Wogonin

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Structural formula
Structural formula of wogonin
General
Surname Wogonin
other names
  • 5,7-dihydroxy-8-methoxy-2-phenyl-4 H -chromen-4-one ( IUPAC )
  • 5,7-dihydroxy-8-methoxyflavone
  • 5,7-dihydroxy-8-methoxy-2-phenyl-4 H -1-benzopyran-4-one
  • WOGONIN ( INCI )
Molecular formula C 15 H 10 O 5
Brief description

yellow crystals

External identifiers / databases
CAS number 632-85-9
PubChem 5281703
ChemSpider 4445020
Wikidata Q409606
properties
Molar mass 284.26 g · mol -1
Physical state

firmly

Melting point

203-204 ° C

solubility

> 20 g l −1 in DMSO

safety instructions
GHS labeling of hazardous substances

hydrate

no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

286 mg kg −1 ( LD 50 ,  rat ,  iv )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Wogonin is a chemical compound from the group of flavones .

Occurrence

Baikal skullcap ( Scutellaria baicalensis )

As a natural flavonoid , it occurs in the roots of the Baikal skullcap ( Scutellaria baicalensis ).

properties

Wogonin is a selective COX-2 inhibitor , which gives it anti-inflammatory properties. COX-1 is not inhibited. The mean inhibitory concentration for COX-2 is 46 µmol. Wogonin exhibits antioxidant , antiviral , antithrombotic and anti-inflammatory properties in vivo . Compared with hepatitis B virus Wogonin is antiviral.

The discovery that wogonin is cytotoxic to various tumor cells and can trigger apoptosis (programmed cell death) caused a sensation . In contrast, it is largely ineffective in healthy cells. Wogonin causes a strong formation of hydrogen peroxide in the degenerated tumor cells , which initiates the signal cascade for apoptosis.

In in-vitro and in-vivo experiments with estrogen-positive and estrogen-negative breast cancer cells , or xenografts of the same on nude mice , wogonin showed promising positive results when administered orally .

Wogonin has not yet been used medicinally .

literature

  • M. Li-Weber: New therapeutic aspects of flavones: the anticancer properties of Scutellaria and its main active constituents Wogonin, Baicalein and Baicalin. In: Cancer Treat Rev 35, 2009, pp. 57-68. PMID 19004559 .
  • J. Peng, Q. Qi, Q. You, R. Hu, W. Liu, F. Feng, G. Wang, Q. Guo: Subchronic toxicity and plasma pharmacokinetic studies on wogonin, a natural flavonoid, in Beagle dogs. In: J Ethnopharmacol 124, 2009, pp. 257-262, PMID 19397969 .
  • HZ Piao et al .: Wogonin inhibits microglial cell migration via suppression of nuclear factor-kappa B activity. In: Int Immunopharmacol 8, 2008, pp. 1658-1662, PMID 18725324 .
  • MC Tai et al.: Therapeutic potential of wogonin: a naturally occurring flavonoid. In: CNS Drug Rev 11, 2005, pp. 141-150, PMID 16007236 .

Individual evidence

  1. ↑ Entry on WOGONIN in the CosIng database of the EU Commission, accessed on March 23, 2020.
  2. ↑ Data sheet Wogonin S. baicalensis (PDF) from Calbiochem, accessed on December 9, 2015.
  3. ↑ P. Singh et al.: Wogonin, 5,7-dihydroxy-8-methoxyflavone as oestrogenic and anti-implantational agent in the rat. In: Phytotherapy Research 4, 1989, pp. 86-89. doi : 10.1002 / ptr.2650040303 .
  4. ↑ a b c data sheet Wogonin hydrate from Sigma-Aldrich , accessed on June 15, 2011 ( PDF ).
  5. ^ Q. Qi et al.: Toxicological studies of wogonin in experimental animals. In: Phytother Res 23, 2009, pp. 417-422. PMID 19003942 .
  6. ↑ Z. Gao et al .: Free radical scavenging and antioxidant activities of flavonoids extracted from the radix of Scutellaria baicalensis Georgi. In: Biochim Biophys Acta 1472, 1999, pp. 643-650, PMID 10564778 .
  7. ↑ SC Ma et al .: Antiviral Chinese medicinal herbs against respiratory syncytial virus. In: J Ethnopharmacol 79, 2002, pp. 205-211, PMID 11801383 .
  8. ↑ Y. Kimura et al: Effects of flavonoids isolated from scutellariae radix on fibrinolytic system induced by trypsin in human umbilical vein endothelial cells. In: J Nat Prod . 60, 1997, pp. 598-601, PMID 9214730 .
  9. ↑ YS Chi et al .: Effects of Wogonin, a plant flavone from Scutellaria radix, on skin inflammation: in vivo regulation of inflammation-associated gene expression. In: Biochem Pharmacol 66, 2003, pp. 1271-1278, PMID 14505806 .
  10. ↑ a b S. Baumann et al .: Wogonin Preferentially Kills Malignant Lymphocytes and Suppresses T-cell Tumor Growth by Inducing PLCgamma1- and Ca2 + -dependent Apoptosis. In: Blood 111, 2008, pp. 2354-2363. doi : 10.1182 / blood-2007-06-096198 PMID 18070986 .
  11. ↑ C. Wohlfarth and T. Efferth: Natural products as promising drug candidates for the treatment of hepatitis B and C. In: Acta Pharmacol Sin 30, 2009, pp. 25-30, PMID 19060918 .
  12. ↑ S. Ikemoto et al.: Antitumor effects of Scutellariae radix and its components baicalein, baicalin, and Wogonin on bladder cancer cell lines. In: Urology 55, 2000, pp. 951-955, PMID 10840124 .
  13. ↑ YC Chen et al .: Wogonin and fisetin induction of apoptosis through activation of caspase 3 cascade and alternative expression of p21 protein in hepatocellular carcinoma cells SK-HEP-1. In: Arch. Toxicol. 76, 2002, pp. 351-359, PMID 12107653 .
  14. ^ WR Lee et al.: Wogonin and fisetin induce apoptosis in human promyeloleukemic cells, accompanied by a decrease of reactive oxygen species, and activation of caspase 3 and Ca (2 +) - dependent endonuclease. In: Biochem Pharmacol 63, 2002, pp. 225-236, PMID 11841797 .
  15. ↑ Sibylle Kohlstädt: Plant ingredient with selective effect on cancer cells. German Cancer Research Center, press release from December 17, 2007 from Informationsdienst Wissenschaft (idw-online.de), accessed on August 24, 2015.
  16. ↑ H. Chung et al: Anticancer effects of wogonin in both estrogen receptor-positive and -negative human breast cancer cell lines in vitro and in nude mice xenografts. In: Int J Cancer 122, 2008, pp. 816-822, PMID 1795778 .