Wogonin

Last updated
Wogonin [1]
Wogonin.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]

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 an binding affinity of Ki 0.92μM and an IC50 value of 1.26μM which is about 100x less potent than diazepam (IC50 value of 0.012μM). [2] [6] The LD50 of pure Wogonin in mice is 3.9 grams per kilogram of body weight suggesting low toxicity [7]

Related Research Articles

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Scutellaria is a genus of flowering plants in the mint family, Lamiaceae. They are known commonly as skullcaps. The generic name is derived from the Latin scutella, meaning "a small dish, tray or platter", or "little dish", referring to the shape of the calyx. The common name alludes to the resemblance of the same structure to "miniature medieval helmets". The genus has a subcosmopolitan distribution, with species occurring nearly worldwide, mainly in temperate regions.

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<i>Scutellaria baicalensis</i> Species of flowering plant

Scutellaria baicalensis, with the common name Baikal skullcap or Chinese skullcap, is a species of flowering plant in the family Lamiaceae.

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<span class="mw-page-title-main">Baicalin</span> Chemical compound

As baicalin is a flavone glycoside, it is a flavonoid. It is the glucuronide of baicalein.

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Tracazolate (ICI-136,753) is an anxiolytic drug which is used in scientific research. It is a pyrazolopyridine derivative, most closely related to pyrazolopyrimidine drugs such as zaleplon, and is one of a structurally diverse group of drugs known as the nonbenzodiazepines which act at the same receptor targets as benzodiazepines but have distinct chemical structures.

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<span class="mw-page-title-main">Baicalein</span> Chemical compound

Baicalein (5,6,7-trihydroxyflavone) is a flavone, a type of flavonoid, originally isolated from the roots of Scutellaria baicalensis and Scutellaria lateriflora. It is also reported in Oroxylum indicum and Thyme. It is the aglycone of baicalin. Baicalein is one of the active ingredients of Sho-Saiko-To, which is a Chinese classic herbal formula, and listed in Japan as Kampo medicine. As a Chinese herbal supplement, it is believed to enhance liver health.

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<span class="mw-page-title-main">Oroxylin A</span> Chemical compound

Oroxylin A is an O-methylated flavone, a chemical compound that can be found in the medicinal plants Scutellaria baicalensis and Scutellaria lateriflora, and the Oroxylum indicum tree. It has demonstrated activity as a dopamine reuptake inhibitor, and is also a negative allosteric modulator of the benzodiazepine site of the GABAA receptor. Oroxylin A has been found to improve memory consolidation in mice by elevating brain-derived neurotrophic factor (BDNF) levels in the hippocampus.

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<span class="mw-page-title-main">Cartazolate</span> Chemical compound

Cartazolate (SQ-65,396) is a drug of the pyrazolopyridine class. It acts as a GABAA receptor positive allosteric modulator at the barbiturate binding site of the complex and has anxiolytic effects in animals. It is also known to act as an adenosine antagonist at the A1 and A2 subtypes and as a phosphodiesterase inhibitor. Cartazolate was tested in human clinical trials and was found to be efficacious for anxiety but was never marketed. It was developed by a team at E.R. Squibb and Sons in the 1970s.

Baicalin-beta-D-glucuronidase (EC 3.2.1.167, baicalinase) is an enzyme with systematic name 5,6,7-trihydroxyflavone-7-O-beta-D-glucupyranosiduronate glucuronosylhydrolase. This enzyme catalyses the following chemical reaction

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. 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.