methyl-5-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione
	Other names Thymoquinone
Identifiers
CAS Number	490-91-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:113532;
ChEMBL	ChEMBL1672002 ;
ChemSpider	9861 ;
PubChem CID	10281;
UNII	O60IE26NUF ;
	InChI InChI=1S/C10H12O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6H,1-3H3 Key: KEQHJBNSCLWCAE-UHFFFAOYSA-N ;
	SMILES CC1=CC(=O)C(=CC1=O)C(C)C;
Properties
Chemical formula	C10H12O2
Molar mass	164.204 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Ahjinyoo0804
Names
	Preferred IUPAC name 2-Methyl-5-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione
	Other names Thymoquinone
Identifiers
CAS Number	490-91-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:113532;
ChEMBL	ChEMBL1672002 ;
ChemSpider	9861 ;
PubChem CID	10281;
UNII	O60IE26NUF ;
	InChI InChI=1S/C10H12O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6H,1-3H3 Key: KEQHJBNSCLWCAE-UHFFFAOYSA-N ;
	SMILES CC1=CC(=O)C(=CC1=O)C(C)C;
Properties
Chemical formula	C10H12O2
Molar mass	164.204 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Thymoquinone is a phytochemical compound found in the plant Nigella sativa. It is also found in select cultivated Monarda fistulosa plants which can be steam distilled to produce an essential oil commonly known as black seed oil.

It has been classified as a pan-assay interference compound, which binds indiscriminately to many proteins.^[1] It is under preliminary research to identify its possible biological properties.^[2]^[3]^[4]

Biosynthesis

Thymoquinone is biosynthesized by plants through the terpene biosynthetic pathway as a secondary metabolite. It belongs to the class of monoterpenes which stem from condensation of two isoprene units.^[5] For thymoquinone, geranyl disphosphate cyclizes and is converted to "Gamma"-terpinene by gamma-terpinene synthase (during seed maturation).^[6] Cytochrome p450 monooxygenases (P450s) then oxidizes gamma-terpinene into p-cymene. Hydroxylation leads to the formation of carvacrol and further hydroxylation produces thymohydroquinone. Thymohydroquinone then undergoes oxidation to form thymoquinone.^[7]

An alternative biosynthetic pathway may occur if some species of the plant accumulate thymol instead of carvacrol, where p-cymene hydroxylates to thymol. ^[5]

Chemical Synthesis

Thymoquinone was first extracted and isolated in 1963 by an Egyptian chemist Mostafa M. El-Dakhakhny.^[8]

Therapeutic Effects

Antioxidant, Anti-Inflammatory Activity

Thymoquinone is considered an anti-oxidant, which defends against reactive oxygen species (ROS) which are continuously produced in cells through aerobic metabolism. The presence of ROS induces oxidation of biomolecules which can be harmful to the host. Thymoquinone neutralizes the free radical-induced oxidative damage as an anti-oxidant enzyme in a variety of organs, including the liver, stomach, and kidney.^[9]

Inflammation in the body is mainly mediated by cyclooxygenase and lipoxygenase, enzymes that generate prostaglandins and leukotrienes. Thymoquinone has the ability to inhibit both enzymes in their pathways of arachidonic acid metabolism specifically in rats, causing anti-inflammatory effects.^[8]^[10]

Effects on the Respiratory System

Known for its effects on alleviating asthma, thymoquinone has been tested in its volatile oil form in guinea pigs and dogs. It was concluded that (i.m) or (i.p) injection of thymoquinone in doses of 200ul/kg induced bronchodilation, reversing the effects of histamine-induced bronchoconstriction.^[8] Thymoquinone also induced relaxation of subject's isolated trachea by inhibiting lipoxygenase products and by non-selective blocking of histamine and serotonin receptors.^[9]

