| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 250mg | |||
| Other Sizes |
Purity: =98.03%
| Targets |
Natural lignans; HSV-1/herpes simplex virus type 1
The primary molecular targets of Yatein are multifaceted. Its most well-characterized mechanism is the inhibition of herpes simplex virus type 1 (HSV-1) replication. Yatein achieves this by disrupting the viral life cycle at the transcriptional level, specifically by interrupting the expression of immediate-early (α) genes, including the crucial regulatory genes ICP0 and ICP4. This intervention halts the viral replication cascade at an early stage. Additionally, Yatein has demonstrated significant antiproliferative activity by arresting the cell cycle at the G2/M phase in various cancer cell lines. This is partly attributed to its ability to inhibit tubulin polymerization, affecting microtubule dynamics essential for mitosis, and to induce DNA damage. Furthermore, Yatein has been identified as an inhibitor of the cytochrome P450 enzyme CYP3A4, an important drug-metabolizing enzyme, which has implications for its potential to modulate the metabolism of other co-administered drugs. |
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| ln Vitro |
In human lung adenocarcinoma A549 and CL1-5 cells, yatein promotes cell cycle arrest in the G2/M phase (5 μM; 24 hours) and increases G2/M phase-related protein expression (5 μM; 6–12 hours) [3]. In human A549 and CL1-5 cells, atein (5 μM; 6–12 hours) causes DNA damage by triggering the ATM/ATR pathway [3]. Yatein (5 μM; 6 h) inhibits tubulin polymerization, which changes microtubule dynamics [3].
In vitro studies have extensively characterized Yatein's biological activities. It significantly suppresses HSV-1 multiplication in HeLa cells without apparent cytotoxicity, confirming its selective antiviral action. The mechanisms of this antiviral effect are mediated by inhibiting HSV-1 α-gene expression, which includes the critical ICP0 and ICP4 genes, and by arresting HSV-1 DNA synthesis and structural protein expression. In the context of cancer research, Yatein has been shown to promote cell cycle arrest at the G2/M phase in human lung adenocarcinoma A549 and CL1-5 cells at a concentration of 5 μM. This is accompanied by an increase in G2/M phase-related protein expression and affects microtubule dynamics by inhibiting tubulin polymerization. These in vitro findings highlight its potential as a dual-action agent with both antiviral and anticancer properties, making it a valuable probe for studying these disease pathways at the cellular level. |
| ln Vivo |
In a human lung cancer xenograft mice model, yatein (20 mg/kg; intraperitoneal injection; five times per week; for 42 days) showed in vivo antitumor effects [3].
In vivo studies on Yatein are limited, as it is primarily used as a research tool. However, its pharmacological potential has been suggested by its in vitro activities. The compound's antiproliferative and antiviral mechanisms are expected to translate to in vivo models, but specific data on its efficacy in animal models of cancer or viral infection are not widely published. Its ability to inhibit tubulin polymerization and induce cell cycle arrest suggests it could have anti-tumor activity in vivo, similar to other lignans. However, without comprehensive animal studies, its pharmacokinetic and pharmacodynamic profiles in living organisms remain largely uncharacterized. As a natural product with a complex mechanism of action, further in vivo research is necessary to fully explore its therapeutic potential and safety profile. |
| Enzyme Assay |
Isolation of Microtubule Proteins[3]
The A549 and CL1-5 cells (1 × 106 cells) were seeded onto culture dishes (10 cm) overnight and treated with 5 μM Yatein. The cells were harvested through trypsinization and washed with PBS. After centrifugation, the supernatant was removed and the cell pellets were mixed with 200 μL of microtubule stabilizing buffer (1 mM MgCl2, 2 mM Tris-HCl, 2 mM EGTA, and 0.5% Triton-100 in ddH2O) and incubated at RT for 20 min. Subsequently, the mixture was centrifuged at 12,000× g for 10 min (4 °C) to obtain the supernatant (monomer tubulin fraction). The remaining cell pellets were washed using the microtubule stabilizing buffer and lysed in a radioimmunoprecipitation assay buffer containing 10% proteinase inhibitor and 10% phosphatase inhibitor at 4 °C for 30 min to obtain the polymer tubulin fraction. The monomer tubulin and polymer tubulin fractions were transferred into microtubes (1.5 mL) and stored at −20 °C until further analysis. The in vitro enzyme/receptor binding assays