Wogonin

Wogonin[1]

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

CAS Number

* 632-85-9 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:10043 N

ChEMBL |

* ChEMBL16171 N

ChemSpider |

* 4445020 N

KEGG |

* C10197 N

PubChem CID

* 5281703

UNII |

* POK93PO28W Y

InChI

* 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 N

Key: XLTFNNCXVBYBSX-UHFFFAOYSA-N N

* 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

SMILES

* COC1=C(C=C(C2=C1OC(=CC2=O)C3=CC=CC=C3)O)O

Properties

Chemical formula

| 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).

N verify (what is YN ?)
Infobox references

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]

## References

1. ↑ Wogonin at chemblink.com
2. ↑ 2.0 2.1 2.2 "Anxiolytic effect of wogonin, a benzodiazepine receptor ligand isolated from Scutellaria baicalensis Georgi". Biochem. Pharmacol. 64 (9): 1415–24. 2002. 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.
4. ↑ "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. 2011. doi:10.3892/ijo.2011.1027. PMID 21573491.
5. ↑ "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. 2011. doi:10.1016/j.taap.2011.03.016. PMID 21457722.
6. ↑ 6.0 6.1 "Anticonvulsant effect of wogonin isolated from Scutellaria baicalensis". European Journal of Pharmacology 574 (2–3): 112–9. 2007. 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 et al. (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. https://www.sciencedirect.com/science/article/abs/pii/S0006295202013473.

* v
* t
* e

GABAA receptor positive modulators

Alcohols|

* Brometone
* Butanol
* Chloralodol
* Chlorobutanol (cloretone)
* Ethanol (alcohol) (alcoholic drink)
* Ethchlorvynol
* Isobutanol
* Isopropanol
* Menthol
* Methanol
* Methylpentynol
* Pentanol
* Petrichloral
* Propanol
* tert-Butanol (2M2P)
* tert-Pentanol (2M2B)
* Tribromoethanol
* Trichloroethanol
* Triclofos
* Trifluoroethanol

Barbiturates|

* (-)-DMBB
* Allobarbital
* Alphenal
* Amobarbital
* Aprobarbital
* Barbexaclone
* Barbital
* Benzobarbital
* Benzylbutylbarbiturate
* Brallobarbital
* Brophebarbital
* Butabarbital/Secbutabarbital
* Butalbital
* Buthalital
* Butobarbital
* Butallylonal
* Carbubarb
* Crotylbarbital
* Cyclobarbital
* Cyclopentobarbital
* Difebarbamate
* Enallylpropymal
* Ethallobarbital
* Eterobarb
* Febarbamate
* Heptabarb
* Heptobarbital
* Hexethal
* Hexobarbital
* Metharbital
* Methitural
* Methohexital
* Methylphenobarbital
* Narcobarbital
* Nealbarbital
* Pentobarbital
* Phenallymal
* Phenobarbital
* Phetharbital
* Primidone
* Probarbital
* Propallylonal
* Propylbarbital
* Proxibarbital
* Reposal
* Secobarbital
* Sigmodal
* Spirobarbital
* Talbutal
* Tetrabamate
* Tetrabarbital
* Thialbarbital
* Thiamylal
* Thiobarbital
* Thiobutabarbital
* Thiopental
* Thiotetrabarbital
* Valofane
* Vinbarbital
* Vinylbital

