Wogonin

Last updated
Wogonin [1]
Wogonin v2.svg
Wogonin molecule ball.png
Names
IUPAC name
5,7-Dihydroxy-8-methoxyflavone
Systematic IUPAC name
5,7-Dihydroxy-8-methoxy-2-phenyl-4H-1-benzopyran-4-one
Other names
Vogonin
Norwogonin 8-methyl ether
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C16H12O5/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9/h2-8,17,19H,1H3 X mark.svgN
    Key: XLTFNNCXVBYBSX-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C16H12O5/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9/h2-8,17,19H,1H3
    Key: XLTFNNCXVBYBSX-UHFFFAOYAQ
  • COC1=C(C=C(C2=C1OC(=CC2=O)C3=CC=CC=C3)O)O
Properties
C16H12O5
Molar mass 284.267 g·mol−1
Melting point 203 to 206 °C (397 to 403 °F; 476 to 479 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Wogonin is an O-methylated flavone, a flavonoid-like chemical compound which is found in Scutellaria baicalensis . [2]

Contents

The glycosides of wogonin are known as wogonosides. For example, oroxindin is a wogonin glucuronide isolated from Oroxylum indicum . [3] It is one of the active ingredients of Sho-Saiko-To, a Japanese herbal supplement.

Pharmacology

Wogonin has been found in one study to have anxiolytic properties in mice at doses of 7.5 to 30 mg/kg, without exhibiting the sedative and muscle-relaxing properties of benzodiazepines. [2] Preliminary in vitro studies have shown pharmacological effects that indicate wogonin may have anti-tumor properties. [4] [5] Wogonin has also been found to possess anticonvulsant effects. [6] It acts as a positive allosteric modulator of the benzodiazepine site of the GABAA receptor with a binding affinity of Ki 0.92 μM and an IC50 value of 1.26 μM which is about 100 times less potent than diazepam (IC50 value of 0.012 μM). [2] [6] The LD50 of pure Wogonin in mice is 3.9 g/kg of body weight suggesting low toxicity. [7]

CNS review: [8]

See also

References

  1. ↑ Wogonin at chemblink.com
  2. 1 2 3 Hui KM, Huen MS, Wang HY, Zheng H, Sigel E, Baur R, Ren H, Li ZW, Wong JT, Xue H (2002). "Anxiolytic effect of wogonin, a benzodiazepine receptor ligand isolated from Scutellaria baicalensis Georgi". Biochem. Pharmacol. 64 (9): 1415–24. doi:10.1016/s0006-2952(02)01347-3. PMID   12392823.
  3. ↑ Ramachandran Nair AG; Joshi BS (October 1979). "Oroxindin—A new flavone glucuronide from Oroxylum indicum". Proceedings of the Indian Academy of Sciences - Chemical Sciences. 88: 323–327. doi:10.1007/BF02844710. S2CID   90414405.
  4. ↑ Lin CC, Kuo CL, Lee MH, Lai KC, Lin JP, Yang JS, Yu CS, Lu CC, Chiang JH, Chueh FS, Chung JG (2011). "Wogonin triggers apoptosis in human osteosarcoma U-2 OS cells through the endoplasmic reticulum stress, mitochondrial dysfunction and caspase-3-dependent signaling pathways". International Journal of Oncology. 39 (1): 217–224. doi: 10.3892/ijo.2011.1027 . PMID   21573491.
  5. ↑ Gao J, Morgan WA, Sanchez-Medina A, Corcoran O (2011). "The ethanol extract of Scutellaria baicalensis and the active compounds induce cell cycle arrest and apoptosis including upregulation of p53 and Bax in human lung cancer cells". Toxicology and Applied Pharmacology. 254 (3): 221–8. Bibcode:2011ToxAP.254..221G. doi:10.1016/j.taap.2011.03.016. PMID   21457722.
  6. 1 2 Park HG, Yoon SY, Choi JY, Lee GS, Choi JH, Shin CY, Son KH, Lee YS, Kim WK, Ryu JH, Ko KH, Cheong JH (2007). "Anticonvulsant effect of wogonin isolated from Scutellaria baicalensis". European Journal of Pharmacology. 574 (2–3): 112–9. doi:10.1016/j.ejphar.2007.07.011. PMID   17692312.
  7. ↑ Hui, Kwok Min; Huen, Michael S.Y.; Wang, Hong Yan; Zheng, Hui; Sigel, Erwin; Baur, Roland; Ren, Hong; Li, Zhi Wang; Wong, J.Tze-Fei; Xue, Hong (2002). "Anxiolytic effect of wogonin, a benzodiazepine receptor ligand isolated from Scutellaria baicalensis Georgi" . Biochemical Pharmacology. 64 (9): 1415–1424. doi:10.1016/S0006-2952(02)01347-3. PMID   12392823.
  8. ↑ Tai, M. C., Tsang, S. Y., Chang, L. Y. F., Xue, H. (March 2005). "Therapeutic Potential of Wogonin: A Naturally Occurring Flavonoid". CNS Drug Reviews. 11 (2): 141–150. doi:10.1111/j.1527-3458.2005.tb00266.x.
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