SMILAGENIN 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 Information

WGK Germany 

3

F 

10

MSDS

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SMILAGENIN Usage And Synthesis

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

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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