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| 5mg |
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| Targets |
Ophiopogonin D' targets multiple proteins and enzymes. It activates SIRT1 (sirtuin 1), a NAD⁺-dependent deacetylase involved in cellular stress responses, metabolism, and aging. The compound also noncompetitively inhibits UGT1A6 and UGT1A10, two important UDP-glucuronosyltransferases involved in phase II drug metabolism. As a C₂₉ steroidal glycoside, Ophiopogonin D' interacts with cellular membranes and may modulate various signaling pathways. Its cytotoxic activity against cancer cells is likely mediated through SIRT1 activation and other mechanisms, although the precise molecular targets responsible for its anticancer effects require further elucidation.
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| ln Vitro |
In vitro studies have demonstrated that Ophiopogonin D' exhibits potent cytotoxic activity against two human tumor cell lines: MG-63 (osteosarcoma) and SNU387 (hepatocellular carcinoma), with IC₅₀ values of 3.09 μM and 3.63 μM, respectively. The compound activates SIRT1 in a dose-dependent fashion, suggesting that its biological effects may be mediated through sirtuin activation. Ophiopogonin D' also noncompetitively inhibits UGT1A6 and UGT1A10, indicating potential interactions with drug metabolism pathways. The compound's potent cytotoxicity against cancer cell lines makes it a promising lead compound for anticancer drug development.
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| ln Vivo |
In vivo activity data for Ophiopogonin D' are limited, as the compound is predominantly used in in vitro research settings. Based on its potent in vitro cytotoxicity and SIRT1 activation, the compound may have potential therapeutic applications in cancer and metabolic diseases. However, specific published in vivo studies evaluating the efficacy and pharmacokinetics of Ophiopogonin D' in animal models are not well documented. The compound's complex steroidal glycoside structure may present challenges for oral bioavailability and systemic delivery.
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| Enzyme Assay |
In vitro non-cell enzyme assays for Ophiopogonin D' typically involve measuring SIRT1 activation using fluorometric or luminescent assays. Purified SIRT1 enzyme is incubated with the compound, NAD⁺, and a fluorogenic peptide substrate, and deacetylase activity is measured by fluorescence intensity. UGT inhibition assays are performed using recombinant UGT1A6 and UGT1A10 enzymes incubated with the compound and a fluorogenic substrate (e.g., 4-methylumbelliferone), with product formation measured by fluorescence or HPLC. IC₅₀ values are calculated from dose-response curves.
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| Cell Assay |
In vitro cell-based assays for Ophiopogonin D' use MG-63 osteosarcoma cells and SNU387 hepatocellular carcinoma cells. Cells are cultured in appropriate media and treated with Ophiopogonin D' at varying concentrations for 24-72 hours. Cell viability is assessed using MTT, CCK-8, or SRB assays to determine IC₅₀ values. Apoptosis is evaluated by Annexin V/PI staining and flow cytometry. SIRT1 activation is assessed by measuring acetylation levels of SIRT1 substrates (e.g., p53, FOXO) by Western blotting using acetylation-specific antibodies.
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| Animal Protocol |
In vivo animal studies for Ophiopogonin D' are limited. Standard protocols for evaluating anticancer compounds would involve administration of the compound to tumor-bearing mouse models (xenograft models using MG-63 or SNU387 cells) via intraperitoneal or intravenous injection. Parameters assessed would include tumor volume measurements, survival analysis, histopathological examination of tumors, assessment of SIRT1 activation and apoptosis markers in tumor tissues, and evaluation of systemic toxicity. However, specific published in vivo data for this compound are not well documented.
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| ADME/Pharmacokinetics |
Ophiopogonin D' has a molecular weight of 855.02 g/mol and a molecular formula of C₄₄H₇₀O₁₆. It has a high LogP of 6.69, indicating significant lipophilicity. The compound should be stored at -20°C. It is soluble in organic solvents such as DMSO. Due to its high molecular weight and complex glycosidic structure, Ophiopogonin D' is expected to have poor oral bioavailability. The compound's pharmacokinetic properties, including absorption, distribution, metabolism, and excretion, have not been extensively characterized.
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| Toxicity/Toxicokinetics |
The toxicity profile of Ophiopogonin D' has not been comprehensively evaluated in published studies. As a natural component of Ophiopogon japonicus, which has a long history of use in traditional Chinese medicine, it is generally considered to have low toxicity at therapeutic doses. However, the compound's potent cytotoxicity against cancer cells suggests that it may have significant biological activity that requires careful evaluation. The compound is classified as a research reagent and is not intended for human therapeutic use. Comprehensive toxicological studies have not been reported.
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| References |
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| Additional Infomation |
See also: Ophiopogonin D (note moved to).
Ophiopogonin D' is a rare naturally occurring C₂₉ steroidal glycoside extracted from the tubers of Ophiopogon japonicus. It is also known as Diosgenin 3-O-[α-L-rhamnopyranosyl-(1-2)][β-D-xylopyranosyl-(1-3)]-β-D-glucopyranoside. The compound activates SIRT1 in a dose-dependent fashion and noncompetitively inhibits UGT1A6 and UGT1A10. It exhibits potent cytotoxic activity against MG-63 osteosarcoma and SNU387 hepatocellular carcinoma cells. Not approved for clinical use; intended for research purposes only. |
| Molecular Formula |
C44H70O16
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|---|---|
| Molecular Weight |
855.0170
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| Exact Mass |
854.466
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| CAS # |
65604-80-0
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| PubChem CID |
10033524
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Index of Refraction |
1.618
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| LogP |
6.69
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| Hydrogen Bond Donor Count |
8
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| Hydrogen Bond Acceptor Count |
16
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
60
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| Complexity |
1570
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| Defined Atom Stereocenter Count |
25
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| SMILES |
C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O)C)C)C)OC1
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| InChi Key |
DQYACEDUQHWXQZ-QOYNBSPSSA-N
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| InChi Code |
InChI=1S/C44H70O16/c1-19-8-13-44(54-17-19)20(2)30-28(60-44)15-26-24-7-6-22-14-23(9-11-42(22,4)25(24)10-12-43(26,30)5)56-41-38(59-40-36(52)34(50)31(47)21(3)55-40)37(33(49)29(16-45)57-41)58-39-35(51)32(48)27(46)18-53-39/h6,19-21,23-41,45-52H,7-18H2,1-5H3/t19-,20+,21+,23+,24-,25+,26+,27-,28+,29-,30+,31+,32+,33-,34-,35-,36-,37+,38-,39+,40+,41-,42+,43+,44-/m1/s1
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| Chemical Name |
(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
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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 | 1.1696 mL | 5.8478 mL | 11.6956 mL | |
| 5 mM | 0.2339 mL | 1.1696 mL | 2.3391 mL | |
| 10 mM | 0.1170 mL | 0.5848 mL | 1.1696 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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