MAGNOLOL

Possibly Marketed Outside US

First approved in 2021

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

Structure Search

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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11430926 | https://www.ncbi.nlm.nih.gov/pubmed/28919715 | https://www.ncbi.nlm.nih.gov/pubmed/21518336 | https://www.ncbi.nlm.nih.gov/pubmed/22474400

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
GABA-A receptor; benzodiazepine site 38 Target ID: CHEMBL2109243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21518336	Modulator 828
Peroxisome proliferator-activated receptor gamma 111 Target ID: P37231\|\|\|Q15179 Gene ID: 5468.0 Gene Symbol: PPARG Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22140563	Agonist 2678
Retinoic acid receptor RXR-alpha 2 Target ID: P19793 Gene ID: 6256.0 Gene Symbol: RXRA Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22140563	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Refractory Candida infection 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28919715	Curative	Basic research	Unknown Approved Use Unknown
Myocardial ischemia-reperfusion injury 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11430926	Preventing	Preclinical	Unknown Approved Use Unknown
Osteoporosis 97 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22474400	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antimicrobial and cytotoxic activities of neolignans from Magnolia officinalis.	2004 Mar	17191867
Signaling pathways of magnolol-induced adrenal steroidogensis.	2005 Aug 15	16061232
Elucidating the inhibitory mechanisms of magnolol on rat smooth muscle cell proliferation.	2005 Dec	16340156
[Studies on HPLC chromatogram of phenolic constituents of Cortex Magnoliae Officinalis].	2005 Jul	16161419
Effects of magnolol and honokiol derived from traditional Chinese herbal remedies on gastrointestinal movement.	2005 Jul 28	16038044
Prokinetic effect of a Kampo medicine, Hange-koboku-to (Banxia-houpo-tang), on patients with functional dyspepsia.	2005 Nov	16323291
Neurotrophic effect of magnolol in the hippocampal CA1 region of senescence-accelerated mice (SAMP1).	2005 Sep	16141555
Differential inhibitory effects of honokiol and magnolol on excitatory amino acid-evoked cation signals and NMDA-induced seizures.	2005 Sep	15921707
Inhibitory effects of magnolol on distal colon of guinea pig in vitro.	2006 Apr	16595919
Separation and determination of honokiol and magnolol in herbal medicines by flow injection-capillary electrophoresis.	2006 Apr	16525846
[Inhibition of extracts from 17 Chinese herbs on periodontal pathogenic microbes].	2006 Aug	16955176
Carbon nanotube/poly(methyl methacrylate) composite electrode for capillary electrophoretic measurement of honokiol and magnolol in Cortex Magnoliae Officinalis.	2006 Aug	16850507
Ethnoveterinary medicines used for horses in Trinidad and in British Columbia, Canada.	2006 Aug 7	16893454
Anti-inflammatory effects of different drugs/agents with antioxidant property on endothelial expression of adhesion molecules.	2006 Dec	17378773
[Investigate into of effective constituent transference of herba Ephedrae and cortex Magnoliae officinalis in preparation course of Shujin Kechuan capsule].	2006 Dec	17348186
Targeting signal-transducer-and-activator-of-transcription-3 for prevention and therapy of cancer: modern target but ancient solution.	2006 Dec	17341611
Magnolol-induced apoptosis is mediated via the intrinsic pathway with release of AIF from mitochondria in U937 cells.	2006 Dec	17142989
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	16544875
Facile purification of honokiol and its antiviral and cytotoxic properties.	2006 Jun 1	16722664
Determination of honokiol and magnolol in cortex Magnoliae Officinalis by capillary electrophoresis with electrochemical detection.	2006 Jun 16	16704915
Herbal remedy magnolol suppresses IL-6-induced STAT3 activation and gene expression in endothelial cells.	2006 May	16520748
Neuroprotective activity of honokiol and magnolol in cerebellar granule cell damage.	2006 May 10	16631734
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	17077620
