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]

References

^ "Flavonoids". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2024. Retrieved 9 May 2024.
^ Matsumoto T (2008). Phytochemistry Research Progress. Nova Publishers. ISBN 9781604562323.
^ 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.
^ 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. doi:10.1055/s-2006-957517. PMID 9776664. S2CID 260251315.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

[lpi-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.

[pmid23686791-3] 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.

[pmid9776664-4] 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. doi:10.1055/s-2006-957517. PMID 9776664. S2CID 260251315.

[Roberts_2004-5] 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.

[pmid18723037-6] 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.

[Si_2009-8] 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.

[1]

Baicalein

Pharmacology

See also

References