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
| Molecular Formula | C18H18O2 |
| Molecular Weight | 266.3343 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Spectroscopic investigation of inner filter effect by magnolol solutions. | 2007-12-31 |
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| Evaluation of the in vitro and in vivo genotoxicity of magnolia bark extract. | 2007-12 |
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| Compressed mints and chewing gum containing magnolia bark extract are effective against bacteria responsible for oral malodor. | 2007-11-14 |
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| Agmatine protects retinal ganglion cells from hypoxia-induced apoptosis in transformed rat retinal ganglion cell line. | 2007-10-02 |
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| Effects of honokiol and magnolol on acute and inflammatory pain models in mice. | 2007-09-08 |
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| Synthesis, cytotoxicity, and antiviral activities of new neolignans related to honokiol and magnolol. | 2007-08-15 |
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| Inhibitory role of magnolol on proliferative capacity and matrix metalloproteinase-9 expression in TNF-alpha-induced vascular smooth muscle cells. | 2007-08 |
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| Mechanisms for the magnolol-induced cell death of CGTH W-2 thyroid carcinoma cells. | 2007-07-01 |
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| Protective effect of magnolol on TBHP-induced injury in H460 cells partially via a p53 dependent mechanism. | 2007-07 |
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| Magnolia ovovata extract and its active component magnolol prevent skin photoaging via inhibition of nuclear factor kappaB. | 2007-06-22 |
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| [Effects of the active compounds of M. officinalis on cariogenic bacteria]. | 2007-06 |
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| Protective effects of magnolol against oxidized LDL-induced apoptosis in endothelial cells. | 2007-06 |
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| Effect of magnolol on TGF-beta1 and fibronectin expression in human retinal pigment epithelial cells under diabetic conditions. | 2007-05-07 |
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| Involvement of Ras/Raf-1/ERK actions in the magnolol-induced upregulation of p21 and cell-cycle arrest in colon cancer cells. | 2007-04 |
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| Magnolol suppresses NF-kappaB activation and NF-kappaB regulated gene expression through inhibition of IkappaB kinase activation. | 2007-04 |
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| Analysis of magnolol and honokiol in biological fluids by capillary zone electrophoresis. | 2007-02-23 |
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| Rapid purification and scale-up of honokiol and magnolol using high-capacity high-speed counter-current chromatography. | 2007-02-23 |
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| Antiproliferative and pro-apoptotic activity of eugenol-related biphenyls on malignant melanoma cells. | 2007-01-18 |
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| Effects of magnolol (5,5'-diallyl-2,2'-dihydroxybiphenyl) on diabetic nephropathy in type 2 diabetic Goto-Kakizaki rats. | 2007-01-09 |
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| Oxidative stress and ischemic injuries in heat stroke. | 2007 |
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| Anti-inflammatory effects of different drugs/agents with antioxidant property on endothelial expression of adhesion molecules. | 2006-12 |
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| [Investigate into of effective constituent transference of herba Ephedrae and cortex Magnoliae officinalis in preparation course of Shujin Kechuan capsule]. | 2006-12 |
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| Targeting signal-transducer-and-activator-of-transcription-3 for prevention and therapy of cancer: modern target but ancient solution. | 2006-12 |
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| Magnolol-induced apoptosis is mediated via the intrinsic pathway with release of AIF from mitochondria in U937 cells. | 2006-12 |
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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. | 2006-11 |
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| Nitric oxide-independent lipid metabolism in RAW 264.7 macrophages loaded with oleic acid. | 2006-11 |
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| In vitro anti-mutagenic effect of magnolol against direct and indirect mutagens. | 2006-10-10 |
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| [Optimization of preparative technique for banxia-houpu effervescent tablets by orthogonal design]. | 2006-10 |
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| [Evaluation of antioxidant activity of Radix Linderae and other two Chinese drugs using TLC-bioautography]. | 2006-10 |
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| The inhibitory effect of magnolol from Magnolia officinalis on glucosyltransferase. | 2006-10 |
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| Simultaneous determination of honokiol and magnolol in Magnolia officinalis by liquid chromatography with tandem mass spectrometric detection. | 2006-10 |
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| Honokiol potentiates apoptosis, suppresses osteoclastogenesis, and inhibits invasion through modulation of nuclear factor-kappaB activation pathway. | 2006-09 |
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| Ethnoveterinary medicines used for horses in Trinidad and in British Columbia, Canada. | 2006-08-07 |
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| [Inhibition of extracts from 17 Chinese herbs on periodontal pathogenic microbes]. | 2006-08 |
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| Carbon nanotube/poly(methyl methacrylate) composite electrode for capillary electrophoretic measurement of honokiol and magnolol in Cortex Magnoliae Officinalis. | 2006-08 |
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| Determination of honokiol and magnolol in cortex Magnoliae Officinalis by capillary electrophoresis with electrochemical detection. | 2006-06-16 |
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| Facile purification of honokiol and its antiviral and cytotoxic properties. | 2006-06-01 |
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| Neuroprotective activity of honokiol and magnolol in cerebellar granule cell damage. | 2006-05-10 |
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| Herbal remedy magnolol suppresses IL-6-induced STAT3 activation and gene expression in endothelial cells. | 2006-05 |
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| Inhibitory effects of magnolol on distal colon of guinea pig in vitro. | 2006-04 |
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| Separation and determination of honokiol and magnolol in herbal medicines by flow injection-capillary electrophoresis. | 2006-04 |
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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. | 2006-02 |
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| Elucidating the inhibitory mechanisms of magnolol on rat smooth muscle cell proliferation. | 2005-12 |
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| Prokinetic effect of a Kampo medicine, Hange-koboku-to (Banxia-houpo-tang), on patients with functional dyspepsia. | 2005-11 |
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| Neurotrophic effect of magnolol in the hippocampal CA1 region of senescence-accelerated mice (SAMP1). | 2005-09 |
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| Differential inhibitory effects of honokiol and magnolol on excitatory amino acid-evoked cation signals and NMDA-induced seizures. | 2005-09 |
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| Signaling pathways of magnolol-induced adrenal steroidogensis. | 2005-08-15 |
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| Effects of magnolol and honokiol derived from traditional Chinese herbal remedies on gastrointestinal movement. | 2005-07-28 |
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| [Studies on HPLC chromatogram of phenolic constituents of Cortex Magnoliae Officinalis]. | 2005-07 |
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| Antimicrobial and cytotoxic activities of neolignans from Magnolia officinalis. | 2004-03 |
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.
| Substance Class |
Chemical
Created
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admin
on
Edited
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| Record UNII |
001E35HGVF
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| Record Status |
Validated (UNII)
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| Record Version |
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JECFA EVALUATION |
MAGNOLOL
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MAGNOLOL
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PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT |
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| ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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