Baicalein

Baicalein

Clinical data
Other names	Biacalein; Noroxylin
Identifiers
IUPAC name 5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one
CAS Number	491-67-8
PubChem CID	5281605
IUPHAR/BPS	5144
ChemSpider	4444924
UNII	49QAH60606
KEGG	C10023
ChEBI	CHEBI:2979
ChEMBL	ChEMBL8260
CompTox Dashboard (EPA)	DTXSID2022389
ECHA InfoCard	100.164.911
Chemical and physical data
Formula	C15H10O5
Molar mass	270.240 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C\1c3c(O)c(O)c(O)cc3O/C(=C/1)c2ccccc2
InChI InChI=1S/C15H10O5/c16-9-6-11(8-4-2-1-3-5-8)20-12-7-10(17)14(18)15(19)13(9)12/h1-7,17-19H Key:FXNFHKRTJBSTCS-UHFFFAOYSA-N

Baicalein (5,6,7-trihydroxyflavone) is a flavone, a type of flavonoid, ^[1] originally isolated from the roots of Scutellaria baicalensis and Scutellaria lateriflora . It is also a constituent of Oroxylum indicum (Indian trumpetflower) and thyme . ^[2] It is the aglycone of baicalin.

Pharmacology

Baicalein, along with its glucuronide baicalin, is a positive allosteric modulator of the benzodiazepine site and a non-benzodiazepine site of the GABA_A receptor, but with an affinity over 250× lower than diazepam. ^{[3] [4] [5]} It displays subtype selectivity for α₂ and α₃ subunit-containing GABA_A receptors. ^[6]

The flavonoid has been shown to inhibit certain types of lipoxygenases. ^[7]

Baicalein is an inhibitor of CYP2C9, ^[8] an enzyme of the cytochrome P450 system that metabolizes drugs in the body.

A derivative of baicalin is a known prolyl endopeptidase inhibitor. ^[9]

See also

• List of compounds with carbon number 15

References

1. "Flavonoids". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2024. Retrieved 9 May 2024.
2. Matsumoto T (2008). Phytochemistry Research Progress. Nova Publishers. ISBN   9781604562323.
3. Zhang SQ, Obregon D, Ehrhart J, Deng J, Tian J, Hou H, et al. (September 2013). "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. doi:10.1002/jnr.23244. PMC   3810722 . PMID   23686791.
4. Liao JF, Wang HH, Chen MC, Chen CC, Chen CF (August 1998). "Benzodiazepine binding site-interactive flavones from Scutellaria baicalensis root". Planta Medica. 64 (6): 571–572. Bibcode:1998PlMed..64..571L. doi:10.1055/s-2006-957517. PMID   9776664. S2CID   260251315.
5. Roberts AA (2004). "Testing efficacy of natural anxiolytic compounds". In Cooper EL, Yamaguchi N (eds.). Complementary and Alternative Approaches to Biomedicine. Advances in Experimental Medicine and Biology. Vol. 546. pp. 181–191. doi:10.1007/978-1-4757-4820-8_13. ISBN   978-1-4419-3441-3. PMID   15584374.
6. Wang F, Xu Z, Ren L, Tsang SY, Xue H (December 2008). "GABA A receptor subtype selectivity underlying selective anxiolytic effect of baicalin". Neuropharmacology. 55 (7): 1231–1237. doi:10.1016/j.neuropharm.2008.07.040. PMID   18723037. S2CID   20133964.
7. 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". Bioorganic & Medicinal Chemistry. 14 (12): 4295–4301. doi:10.1016/j.bmc.2006.01.057. PMID   16500106. S2CID   645610.
8. Si D, Wang Y, Zhou YH, Guo Y, Wang J, Zhou H, et al. (March 2009). "Mechanism of CYP2C9 inhibition by flavones and flavonols" (PDF). Drug Metabolism and Disposition. 37 (3): 629–634. doi:10.1124/dmd.108.023416. PMID   19074529. S2CID   285706. Archived from the original (PDF) on 2008-12-17. Retrieved 2009-02-19.
9. Tarragó T, Kichik N, Claasen B, Prades R, Teixidó M, Giralt E (August 2008). "Baicalin, a prodrug able to reach the CNS, is a prolyl oligopeptidase inhibitor". Bioorganic & Medicinal Chemistry. 16 (15): 7516–7524. doi:10.1016/j.bmc.2008.04.067. PMID   18650094.