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4-O-Methylhonokiol

CAS# 68592-15-4

4-O-Methylhonokiol

Catalog No. BCN8474----Order now to get a substantial discount!

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Quality Control of 4-O-Methylhonokiol

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Chemical structure

4-O-Methylhonokiol

3D structure

Chemical Properties of 4-O-Methylhonokiol

Cas No. 68592-15-4 SDF Download SDF
PubChem ID 155160 Appearance Bright yellow oil
Formula C19H20O2 M.Wt 280.367
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 2-(4-methoxy-3-prop-2-enylphenyl)-4-prop-2-enylphenol
SMILES COC1=C(C=C(C=C1)C2=C(C=CC(=C2)CC=C)O)CC=C
Standard InChIKey OQFHJKZVOALSPV-UHFFFAOYSA-N
Standard InChI InChI=1S/C19H20O2/c1-4-6-14-8-10-18(20)17(12-14)15-9-11-19(21-3)16(13-15)7-5-2/h4-5,8-13,20H,1-2,6-7H2,3H3
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

4-O-Methylhonokiol Dilution Calculator

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4-O-Methylhonokiol Molarity Calculator

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Preparing Stock Solutions of 4-O-Methylhonokiol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.5668 mL 17.8338 mL 35.6675 mL 71.3351 mL 89.1688 mL
5 mM 0.7134 mL 3.5668 mL 7.1335 mL 14.267 mL 17.8338 mL
10 mM 0.3567 mL 1.7834 mL 3.5668 mL 7.1335 mL 8.9169 mL
50 mM 0.0713 mL 0.3567 mL 0.7134 mL 1.4267 mL 1.7834 mL
100 mM 0.0357 mL 0.1783 mL 0.3567 mL 0.7134 mL 0.8917 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 4-O-Methylhonokiol

RANKL-induced osteoclastogenesis is suppressed by 4-O-methylhonokiol in bone marrow-derived macrophages.[Pubmed:28736799]

Arch Pharm Res. 2017 Aug;40(8):933-942.

Magnolol, honokiol, and obovatol are well known bioactive constituents of the bark of Magnolia officinalis and have been reported to have beneficial effects in various diseases. We recently isolated a novel active compound, 4-O-Methylhonokiol (4-O-MH) from the ethanol extract of M. officinalis, which was previously reported to have pharmacological effects including anti-inflammatory, anti-oxidative, and anti-aging activities. Here, we examined the pharmacological properties of 4-O-MH on osteoblast (bone-forming cells) and osteoclast (bone-resorbing cells) differentiation, and its underlying signaling pathways in primary cultured pre-osteoblasts and bone marrow macrophages. Our results showed that 4-O-MH did not affect cell viability in pre-osteoblasts and did not influence osteoblast differentiation and mineralized nodule formation, as assessed by alkaline phosphatase activity and Alizarin red staining. However, 4-O-MH significantly inhibited TRAP-positive multinuclear osteoclasts and F-actin ring formation during Receptor activator of NF-kappaB ligand (RANKL)-mediated osteoclastogenesis without cytotoxicity. In addition, 4-O-MH suppressed RANKL-induced critical factors (c-Fos, NF-ATc1, TRAP, and ITB3) for osteoclast differentiation and function. Furthermore, RANKL-mediated signaling, including ERK1/2, AKT, and NF-kB pathways was attenuated by 4-O-MH. Taken together, 4-O-MH has an inhibitory role in RANKL-mediated osteoclastogenesis but not osteoblast differentiation, and our findings also suggest that 4-O-MH is a potential therapeutic agent for bone-destructive diseases such as osteoporosis, alveolar bone resorption, and osteoarthritis.

Novel positive allosteric modulators of GABAA receptors with anesthetic activity.[Pubmed:27198062]

Sci Rep. 2016 May 20;6:25943.

GABAA receptors are the main inhibitory neurotransmitter receptors in the brain and are targets for numerous clinically important drugs such as benzodiazepines, anxiolytics and anesthetics. We previously identified novel ligands of the classical benzodiazepine binding pocket in alpha1beta2gamma2 GABAA receptors using an experiment-guided virtual screening (EGVS) method. This screen also identified novel ligands for intramembrane low affinity diazepam site(s). In the current study we have further characterized compounds 31 and 132 identified with EGVS as well as 4-O-Methylhonokiol. We investigated the site of action of these compounds in alpha1beta2gamma2 GABAA receptors expressed in Xenopus laevis oocytes using voltage-clamp electrophysiology combined with a benzodiazepine site antagonist and transmembrane domain mutations. All three compounds act mainly through the two beta+/alpha- subunit transmembrane interfaces of the GABAA receptors. We then used concatenated receptors to dissect the involvement of individual beta+/alpha- interfaces. We further demonstrated that these compounds have anesthetic activity in a small aquatic animal model, Xenopus laevis tadpoles. The newly identified compounds may serve as scaffolds for the development of novel anesthetics.

4-O-Methylhonokiol Protects HaCaT Cells from TGF-beta1-Induced Cell Cycle Arrest by Regulating Canonical and Non-Canonical Pathways of TGF-beta Signaling.[Pubmed:28190316]

Biomol Ther (Seoul). 2017 Jul 1;25(4):417-426.

