Honokiol

Modify Date: 2024-01-02 07:24:34

Honokiol Structure
Honokiol structure
 Common Name Honokiol
CAS Number 35354-74-6 Molecular Weight 266.334
Density 1.1±0.1 g/cm3 Boiling Point 400.1±40.0 °C at 760 mmHg
Molecular Formula C18H18O2 Melting Point 87.5ºC
MSDS Chinese USA Flash Point 184.0±21.9 °C
Symbol GHS05
GHS05		 Signal Word Danger

 Use of Honokiol


Honokiol is a bioactive, biphenolic phytochemical that possesses potent antioxidative, anti-inflammatory, antiangiogenic, and anticancer activities by targeting a variety of signaling molecules. It inhibits the activation of Akt and enhances the phosphorylation of ERK1/ERK2.

 Names

Name Honokiol
Synonym More Synonyms

 Honokiol Biological Activity

Description Honokiol is a bioactive, biphenolic phytochemical that possesses potent antioxidative, anti-inflammatory, antiangiogenic, and anticancer activities by targeting a variety of signaling molecules. It inhibits the activation of Akt and enhances the phosphorylation of ERK1/ERK2.
Related Catalog
Target

Akt

ERK1

ERK2

Autophagy
In Vitro Honokiol (0, 12.5, 25 and 50 μM) inhibits the growth of GBM cells and induces apoptosis, with IC50 of appr against 30 μM DBTRG-05MG cell. Honokiol-induced apoptosis of GBM cells is associated with the downregulation of the Rb protein and cleavage of PARP and Bcl-x (S/L). Honokiol (50 μM) increases the level of autophagy markers in GBM cells[1]. Honokiol has anticancer effect, and the IC50 values with MDA-MB-231, MDA-MB-468, and MDA-MB-453 cell lines is 16.99 ± 1.28 μM, 15.94 ± 2.35 μM and 20.11 ±3.13 μM respectively. Honokiol (3, 10 μM) produces significant inhibition on the spheroid number and spheroid sizes in the clonogenic assay[2]. Honokiol (0.1-1.0 μM) specifically inhibits washed human platelet aggregation stimulated by collagen, but not by other agonists. honokiol (0.6 and 1.0 μM) can concentration-dependently inhibit the collagen-induced ATP-release reaction in washed human platelets. Honokiol specifically inhibits platelet aggregation and the phosphorylation of Lyn, PLCγ2, and PKC stimulated with convulxin. Honokiol (5, 10 μM) significantly inhibits convulxin-stimulated MAPKs and Akt activation[3]. Honokiol (10, 20 μM) increases ERK1/2 phosphorylation in a dose-dependent manner depending on CaMK II activation[4].
In Vivo Honokiol-NM (40 mg/kg, p.o.) produces superior anticancer effects, and the PCNA, Cyclin D1 and cleaved caspase 3 expressions are 2.12, 1.92 and 1.68-fold significantly altered in this treated group[2].
Cell Assay In cytotoxicity assays, 10,000 cells/well are added to 96 wells plates and incubated overnight, thereafter cells are treated with different concentrations of Honokiol dissolved in dimethylsulphoxide (DMSO). Since Honokiol is not soluble in aqueous solvents, for in vitro studies Honokiol is dissolved in DMSO. To study the possible effect of DMSO on cells, solvent (DMSO) control is used at highest concentration of <0.1%. After 72 h treatment, cells are fixed and cell viability is measured by crystal violet staining (0.05%).
Animal Admin For anticancer in vivo studies, the MDA-MB-231 cells (2 million) are injected into mammary fat tissue. Two weeks after the tumor cell injections, palpable tumors are observed in mammary tissues, which is an indication of tumor formation. Then drug treatment either in free form or in nanomicellar forms is given orally at the dose of 40 and 80 mg/kg daily. The drug treatment is continued for 4 weeks, and the tumor volumes and body weights are recorded weekly. After 4 weeks of treatment, animals are sacrificed; final tumor volumes and weights are measured. These tumors are used for western blot and immunohistochemical analysis. For western blot experiments, tumor tissues are stored at −80°C till the analysis is done. For IHC, tumors are fixed in formal saline.
References

[1]. Chang KH, et al. Honokiol-induced apoptosis and autophagy in glioblastoma multiforme cells. Oncol Lett. 2013 Nov;6(5):1435-1438.

