Baicalein

From Wikipedia, the free encyclopedia
Baicalein
IUPAC name

5,6,7-Trihydroxy-2-phenyl-chromen-4-one

Other names

5,6,7-Trihydroxyflavone

Identifiers
CAS number 491-67-8 YesY
PubChem 5281605
ChemSpider 4444924 YesY
UNII 49QAH60606 YesY
ChEBI CHEBI:2979 YesY
ChEMBL CHEMBL8260 YesY
Jmol-3D images Image 1
Properties
Molecular formula C15H10O5
Molar mass 270.24 g mol−1
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Baicalein (5,6,7-trihydroxyflavone) is a flavone, a type of flavonoid, originally isolated from the roots of Scutellaria baicalensis. It is also reported in Oroxylum indicum or Indian trumpetflower. It is the aglycone of baicalin.

The flavonoid has been shown to inhibit certain types of lipoxygenases[1] and act as an anti-inflammatory agent.[2]It has antiproliferative effects on ET-1-induced proliferation of pulmonary artery smooth muscle cell proliferation via inhibition of TRPC1 channel expression.[3] Possible antidepressant effects have also been attributed to baicalein in animal research.[4]

Baicalein is an inhibitor of CYP2C9,[5] an enzyme of the cytochrome P450 system that metabolizes drugs in the body.

A derivative of baicalin is a known prolyl endopeptidase inhibitor.[6]

It is one of the active ingredients of Sho-Saiko-To, a Japanese herbal supplement believed to enhance liver health.

Glycosides

Tetuin is the 6-glucoside of baicalein.

See also

References

  1. ↑ 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". Bioorg. Med. Chem. 14 (12): 4295–301. doi:10.1016/j.bmc.2006.01.057. PMID 16500106. 
  2. ↑ Hsieh CJ, Hall K, Ha T, Li C, Krishnaswamy G, Chi DS (2007). "Baicalein inhibits IL-1β- and TNF-α-induced inflammatory cytokine production from human mast cells via regulation of the NF-κB pathway". Clin Mol Allergy 5 (1): 5. doi:10.1186/1476-7961-5-5. PMC 2206049. PMID 18039391. 
  3. ↑ Yi-Ling Lin, Rong-Jyh Lin, Kuo-Pyng Shen, Zen-Kong Dai, Ing-Jun Chen, Jiunn-Ren Wu, Bin-Nan Wu, Baicalein, isolated from Scutellaria baicalensis, protects against endothelin-1-induced pulmonary artery smooth muscle cell proliferation via inhibition of TRPC1 channel expression, Journal of Ethnopharmacology, Volume 138, Issue 2, 18 November 2011, Pages 373-381, ISSN 0378-8741, 10.1016/j.jep.2011.09.014. (http://www.sciencedirect.com/science/article/pii/S0378874111006842)
  4. ↑ Xiong Z, Jiang B, Wu PF, et al. (2011). "Antidepressant effects of a plant-derived flavonoid baicalein involving extracellular signal-regulated kinases cascade". Biol. Pharm. Bull. 34 (2): 253–9. PMID 21415537. 
  5. ↑ Si Dayong, Wang Y, Zhou Y-H, Guo Y, Wang J, Zhou H, Li Z-S, Fawcett JP (March 2009). "Mechanism of CYP2C9 inhibition by flavones and flavonols". Drug Metabolism and Disposition 37 (3): 629–34. doi:10.1124/dmd.108.023416. PMID 19074529. 
  6. ↑ 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 and Medicinal Chemistry. 2008 Aug 1;16(15):7516-24. PMID 18650094
Flavones and their conjugates
Aglycones
Monohydroxyflavone
Dihydroxyflavones
Trihydroxyflavones
Tetrahydroxyflavones
Pentahydroxyflavones
O-methylated flavones
  • Acacetin (Apigenin 4'-methyl ether)
  • Artocarpetin (Norartocarpetin 7-methyl ether)
  • Diosmetin (Luteolin 4'-methyl ether)
  • Eupatilin (5,7-Dihydroxy-3',4',6-trimethoxyflavone)
  • Genkwanin (Apigenin 7-methyl ether)
  • Nepetin (Luteolin 6-methyl ether)
  • Nobiletin (3',4',5,6,7,8-Hexamethoxyflavone)
  • Oroxylin A (Baicalein 6-methyl ether)
  • Pratol (7-Hydroxy-4-methoxyflavone)
  • Sinensetin (3',4',5,6,7-Pentamethoxyflavone)
  • Tangeritin (4',5,6,7,8-Pentamethoxyflavone)
  • Techtochrysin (Chrysin 7-methyl ether)
  • Tricin (Tricetin 3',5'-dimethyl ether)
  • Wogonin (Norwogonin 8-methyl ether)
  • Zapotin (2,6,5,6-tetramethoxyflavone)
Glycosides
of apigenin
  • Apiin (Apigenin-7-O-apioglucoside)
  • Apigetrin (Apigenin 7-O-glucoside)
  • Isovitexin (Apigenin 6-C-glucoside)
  • Rhoifolin (Apigenin 7-O-neohesperidoside)
  • Saponarin (Isovitexin-7-O-glucoside)
  • Schaftoside (Apigenin 6-C-glucoside 8-C-arabinoside)
  • Vicenin-2 (Apigenin 6,8-di-C-glucoside)
  • Vitexin (Apigenin-8-C-glucoside)
of baicalein
  • Baicalin (Baicalein 7-O-glucuronide)
  • Tetuin (Baicalein 6-O-glucoside)
of hypolaetin
  • Hypolaetin 8-glucoside
  • Hypolaetin 8-glucuronide
of luteolin
  • Giraldiin A (4',5,5',7-Tetrahydroxy-3-methoxy-3'-O-α-L-arabinopyranosyloxyflavone) and B (5,5',7'-Trihydroxy-2',3-dimethoxy-4'-O-β-D-glucopyranosyloxyflavone)
  • Nepitrin (Nepetin 7-O-glucoside)
  • Oroxindin (Wogonin 7-O-glucuronide)
  • Scutellarin (Scutellarein 7-O-glucuronide)
Acetylated
  • Artocarpetin A (prenylated artocarpetin)
  • Artoindonesianin P (prenylated)
Sulfated glycosides
Theograndin I (sulfated glucuronide of isoscutellarein) and II
Polymers
Synthetic
This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.