Benzodiazepines|

* 2-Oxoquazepam
* 3-Hydroxyphenazepam
* Adinazolam
* Alprazolam
* Arfendazam
* Avizafone
* Bentazepam
* Bretazenil
* Bromazepam
* Brotizolam
* Camazepam
* Carburazepam
* Chlordiazepoxide
* Ciclotizolam
* Cinazepam
* Cinolazepam
* Clazolam
* Climazolam
* Clobazam
* Clonazepam
* Clonazolam
* Cloniprazepam
* Clorazepate
* Clotiazepam
* Cloxazolam
* CP-1414S
* Cyprazepam
* Delorazepam
* Demoxepam
* Diazepam
* Diclazepam
* Doxefazepam
* Elfazepam
* Estazolam
* Ethyl carfluzepate
* Ethyl dirazepate
* Ethyl loflazepate
* Etizolam
* EVT-201
* FG-8205
* Fletazepam
* Flubromazepam
* Flubromazolam
* Fludiazepam
* Flunitrazepam
* Flunitrazolam
* Flurazepam
* Flutazolam
* Flutemazepam
* Flutoprazepam
* Fosazepam
* Gidazepam
* Halazepam
* Haloxazolam
* Iclazepam
* Imidazenil
* Irazepine
* Ketazolam
* Lofendazam
* Lopirazepam
* Loprazolam
* Lorazepam
* Lormetazepam
* Meclonazepam
* Medazepam
* Menitrazepam
* Metaclazepam
* Mexazolam
* Midazolam
* Motrazepam
* N-Desalkylflurazepam
* Nifoxipam
* Nimetazepam
* Nitrazepam
* Nitrazepate
* Nitrazolam
* Nordazepam
* Nortetrazepam
* Oxazepam
* Oxazolam
* Phenazepam
* Pinazepam
* Pivoxazepam
* Prazepam
* Premazepam
* Proflazepam
* Pyrazolam
* QH-II-66
* Quazepam
* Reclazepam
* Remimazolam
* Rilmazafone
* Ripazepam
* Ro48-6791
* Ro48-8684
* SH-053-R-CH3-2′F
* Sulazepam
* Temazepam
* Tetrazepam
* Tolufazepam
* Triazolam
* Triflubazam
* Triflunordazepam (Ro5-2904)
* Tuclazepam
* Uldazepam
* Zapizolam
* Zolazepam
* Zomebazam

Carbamates|

* Carisbamate
* Carisoprodol
* Clocental
* Cyclarbamate
* Difebarbamate
* Emylcamate
* Ethinamate
* Febarbamate
* Felbamate
* Hexapropymate
* Lorbamate
* Mebutamate
* Meprobamate
* Nisobamate
* Pentabamate
* Phenprobamate
* Procymate
* Styramate
* Tetrabamate
* Tybamate

Flavonoids|

* 6-Methylapigenin
* Ampelopsin (dihydromyricetin)
* Apigenin
* Baicalein
* Baicalin
* Catechin
* EGC
* EGCG
* Hispidulin
* Linarin
* Luteolin
* Rc-OMe
* Skullcap constituents (e.g., baicalin)
* Wogonin

Imidazoles|

* Etomidate
* Metomidate
* Propoxate

Kava constituents|

* 10-Methoxyyangonin
* 11-Methoxyyangonin
* 11-Hydroxyyangonin
* Desmethoxyyangonin
* 11-Methoxy-12-hydroxydehydrokavain
* 7,8-Dihydroyangonin
* Kavain
* 5-Hydroxykavain
* 5,6-Dihydroyangonin
* 7,8-Dihydrokavain
* 5,6,7,8-Tetrahydroyangonin
* 5,6-Dehydromethysticin
* Methysticin
* 7,8-Dihydromethysticin
* Yangonin

Monoureides|

* Acecarbromal
* Apronal (apronalide)
* Bromisoval
* Carbromal
* Capuride
* Ectylurea

Neuroactive steroids|

* Acebrochol
* Allopregnanolone (brexanolone)
* Alfadolone
* Alfaxalone
* 3α-Androstanediol
* Androstenol
* Androsterone
* Certain anabolic-androgenic steroids
* Cholesterol
* DHDOC
* 3α-DHP
* 5α-DHP
* 5β-DHP
* DHT
* Etiocholanolone
* Ganaxolone
* Hydroxydione
* Minaxolone
* ORG-20599
* ORG-21465
* P1-185
* Pregnanolone (eltanolone)
* Progesterone
* Renanolone
* SAGE-105
* SAGE-324
* SAGE-516
* SAGE-689
* SAGE-872
* Testosterone
* THDOC
* Zuranolone

