Baicalein

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Baicalein
Baicalein.svg
Baicalein-3D-balls.png
Names
IUPAC name
5,6,7-Trihydroxy-2-phenyl-chromen-4-one
Other names
5,6,7-Trihydroxyflavone
Identifiers
491-67-8 YesY
ChEBI CHEBI:2979 YesY
ChEMBL ChEMBL8260 YesY
ChemSpider 4444924 YesY
5144
Jmol 3D model Interactive image
PubChem 5281605
UNII 49QAH60606 YesY
  • 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 YesY
    Key: FXNFHKRTJBSTCS-UHFFFAOYSA-N YesY
  • InChI=1/C15H10O5/c16-9-6-11(8-4-2-1-3-5-8)20-12-7-10(17baic)14(18)15(19)13(9)12/h1-7,17-19H
    Key: FXNFHKRTJBSTCS-UHFFFAOYAX
  • O=C\1c3c(O)c(O)c(O)cc3O/C(=C/1)c2ccccc2
Properties
C15H10O5
Molar mass 270.24 g·mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
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

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