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 |
|---|---|---|
| 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 action of ICI-182,780, an estrogen receptor antagonist, on BK(Ca) channel activity in cultured endothelial cells of human coronary artery. | 2003 Nov 15 |
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| The mechanism of honokiol-induced and magnolol-induced inhibition on muscle contraction and Ca2+ mobilization in rat uterus. | 2003 Oct |
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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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| Effects of Magnolol and Honokiol on the activities of streptococcal glucosyltransferases both in solution and adsorbed on an experimental pellicle. | 2004 |
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| Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones. | 2004 Apr |
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| Signaling pathway of magnolol-stimulated lipolysis in sterol ester-loaded 3T3-L1 preadipocyes. | 2004 Apr 1 |
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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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| Antimicrobial and cytotoxic activities of neolignans from Magnolia officinalis. | 2004 Mar |
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| Mechanisms of the influence of magnolol on eicosanoid metabolism in neutrophils. | 2004 Mar 1 |
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| Isolation and purification of honokiol and magnolol from cortex Magnoliae officinalis by high-speed counter-current chromatography. | 2004 May 21 |
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| Magnolol alters the course of endotoxin tolerance and provides early protection against endotoxin challenge following sublethal hemorrhage in rats. | 2004 Oct |
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| Magnolol stimulates lipolysis in lipid-laden RAW 264.7 macrophages. | 2005 Apr 1 |
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| Magnolol and honokiol enhance HL-60 human leukemia cell differentiation induced by 1,25-dihydroxyvitamin D3 and retinoic acid. | 2005 Feb |
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| Cytotoxic neolignans: an SAR study. | 2005 Jan 3 |
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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 induces the distributional changes of p160 and adipose differentiation-related protein in adrenal cells. | 2005 Jun |
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| Determination of honokiol and magnolol by micro HPLC with electrochemical detection and its application to the distribution analysis in branches and leaves of Magnolia obovata. | 2005 Mar |
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| Prokinetic effect of a Kampo medicine, Hange-koboku-to (Banxia-houpo-tang), on patients with functional dyspepsia. | 2005 Nov |
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| Differential inhibitory effects of honokiol and magnolol on excitatory amino acid-evoked cation signals and NMDA-induced seizures. | 2005 Sep |
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| Inhibitory effects of magnolol on distal colon of guinea pig in vitro. | 2006 Apr |
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| Separation and determination of honokiol and magnolol in herbal medicines by flow injection-capillary electrophoresis. | 2006 Apr |
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| [Inhibition of extracts from 17 Chinese herbs on periodontal pathogenic microbes]. | 2006 Aug |
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| Carbon nanotube/poly(methyl methacrylate) composite electrode for capillary electrophoretic measurement of honokiol and magnolol in Cortex Magnoliae Officinalis. | 2006 Aug |
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| Ethnoveterinary medicines used for horses in Trinidad and in British Columbia, Canada. | 2006 Aug 7 |
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| Anti-inflammatory effects of different drugs/agents with antioxidant property on endothelial expression of adhesion molecules. | 2006 Dec |
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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 Dec |
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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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| Facile purification of honokiol and its antiviral and cytotoxic properties. | 2006 Jun 1 |
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| Determination of honokiol and magnolol in cortex Magnoliae Officinalis by capillary electrophoresis with electrochemical detection. | 2006 Jun 16 |
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| Neuroprotective activity of honokiol and magnolol in cerebellar granule cell damage. | 2006 May 10 |
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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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| Nitric oxide-independent lipid metabolism in RAW 264.7 macrophages loaded with oleic acid. | 2006 Nov |
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| The inhibitory effect of magnolol from Magnolia officinalis on glucosyltransferase. | 2006 Oct |
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| Simultaneous determination of honokiol and magnolol in Magnolia officinalis by liquid chromatography with tandem mass spectrometric detection. | 2006 Oct |
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| In vitro anti-mutagenic effect of magnolol against direct and indirect mutagens. | 2006 Oct 10 |
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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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| Oxidative stress and ischemic injuries in heat stroke. | 2007 |
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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 Apr |
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| Magnolol suppresses NF-kappaB activation and NF-kappaB regulated gene expression through inhibition of IkappaB kinase activation. | 2007 Apr |
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| Evaluation of the in vitro and in vivo genotoxicity of magnolia bark extract. | 2007 Dec |
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| Spectroscopic investigation of inner filter effect by magnolol solutions. | 2007 Dec 31 |
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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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| Magnolia ovovata extract and its active component magnolol prevent skin photoaging via inhibition of nuclear factor kappaB. | 2007 Jun 22 |
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| Effect of magnolol on TGF-beta1 and fibronectin expression in human retinal pigment epithelial cells under diabetic conditions. | 2007 May 7 |
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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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:32:56 GMT 2023
by
admin
on
Fri Dec 15 18:32:56 GMT 2023
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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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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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SPECIES BIOLOGICAL |
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