Baicalein

Baicalein
Names
IUPAC name
5,6,7-Trihydroxy-2-phenyl-chromen-4-one
Other names
5,6,7-Trihydroxyflavone
Identifiers
491-67-8 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:2979 YesY
ChEMBL ChEMBL8260 YesY
ChemSpider 4444924 YesY
ECHA InfoCard 100.164.911
5144
PubChem 5281605
UNII 49QAH60606 YesY
Properties
C15H10O5
Molar mass 270.24 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 or Indian trumpetflower. It is the aglycone of baicalin. Baicalein is one of the active ingredients of Sho-Saiko-To, a Japanese herbal supplement believed to enhance liver health.

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.[1][2][3][4][5][6] It displays subtype selectivity for α2 and α3 subunit-containing GABAA receptors.[7] In accordance, baicalein shows anxiolytic effects in mice without incidence of sedation or myorelaxation.[6][7][8] It is thought that baicalein, along with other flavonoids, may underlie the anxiolytic effects of S. baicalensis and S. lateriflora.[9][10] Baicalein is also an antagonist of the estrogen receptor, or an antiestrogen.[10]

The flavonoid has been shown to inhibit certain types of lipoxygenases[11] and act as an anti-inflammatory agent.[12] It has antiproliferative effects on ET-1-induced proliferation of pulmonary artery smooth muscle cell proliferation via inhibition of TRPC1 channel expression.[13] Possible antidepressant effects have also been attributed to baicalein in animal research.[14]

Baicalein is an inhibitor of CYP2C9,[15] an enzyme of the cytochrome P450 system that metabolizes drugs in the body.

A derivative of baicalin is a known prolyl endopeptidase inhibitor.[16]

Baicalein has been shown to inhibit Staphylococcus aureus biofilm formation and the quorum sensing system in vitro.[17]

Glycosides

Tetuin is the 6-glucoside of baicalein.

See also

References

  1. ↑ Wang H, Hui KM, Xu S, Chen Y, Wong JT, Xue H (2002). "Two flavones from Scutellaria baicalensis Georgi and their binding affinities to the benzodiazepine site of the GABAA receptor complex". Pharmazie. 57 (12): 857–8. PMID 12561253.
  2. ↑ Hui KM, Wang XH, Xue H (2000). "Interaction of flavones from the roots of Scutellaria baicalensis with the benzodiazepine site". Planta Med. 66 (1): 91–3. doi:10.1055/s-0029-1243121. PMID 10705749.
  3. ↑ Zhang SQ, Obregon D, Ehrhart J, Deng J, Tian J, Hou H, Giunta B, Sawmiller D, Tan J (2013). "Baicalein reduces β-amyloid and promotes nonamyloidogenic amyloid precursor protein processing in an Alzheimer's disease transgenic mouse model". J. Neurosci. Res. 91 (9): 1239–46. doi:10.1002/jnr.23244. PMC 3810722Freely accessible. PMID 23686791.
  4. ↑ Liao JF, Wang HH, Chen MC, Chen CC, Chen CF (1998). "Benzodiazepine binding site-interactive flavones from Scutellaria baicalensis root". Planta Med. 64 (6): 571–2. doi:10.1055/s-2006-957517. PMID 9776664.
  5. ↑ Edwin Lowell Cooper; Nobuo Yamaguchi (1 January 2004). Complementary and Alternative Approaches to Biomedicine. Springer Science & Business Media. pp. 188–. ISBN 978-0-306-48288-5.
  6. 1 2 de Carvalho RS, Duarte FS, de Lima TC (2011). "Involvement of GABAergic non-benzodiazepine sites in the anxiolytic-like and sedative effects of the flavonoid baicalein in mice". Behav. Brain Res. 221 (1): 75–82. doi:10.1016/j.bbr.2011.02.038. PMID 21377498.
  7. 1 2 Wang F, Xu Z, Ren L, Tsang SY, Xue H (2008). "GABA A receptor subtype selectivity underlying selective anxiolytic effect of baicalin". Neuropharmacology. 55 (7): 1231–7. doi:10.1016/j.neuropharm.2008.07.040. PMID 18723037.
  8. ↑ Liao JF, Hung WY, Chen CF (2003). "Anxiolytic-like effects of baicalein and baicalin in the Vogel conflict test in mice". Eur. J. Pharmacol. 464 (2-3): 141–6. doi:10.1016/s0014-2999(03)01422-5. PMID 12620506.
  9. ↑ Awad R, Arnason JT, Trudeau V, Bergeron C, Budzinski JW, Foster BC, Merali Z (2003). "Phytochemical and biological analysis of skullcap (Scutellaria lateriflora L.): a medicinal plant with anxiolytic properties". Phytomedicine. 10 (8): 640–9. doi:10.1078/0944-7113-00374. PMID 14692724.
  10. 1 2 Stefanie Schwartz (9 January 2008). Psychoactive Herbs in Veterinary Behavior Medicine. John Wiley & Sons. pp. 139–. ISBN 978-0-470-34434-7.
  11. ↑ Deschamps JD, Kenyon VA, Holman TR (June 2006). "Baicalein is a potent in vitro inhibitor against both reticulocyte 15-human and platelet 12-human lipoxygenases". Bioorg. Med. Chem. 14 (12): 4295–301. doi:10.1016/j.bmc.2006.01.057. PMID 16500106.
  12. ↑ Hsieh CJ, Hall K, Ha T, Li C, Krishnaswamy G, Chi DS (2007). "Baicalein inhibits IL-1β- and TNF-α-induced inflammatory cytokine production from human mast cells via regulation of the NF-κB pathway". Clin Mol Allergy. 5 (1): 5. doi:10.1186/1476-7961-5-5. PMC 2206049Freely accessible. PMID 18039391.
  13. ↑ Lin Y-L, Lin R-J, Shen K-P, Dai Z-K, Chen I-J, Wu J-R, Wu B-N (2011). "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. doi:10.1016/j.jep.2011.09.014.
  14. ↑ Xiong Z, Jiang B, Wu PF, et al. (2011). "Antidepressant effects of a plant-derived flavonoid baicalein involving extracellular signal-regulated kinases cascade". Biol. Pharm. Bull. 34 (2): 253–9. doi:10.1248/bpb.34.253. PMID 21415537.
  15. ↑ Si D, Wang Y, Zhou Y-H, Guo Y, Wang J, Zhou H, Li Z-S, Fawcett JP (March 2009). "Mechanism of CYP2C9 inhibition by flavones and flavonols" (PDF). Drug Metabolism and Disposition. 37 (3): 629–34. doi:10.1124/dmd.108.023416. PMID 19074529.
  16. ↑ Tarragó T, Kichik N, Claasen B, Prades R, Teixidó M, Giralt E (Aug 2008). "Baicalin, a prodrug able to reach the CNS, is a prolyl oligopeptidase inhibitor". Bioorganic and Medicinal Chemistry. 16 (15): 7516–24. doi:10.1016/j.bmc.2008.04.067. PMID 18650094.
  17. ↑ Chen Y, Liu T, Wang K, Hou C, Cai S, Huang Y, Du Z, Huang H, Kong J, Chen Y (April 2016). "Baicalein Inhibits Staphylococcus aureus Biofilm Formation and the Quorum Sensing System In Vitro.". PLOS ONE. 11 (4): e0153468. doi:10.1371/journal.pone.0153468. PMC 4851419Freely accessible. PMID 27128436.
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