Ophiopogonin D is a C29 steroidal glycoside that occurs naturally and has the potential to be used in the treatment of cardiovascular and inflammatory conditions.
Physicochemical Properties
| Molecular Formula | C₄₄H₇₀O₁₆ |
| Molecular Weight | 855.02 |
| Exact Mass | 854.466 |
| Elemental Analysis | C, 61.81; H, 8.25; O, 29.94 |
| CAS # | 945619-74-9 |
| Related CAS # | 945619-74-9 |
| PubChem CID | 46173859 |
| Appearance | White to off-white solid powder |
| Density | 1.4±0.1 g/cm3 |
| Index of Refraction | 1.617 |
| LogP | 5.54 |
| Hydrogen Bond Donor Count | 8 |
| Hydrogen Bond Acceptor Count | 16 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 60 |
| Complexity | 1590 |
| Defined Atom Stereocenter Count | 26 |
| SMILES | C[C@]12CC[C@@H]3[C@@]4(C(=CC[C@H]3[C@@H]1C[C@@H]1O[C@@]3(OC[C@H](C)CC3)[C@H]([C@H]21)C)C[C@@H](O)C[C@H]4O[C@@H]1O[C@H](C)[C@H](O)[C@H](O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O)C |
| InChi Key | FHKHGNFKBPFJCB-LYLKFOBISA-N |
| InChi Code | InChI=1S/C44H70O16/c1-18-9-12-44(54-16-18)19(2)30-28(60-44)15-26-24-8-7-22-13-23(45)14-29(43(22,6)25(24)10-11-42(26,30)5)57-41-38(59-40-36(52)34(50)31(47)20(3)55-40)37(32(48)21(4)56-41)58-39-35(51)33(49)27(46)17-53-39/h7,18-21,23-41,45-52H,8-17H2,1-6H3/t18-,19+,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 |
| Chemical Name | (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-2-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,14R,16R)-16-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-14-yl]oxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol |
| Synonyms | Ophiopogonin-D; Ophiopogonin D; Deacetylophiopogonin-C; Deacetylophiopogonin C; OJV V; OJV-V; OJVV |
| HS Tariff Code | 2934.99.9001 |
| 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) |
Biological Activity
| Targets | PPARα; NF-κB |
| Enzyme Assay | Assays measuring the enzyme-catalyzed phosphorylation of GST-IκBα are performed by adding enzyme (a final concentration of 0.5 μg/mL) at 30 ℃ to solutions of 100 μg/mL GST- IκBα and 5 μM [33P]ATP in 40 mM Tris HCl, pH 7.5, containing 4 mM MgCl2, 34mM sodium phosphate, 3 mM NaCl, 0.6 mM potassium phosphate, 1 mM KCl, 1 mM dithiothreitol, 3% (w/v) glycerol, and 250 μg/mL bovine serum albumin. The specific activity of [33P]ATP used in the assay is 100 Ci/mmol. After 5 min, the kinase reactions are stopped by the addition of 2× Laemmli sample buffer and heat-treated at 90 ℃ for 1 min. The samples are then loaded on to NuPAGE 10% BisTris gels. After completion of SDS-PAGE, gels are dried on a slab gel dryer. The bands are then detected using a 445Si PhosphorImager, and the radioactivity is quantified using ImageQuant software. Under these conditions, the degree of phosphorylation of GST-IκBα is linear with time and concentration of enzyme. |
| Cell Assay | 1×105 cells (Metastatic human melanoma cells SK-MEL-5) per well are plated in six-well plates with 10% fetal bovine serum medium overnight to allow cell adhesion. Cells ae cultured in medium containing BMS-345541 for 72 hours of treatment. Cells are counted with a hemocytometer. |
| References |
[1]. Homo-aro-cholestane, furostane and spirostane saponins from the tubers of Ophiopogonjaponicus. Phytochemistry. 2017 Apr;136:125-132. [2]. Ophiopogonin D and EETs ameliorate Ang II-induced inflammatory responses via activating PPARα in HUVECs. Biochem Biophys Res Commun. 2017 Aug 19;490(2):123-133. |
| Additional Infomation |
Ophiopogonin D is a steroid saponin. Ophiopogonin D has been reported in Liriope muscari, Ophiopogon jaburan, and Ophiopogon japonicus with data available. |
Solubility Data
| Solubility (In Vitro) |
DMSO: ~100 mg/mL (~117 mM) Ethanol: ~100 mg/mL (~117 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (2.92 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly. (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 |