4-O-Methylhonokiol, a neolignan compound from Magnolia Officinalis, has been reported to have various biological activities including hair growth promoting effect. However, although transforming growth factor-beta (TGF-beta) signal pathway has an essential role in the regression induction of hair growth, the effect of 4-O-Methylhonokiol on the TGF-beta signal pathway has not yet been elucidated. We thus examined the effect of 4-O-Methylhonokiol on TGF-beta-induced canonical and noncanonical pathways in HaCaT human keratinocytes. When HaCaT cells were pretreated with 4-O-Methylhonokiol, TGF-beta1-induced G1/G0 phase arrest and TGF-beta1-induced p21 expression were decreased. Moreover, 4-O-Methylhonokiol inhibited nuclear translocation of Smad2/3, Smad4 and Sp1 in TGF-beta1-induced canonical pathway. We observed that ERK phosphorylation by TGF-beta1 was significantly attenuated by treatment with 4-O-Methylhonokiol. 4-O-Methylhonokiol inhibited TGF-beta1-induced reactive oxygen species (ROS) production and reduced the increase of NADPH oxidase 4 (NOX4) mRNA level in TGF-beta1-induced noncanonical pathway. These results indicate that 4-O-Methylhonokiol could inhibit TGF-beta1-induced cell cycle arrest through inhibition of canonical and noncanonical pathways in human keratinocyte HaCaT cell and that 4-O-Methylhonokiol might have protective action on TGF-beta1-induced cell cycle arrest.

Antitumor activity of 4-O-Methylhonokiol in human oral cancer cells is mediated via ROS generation, disruption of mitochondrial potential, cell cycle arrest and modulation of Bcl-2/Bax proteins.[Pubmed:29332355]

J BUON. 2017 Nov-Dec;22(6):1577-1581.

PURPOSE: The plant-derived natural product 4-O-Methylhonokiol (MH) has been reported to possess tremendous pharmacological potential ranging from neuroprotection to anticancer activity. However, the anticancer activity of MH in oral squamous cell carcinoma (OSCC) cells has not been evaluated. In the present study, MH was evaluated for its anticancer activity against OSSC PE/CA-PJ41 cells and the possible underlying mechanism was determined. METHODS: Cell cytotoxicity was evaluated by colorimetrybased MTT assay while the effects on cell cycle phase distribution were assessed by flow cytometry. Effects of MH on reactive oxygen species (ROS) production and mitochondrial membrane potential (MMP) were evaluated by flow cytometry. Western blot assay was finally utilized to study the effects of MH on key cancer and apoptosis-linked proteins including Bax and Bcl-2. RESULTS: MH induced cytotoxicity in OSCC PE/CA-PJ41 cells with an observed IC50 of 1.25 muM. It also caused significant increase in the production of ROS and disrupted the MMP in a dose-dependent manner. The reduction in MMP favored mitochondrial apoptotic pathway which was further confirmed by determining the expression of Bax and Bcl-2. It was observed that MH downregulated the expression of Bax and upregulated the expression of MMP, ultimately leading to apoptosis of OSSC PE/CA-PJ41 cells. Additionally, MH also caused G2/M cell cycle arrest in a dose-dependent manner. CONCLUSION: Taken together, our results indicate that 4-Omethylhonokiol may prove a potential natural anticancer molecule against human oral carcinoma cells.

Phytochemicals as inhibitors of NF-kappaB for treatment of Alzheimer's disease.[Pubmed:29179999]

Pharmacol Res. 2018 Mar;129:262-273.

Alzheimer's disease (AD) is the most prevalent form of dementia. The exact pathophysiology of this disease remains incompletely understood and safe and effective therapies are required. AD is highly correlated with neuroinflammation and oxidative stress in brain causing neuronal loss. Nuclear factor of activated B-cells (NF-kappaB) is involved in physiological inflammatory processes and thus representing a promising target for inflammation-based AD therapy. Phytochemicals are able to interfere with the NF-kappaB pathway. They inhibit the phosphorylation or the ubiquitination of signaling molecules, and thus, inhibit the degradation of IkappaB. The translocation of NF-kappaB to the nucleus and subsequent transcription of pro-inflammatory cytokines are inhibited by the actions of phytochemicals. Additionally, natural compounds preventing the interaction of NF-kappaB can block NF-kappaB's transcriptional activity by inhibiting its binding to target DNA. Many polyphenols including curcumin, resveratrol, pterostilbene, punicalagin, macranthoin G, salidroside, 4-O-Methylhonokiol, lycopene, genistein, obovatol and gallic acid were reported as potent NF-kappaB inhibitors for AD treatment. Several alkaloids such as galantamine, glaucocalyxin B, tetrandrine, berberine, oridonin, anatabine have been shown anti-inflammatory effects in AD models in vitro as well as in vivo. Besides, vitamins, tanshinone IIA, artemisinin, dihydroasparagusic acid, geniposide, xanthoceraside, l-theranine, 1,8-cineole and paeoniflorin were described as promising NF-kappaB inhibitors. In conclusion, natural products from plants represent interesting candidates for AD treatment. They may qualify as promising compounds for the development of derivatives providing enhanced pharmacological features.

Description

4-O-Methyl honokiol is a natural neolignan isolated from Magnolia officinalis, acts as a PPARγ agonist, and inhibtis NF-κB activity, used for cancer and inflammation research.

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