 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C51H84O22 |
| Molecular Weight | 1049.20 |
| Exact Mass | 1048.545 |
| CAS # | 55056-80-9 |
| PubChem CID | 441891 |
| Appearance | White to off-white solid powder |
| Density | 1.5±0.1 g/cm3 |
| Index of Refraction | 1.632 |
| LogP | 3.64 |
| Hydrogen Bond Donor Count | 13 |
| Hydrogen Bond Acceptor Count | 22 |
| Rotatable Bond Count | 14 |
| Heavy Atom Count | 73 |
| Complexity | 1900 |
| Defined Atom Stereocenter Count | 31 |
| SMILES | C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O[C@H]7[C@@H]([C@@H]([C@H]([C@@H](O7)C)O)O)O)O)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)C)C)O[C@@]1(CC[C@@H](C)CO[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O |
| InChi Key | LVTJOONKWUXEFR-UEZXSUPNSA-N |
| InChi Code | InChI=1S/C51H84O22/c1-20(19-65-45-39(60)38(59)35(56)30(17-52)69-45)9-14-51(64)21(2)32-29(73-51)16-28-26-8-7-24-15-25(10-12-49(24,5)27(26)11-13-50(28,32)6)68-48-44(72-47-41(62)37(58)34(55)23(4)67-47)42(63)43(31(18-53)70-48)71-46-40(61)36(57)33(54)22(3)66-46/h7,20-23,25-48,52-64H,8-19H2,1-6H3/t20-,21+,22+,23+,25+,26-,27+,28+,29+,30-,31-,32+,33+,34+,35-,36-,37-,38+,39-,40-,41-,42+,43-,44-,45-,46+,47+,48-,49+,50+,51-/m1/s1 |
| Chemical Name | (2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-6-hydroxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-en-16-yl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol |
| 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 |
| 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 | Human Endogenous Metabolite |
| ln Vivo | Significant improvements in glucose intolerance are observed with protodioscin (5 and 10 mg/kg), which also lowers serum levels of UA, BUN, Cr, TC, and TG. By suppressing the activation of nuclear factor-κB, c-Jun N-terminal kinase, p38 mitogen-activated protein kinase, extracellular signal-regulated kinase, and p38, protodioscin dramatically lowers renal concentrations of IL-1β, IL-6, and TNF-α[1]. In rats, protodioscin decreases the number of apoptotic nerve cells brought on by MCAO, lowers the death rate, and prevents the rise in neurological impairment scores and infarct volume. Protodioscin reverses the protein expression of NF-κB (in the nucleus and cytoplasm) and IκBα (in the cytoplasm) induced by MCAO in rats, attenuates the alteration of important apoptins, and reduces the release of pro-inflammatory cytokines in serum[2]. Rats fed a high-fat diet have a coagulation time that is approximately 50% longer than that of rats given a protodioscin injection (0.5 mg/kg, ip). Protodioscin shows promise in reducing blood levels of both lipoproteins, particularly LDL, which raises the HDL/LDL ratio[3]. |
| References |
[1]. Protodioscin ameliorates fructose-induced renal injury via inhibition of the mitogen activated protein kinase pathway. Phytomedicine. 2016 Nov 15;23(12):1504-1510. [2]. Potential neuroprotection of protodioscin against cerebral ischemia-reperfusion injury in rats through intervening inflammation and apoptosis. Steroids. 2016 Sep;113:52-63. [3]. Antihyperlipidemic effect of protodioscin, an active ingredient isolated from the rhizomes of Dioscorea nipponica. Planta Med. 2010 Oct;76(15):1642-6. |
| Additional Infomation |
Protodioscin is a spirostanyl glycoside that consists of the trisaccharide alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc attached to position 3 of 26-(beta-D-glucopyranosyloxy)-3beta,22-dihydroxyfurost-5-ene via a glycosidic linkage. Found in several plant species including yams, asparagus and funugreek. It has a role as a metabolite. It is a steroid saponin, a trisaccharide derivative, a beta-D-glucoside, a pentacyclic triterpenoid and a cyclic hemiketal. It is functionally related to a diosgenin. It derives from a hydride of a spirostan. Protodioscin has been reported in Dioscorea collettii, Dioscorea deltoidea, and other organisms with data available. See also: Fenugreek seed (part of). |
Solubility Data
| Solubility (In Vitro) |
H2O: 50 mg/mL (47.66 mM) DMSO: 50 mg/mL (47.66 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (2.38 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 (2.38 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (2.38 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 | 0.9531 mL | 4.7655 mL | 9.5311 mL | |
| 5 mM | 0.1906 mL | 0.9531 mL | 1.9062 mL | |
| 10 mM | 0.0953 mL | 0.4766 mL | 0.9531 mL |