Nitric oxide-independent lipid metabolism in RAW 264.7 macrophages loaded with oleic acid.	2006 Nov	16891132
[Optimization of preparative technique for banxia-houpu effervescent tablets by orthogonal design].	2006 Oct	17326411
[Evaluation of antioxidant activity of Radix Linderae and other two Chinese drugs using TLC-bioautography].	2006 Oct	17184113
The inhibitory effect of magnolol from Magnolia officinalis on glucosyltransferase.	2006 Oct	16797479
Simultaneous determination of honokiol and magnolol in Magnolia officinalis by liquid chromatography with tandem mass spectrometric detection.	2006 Oct	16583454
In vitro anti-mutagenic effect of magnolol against direct and indirect mutagens.	2006 Oct 10	16884943
Honokiol potentiates apoptosis, suppresses osteoclastogenesis, and inhibits invasion through modulation of nuclear factor-kappaB activation pathway.	2006 Sep	16966432
Oxidative stress and ischemic injuries in heat stroke.	2007	17645935
Involvement of Ras/Raf-1/ERK actions in the magnolol-induced upregulation of p21 and cell-cycle arrest in colon cancer cells.	2007 Apr	17295239
Magnolol suppresses NF-kappaB activation and NF-kappaB regulated gene expression through inhibition of IkappaB kinase activation.	2007 Apr	17240450
Inhibitory role of magnolol on proliferative capacity and matrix metalloproteinase-9 expression in TNF-alpha-induced vascular smooth muscle cells.	2007 Aug	17570325
Synthesis, cytotoxicity, and antiviral activities of new neolignans related to honokiol and magnolol.	2007 Aug 15	17587572
Evaluation of the in vitro and in vivo genotoxicity of magnolia bark extract.	2007 Dec	17692444
Spectroscopic investigation of inner filter effect by magnolol solutions.	2007 Dec 31	17374565
Analysis of magnolol and honokiol in biological fluids by capillary zone electrophoresis.	2007 Feb 23	17234199
Rapid purification and scale-up of honokiol and magnolol using high-capacity high-speed counter-current chromatography.	2007 Feb 23	17222860
Antiproliferative and pro-apoptotic activity of eugenol-related biphenyls on malignant melanoma cells.	2007 Jan 18	17233906
Effects of magnolol (5,5'-diallyl-2,2'-dihydroxybiphenyl) on diabetic nephropathy in type 2 diabetic Goto-Kakizaki rats.	2007 Jan 9	17070554
Protective effect of magnolol on TBHP-induced injury in H460 cells partially via a p53 dependent mechanism.	2007 Jul	17703737
Mechanisms for the magnolol-induced cell death of CGTH W-2 thyroid carcinoma cells.	2007 Jul 1	17390340
[Effects of the active compounds of M. officinalis on cariogenic bacteria].	2007 Jun	17593830
Protective effects of magnolol against oxidized LDL-induced apoptosis in endothelial cells.	2007 Jun	17216433
Magnolia ovovata extract and its active component magnolol prevent skin photoaging via inhibition of nuclear factor kappaB.	2007 Jun 22	17346696
Effect of magnolol on TGF-beta1 and fibronectin expression in human retinal pigment epithelial cells under diabetic conditions.	2007 May 7	17321517
Compressed mints and chewing gum containing magnolia bark extract are effective against bacteria responsible for oral malodor.	2007 Nov 14	17949053
Agmatine protects retinal ganglion cells from hypoxia-induced apoptosis in transformed rat retinal ganglion cell line.	2007 Oct 2	17908330
Effects of honokiol and magnolol on acute and inflammatory pain models in mice.	2007 Sep 8	17826802

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Fri Dec 15 18:32:56 GMT 2023` Edited by `admin` on `Fri Dec 15 18:32:56 GMT 2023`
Record UNII	001E35HGVF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MAGNOLOL

Official Name

English

MAGNOLOL [INCI]

Common Name

English

DEHYDRODICHAVICOL

Common Name

English

5,5'-DIALLYL-2,2'-BIPHENYLDIOL

Systematic Name

English

FEMA NO. 4559

Code

English

MAGNOLOL [HSDB]

Common Name

English

5,5'-DI-2-PROPEN-1-YL-(1,1'-BIPHENYL)-2,2'-DIOL

Systematic Name

English

MAGNOLOL [MI]

Common Name

English

2,2'-BICHAVICOL

Common Name

English

NSC-293099

Code

English

2,2'-DIHYDROXY-5,5'-DIALLYLBIPHENYL

Systematic Name

English

Classification Tree Code System Code

JECFA EVALUATION

MAGNOLOL