for Yatein focus on its antiviral and cytotoxic mechanisms. Its anti-HSV-1 activity is assessed in viral replication assays, where the compound's ability to inhibit the expression of immediate-early viral genes (ICP0 and ICP4) is measured using techniques like quantitative PCR or Western blotting. The compound's effect on tubulin polymerization can be evaluated in cell-free assays using purified tubulin, where the inhibition of polymerization is monitored spectrophotometrically. Additionally, its interaction with the cytochrome P450 enzyme CYP3A4 can be assessed using standard inhibition assays with a fluorogenic or chromogenic substrate. These assays help to define the molecular mechanisms underlying its observed biological effects. |
| Cell Assay |
Cell cycle analysis [3]
Cell Types: A549 cells, CL1-5 cells Tested Concentrations: 1.25 μM, 2.5 μM, 5 μM Incubation Duration: 24 hrs (hours) Experimental Results: Both cell lines induced cell cycle arrest in the G2/M phase. Western Blot Analysis [3] Cell Types: A549 cells, CL1-5 cells Tested Concentrations: 5 μM Incubation Duration: 6 hrs (hours), 12 hrs (hours) Experimental Results: Up-regulates the expression of cyclin B1, but does not up-regulate the expression of Cdc2 and Cdc25c, and induces Cdc2 phosphorylation. Cellular assays for Yatein are conducted in various cell lines to evaluate its antiviral and anticancer activities. For antiviral studies, HeLa cells are infected with HSV-1 and treated with Yatein. Viral replication is quantified by plaque assays or by measuring viral DNA or RNA levels. Cytotoxicity is assessed using standard cell viability assays like MTT to ensure the observed antiviral effects are not due to general toxicity. For anticancer studies, cell lines such as A549 and CL1-5 are treated with Yatein, and cell cycle analysis is performed using flow cytometry to measure the accumulation of cells in the G2/M phase. The expression of cell cycle-related proteins is also examined by Western blotting. These cell-based assays are crucial for confirming the compound's mechanism of action and determining its potency. |
| Animal Protocol |
Animal/Disease Models: Male NOD/SCID (severe combined immunodeficient) mouse (6-8 weeks), A549 cell xenografts [3]
Doses: 20 mg/kg Route of Administration: intraperitoneal (ip) injection, 5 times a week for 42 days Experimental Results: Significant tumor growth Slows down and modestly increases cyclin B1 expression and Cdc2 phosphorylation. In Vivo Antitumor Activity[3] The A549-luc cells were mixed with Matrigel (Sigma-Aldrich) at a 1:1 ratio. The cells were injected subcutaneously into the back of nonobese diabetic and severe combined immunodeficiency (NOD/SCID) mice (male, 6–8 weeks old) at a density of 3.5 × 106 cells/mouse. Tumors were allowed to grow for 10 days and were then treated with an intraperitoneal (i.p.) injection of either 0.5% DMSO in ddH2O to the mice in the vehicle control group (n = 5) or 20 mg/kg of yatein (dissolved in 0.5% DMSO in ddH2O) to the mice in the yatein group (n = 5). The tumor-bearing mice were sacrificed after 42 days. Tumor volume was measured five times/week and calculated using the following formula: Length × width × thickness × 0.5 (mm3). An IVIS (Caliper lifescience IVIS Spectrum CT) was used to analyze the luminescence of tumor tissue. In vivo animal experiments for Yatein are not well-documented in the available literature. As a research-grade compound, its primary use is in vitro to elucidate mechanisms of action. While its antiproliferative and antiviral activities suggest potential for in vivo efficacy, specific animal models, such as xenograft models for cancer or mouse models of HSV-1 infection, have not been widely reported. The lack of published in vivo data underscores that Yatein is still in the early stages of pharmacological investigation and is not yet ready for preclinical development as a therapeutic candidate. |
| ADME/Pharmacokinetics |
Yatein is a small molecule with a molecular weight of 400.4 g/mol and a molecular formula of C22H24O7. Its physicochemical properties, such as solubility, are typical of lignans. It is recommended to be stored as a powder at -20°C for up to 3 years or in solvent at -80°C for up to 6 months, and it requires protection from light. It may dissolve in DMSO, and for in vivo studies, common formulations include suspensions in 0.5% carboxymethylcellulose sodium (CMC-Na) for oral administration. Detailed pharmacokinetic parameters, such as bioavailability, half-life, and tissue distribution, have not been extensively reported, as its primary application remains as a research tool.