Toxicity

References

^ Baell JB (March 2016). "Feeling Nature's PAINS: Natural Products, Natural Product Drugs, and Pan Assay Interference Compounds (PAINS)". Journal of Natural Products. 79 (3): 616–28. doi:10.1021/acs.jnatprod.5b00947. PMID 26900761.
^ Farkhondeh T, Samarghandian S, Borji A (September 2017). "An overview on cardioprotective and anti-diabetic effects of thymoquinone". Asian Pacific Journal of Tropical Medicine. 10 (9): 849–854. doi:10.1016/j.apjtm.2017.08.020. PMID 29080612.
^ Leong, Xin-Fang; Choy, Ker Woon; Alias, Aspalilah (2021-12-15). "Anti-Inflammatory Effects of Thymoquinone in Atherosclerosis: A Mini Review". Frontiers in Pharmacology. 12: 758929. doi:10.3389/fphar.2021.758929. ISSN 1663-9812. PMC 8715035. PMID 34975474.
^ Ali, Md Yousuf; Akter, Zakia; Mei, Zhiqiang; Zheng, Meiling; Tania, Mousumi; Khan, Md Asaduzzaman (February 2021). "Thymoquinone in autoimmune diseases: Therapeutic potential and molecular mechanisms". Biomedicine & Pharmacotherapy. 134: 111157. doi:10.1016/j.biopha.2020.111157. ISSN 1950-6007. PMID 33370631. S2CID 229714190.
^ ^a ^b Ahmad, Anas; Mishra, Rakesh Kumar; Vyawahare, Akshay; Kumar, Ajay; Rehman, Muneeb U.; Qamar, Wajhul; Khan, Abdul Quaiyoom; Khan, Rehan (2019-12). "Thymoquinone (2-Isopropyl-5-methyl-1, 4-benzoquinone) as a chemopreventive/anticancer agent: Chemistry and biological effects". Saudi Pharmaceutical Journal. 27 (8): 1113–1126. doi:10.1016/j.jsps.2019.09.008. PMC 6921197. PMID 31885471. {{cite journal}}: Check date values in: |date= (help)CS1 maint: PMC format (link)
^ Elyasi, Rizan; Majdi, Mohammad; Krause, Sandra T.; Kücükay, Nagihan; Azizi, Abdolbaset; Degenhardt, Jörg (2022-10-01). "Identification and functional characterization of a γ-terpinene synthase in Nigella sativa L (black cumin)". Phytochemistry. 202: 113290. doi:10.1016/j.phytochem.2022.113290. ISSN 0031-9422.
^ Krause, Sandra T.; Liao, Pan; Crocoll, Christoph; Boachon, Benoît; Förster, Christiane; Leidecker, Franziska; Wiese, Natalie; Zhao, Dongyan; Wood, Joshua C.; Buell, C. Robin; Gershenzon, Jonathan; Dudareva, Natalia; Degenhardt, Jörg (2021-12-28). "The biosynthesis of thymol, carvacrol, and thymohydroquinone in Lamiaceae proceeds via cytochrome P450s and a short-chain dehydrogenase". Proceedings of the National Academy of Sciences. 118 (52): e2110092118. doi:10.1073/pnas.2110092118. ISSN 0027-8424. PMC 8719858. PMID 34930840.{{cite journal}}: CS1 maint: PMC format (link)
^ ^a ^b ^c Hussein El-Tahir, Kamal El-Din; Bakeet, Dana M. (2006-01-01). "The Black Seed Nigella sativa Linnaeus - A Mine for Multi Cures: A Plea for Urgent Clinical Evaluation of its Volatile Oil". Journal of Taibah University Medical Sciences. 1 (1, Supplement C): 1–19. doi:10.1016/S1658-3612(06)70003-8. ISSN 1658-3612.
^ ^a ^b Darakhshan, Sara; Bidmeshki Pour, Ali; Hosseinzadeh Colagar, Abasalt; Sisakhtnezhad, Sajjad (2015-05). "Thymoquinone and its therapeutic potentials". Pharmacological Research. 95–96: 138–158. doi:10.1016/j.phrs.2015.03.011. {{cite journal}}: Check date values in: |date= (help)
^ Khan, M. Akram (1999-03). "Chemical composition and medicinal properties of Nigella sativa Linn". Inflammopharmacology. 7 (1): 15–35. doi:10.1007/s10787-999-0023-y. ISSN 0925-4692. {{cite journal}}: Check date values in: |date= (help)

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[1] Baell JB (March 2016). "Feeling Nature's PAINS: Natural Products, Natural Product Drugs, and Pan Assay Interference Compounds (PAINS)". Journal of Natural Products. 79 (3): 616–28. doi:10.1021/acs.jnatprod.5b00947. PMID 26900761.

