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4-O-Methylhonokiol

From Wikipedia, the free encyclopedia
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
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
  • COC1=C(C=C(C=C1)C2=C(C=CC(=C2)CC=C)O)CC=C
Properties
C19H20O2
Molar mass280.367 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

4-O-Methylhonokiol is aneolignan, a type ofphenolic compound. It isfound in the bark ofMagnolia grandiflora[1] and inM. virginiana flowers.[2]

4-O-Methylhonokiol is aCB2 receptor ligand (Ki = 50 nM), showinginverse agonism andpartial agonism via different pathways (cAMP and Ca2+), which potently inhibits osteoclastogenesis.[3] 4-O-Methylhonokiol further attenuates memory impairment inpresenilin 2 mutant mice through reduction of oxidative damage and inactivation ofastrocytes and the ERK pathway.[4] The different neuroprotective effects reported inrodent models may be mediated via CB2 receptors.[5] 4-O-Methylhonokiol activates CB2 receptors and also inhibits the oxygenation of the major endocannabinoid2-AG viaCOX-2 in a substrate-selective manner, thus leading to potential synergistic effects at CB receptors.[6] The same study also provided data that 4-O-methylhonokiol can readily pass the blood–brain barrier.

References

[edit]
  1. ^Clark, Alice M.; El-Feraly, Arouk S.; Li, Wen-Shyong (1981). "Antimicrobial activity of phenolic constituents ofmagnolia grandiflora L".Journal of Pharmaceutical Sciences.70 (8):951–2.doi:10.1002/jps.2600700833.PMID 7310672.
  2. ^Chandra, Amitabh; Nair, Muraleedharan (2007). "Supercritical Carbon Dioxide Extraction and Quantification of Bioactive Neolignans from Magnolia virginiana Flowers".Planta Medica.61 (2):192–5.doi:10.1055/s-2006-958051.PMID 7753933.S2CID 28117395.
  3. ^Schuehly, Paredes; Kleyer, Huefner; Anavi-Goffer, Raduner; Altmann, Gertsch (2011). "Mechanisms of osteoclastogenesis inhibition by a novel class of biphenyl-type cannabinoid CB(2) receptor inverse agonists".Chemistry and Biology.18 (8):1053–64.doi:10.1016/j.chembiol.2011.05.012.PMID 21867920.
  4. ^Lee, Y. J.; Choi, I. S.; Park, M. H.; Lee, Y. M.; Song, J. K.; Kim, Y. H.; Kim, K. H.; Hwang, D. Y.; Jeong, J. H.; Yun, Y. P.; Oh, K. W.; Jung, J. K.; Han, S. B.; Hong, J. T. (2011). "4-O-Methylhonokiol attenuates memory impairment in presenilin 2 mutant mice through reduction of oxidative damage and inactivation of astrocytes and the ERK pathway".Free Radical Biology and Medicine.50 (1):66–77.doi:10.1016/j.freeradbiomed.2010.10.698.PMID 20974250.
  5. ^Gertsch, Anavi-Goffer (2012)."Methylhonokiol attenuates neuroinflammation: a role for cannabinoid receptors?".Journal of Neuroinflammation.9 (135):1053–64.doi:10.1186/1742-2094-9-135.PMC 3419612.PMID 22716035.
  6. ^Chicca, A.; Gachet, M. S.; Petrucci, V.; Schuehly, W.; Charles, R. -P.; Gertsch, J. R. (2015)."4′-O-methylhonokiol increases levels of 2-arachidonoyl glycerol in mouse brain via selective inhibition of its COX-2-mediated oxygenation".Journal of Neuroinflammation.12: 89.doi:10.1186/s12974-015-0307-7.PMC 4490613.PMID 25962384.
Types oflignans
Lignans
Lignanglycosides
Mammalian lignans (enterolignans)
Neolignans
Flavonolignans
Receptor
(ligands)
CB1Tooltip Cannabinoid receptor type 1
Agonists
(abridged,
full list)
Inverse agonists
Antagonists
CB2Tooltip Cannabinoid receptor type 2
Agonists
Antagonists
NAGly
(
GPR18)
Agonists
Antagonists
GPR55
Agonists
Antagonists
GPR119
Agonists
Transporter
(modulators)
eCBTsTooltip Endocannabinoid transporter
Enzyme
(modulators)
FAAHTooltip Fatty acid amide hydrolase
MAGL
ABHD6
ABHD12
Others
  • Others:2-PG(directly potentiates activity of 2-AG at CB1 receptor)
  • ARN-272(FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)
Alcohols
Barbiturates
Benzodiazepines
Carbamates
Flavonoids
Imidazoles
Kava constituents
Monoureides
Neuroactive steroids
Nonbenzodiazepines
Phenols
Piperidinediones
Pyrazolopyridines
Quinazolinones
Volatiles/gases
Others/unsorted
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