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MedKoo Cat#: 584363 | Name: Smilagenin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Smilagenin, also known as PYM50028, is an orally active, nonpeptide neurotrophic factor inducer, prevents and reverses neuronal damage induced by MPP+ in mesencephalic neurons and by MPTP in a mouse model of Parkinson's disease.

Chemical Structure

Smilagenin
Smilagenin
CAS#126-18-1

Theoretical Analysis

MedKoo Cat#: 584363

Name: Smilagenin

CAS#: 126-18-1

Chemical Formula: C27H44O3

Exact Mass: 416.3290

Molecular Weight: 416.65

Elemental Analysis: C, 77.84; H, 10.65; O, 11.52

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
50mg USD 550.00 2 Weeks
100mg USD 950.00 2 Weeks
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Synonym
Smilagenin; PYM50028; PYM 50028; AI3-44895; Cogane
IUPAC/Chemical Name
(25R)-5beta-Spirostan-3beta-ol
InChi Key
GMBQZIIUCVWOCD-UQHLGXRBSA-N
InChi Code
InChI=1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17+,18-,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1
SMILES Code
[H][C@]1(O[C@@]2(OC[C@H](C)CC2)[C@H]3C)C[C@@]4([H])[C@]5([H])CC[C@]6([H])C[C@@H](O)CC[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Smilagenin improves memory of aged rats by increasing the muscarinic receptor subtype 1 (M1)-receptor density. Smilagenin attenuates Aβ(25-35)-induced neurodegeneration via stimulating the gene expression of brain-derived neurotrophic factor.
In vitro activity:
Smilagenin has shown promise in alleviating neurodegenerative changes associated with Alzheimer's disease (AD). In experiments with cultured rat cortical neurons and SH-SY5Y neuroblastoma cells, smilagenin pretreatment countered the negative effects induced by Aβ(25-35), such as reduced cholinergic neuron count, shortened neurite outgrowth, and decreased muscarinic receptor density. Smilagenin also increased brain-derived neurotrophic factor (BDNF) levels. Reference: Neuroscience. 2012 May 17;210:275-85. https://pubmed.ncbi.nlm.nih.gov/22441042/
In vivo activity:
Smilagenin has demonstrated significant neuroprotective effects, particularly in the context of AD. In a murine model of AD, smilagenin improved learning and memory abilities, reduced the deposition of β-amyloid plaques in the cortex and hippocampus, and inhibited the secretion of Aβ1-42. Smilagenin enhanced BDNF expression and influenced histone acetylation, elevating global levels of H3AC and H4AC. Additionally, smilagenin increased the expression of P300. Reference: Phytomedicine. 2023 Sep;118:154956. https://pubmed.ncbi.nlm.nih.gov/37499345/
Solvent mg/mL mM comments
Solubility
DMSO 5.0 12.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 416.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Zhang C, Wu Y, Li J, Yang GX, Su L, Huang Y, Wang R, Ma L. Synthesis and biological evaluation of 3-carbamate smilagenin derivatives as potential neuroprotective agents. Bioorg Med Chem Lett. 2019 Oct 1;29(19):126622. doi: 10.1016/j.bmcl.2019.08.026. Epub 2019 Aug 13. PMID: 31444084. 2. Zhang R, Wang Z, Howson PA, Xia Z, Zhou S, Wu E, Xia Z, Hu Y. 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. Epub 2012 Mar 13. PMID: 22441042. 3. Yang S, Fan L, Zhang R, Song C, Shi J, Wang J, Zhang P, Wang H, Zhang Y. Smilagenin induces expression and epigenetic remodeling of BDNF in alzheimer's disease. Phytomedicine. 2023 Sep;118:154956. doi: 10.1016/j.phymed.2023.154956. Epub 2023 Jul 17. PMID: 37499345. 4. He X, Yang S, Zhang R, Hou L, Xu J, Hu Y, Xu R, Wang H, Zhang Y. 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. PMID: 30804756; PMCID: PMC6371654.
In vitro protocol:
1. Zhang C, Wu Y, Li J, Yang GX, Su L, Huang Y, Wang R, Ma L. Synthesis and biological evaluation of 3-carbamate smilagenin derivatives as potential neuroprotective agents. Bioorg Med Chem Lett. 2019 Oct 1;29(19):126622. doi: 10.1016/j.bmcl.2019.08.026. Epub 2019 Aug 13. PMID: 31444084. 2. Zhang R, Wang Z, Howson PA, Xia Z, Zhou S, Wu E, Xia Z, Hu Y. 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. Epub 2012 Mar 13. PMID: 22441042.
In vivo protocol:
