| Identification | Back Directory | [Name]
SMILAGENIN | [CAS]
126-18-1 | [Synonyms]
Nsc93747
SMILAGENIN
ESMILAGENIN
Smilax china L
ISOSARSAPOGENIN
ISOSARSAPOGENINE
ISOSARSASAPOGENIN
SMILAGENIN USP/EP/BP
(25r)-spirostan-3β-ol
(25R)-SPIROSTAN-3BETA-OL
(25R)-5β-spirostan-3β-ol
(3β,5β,25R)-Spirostan-3-ol
Spirostan-3-ol, (3β,5β,25R)-
25R,5BETA-SPIROSTAN-3BETA-OL
5.beta.-Spirostan-3.beta.-ol, (25R)-
16,22:22,26-Bis(epoxy)cholestan-3β-ol
Spirostan-3-ol, (3.beta.,5.beta.,25R)-
16,22:22,26-BIS(EPOXY)CHOLESTAN-3BETA-OL
5BETA,20ALPHA,22ALPHA,25D-SPIRANOSTAN-3BETA-OL
5-BETA, 20-ALPHA, 22-ALPHA, 25D-SPIROSTAN-3-BETA-OL
(25R)-Spirostan-3β-ol, 16,22:22,26-Bis(epoxy)cholestan-3β-ol | [EINECS(EC#)]
204-775-8 | [Molecular Formula]
C27H44O3 | [MDL Number]
MFCD00037845 | [MOL File]
126-18-1.mol | [Molecular Weight]
416.64 |
| Chemical Properties | Back Directory | [Melting point ]
~185 °C
| [alpha ]
D25 -69° (c = 0.5 in chloroform) | [Boiling point ]
474.91°C (rough estimate) | [density ]
1.0362 (rough estimate) | [refractive index ]
1.4700 (estimate) | [storage temp. ]
Store at -20°C | [solubility ]
Ethanol: ≥ 10 mg/mL (24.00 mM); DMSO: < 1 mg/mL (insoluble or slightly soluble) | [form ]
Solid | [pka]
15.14±0.70(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Uses]
Smilagenin (SMI) is a small-molecule steroidal sapogenin from Anemarrhena asphodeloides and Pelargonium hortorum widely used in traditional Chinese medicine for treating chronic neurodegeneration diseases[1].
Smilagenin (SMI) improves memory of aged rats by increasing the muscarinic receptor subtype 1 (M1)-receptor density[2].
Smilagenin (SMI) attenuates Aβ(25-35)-induced neurodegenerationvia stimulating the gene expression of brain-derived neurotrophic factor, may represents a novel therapeutic strategy for AD[3]. | [Definition]
ChEBI: An oxaspiro compound that is(5beta,25R)-spirostan substituted by a beta-hydroxy group at position 3. | [in vivo]
Smilagenin (intragastric administration; 10 or 26 mg/kg, once daily; 60 days) prevents the impairment of dopaminergic neurons in chronic MPTP/probenecid-induced mouse model[2]. | Animal Model: | MPTP/probenecid-induced mouse model[2] | | Dosage: | 10 or 26 mg/kg | | Administration: | Intragastric administration; 10 or 26 mg/kg; once daily; 60 days | | Result: | Ameliorated locomotor ability of MPTP/probenecid-lesioned mice. |
| [IC 50]
mAChR1 | [Purification Methods]
Chromatograph smilagenin on active Al2O3 and elute with *C6H6, then recrystallise it from Me2CO, aqueous EtOH (m 187-188o) or MeOH. The acetate crystallises from MeOH with m 152o and [] D 25 -59.6o, [] 546 25 –68.9o (c 0.25, CHCl3). [Askew J Chem Soc 1399 1936 and 1402 1936, Scheer et al. J Am Chem Soc 77 6411955, Beilstein 19 III/IV 826.] | [References]
[1] He X, et al. Smilagenin Protects Dopaminergic Neurons in Chronic MPTP/Probenecid-Lesioned Parkinson's Disease Models. Front Cell Neurosci. 2019 Feb 5;13:18. DOI:10.3389/fncel.2019.00018
[2] Hu Y, et al. Regulation of M1-receptor mRNA stability by smilagenin and its significance in improving memory of aged rats. Neurobiol Aging. 2010 Jun;31(6):1010-9. DOI:10.1016/j.neurobiolaging.2008.06.008
[3] Zhang R, et al. Smilagenin attenuates beta amyloid (25-35)-induced degeneration of neuronal cells via stimulating the gene expression of brain-derived neurotrophic factor. Neuroscience. 2012 May 17;210:275-85 DOI:10.1016/j.neuroscience.2012.03.017 |
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