Magnolol
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| Names | |
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| IUPAC name
3,3′-Neoligna-8,8′-diene-4,4′-diol
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| 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)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.127.908 |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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.[2]
Magnolol is a compound that acts on GABA_A 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
[edit]It is known to act on the GABAA receptors in rat cells in 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 of GABAA.[7]
Magnolol is also binding in dimeric mode to PPARγ, acting as an agonist of this nuclear receptor.[8]
Magnolol may interact with cannabinoid receptors, acting as a partial agonist of CB2 receptors, with lower affinity for the CB1 receptor.[9]
References
[edit]- ^ Magnolol at Sigma-Aldrich
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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]- Squires, Richard F.; Ai, Jinglu; Witt, Michael-Robin; Kahnberg, Pia; Saederup, Else; Sterner, Olov; Nielsen, Mogens (1999). "Honokiol and magnolol increase the number of 3H muscimol binding sites three-fold in rat forebrain membranes in vitro using a filtration assay, by allosterically increasing the affinities of low-affinity sites". Neurochemical Research. 24 (12): 1593–602. doi:10.1023/A:1021116502548. PMID 10591411. S2CID 9070185.
- Rycek L, Puthenkalam R, Schnürch M, Ernst M, Mihovilovic MD (2015). "Metal-assisted synthesis of unsymmetrical magnolol and honokiol analogs and their biological assessment as GABAA receptor ligands". Bioorg. Med. Chem. Lett. 25 (2): 400–3. doi:10.1016/j.bmcl.2014.10.091. PMC 4297288. PMID 25510374.