1. Yang S, Fan L, Zhang R, Song C, Shi J, Wang J, Zhang P, Wang H, Zhang Y. Smilagenin induces expression and epigenetic remodeling of BDNF in alzheimer's disease. Phytomedicine. 2023 Sep;118:154956. doi: 10.1016/j.phymed.2023.154956. Epub 2023 Jul 17. PMID: 37499345. 2. He X, Yang S, Zhang R, Hou L, Xu J, Hu Y, Xu R, Wang H, Zhang Y. 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. PMID: 30804756; PMCID: PMC6371654.
1: Alotaibi MO, Alotaibi NM, Alwaili MA, Alshammari N, Adnan M, Patel M. Natural sapogenins as potential inhibitors of aquaporins for targeted cancer therapy: computational insights into binding and inhibition mechanism. J Biomol Struct Dyn. 2024 Jan 4:1-22. doi: 10.1080/07391102.2023.2299743. Epub ahead of print. PMID: 38174738. 2: Xue A, Zhao D, Zhao C, Li X, Yang M, Zhao H, Zhao C, Lei X, Wu J, Zhang N. Study on the neuroprotective effect of Zhimu-Huangbo extract on mitochondrial dysfunction in HT22 cells induced by D-galactose by promoting mitochondrial autophagy. J Ethnopharmacol. 2024 Jan 10;318(Pt B):117012. doi: 10.1016/j.jep.2023.117012. Epub 2023 Aug 9. PMID: 37567426. 3: Yang S, Fan L, Zhang R, Song C, Shi J, Wang J, Zhang P, Wang H, Zhang Y. Smilagenin induces expression and epigenetic remodeling of BDNF in alzheimer's disease. Phytomedicine. 2023 Sep;118:154956. doi: 10.1016/j.phymed.2023.154956. Epub 2023 Jul 17. PMID: 37499345. 4: Lu BW, Liang XZ, Wen MT, Li G. Exploration at the network pharmacology level of possible targeting mechanisms of Smilacis Glabrae Rhixoma for the treatment of osteoporosis. Eur Rev Med Pharmacol Sci. 2023 Apr;27(8):3681-3698. doi: 10.26355/eurrev_202304_32165. PMID: 37140318. 5: Senol Deniz FS, Eren G, Orhan IE, Sener B, Ozgen U, Aldaba R, Calis I. Outlining In Vitro and In Silico Cholinesterase Inhibitory Activity of Twenty- Four Natural Products of Various Chemical Classes: Smilagenin, Kokusaginine, and Methyl Rosmarinate as Emboldening Inhibitors. Molecules. 2021 Apr 1;26(7):2024. doi: 10.3390/molecules26072024. PMID: 33916300; PMCID: PMC8037418. 6: Love J, Simons CR. Acid hydrolysis of saponins extracted in tincture. PLoS One. 2020 Dec 31;15(12):e0244654. doi: 10.1371/journal.pone.0244654. PMID: 33382809; PMCID: PMC7774937. 7: Cortés A J, Sánchez-Mendoza E, Zamilpa A, González-Cortazar M, Herrera-Ruiz M, Almanza-Pérez JC, Terán-Cabanillas E, Condé R, Domínguez-Ramírez L, Arcos EM, Jiménez-Ferrer JE. Steroidal saponin from Agave marmorata Roezl modulates inflammatory response by inhibiting NF-κB and AP-1. Nat Prod Res. 2022 Feb;36(4):1123-1128. doi: 10.1080/14786419.2020.1855638. Epub 2020 Dec 21. PMID: 33342288. 8: Zhang C, Wu Y, Li J, Yang GX, Su L, Huang Y, Wang R, Ma L. Synthesis and biological evaluation of 3-carbamate smilagenin derivatives as potential neuroprotective agents. Bioorg Med Chem Lett. 2019 Oct 1;29(19):126622. doi: 10.1016/j.bmcl.2019.08.026. Epub 2019 Aug 13. PMID: 31444084. 9: Czajkowska-Szczykowska D, Corona Díaz A, Aleksiejczuk G, López Castro Y, Morzycki JW. Access to 27-Nortomatidine and 27-Norsoladulcidine Derivatives. J Org Chem. 2019 Apr 5;84(7):4104-4111. doi: 10.1021/acs.joc.9b00103. Epub 2019 Mar 20. PMID: 30855957. 10: He X, Yang S, Zhang R, Hou L, Xu J, Hu Y, Xu R, Wang H, Zhang Y. 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. PMID: 30804756; PMCID: PMC6371654. 11: Fuentes-Aguilar A, Romero-Hernández LL, Arenas-González A, Merino-Montiel P, Montiel-Smith S, Meza-Reyes S, Vega-Báez JL, Plata GB, Padrón JM, López Ó, Fernández-Bolaños JG. New selenosteroids as antiproliferative agents. Org Biomol Chem. 2017 Jun 14;15(23):5041-5054. doi: 10.1039/c7ob00458c. PMID: 28574071. 12: Li J, Xia Z, Sun X, Zhang R, Huang G, Hickling R, Xia Z, Hu Y, Zhang Y. Reversal of dopamine neurons and locomotor ability degeneration in aged rats with smilagenin. Neuroscience. 2013 Aug 15;245:90-8. doi: 10.1016/j.neuroscience.2013.04.028. Epub 2013 Apr 23. PMID: 23624370. 13: Zhang R, Wang Z, Howson PA, Xia Z, Zhou S, Wu E, Xia Z, Hu Y. Smilagenin attenuates beta amyloid (25-35)-induced degeneration of neuronal cells via stimulating the gene expression of brain-derived neurotrophic factor. 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