Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H18O2 |
| Molecular Weight | 266.3343 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=C(CC=C)C=C1C2=CC(CC=C)=CC=C2O
InChI
InChIKey=VVOAZFWZEDHOOU-UHFFFAOYSA-N
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
Magnolol is a small polyphenolic molecule with low toxicity that is isolated from the herb genus Magnolia. In preclinical experiments, magnolol was found to have anti-oxidative, anti-inflammatory, anti-tumorigenic, anti-diabetic, anti-microbial, anti-neurodegenerative and anti-depressant properties. Magnolol is a dual agonist targeting both nuclear receptors retinoic X receptor α (RXRα) and peroxisome proliferator activated receptor γ (PPARγ). These proteins function potently in metabolic diseases and are both important targets for anti-diabetic drugs. In addition, was made a suggestion, that magnolol might exert antiepileptic activity by acting at the GABAA/benzodiazepine receptor complex. Magnolol might be of benefit to the treatment of refractory Candida infection. In addition, it might be a candidate as an agent for the prevention of bone disorders such as osteoporosis. It is known, that the accumulation of oxygen-free radicals and activation of neutrophils are strongly implicated as important pathophysiological mechanisms mediating myocardial ischemia/reperfusion injury. It has been proven that various antioxidants have cardioprotective effects, including magnolol. Its properties were studied in the rat model of myocardial ischemia/reperfusion injury.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2109243 |
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Target ID: P37231|||Q15179 Gene ID: 5468.0 Gene Symbol: PPARG Target Organism: Homo sapiens (Human) |
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Target ID: P19793 Gene ID: 6256.0 Gene Symbol: RXRA Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Unknown Approved UseUnknown |
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| Preventing | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Inhibitory effect of magnolol and honokiol from Magnolia obovata on human fibrosarcoma HT-1080. Invasiveness in vitro. | 2001 Nov |
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| Molecular mechanisms of apoptosis induced by magnolol in colon and liver cancer cells. | 2001 Oct |
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| Stimulation of the BK(Ca) channel in cultured smooth muscle cells of human trachea by magnolol. | 2002 Jan |
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| Magnolol induces apoptosis in vascular smooth muscle. | 2003 Aug |
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| Protective effects of honokiol and magnolol on tertiary butyl hydroperoxide- or D-galactosamine-induced toxicity in rat primary hepatocytes. | 2003 Jan |
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| Effector mechanism of magnolol-induced apoptosis in human lung squamous carcinoma CH27 cells. | 2003 Jan |
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| Metabolites of orally administered Magnolia officinalis extract in rats and man and its antidepressant-like effects in mice. | 2003 Nov |
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| Inhibitory effect of magnolol on tumour metastasis in mice. | 2003 Sep |
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| Magnolol alters cytokine response after hemorrhagic shock and increases survival in subsequent intraabdominal sepsis in rats. | 2003 Sep |
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| In vitro antibacterial and anti-inflammatory effects of honokiol and magnolol against Propionibacterium sp. | 2004 Aug 2 |
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| Mechanisms of the influence of magnolol on eicosanoid metabolism in neutrophils. | 2004 Mar 1 |
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| Signaling pathways of magnolol-induced adrenal steroidogensis. | 2005 Aug 15 |
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| Cytotoxic neolignans: an SAR study. | 2005 Jan 3 |
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| [Studies on HPLC chromatogram of phenolic constituents of Cortex Magnoliae Officinalis]. | 2005 Jul |
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| Effects of magnolol and honokiol derived from traditional Chinese herbal remedies on gastrointestinal movement. | 2005 Jul 28 |
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| Magnolol-induced apoptosis is mediated via the intrinsic pathway with release of AIF from mitochondria in U937 cells. | 2006 Dec |
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| A comparative study of upright counter-current chromatography and high-performance liquid chromatograpohy for preparative isolation and purification ofphenolic compounds from Magnoliae officinalis. | 2006 Feb |
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| Herbal remedy magnolol suppresses IL-6-induced STAT3 activation and gene expression in endothelial cells. | 2006 May |
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| Determination of liquiritin, naringin, hesperidin, thymol, imperatorin, honokiol, isoimperatorin, and magnolol in the traditional Chinese medicinal preparation Huoxiang-zhengqi liquid using high-performance liquid chromatography. | 2006 Nov |
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| Honokiol potentiates apoptosis, suppresses osteoclastogenesis, and inhibits invasion through modulation of nuclear factor-kappaB activation pathway. | 2006 Sep |
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| Inhibitory role of magnolol on proliferative capacity and matrix metalloproteinase-9 expression in TNF-alpha-induced vascular smooth muscle cells. | 2007 Aug |
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| Synthesis, cytotoxicity, and antiviral activities of new neolignans related to honokiol and magnolol. | 2007 Aug 15 |
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| Rapid purification and scale-up of honokiol and magnolol using high-capacity high-speed counter-current chromatography. | 2007 Feb 23 |
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| Effects of magnolol (5,5'-diallyl-2,2'-dihydroxybiphenyl) on diabetic nephropathy in type 2 diabetic Goto-Kakizaki rats. | 2007 Jan 9 |
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| [Effects of the active compounds of M. officinalis on cariogenic bacteria]. | 2007 Jun |
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| Protective effects of magnolol against oxidized LDL-induced apoptosis in endothelial cells. | 2007 Jun |
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| Compressed mints and chewing gum containing magnolia bark extract are effective against bacteria responsible for oral malodor. | 2007 Nov 14 |
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| Agmatine protects retinal ganglion cells from hypoxia-induced apoptosis in transformed rat retinal ganglion cell line. | 2007 Oct 2 |
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| Effects of honokiol and magnolol on acute and inflammatory pain models in mice. | 2007 Sep 8 |
Sample Use Guides
in mice: magnolol protects against trimethyltin-induced neuronal damage and glial activation: 25 mg/kg i.p
in rats: pretreatment with magnolol (0.2 and 0.5 microg/kg, i.v. bolus) at 10 min before 45 min of left coronary artery occlusion, significantly suppressed the incidence of ventricular fibrillation and mortality when compared with the control group
Route of Administration:
Other
The antifungal activity of magnolol was demonstrated in planktonic C. albicans and non-albicans Candida species, especially fluconazole-resistant Candida krusei, with the minimum inhibitory concentrations ranging from 10 to 40 μg/mL. The BMIC90 (minimum concentration with 90% Candida biofilm inhibited) values of magnolol ranged from 20 to 160 μg/mL. As an alternative and broad-spectrum antifungal agent, magnolol might be of benefit to the treatment of refractory Candida infection. Susceptibility testing of planktonic yeast cells to magnolol was performed following the CLSI M-27A broth micro-dilution method. The frozen magnolol solution was thawed and diluted in Roswell Park Memorial Institute (RPMI) 1640, which was buffered to pH =7.0 using 0.165 M 3-morpholinopropane-1-sulfonic acid. The magnolol solution (100 μL of a 2-fold dilution) was pipetted into each well of a 96-well microtiter plate. The final concentration of magnolol ranged from 2.5 to 1,280 μg/mL.
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JECFA EVALUATION |
MAGNOLOL
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METABOLITE (PARENT)
SUBSTANCE RECORD
