Smilagenin
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Hodoodo CAT#: H584363

CAS#: 126-18-1

Description: 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

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Smilagenin
CAS# 126-18-1

Theoretical Analysis

Hodoodo Cat#: H584363
Name: Smilagenin
CAS#: 126-18-1
Chemical Formula: C27H44O3
Exact Mass: 416.33
Molecular Weight: 416.650
Elemental Analysis: C, 77.84; H, 10.65; O, 11.52

Price and Availability

Size Price Availability Quantity
10mg USD 350 2 Weeks
50mg USD 710 2 Weeks
100mg USD 1050 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:

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/

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.

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1: 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. PubMed PMID: 23624370.

2: Visanji NP, Orsi A, Johnston TH, Howson PA, Dixon K, Callizot N, Brotchie JM, Rees DD. PYM50028, a novel, 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. FASEB J. 2008 Jul;22(7):2488-97. doi: 10.1096/fj.07-095398. Epub 2008 Mar 25. PubMed PMID: 18364399.

3: Lim SM, Jeong JJ, Kang GD, Kim KA, Choi HS, Kim DH. Timosaponin AIII and its metabolite sarsasapogenin ameliorate colitis in mice by inhibiting NF-κB and MAPK activation and restoring Th17/Treg cell balance. Int Immunopharmacol. 2015 Apr;25(2):493-503. doi: 10.1016/j.intimp.2015.02.016. Epub 2015 Feb 16. PubMed PMID: 25698557.

4: Athauda D, Foltynie T. The ongoing pursuit of neuroprotective therapies in Parkinson disease. Nat Rev Neurol. 2015 Jan;11(1):25-40. doi: 10.1038/nrneurol.2014.226. Epub 2014 Dec 2. Review. PubMed PMID: 25447485.

5: Yin Y, Zhao XC, Wang SJ, Gao PY, Li LZ, Ikejima T, Song SJ. Synthesis and biological evaluation of novel sarsasapogenin derivatives as potential anti-tumor agents. Steroids. 2015 Jan;93:25-31. doi: 10.1016/j.steroids.2014.09.007. Epub 2014 Oct 19. PubMed PMID: 25456170.

6: Worth PF. How to treat Parkinson's disease in 2013. Clin Med (Lond). 2013 Feb;13(1):93-6. Review. PubMed PMID: 23472504.

7: Sengupta R, Barone A, Marasa J, Taylor S, Jackson E, Warrington NM, Rao S, Kim AH, Leonard JR, Piwnica-Worms D, Rubin JB. Novel chemical library screen identifies naturally occurring plant products that specifically disrupt glioblastoma-endothelial cell interactions. Oncotarget. 2015 Jul 30;6(21):18282-92. PubMed PMID: 26286961; PubMed Central PMCID: PMC4621891.

8: Li GL, Yang J, Duan JA, Liu HB, Zhu ZH, Qian DW, Tang ZS. [Quality Analysis and Evaluation of Anemarrhena asphodeloides Rhizome from Different Habitats]. Zhong Yao Cai. 2015 Jun;38(6):1148-52. Chinese. PubMed PMID: 26762052.

9: Gu G, An L, Fang M, Guo Z. Efficient one-pot synthesis of tigogenin saponins and their antitumor activities. Carbohydr Res. 2014 Jan 13;383:21-6. doi: 10.1016/j.carres.2013.10.015. Epub 2013 Oct 30. PubMed PMID: 24239606.

10: Sánchez-Flores J, Romero-Ávila M, Rosado-Abón A, Flores-Álamo M, Iglesias-Arteaga MA. Diacetoxyiodobenzene-mediated synthesis of unnatural furospirostane sapogenins derived from diosgenin and tigogenin. Steroids. 2013 Sep;78(9):798-802. doi: 10.1016/j.steroids.2013.05.013. Epub 2013 May 23. PubMed PMID: 23707570.

11: Shen S, Zhang Y, Zhang R, Gong X. Sarsasapogenin induces apoptosis via the reactive oxygen species-mediated mitochondrial pathway and ER stress pathway in HeLa cells. Biochem Biophys Res Commun. 2013 Nov 15;441(2):519-24. PubMed PMID: 24383086.

12: Sun Y, Liu L, Peng Y, Liu B, Lin D, Li L, Song S. Metabolites characterization of timosaponin AIII in vivo and in vitro by using liquid chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Aug 1;997:236-43. doi: 10.1016/j.jchromb.2015.06.015. Epub 2015 Jun 19. PubMed PMID: 26134298.

13: Shen S, Zhang Y, Zhang R, Gong X. Sarsasapogenin induces apoptosis via the reactive oxygen species-mediated mitochondrial pathway and ER stress pathway in HeLa cells. Biochem Biophys Res Commun. 2013 Oct 26. pii: S0006-291X(13)01782-8. doi: 10.1016/j.bbrc.2013.10.101. [Epub ahead of print] PubMed PMID: 24513212.

14: Duckstein SM, Stintzing FC. LC-MS(n) characterization of steroidal saponins in Helleborus niger L. roots and their conversion products during fermentation. Steroids. 2015 Jan;93:47-59. doi: 10.1016/j.steroids.2014.09.011. Epub 2014 Nov 20. PubMed PMID: 25449769.

15: Xiao SF, Xue HB, Li X, Chen C, Li GJ, Yuan CM, Zhang MY. A double-blind, placebo-controlled study of traditional Chinese medicine sarsasapogenin added to risperidone in patients with negative symptoms dominated schizophrenia. Neurosci Bull. 2011 Aug;27(4):258-68. doi: 10.1007/s12264-011-1417-6. PubMed PMID: 21788997; PubMed Central PMCID: PMC5560307.

16: Yang B, Liu Z, Hu J, Lai X, Xia P. Quantitative determination of sarsasapogenin in rat plasma using liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Jun 1;1022:213-219. doi: 10.1016/j.jchromb.2016.04.020. Epub 2016 Apr 14. PubMed PMID: 27107248.

17: Cheng L, Pan GF, Sun XB, Huang YX, Peng YS, Zhou LY. Evaluation of anxiolytic-like effect of aqueous extract of asparagus stem in mice. Evid Based Complement Alternat Med. 2013;2013:587260. doi: 10.1155/2013/587260. Epub 2013 Nov 20. PubMed PMID: 24348707; PubMed Central PMCID: PMC3853311.

18: Wang L, Wang X, Yuan X, Zhao B. Simultaneous analysis of diosgenin and sarsasapogenin in Asparagus officinalis byproduct by thin-layer chromatography. Phytochem Anal. 2011 Jan-Feb;22(1):14-7. doi: 10.1002/pca.1244. Epub 2010 Aug 26. PubMed PMID: 20799270.

19: Xu Y, Liu JH, Wang J, Zhang J, Yu BY. A monoclonal antibody-based competitive ELISA for the determination of ruscogenin in Chinese traditional medicines and biological samples. Chin J Nat Med. 2014 Oct;12(10):794-9. doi: 10.1016/S1875-5364(14)60121-7. Epub 2014 Oct 31. PubMed PMID: 25443374.

20: 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. PubMed PMID: 22441042.