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6-Methylapigenin

From Wikipedia, the free encyclopedia
GABAA PAM, flavonoid
6-Methylapigenin
Names
IUPAC name
5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-methylchromen-4-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • Key: ZLGRXDWWYMFIGI-UHFFFAOYSA-N
  • InChI=1S/C16H12O5/c1-8-11(18)6-14-15(16(8)20)12(19)7-13(21-14)9-2-4-10(17)5-3-9/h2-7,17-18,20H,1H3
  • CC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC=C(C=C3)O)O
Properties
C16H12O5
Molar mass284.267 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

6-Methylapigenin is a naturally occurringflavonoid and a derivative ofapigenin. It has activity atGABAA receptors as a positive modulator.

Natural occurrence

[edit]

6-Methylapigenin can be found in multiple plants, such asValeriana officinalis,Valeriana jatamansi, andPicea neoveitchii.[1]

Biological activity

[edit]

6-Methylapigenin binds to theGABAA receptor on thebenzodiazepine binding site. This compound possessesanxiolytic effects. In a mouse model, it is also able to potentiate sleep induced byhesperidin, anotherflavonoid.[2][3] However, since it does not have the chemical structure ofbenzodiazepines, it can therefore be classed as anonbenzodiazepine.

References

[edit]
  1. ^PubChem."6-Methylapigenin".pubchem.ncbi.nlm.nih.gov. Retrieved2024-02-04.
  2. ^Fernández, Sebastián P.; Wasowski, Cristina; Paladini, Alejandro C.; Marder, Mariel (2005-04-11). "Synergistic interaction between hesperidin, a natural flavonoid, and diazepam".European Journal of Pharmacology.512 (2–3):189–198.doi:10.1016/j.ejphar.2005.02.039.ISSN 0014-2999.PMID 15840404.
  3. ^Marder, Mariel; Viola, Haydeé; Wasowski, Cristina; Fernández, Sebastián; Medina, Jorge H.; Paladini, Alejandro C. (2003). "6-methylapigenin and hesperidin: new valeriana flavonoids with activity on the CNS".Pharmacology, Biochemistry, and Behavior.75 (3):537–545.doi:10.1016/s0091-3057(03)00121-7.ISSN 0091-3057.PMID 12895671.S2CID 37559366.
Alcohols
Barbiturates
Benzodiazepines
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Imidazoles
Kava constituents
Monoureides
Neuroactive steroids
Nonbenzodiazepines
Phenols
Piperidinediones
Pyrazolopyridines
Quinazolinones
Volatiles/gases
Others/unsorted
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