ChemicalBook CAS DataBase List 126-18-1

126-18-1

Name	SMILAGENIN
CAS	126-18-1
EINECS(EC#)	204-775-8
Molecular Formula	C27H44O3
MDL Number	MFCD00037845
Molecular Weight	416.64
MOL File	126-18-1.mol

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

Chemical Properties

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

Safety Data

WGK Germany	3
F	10

Hazard Information

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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