Baicalein Explained
| Drug Name: | Baicalein |
| Cas Number: | 491-67-8 |
| Pubchem: | 5281605 |
| Iuphar Ligand: | 5144 |
| Chemspiderid: | 4444924 |
| Unii: | 49QAH60606 |
| Kegg: | C10023 |
| Chebi: | 2979 |
| Chembl: | 8260 |
| Synonyms: | Biacalein; Noroxylin |
| Iupac Name: | 5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one |
| C: | 15 |
| H: | 10 |
| O: | 5 |
| Smiles: | O=C\1c3c(O)c(O)c(O)cc3O/C(=C/1)c2ccccc2 |
| Stdinchi: | 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 |
| Stdinchikey: | 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 GABAA receptor, but with an affinity over 250× lower than diazepam.[3] [4] [5] It displays subtype selectivity for α2 and α3 subunit-containing GABAA 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
Notes and References
- Web site: Flavonoids . Micronutrient Information Center, Linus Pauling Institute, Oregon State University . 9 May 2024 . 2024.
- Book: Phytochemistry Research Progress. 9781604562323. Matsumoto T . 2008. Nova Publishers.
- Zhang SQ, Obregon D, Ehrhart J, Deng J, Tian J, Hou H, Giunta B, Sawmiller D, Tan J . 6 . 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 . September 2013 . 23686791 . 3810722 . 10.1002/jnr.23244 .
- Liao JF, Wang HH, Chen MC, Chen CC, Chen CF . Benzodiazepine binding site-interactive flavones from Scutellaria baicalensis root . Planta Medica . 64 . 6 . 571–572 . August 1998 . 9776664 . 10.1055/s-2006-957517 . 260251315 .
- Book: Roberts AA . Complementary and Alternative Approaches to Biomedicine . Testing efficacy of natural anxiolytic compounds . Cooper EL, Yamaguchi N . Advances in Experimental Medicine and Biology . 546 . 181–191 . 2004 . 15584374 . 10.1007/978-1-4757-4820-8_13 . 978-1-4419-3441-3 .
- Wang F, Xu Z, Ren L, Tsang SY, Xue H . GABA A receptor subtype selectivity underlying selective anxiolytic effect of baicalin . Neuropharmacology . 55 . 7 . 1231–1237 . December 2008 . 18723037 . 10.1016/j.neuropharm.2008.07.040 . 20133964 .
- Deschamps JD, Kenyon VA, Holman TR . Baicalein is a potent in vitro inhibitor against both reticulocyte 15-human and platelet 12-human lipoxygenases . Bioorganic & Medicinal Chemistry . 14 . 12 . 4295–4301 . June 2006 . 16500106 . 10.1016/j.bmc.2006.01.057 . 645610 .
- Si D, Wang Y, Zhou YH, Guo Y, Wang J, Zhou H, Li ZS, Fawcett JP . 6 . Mechanism of CYP2C9 inhibition by flavones and flavonols . Drug Metabolism and Disposition . 37 . 3 . 629–634 . March 2009 . 19074529 . 10.1124/dmd.108.023416 . 2009-02-19 . dead . 285706 . https://web.archive.org/web/20081217093507/http://p4502c.googlepages.com/dmd2.pdf . 2008-12-17 .
- Tarragó T, Kichik N, Claasen B, Prades R, Teixidó M, Giralt E . Baicalin, a prodrug able to reach the CNS, is a prolyl oligopeptidase inhibitor . Bioorganic & Medicinal Chemistry . 16 . 15 . 7516–7524 . August 2008 . 18650094 . 10.1016/j.bmc.2008.04.067 .
