4-O-Methylhonokiol

4-O-Methylhonokiol is a neolignan, a type of phenolic compound. It is found in the bark of Magnolia grandiflora and in M. virginiana flowers.

4-O-Methylhonokiol
Names
Preferred IUPAC name
4′-Methoxy-3′,5-di(prop-2-en-1-yl)[1,1′-biphenyl]-2-ol
Other names
3,5′-Diallyl-2′-hydroxy-4-methoxybiphenyl
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C19H20O2/c1-4-6-14-8-10-18(20)17(12-14)15-9-11-19(21-3)16(13-15)7-5-2/h4-5,8-13,20H,1-2,6-7H2,3H3
    Key: OQFHJKZVOALSPV-UHFFFAOYSA-N
  • InChI=1/C19H20O2/c1-4-6-14-8-10-18(20)17(12-14)15-9-11-19(21-3)16(13-15)7-5-2/h4-5,8-13,20H,1-2,6-7H2,3H3
    Key: OQFHJKZVOALSPV-UHFFFAOYAP
SMILES
  • COC1=C(C=C(C=C1)C2=C(C=CC(=C2)CC=C)O)CC=C
Properties
C19H20O2
Molar mass 280.367 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

4-O-Methylhonokiol is a CB2 receptor ligand (Ki = 50 nM), showing inverse agonism and partial agonism via different pathways (cAMP and Ca2+), which potently inhibits osteoclastogenesis. 4-O-Methylhonokiol further attenuates memory impairment in presenilin 2 mutant mice through reduction of oxidative damage and inactivation of astrocytes and the ERK pathway. The different neuroprotective effects reported in rodent models may be mediated via CB2 receptors. 4-O-Methylhonokiol activates CB2 receptors and also inhibits the oxygenation of the major endocannabinoid 2-AG via COX-2 in a substrate-selective manner, thus leading to potential synergistic effects at CB receptors. The same study also provided data that 4-O-methylhonokiol can readily pass the blood–brain barrier.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.