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Magnolol

From Wikipedia, the free encyclopedia
Magnolol[1]
Names
IUPAC name
3,3′-Neoligna-8,8′-diene-4,4′-diol
Systematic IUPAC name
5,5′-Di(prop-2-en-1-yl)[1,1′-biphenyl]-2,2′-diol
Other names
Dehydrodichavicol
5,5'-Diallyl-2,2'-dihydroxybiphenyl
5,5'-Diallyl-2,2'-biphenyldiol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard100.127.908Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C18H18O2/c1-3-5-13-7-9-17(19)15(11-13)16-12-14(6-4-2)8-10-18(16)20/h3-4,7-12,19-20H,1-2,5-6H2 ☒N
    Key: VVOAZFWZEDHOOU-UHFFFAOYSA-N ☒N
  • InChI=1/C18H18O2/c1-3-5-13-7-9-17(19)15(11-13)16-12-14(6-4-2)8-10-18(16)20/h3-4,7-12,19-20H,1-2,5-6H2
    Key: VVOAZFWZEDHOOU-UHFFFAOYAE
  • C=CCC1=CC(=C(C=C1)O)C2=C(C=CC(=C2)CC=C)O
Properties
C18H18O2
Molar mass266.340 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Magnolol is anorganic compound that is classified aslignan. It is abioactive compoundfound in the bark of the Houpu magnolia (Magnolia officinalis) and inM. grandiflora.[2]

Magnolol is a compound that acts onGABA_A receptors and functions as an allosteric modulator. It hasantifungal properties and demonstrates anti-periodontal disease effects in animal models. In cell cultures, magnolol stimulatesosteoblasts and inhibitsosteoclasts, indicating potential for anti-osteoporosis treatment. It also binds in a dimeric form toPPARγ, acting as an agonist of this nuclear receptor. Additionally, magnolol may interact withcannabinoid receptors, acting as a partial agonist of CB2 receptors with lower affinity for CB1 receptors.

Bioactivity

[edit]

It is known to act on theGABAA receptors in rat cellsin vitro[3] as well as having antifungal properties.[4] Magnolol has a number of osteoblast-stimulating and osteoclast-inhibiting activities in cell culture and has been suggested as a candidate for screening for anti-osteoporosis activity.[5] It has anti-periodontal disease activity in a rat model.[6] Structural analogues have been studied and found to be strong allosteric modulators ofGABAA.[7]

Magnolol is also binding in dimeric mode toPPARγ, acting as an agonist of this nuclear receptor.[8]

Magnolol may interact withcannabinoid receptors, acting as a partial agonist ofCB2 receptors, with lower affinity for theCB1 receptor.[9]

References

[edit]
  1. ^Magnolol at Sigma-Aldrich
  2. ^Lee, Young-Jung; Lee, Yoot Mo; Lee, Chong-Kil; Jung, Jae Kyung; Han, Sang Bae; Hong, Jin Tae (2011). "Therapeutic applications of compounds in theMagnolia family".Pharmacology & Therapeutics.130 (2):157–76.doi:10.1016/j.pharmthera.2011.01.010.PMID 21277893.
  3. ^Ai, Jinglu; Wang, Xiaomei; Nielsen, Mogens (2001). "Honokiol and Magnolol Selectively Interact with GABAA Receptor Subtypes in vitro".Pharmacology.63 (1):34–41.doi:10.1159/000056110.PMID 11408830.S2CID 19327464.
  4. ^Bang, Kyu Ho; Kim, Yoon Kwan; Min, Byung Sun; Na, Min Kyun; Rhee, Young Ha; Lee, Jong Pill; Bae, Ki Hwan (2000). "Antifungal activity of magnolol and honokiol".Archives of Pharmacal Research.23 (1):46–9.doi:10.1007/BF02976465.PMID 10728656.S2CID 22754315.
  5. ^Kwak, Eun Jung; Lee, Young Soon; Choi, Eun Mi (2012)."Effect of Magnolol on the Function of Osteoblastic MC3T3-E1 Cells".Mediators of Inflammation.2012:1–7.doi:10.1155/2012/829650.PMC 3306956.PMID 22474400.
  6. ^Lu, Sheng-Hua; Huang, Ren-Yeong; Chou, Tz-Chong (2013)."Magnolol Ameliorates Ligature-Induced Periodontitis in Rats and Osteoclastogenesis: In Vivo and in Vitro Study".Evidence-Based Complementary and Alternative Medicine.2013:1–12.doi:10.1155/2013/634095.PMC 3618931.PMID 23573141.
  7. ^Fuchs, Alexander; Baur, Roland; Schoeder, Clara; Sigel, Erwin; Müller, Christa E. (December 2014). "Structural analogues of the natural products magnolol and honokiol as potent allosteric potentiators of GABAA receptors".Bioorganic & Medicinal Chemistry.22 (24):6908–6917.doi:10.1016/j.bmc.2014.10.027.PMID 25456080.
  8. ^Dreier, Dominik; Latkolik, Simone; Rycek, Lukas; Schnürch, Michael; Dymáková, Andrea; Atanasov, Atanas G.; Ladurner, Angela; Heiss, Elke H.; Stuppner, Hermann; Schuster, Daniela; Mihovilovic, Marko D.; Dirsch, Verena M. (20 October 2017)."Linked magnolol dimer as a selective PPARγ agonist – Structure-based rational design, synthesis, and bioactivity evaluation".Scientific Reports.7 (1): 13002.doi:10.1038/s41598-017-12628-5.PMC 5651862.PMID 29057944.S2CID 256897195.
  9. ^Rempel, Viktor; Fuchs, Alexander; Hinz, Sonja; Karcz, Tadeusz; Lehr, Matthias; Koetter, Uwe; Müller, Christa E. (10 January 2013)."Magnolia Extract, Magnolol, and Metabolites: Activation of Cannabinoid CB 2 Receptors and Blockade of the Related GPR55".ACS Medicinal Chemistry Letters.4 (1):41–45.doi:10.1021/ml300235q.PMC 4027495.PMID 24900561.

Further reading

[edit]
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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