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, originally isolated from the roots of Scutellaria baicalensis and Scutellaria lateriflora. It is also reported in Oroxylum indicum (Indian trumpetflower) and Thyme. 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.

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

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

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

A derivative of baicalin is a known prolyl endopeptidase inhibitor.

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

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

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