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| Toxicity/Toxicokinetics |
Comprehensive toxicology data for Yatein are not widely available. However, in vitro studies have indicated that it does not exhibit apparent cytotoxicity in HeLa cells at concentrations effective against HSV-1. Cytotoxicity data for other human cell lines, such as A431, Col2, HT, KB, and KB-V1, have been reported with ED50 values ranging from >20 μg/mL to as low as 0.06 μg/mL, indicating variable potency depending on the cell type. These findings suggest that Yatein's cytotoxic effects may be cell-type specific and dose-dependent. As a research compound, comprehensive toxicological evaluations, including genotoxicity, cardiotoxicity, and long-term safety studies, have not been published, and it is not intended for human or veterinary use.
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| References |
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| Additional Infomation |
Dihydroanhydropodorhizol is a buty-4-lactone compound with 3,4,5-trimethoxybenzyl and (1,3-benzodioxane-5-yl)methyl substituents at positions 3 and 4, respectively. It is a plant metabolite. It is a lignan, buty-4-lactone, methoxybenzene compound, and benzodioxane compound. It has been reported that yatein is present in Eleutherococcus divaricatus, Illigera luzonensis, and other organisms with relevant data.
Yatein is a bioactive lignan of significant research interest due to its dual antiviral and anticancer activities. Its primary mechanism involves suppressing HSV-1 replication by interrupting immediate-early gene expression and inducing G2/M cell cycle arrest through the inhibition of tubulin polymerization. It also inhibits the drug-metabolizing enzyme CYP3A4. Despite its promising in vitro profile, Yatein remains a research-grade compound and has not progressed to clinical trials. It is not approved for therapeutic use and is exclusively available for laboratory research purposes. Its value lies in its potential as a lead compound for developing novel antiviral and anticancer therapies and as a pharmacological tool to study the molecular mechanisms of these diseases. |
| Molecular Formula |
C22H24O7
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|---|---|
| Molecular Weight |
400.427
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| Exact Mass |
400.152
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| Elemental Analysis |
C, 65.99; H, 6.04; O, 27.97
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| CAS # |
40456-50-6
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| PubChem CID |
442835
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| Appearance |
Colorless to light yellow ointment
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
564.9±45.0 °C at 760 mmHg
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| Flash Point |
246.2±28.8 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.577
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| Source |
C. formosana leaves ; Fitzroya cupressoides (Molina) I. M. Johnst.; Austrocedrus chilensis (D. Don) Pic.Serm. & Bizzarri; Chamaecyparis obtusa; Chilean Cupressaceae
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| LogP |
3.06
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
29
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| Complexity |
541
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| Defined Atom Stereocenter Count |
2
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| SMILES |
COC1=C(C(=CC(=C1)C[C@@H]2[C@@H](CC3=CC4=C(C=C3)OCO4)COC2=O)OC)OC
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| InChi Key |
GMLDZDDTZKXJLU-JKSUJKDBSA-N
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| InChi Code |
InChI=1S/C22H24O7/c1-24-19-9-14(10-20(25-2)21(19)26-3)7-16-15(11-27-22(16)23)6-13-4-5-17-18(8-13)29-12-28-17/h4-5,8-10,15-16H,6-7,11-12H2,1-3H3/t15-,16+/m0/s1
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| Chemical Name |
(3R,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one
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| Synonyms |
Dihydroanhydropodorhizol; (-)-yatein; (-)-deoxypodorhizone; Deoxypodorhizone; CHEBI:4553; CHEMBL471067; Yatein
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4973 mL | 12.4866 mL | 24.9732 mL | |
| 5 mM | 0.4995 mL | 2.4973 mL | 4.9946 mL | |
| 10 mM | 0.2497 mL | 1.2487 mL | 2.4973 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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