Baicalin
Baicalin | |
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IUPAC name (2S,3S,4S,5R,6S)-6-(5,6-dihydroxy-4-oxo-2-phenyl-chromen-7-yl)oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid | |
Other names Baicalein 7-O-glucuronide; 5,6-Dihydroxy-4-oxygen-2-phenyl-4H-1-benzopyran-7-beta-D-glucopyranose acid | |
Identifiers | |
CAS number | 21967-41-9 |
PubChem | 64982 |
ChemSpider | 58507 |
UNII | 347Q89U4M5 |
ChEBI | CHEBI:2981 |
ChEMBL | CHEMBL485818 |
Jmol-3D images | {{#if:O=C3\C=C(/Oc2cc(O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O)c(O)c(O)c23)c4ccccc4|Image 1 |
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Properties | |
Molecular formula | C21H18O11 |
Molar mass | 446.36 g mol−1 |
Melting point | 202 to 205 °C; 396 to 401 °F; 475 to 478 K |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
Infobox references | |
Baicalin is a flavone, a type of flavonoid. It is found in several species in the genus Scutellaria, including Scutellaria lateriflora (blue skullcap). There are 10 mg/g baicalin in Scutellaria galericulata (common skullcap) leaves.[1] Baicalin is the glucuronide of baicalein.
It is a component of Chinese medicinal herb Huang-chin (Scutellaria baicalensis) and one of the chemical ingredients of Sho-Saiko-To, an herbal supplement.
Baicalin is a known prolyl endopeptidase inhibitor,[2] induces apoptosis in pancreatic cancer cells,[3] and affects the GABA receptors.[citation needed]
References
- ↑ P.H. and Horhammer, L., Hager's Handbuch der Pharmazeutischen Praxis, Vols. 2-6, Springer-Verlag, Berlin, 1969-1979
- ↑ Tarragó, T; Kichik, N; Claasen, B; Prades, R; Teixidó, M; Giralt, E (2008). "Baicalin, a prodrug able to reach the CNS, is a prolyl oligopeptidase inhibitor". Bioorganic & medicinal chemistry 16 (15): 7516–24. doi:10.1016/j.bmc.2008.04.067. PMID 18650094.
- ↑ Takahashi H, Chen MC, Pham H, Angst E, King JC, Park J, Brovman EY, Ishiguro H, Harris DM, Reber HA, Hines OJ, Gukovskaya AS, Go VL, Eibl G (2011). "Baicalein, a component of Scutellaria baicalensis, induces apoptosis by Mcl-1 down-regulation in human pancreatic cancer cells". Biochim Biophys Acta 1813 (8): 1465–1474. doi:10.1016/j.bbamcr.2011.05.003. PMC 3123440. PMID 21596068.
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