Chemistry:Baicalein

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Short description: Chemical compound
Baicalein
Baicalein.svg
Baicalein-3D-balls.png
Clinical data
Other namesBiacalein; Noroxylin
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC15H10O5
Molar mass270.240 g·mol−1
3D model (JSmol)

Baicalein (5,6,7-trihydroxyflavone) is a flavone, a type of flavonoid, originally isolated from the roots of Scutellaria baicalensis and Scutellaria lateriflora. It is also reported in Oroxylum indicum (Indian trumpetflower) and Thyme.[1] It is the aglycone of baicalin. Baicalein is one of the active ingredients of Sho-Saiko-To, which is a Chinese classic herbal formula, and listed in Japan as Kampo medicine.[citation needed]

Baicalein, along with its analogue baicalin, is a positive allosteric modulator of the benzodiazepine site and/or a non-benzodiazepine site of the GABAA receptor but with an affinity over 250× lower than diazepam.[2][3][4][5][6][7] It displays subtype selectivity for α2 and α3 subunit-containing GABAA receptors.[8] In accordance, baicalein shows anxiolytic effects in mice without incidence of sedation or myorelaxation.[7][8][9] It is thought that baicalein, along with other flavonoids, may underlie the anxiolytic effects of S. baicalensis and S. lateriflora.[10][11] Baicalein is also an antagonist of the estrogen receptor, or an antiestrogen.[11]

The flavonoid has been shown to inhibit certain types of lipoxygenases[12] and act as an anti-inflammatory agent.[13] It has antiproliferative effects on ET-1-induced proliferation of pulmonary artery smooth muscle cell proliferation via inhibition of TRPC1 channel expression.[14] Possible antidepressant effects have also been attributed to baicalein in animal research.[15]

Baicalein is an inhibitor of CYP2C9,[16] an enzyme of the cytochrome P450 system that metabolizes drugs in the body.

A derivative of baicalin is a known prolyl endopeptidase inhibitor.[17]

Baicalein has been shown to inhibit Staphylococcus aureus biofilm formation and the quorum sensing system in vitro.[18]

It has also been shown to be effective in vitro against all forms of Borrelia burgdorferi and Borrelia garinii.[19]

Glycosides

Tetuin is the 6-glucoside of baicalein.

