Timosaponin AIII is a novel and potent acetylcholinesterase (AChE) inhibitor (IC50 = 35.4 μM) and also an inhibitor of U46619-induced rat platelet aggregation.
Physicochemical Properties
| Molecular Formula | C39H64O13 |
| Molecular Weight | 740.9177 |
| Exact Mass | 740.434 |
| CAS # | 41059-79-4 |
| PubChem CID | 15953793 |
| Appearance | White to off-white solid powder |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 862.8±65.0 °C at 760 mmHg |
| Flash Point | 475.6±34.3 °C |
| Vapour Pressure | 0.0±0.6 mmHg at 25°C |
| Index of Refraction | 1.606 |
| LogP | 3.94 |
| Hydrogen Bond Donor Count | 7 |
| Hydrogen Bond Acceptor Count | 13 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 52 |
| Complexity | 1270 |
| Defined Atom Stereocenter Count | 22 |
| 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[C@H]6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C)C)C)OC1 |
| InChi Key | MMTWXUQMLQGAPC-YXOKLLKRSA-N |
| InChi Code | InChI=1S/C39H64O13/c1-18-7-12-39(47-17-18)19(2)28-25(52-39)14-24-22-6-5-20-13-21(8-10-37(20,3)23(22)9-11-38(24,28)4)48-36-34(32(45)30(43)27(16-41)50-36)51-35-33(46)31(44)29(42)26(15-40)49-35/h18-36,40-46H,5-17H2,1-4H3/t18-,19-,20+,21-,22+,23-,24-,25-,26+,27+,28-,29+,30-,31-,32-,33+,34+,35-,36+,37-,38-,39+/m0/s1 |
| Chemical Name | (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S,16S,18R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-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
| ln Vitro | Acetylcholinesterase (AChE) activity is inhibited by timosaponin AIII, with an IC50 of 35.4 μM[1]. The primary selective cytotoxic effect of BN108 is thought to be mediated by timosaponin AIII, which also induces ER stress, protective autophagy, and mTOR inhibition [2]. |
| ln Vivo | Timosaponin AIII (TA3) was the most successful steroidal saponin in addressing memory impairments among those that were examined. Scopolamine-induced step delay reduction was enhanced by timosaponin AIII by 17% (10 mg/kg), 28% (20 mg/kg), and 43% (40 mg/kg). During acquisition trials, no variations in latency were noticed. The efficient inhibition of acetylcholine decrease in the brains of mice treated with scopolamine is achieved by timosaponin AIII (20, 40 mg/kg, po). Timosaponin AIII's inhibitory effect is similar to that of tacrine, which is employed as a positive control [1]. |
| References |
[1]. Timosaponin AIII, a saponin isolated from Anemarrhena asphodeloides, ameliorates learning and memory deficits in mice. Pharmacol Biochem Behav. 2009 Aug;93(2):121-7. [2]. Timosaponin AIII is preferentially cytotoxic to tumor cells through inhibition of mTOR and induction of ER stress. PLoS One. 2009 Sep 30;4(9):e7283. |
| Additional Infomation |
Timosaponin A-III is a triterpenoid. It has a role as a metabolite. Timosaponin A-III has been reported in Narthecium asiaticum, Yucca schidigera, and other organisms with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~125 mg/mL (~168.71 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (2.81 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 20.8 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 2: ≥ 2.08 mg/mL (2.81 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 20.8 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 | 1.3497 mL | 6.7484 mL | 13.4967 mL | |
| 5 mM | 0.2699 mL | 1.3497 mL | 2.6993 mL | |
| 10 mM | 0.1350 mL | 0.6748 mL | 1.3497 mL |