Nonbenzodiazepines|

* Cyclopyrrolones: Eszopiclone
* Pagoclone
* Pazinaclone
* Suproclone
* Suriclone
* Zopiclone

* Imidazopyridines: Alpidem
* DS-1
* Necopidem
* Saripidem
* Zolpidem

* Pyrazolopyrimidines: Divaplon
* Fasiplon
* Indiplon
* Lorediplon
* Ocinaplon
* Panadiplon
* Taniplon
* Zaleplon

* Others: Adipiplon
* CGS-8216
* CGS-9896
* CGS-13767
* CGS-20625
* CL-218,872
* CP-615,003
* CTP-354
* ELB-139
* GBLD-345
* Imepitoin
* JM-1232
* L-838,417
* Lirequinil (Ro41-3696)
* NS-2664
* NS-2710
* NS-11394
* Pipequaline
* ROD-188
* RWJ-51204
* SB-205,384
* SX-3228
* TGSC01AA
* TP-003
* TPA-023
* TP-13
* U-89843A
* U-90042
* Viqualine
* Y-23684

Phenols|

* Fospropofol
* Propofol
* Thymol

Piperidinediones|

* Glutethimide
* Methyprylon
* Piperidione
* Pyrithyldione

Pyrazolopyridines|

* Cartazolate
* Etazolate
* ICI-190,622
* Tracazolate

Quinazolinones|

* Afloqualone
* Cloroqualone
* Diproqualone
* Etaqualone
* Mebroqualone
* Mecloqualone
* Methaqualone
* Methylmethaqualone
* Nitromethaqualone
* SL-164

Volatiles/gases|

* Acetone
* Acetophenone
* Acetylglycinamide chloral hydrate
* Aliflurane
* Benzene
* Butane
* Butylene
* Centalun
* Chloral
* Chloral betaine
* Chloral hydrate
* Chloroform
* Cryofluorane
* Desflurane
* Dichloralphenazone
* Dichloromethane
* Diethyl ether
* Enflurane
* Ethyl chloride
* Ethylene
* Fluroxene
* Gasoline
* Halopropane
* Halothane
* Isoflurane
* Kerosine
* Methoxyflurane
* Methoxypropane
* Nitric oxide
* Nitrogen
* Nitrous oxide
* Norflurane
* Paraldehyde
* Propane
* Propylene
* Roflurane
* Sevoflurane
* Synthane
* Teflurane
* Toluene
* Trichloroethane (methyl chloroform)
* Trichloroethylene
* Vinyl ether

Others/unsorted|

* 3-Hydroxybutanal
* α-EMTBL
* AA-29504
* Avermectins (e.g., ivermectin)
* Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide)
* Carbamazepine
* Chloralose
* Chlormezanone
* Clomethiazole
* DEABL
* Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine))
* DS2
* Efavirenz
* Etazepine
* Etifoxine
* Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid)
* Fluoxetine
* Flupirtine
* Hopantenic acid
* Lanthanum
* Lavender oil
* Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol)
* Loreclezole
* Menthyl isovalerate (validolum)
* Monastrol
* Niacin
* Nicotinamide (niacinamide)
* Org 25,435
* Phenytoin
* Propanidid
* Retigabine (ezogabine)
* Safranal
* Seproxetine
* Stiripentol
* Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional)
* Terpenoids (e.g., borneol)
* Topiramate
* Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol)

* Unsorted benzodiazepine site positive modulators: α-Pinene
* MRK-409 (MK-0343)
* TCS-1105
* TCS-1205

See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators

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Original source: https://en.wikipedia.org/wiki/Wogonin. Read more

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Wogonin&oldid=825311"
*[CID]: Compound ID
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*[GABAA]: γ-Aminobutyric acid A