[2]. Godugu C, et al. Honokiol nanomicellar formulation produced increased oral bioavailability and anticancer effects in triple negative breast cancer (TNBC). Colloids Surf B Biointerfaces. 2017 Jan 23;153:208-219

[3]. Lee TY, et al. Honokiol as a specific collagen receptor glycoprotein VI antagonist on human platelets: Functional ex vivo and in vivo studies. Sci Rep. 2017 Jan 5;7:40002

[4]. Zhai H, et al. Honokiol-induced neurite outgrowth promotion depends on activation of extracellular signal-regulated kinases (ERK1/2). Eur J Pharmacol. 2005 Jun 1;516(2):112-7.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 400.1±40.0 °C at 760 mmHg
Melting Point 87.5ºC
Molecular Formula C18H18O2
Molecular Weight 266.334
Flash Point 184.0±21.9 °C
Exact Mass 266.130676
PSA 40.46000
LogP 4.20
Vapour Pressure 0.0±1.0 mmHg at 25°C
Index of Refraction 1.602
Storage condition 2-8°C
Water Solubility DMSO: 36 mg/mL

 Safety Information

Symbol GHS05
GHS05
Signal Word Danger
Hazard Statements H318
Precautionary Statements P280-P305 + P351 + P338 + P310
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi:Irritant
Risk Phrases R41;R51/53
Safety Phrases S26-S39-S61
RIDADR UN 3077 9/PG 3
WGK Germany 3
Hazard Class 9.0
HS Code 2932999099

 Synthetic Route

 Customs

HS Code 2907299090
Summary 2907299090 polyphenols; phenol-alcohols。supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward)。VAT:17.0%。tax rebate rate:9.0%。MFN tariff:5.5%。general tariff:30.0%

 Articles21

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Comparison of counter-current chromatography and preparative high performance liquid chromatography applied to separating minor impurities in drug preparations

J. Chromatogr. A. 1344 , 51-8, (2014)

• Impurity separation of honokiol and quercetin by both preparative HPLC and CCC. • Several performance parameters of separation were compared. • CCC provided larger sample loading, especially for a s...
Moderate concentrations of 4-O-methylhonokiol potentiate GABAA receptor currents stronger than honokiol.

Biochim. Biophys. Acta 1840(10) , 3017-21, (2014)

Magnolia bark preparations from Magnolia officinalis of Asian medicinal systems are known for their muscle relaxant effect and anticonvulsant activity. These CNS related effects are ascribed to the pr...

 Synonyms

3',5-Di-2-propenyl-[1,1'-biphenyl]-2,4'-diol
5,3'-DIALLYL-2,4'-DIHYDROXYBIPHENYL
3,3'-DIALLYL-4,6'-DIHYDROXYBIPHENYL
HONEYSUCKLEFLOWEREXTRACT
5,3'-diallyl-biphenyl-2,4'-diol
Honokiol
[1,1'-Biphenyl]-2,4'-diol, 3',5-di-2-propen-1-yl-
2-(4-hydroxy-3-prop-2-enyl-phenyl)-4-prop-2-enyl-phenol
3',5-Diallyl-2,4'-dihydroxybiphenyl
5,3'-DIALLYL-2,4'-DIHYDROXYDIPHENYL
MFCD00016674
3',5-Diallylbiphenyl-2,4'-diol
5,5'-diallyl-2,4'-dihydroxybiphenyl
3',5-Diallyl-2,4'-biphenyldiol
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Related Compounds: More...
Honokiol DCA
1620160-42-0
Honokiol std.
528-43-8
METHYLHONOKIOL
68592-15-4
Dimethylhonokiol
68592-18-7
4-O-methylhonokiol
68592-19-8
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