See also

  • List of compounds with carbon number 15

References

  1. ↑ Phytochemistry Research Progress. Nova Publishers. 2008. ISBN 9781604562323. https://books.google.com/books?id=l5Mo0M5CqQcC&q=%22Baicalein%22+and+%22thymus+vulgaris%22&pg=PA42. 
  2. ↑ "Two flavones from Scutellaria baicalensis Georgi and their binding affinities to the benzodiazepine site of the GABAA receptor complex". Die Pharmazie 57 (12): 857–858. December 2002. PMID 12561253. 
  3. ↑ "Interaction of flavones from the roots of Scutellaria baicalensis with the benzodiazepine site". Planta Medica 66 (1): 91–93. February 2000. doi:10.1055/s-0029-1243121. PMID 10705749. 
  4. ↑ "Baicalein reduces β-amyloid and promotes nonamyloidogenic amyloid precursor protein processing in an Alzheimer's disease transgenic mouse model". Journal of Neuroscience Research 91 (9): 1239–1246. September 2013. doi:10.1002/jnr.23244. PMID 23686791. 
  5. ↑ "Benzodiazepine binding site-interactive flavones from Scutellaria baicalensis root". Planta Medica 64 (6): 571–572. August 1998. doi:10.1055/s-2006-957517. PMID 9776664. 
  6. ↑ "Testing efficacy of natural anxiolytic compounds". Complementary and Alternative Approaches to Biomedicine. Advances in Experimental Medicine and Biology. 546. 2004. pp. 181–191. doi:10.1007/978-1-4757-4820-8_13. ISBN 978-1-4419-3441-3. 
  7. ↑ 7.0 7.1 "Involvement of GABAergic non-benzodiazepine sites in the anxiolytic-like and sedative effects of the flavonoid baicalein in mice". Behavioural Brain Research 221 (1): 75–82. August 2011. doi:10.1016/j.bbr.2011.02.038. PMID 21377498. 
  8. ↑ 8.0 8.1 "GABA A receptor subtype selectivity underlying selective anxiolytic effect of baicalin". Neuropharmacology 55 (7): 1231–1237. December 2008. doi:10.1016/j.neuropharm.2008.07.040. PMID 18723037. 
  9. ↑ "Anxiolytic-like effects of baicalein and baicalin in the Vogel conflict test in mice". European Journal of Pharmacology 464 (2–3): 141–146. March 2003. doi:10.1016/s0014-2999(03)01422-5. PMID 12620506. 
  10. ↑ "Phytochemical and biological analysis of skullcap (Scutellaria lateriflora L.): a medicinal plant with anxiolytic properties". Phytomedicine 10 (8): 640–649. November 2003. doi:10.1078/0944-7113-00374. PMID 14692724. 
  11. ↑ 11.0 11.1 "Native American Psychoactive Herbs". Psychoactive Herbs in Veterinary Behavior Medicine. John Wiley & Sons. 9 January 2008. pp. 139–. ISBN 978-0-470-34434-7. https://books.google.com/books?id=ZP6QVep-x24C&pg=PA139. 
  12. ↑ "Baicalein is a potent in vitro inhibitor against both reticulocyte 15-human and platelet 12-human lipoxygenases". Bioorganic & Medicinal Chemistry 14 (12): 4295–4301. June 2006. doi:10.1016/j.bmc.2006.01.057. PMID 16500106. https://www.escholarship.org/uc/item/8mj512rb. 
  13. ↑ "Baicalein inhibits IL-1beta- and TNF-alpha-induced inflammatory cytokine production from human mast cells via regulation of the NF-kappaB pathway". Clinical and Molecular Allergy 5 (1): 5. November 2007. doi:10.1186/1476-7961-5-5. PMID 18039391. 
  14. ↑ "Baicalein, isolated from Scutellaria baicalensis, protects against endothelin-1-induced pulmonary artery smooth muscle cell proliferation via inhibition of TRPC1 channel expression". Journal of Ethnopharmacology 138 (2): 373–381. November 2011. doi:10.1016/j.jep.2011.09.014. PMID 21963569. 
  15. ↑ "Antidepressant effects of a plant-derived flavonoid baicalein involving extracellular signal-regulated kinases cascade". Biological & Pharmaceutical Bulletin 34 (2): 253–259. 2011. doi:10.1248/bpb.34.253. PMID 21415537. 
  16. ↑ "Mechanism of CYP2C9 inhibition by flavones and flavonols". Drug Metabolism and Disposition 37 (3): 629–634. March 2009. doi:10.1124/dmd.108.023416. PMID 19074529. http://p4502c.googlepages.com/dmd2.pdf. Retrieved 2009-02-19. 
  17. ↑ "Baicalin, a prodrug able to reach the CNS, is a prolyl oligopeptidase inhibitor". Bioorganic & Medicinal Chemistry 16 (15): 7516–7524. August 2008. doi:10.1016/j.bmc.2008.04.067. PMID 18650094. 
  18. ↑ "Baicalein Inhibits Staphylococcus aureus Biofilm Formation and the Quorum Sensing System In Vitro". PLOS ONE 11 (4): e0153468. April 2016. doi:10.1371/journal.pone.0153468. PMID 27128436. Bibcode: 2016PLoSO..1153468C. 
  19. ↑ "In vitro evaluation of antibacterial activity of phytochemicals and micronutrients against Borrelia burgdorferi and Borrelia garinii". Journal of Applied Microbiology 119 (6): 1561–1572. December 2015. doi:10.1111/jam.12970. PMID 26457476. 



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