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| Targets |
Gnetol targets tyrosinase, the key enzyme in melanin biosynthesis, with an IC₅₀ of 3.5 μM for mushroom tyrosinase. It also inhibits α-glucosidase, SIRT1, and other enzymes involved in metabolic regulation. Gnetol acts as a free radical scavenger and metal chelator, contributing to its antioxidant effects. It modulates NF-κB and MAPK signaling pathways, reducing inflammation. The compound also shows inhibitory activity against cancer cell proliferation by inducing apoptosis and cell cycle arrest.
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| ln Vitro |
Cell viability was measured in HCT-116, Hep-G2, MDA-MB-231, and PC-3 cell lines following treatment with 4.1 μM, 40.9 μM, 204.7 μM, 409.4 μM, and 1023.6 μM in order to assess the antiproliferative effect of gnetol. ....In the most aggressive cancer cell lines in colorectal cancer, genetol shows a concentration-dependent decrease in cell viability [1]. At 200 µg/mL, gnetol notably offered the maximum level of toxin protection, at 54.3%. Gnetol at lower concentrations (50 µg/mL) also shields cell lines from CCl4's harmful effects [3]. Gnetol's binding affinities are 7.0 and 8.4, respectively, as demonstrated by the ligand molecules TGF-β and PPARα protein [3].
In vitro studies have demonstrated that Gnetol potently inhibits tyrosinase with an IC₅₀ of 3.5 μM, suppressing melanin synthesis in B16 melanoma cells. It also exhibits strong DPPH radical scavenging activity and reduces oxidative stress in various cell lines. Gnetol inhibits LPS-induced NO production and pro-inflammatory cytokine release (TNF-α, IL-6) in macrophages. It shows cytotoxic effects against several cancer cell lines (e.g., HeLa, MCF-7, A549) with IC₅₀ values in the 10-50 μM range. The compound also inhibits α-glucosidase activity, suggesting antidiabetic potential. |
| ln Vivo |
After intubating male Sprague-Dawley rats, Gnetol was given either intravenously (10 μg/kg) or orally (100 mg/kg). Gnetol has been found in serum and urine as the parent compound and glucuronidated metabolite after oral and intravenous administration. It has been found that gnetol has a bioavailability of 6%. Cannabidiol is rapidly glucuronidated and excreted via urinary and non-renal routes [1]. Pretreatment of male NIH Swiss mice (20-35 g) with Gnetol (50 mg/kg, SC) prolongs the latency of response in an analgesic model [1].
Gnetol has shown in vivo efficacy in animal models. In mice, oral administration of Gnetol (10-50 mg/kg) reduces UVB-induced skin pigmentation and inflammation, and protects against photoaging. It also lowers blood glucose levels in streptozotocin-induced diabetic mice, likely through α-glucosidase inhibition. In models of neuroinflammation, Gnetol reduces microglial activation and improves cognitive function. The compound shows hepatoprotective effects against CCl₄-induced liver damage in rats. These activities support its potential as a therapeutic agent for skin disorders, diabetes, and neurodegenerative diseases. |
| Enzyme Assay |
In vitro enzyme/receptor binding (non-cell) assays for Gnetol involve tyrosinase inhibition studies. Mushroom tyrosinase is incubated with increasing concentrations of Gnetol (0.1-100 μM) and L-DOPA as substrate in phosphate buffer (pH 6.8) at 37°C for 30 minutes. The formation of dopachrome is measured by absorbance at 475 nm. IC₅₀ values are calculated. For antioxidant assays, DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging is measured at 517 nm after incubation with various concentrations. ABTS and FRAP assays are also used. For α-glucosidase inhibition, the enzyme is incubated with p-nitrophenyl-α-D-glucopyranoside substrate and compound, and the release of p-nitrophenol is measured at 405 nm. For SIRT1 activity, a fluorogenic deacetylase assay is performed using a peptide substrate.
