Magnolol

Magnolol
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 InfoCard 100.127.908 Edit 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 X markN
    Key: VVOAZFWZEDHOOU-UHFFFAOYSA-N X markN
  • 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 mass 266.340 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Magnolol is an organic compound that is classified as lignan. It is a bioactive compound found in the bark of the Houpu magnolia (Magnolia officinalis) and in M. grandiflora.

Magnolol is a compound that acts on GABAA receptors and functions as an allosteric modulator. It has antifungal properties and demonstrates anti-periodontal disease effects in animal models. In cell cultures, magnolol stimulates osteoblasts and inhibits osteoclasts, indicating potential for anti-osteoporosis treatment. It also binds in a dimeric form to PPARγ, acting as an agonist of this nuclear receptor. Additionally, magnolol may interact with cannabinoid receptors, acting as a partial agonist of CB2 receptors with lower affinity for CB1 receptors.

Bioactivity

It is known to act on the GABAA receptors in rat cells in vitro as well as having antifungal properties. 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. It has anti-periodontal disease activity in a rat model. Structural analogues have been studied and found to be strong allosteric modulators of GABAA.

Magnolol is also binding in dimeric mode to PPARγ, acting as an agonist of this nuclear receptor.

Magnolol may interact with cannabinoid receptors, acting as a partial agonist of CB2 receptors, with lower affinity for the CB1 receptor.

References

  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 the Magnolia 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