[2] Farkhondeh T, Samarghandian S, Borji A (September 2017). "An overview on cardioprotective and anti-diabetic effects of thymoquinone". Asian Pacific Journal of Tropical Medicine. 10 (9): 849–854. doi:10.1016/j.apjtm.2017.08.020. PMID 29080612.

[3] Leong, Xin-Fang; Choy, Ker Woon; Alias, Aspalilah (2021-12-15). "Anti-Inflammatory Effects of Thymoquinone in Atherosclerosis: A Mini Review". Frontiers in Pharmacology. 12: 758929. doi:10.3389/fphar.2021.758929. ISSN 1663-9812. PMC 8715035. PMID 34975474.

[4] Ali, Md Yousuf; Akter, Zakia; Mei, Zhiqiang; Zheng, Meiling; Tania, Mousumi; Khan, Md Asaduzzaman (February 2021). "Thymoquinone in autoimmune diseases: Therapeutic potential and molecular mechanisms". Biomedicine & Pharmacotherapy. 134: 111157. doi:10.1016/j.biopha.2020.111157. ISSN 1950-6007. PMID 33370631. S2CID 229714190.

[:02-5] Ahmad, Anas; Mishra, Rakesh Kumar; Vyawahare, Akshay; Kumar, Ajay; Rehman, Muneeb U.; Qamar, Wajhul; Khan, Abdul Quaiyoom; Khan, Rehan (2019-12). "Thymoquinone (2-Isopropyl-5-methyl-1, 4-benzoquinone) as a chemopreventive/anticancer agent: Chemistry and biological effects". Saudi Pharmaceutical Journal. 27 (8): 1113–1126. doi:10.1016/j.jsps.2019.09.008. PMC 6921197. PMID 31885471. {{cite journal}}: Check date values in: |date= (help)CS1 maint: PMC format (link)

[6] Elyasi, Rizan; Majdi, Mohammad; Krause, Sandra T.; Kücükay, Nagihan; Azizi, Abdolbaset; Degenhardt, Jörg (2022-10-01). "Identification and functional characterization of a γ-terpinene synthase in Nigella sativa L (black cumin)". Phytochemistry. 202: 113290. doi:10.1016/j.phytochem.2022.113290. ISSN 0031-9422.

[7] Krause, Sandra T.; Liao, Pan; Crocoll, Christoph; Boachon, Benoît; Förster, Christiane; Leidecker, Franziska; Wiese, Natalie; Zhao, Dongyan; Wood, Joshua C.; Buell, C. Robin; Gershenzon, Jonathan; Dudareva, Natalia; Degenhardt, Jörg (2021-12-28). "The biosynthesis of thymol, carvacrol, and thymohydroquinone in Lamiaceae proceeds via cytochrome P450s and a short-chain dehydrogenase". Proceedings of the National Academy of Sciences. 118 (52): e2110092118. doi:10.1073/pnas.2110092118. ISSN 0027-8424. PMC 8719858. PMID 34930840.{{cite journal}}: CS1 maint: PMC format (link)

[:12-8] Hussein El-Tahir, Kamal El-Din; Bakeet, Dana M. (2006-01-01). "The Black Seed Nigella sativa Linnaeus - A Mine for Multi Cures: A Plea for Urgent Clinical Evaluation of its Volatile Oil". Journal of Taibah University Medical Sciences. 1 (1, Supplement C): 1–19. doi:10.1016/S1658-3612(06)70003-8. ISSN 1658-3612.

[:22-9] Darakhshan, Sara; Bidmeshki Pour, Ali; Hosseinzadeh Colagar, Abasalt; Sisakhtnezhad, Sajjad (2015-05). "Thymoquinone and its therapeutic potentials". Pharmacological Research. 95–96: 138–158. doi:10.1016/j.phrs.2015.03.011. {{cite journal}}: Check date values in: |date= (help)

[10] Khan, M. Akram (1999-03). "Chemical composition and medicinal properties of Nigella sativa Linn". Inflammopharmacology. 7 (1): 15–35. doi:10.1007/s10787-999-0023-y. ISSN 0925-4692. {{cite journal}}: Check date values in: |date= (help)

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