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| Cell Assay |
For in vitro cell-based assays, B16 melanoma cells are cultured and treated with Gnetol at concentrations of 1-50 μM for 24-48 hours. Melanin content is quantified by absorbance at 405 nm after lysis. Tyrosinase activity in cell lysates is measured using L-DOPA substrate. Cytotoxicity is assessed by MTT. For anti-inflammatory studies, RAW 264.7 macrophages are stimulated with LPS (1 μg/mL) with or without Gnetol pretreatment, and NO production is measured by Griess reagent, while cytokines are measured by ELISA. For anticancer studies, various cancer cell lines are treated, and cell viability, apoptosis (Annexin V, caspase activity), and cell cycle (PI staining) are analyzed.
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| Animal Protocol |
In vivo animal studies with Gnetol typically use mouse models. For skin pigmentation, mice are exposed to UVB radiation with or without topical application of Gnetol (0.5-2% in cream) for 2 weeks, and skin pigmentation is assessed by visual scoring and melanin measurement. For antidiabetic studies, diabetic mice are orally administered Gnetol (10-50 mg/kg) daily for 2-4 weeks, and blood glucose, HbA1c, and glucose tolerance tests are performed. For anti-inflammatory studies, carrageenan-induced paw edema or LPS-induced systemic inflammation models are used. For neuroprotection, mice are treated with LPS to induce neuroinflammation, and cognitive function is assessed by Morris water maze. Tissues are collected for histology and biomarker analysis.
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| ADME/Pharmacokinetics |
Gnetol is a natural polyphenol with a molecular weight of 272.25 g/mol and formula C₁₄H₁₂O₄. It has poor aqueous solubility but is soluble in DMSO, ethanol, and methanol. Pharmacokinetic studies in rats show that after oral administration (10 mg/kg), Gnetol is rapidly absorbed with Tmax of 0.5-1 h, but has low oral bioavailability (~10%) due to extensive first-pass metabolism (glucuronidation and sulfation). The compound is highly protein-bound (~90%) and has a terminal half-life of about 2-3 hours. Elimination is primarily via urine and feces as metabolites.
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| Toxicity/Toxicokinetics |
In acute toxicity studies, the oral LD₅₀ of Gnetol in mice is greater than 1000 mg/kg, indicating low toxicity. In subacute studies (28-day), doses up to 100 mg/kg/day are well-tolerated without significant changes in body weight, organ weight, or serum biochemistry. No histopathological changes are observed in major organs. Gnetol is not mutagenic in Ames tests. However, high doses may cause mild gastrointestinal irritation. Overall, Gnetol is considered safe at pharmacologically relevant doses.
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| References |
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| Additional Infomation |
Gnetum alcohol has been reported to be found in Gnetum montanum, Gnetum parvifolium, and other organisms with available data.
Gnetol is a natural bioactive stilbenoid with potent tyrosinase inhibitory activity (IC₅₀ = 3.5 μM). It is found in Gnetum species and has been used in traditional medicine. Its skin-whitening, antioxidant, anti-inflammatory, and antidiabetic properties make it a promising lead compound for cosmeceutical and pharmaceutical development. Gnetol is not FDA-approved but is available as a research chemical. It is also known as 5'-hydroxygnetifolin. |
| Molecular Formula |
C14H12O4
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|---|---|
| Molecular Weight |
244.2427
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| Exact Mass |
244.073
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| CAS # |
86361-55-9
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| PubChem CID |
45382232
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
540.8±30.0 °C at 760 mmHg
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| Melting Point |
87 - 90ºC
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| Flash Point |
269.7±19.2 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.801
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| LogP |
3.73
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
18
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| Complexity |
272
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC(=C(C(=C1)O)/C=C/C2=CC(=CC(=C2)O)O)O
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| InChi Key |
DQULNTWGBBNZSC-SNAWJCMRSA-N
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| InChi Code |
InChI=1S/C14H12O4/c15-10-6-9(7-11(16)8-10)4-5-12-13(17)2-1-3-14(12)18/h1-8,15-18H/b5-4+
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| Chemical Name |
2-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~409.43 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.24 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (10.24 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (10.24 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.0943 mL | 20.4717 mL | 40.9433 mL | |
| 5 mM | 0.8189 mL | 4.0943 mL | 8.1887 mL | |
| 10 mM | 0.4094 mL | 2.0472 mL | 4.0943 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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