Solasodine | CAS#126-17-0 | antioxidant

MedKoo Cat#: 461712 | Name: Solasodine

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Description:

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

Solasodine is an antioxidant glycoalkaloid of Solanum species.

Chemical Structure

Solasodine

CAS#126-17-0 (free base)

Theoretical Analysis

MedKoo Cat#: 461712

Name: Solasodine

CAS#: 126-17-0 (free base)

Chemical Formula: C27H43NO2

Exact Mass: 413.3294

Molecular Weight: 413.64

Elemental Analysis: C, 78.40; H, 10.48; N, 3.39; O, 7.74

Price and Availability

Size	Price	Availability
5mg	USD 280.00	2 weeks
10mg	USD 460.00	2 weeks
25mg	USD 700.00	2 Weeks

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Related CAS #

6106-33-8 (HCl) 126-17-0 (free base)

Synonym

Solasodine; Purapuridine; Salasdine; Solancarpidine;

IUPAC/Chemical Name

(4S,5'R,6aR,6bS,8aS,8bR,9R,10R,11aS,12aS,12bS)-5',6a,8a,9-tetramethyl-1,3,4,5,6,6a,6b,7,8,8a,8b,9,11a,12,12a,12b-hexadecahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-piperidin]-4-ol

InChi Key

KWVISVAMQJWJSZ-FIBXIUFESA-N

InChi Code

InChI=1S/C27H43NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28-29H,6-15H2,1-4H3/t16-,17-,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1

SMILES Code

[H][C@]1(O[C@@]2(NC[C@H](C)CC2)[C@@H]3C)C[C@@]4([H])[C@]5([H])CC=C6C[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 DMF and ethanol

Shelf Life

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Solasodine has diverse biological activities.

In vitro activity:

The findings of this study indicate that solasodine can directly suppresses Hh/Gli1 signaling, and is a novel anticancer candidate that targets cancer stem-like cells (CSCs). Solasodine significantly decreased the proliferation of MCF7 tumorspheres and showed a stronger cytotoxicity on breast cancer cells with higher levels of Gli1 expression. Solasodie enhanced expression of CD24 and suppressed expressions of CD44 and ALDH1. Reference: Phytomedicine. 2022 Dec;107:154448. https://pubmed.ncbi.nlm.nih.gov/36116198/

In vivo activity:

In this study, solasodine prevented epithelial-mesenchymal transition by modulating the AMPK/STAT3/NF-κB/CLDN2 signalling pathway, becoming a new solution for inhibiting gastric cancer metastasis. In a xenograft model to investigate the phosphorylation of AMPK and the expression of CLDN2 from tumour tissues, solasodine inhibited tumour growth through AMPK-CLDN2 pathway. Reference: Chem Biol Interact. 2023 Jul 1;379:110520. https://pubmed.ncbi.nlm.nih.gov/37121296/

	Solvent	mg/mL	mM
Solubility
	DMF	1.0	2.42
	Ethanol	1.0	2.42

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 413.64 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.

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. Chen J, Ma D, Zeng C, White LV, Zhang H, Teng Y, Lan P. Solasodine suppress MCF7 breast cancer stem-like cells via targeting Hedgehog/Gli1. Phytomedicine. 2022 Dec;107:154448. doi: 10.1016/j.phymed.2022.154448. Epub 2022 Sep 6. PMID: 36116198. 2. Zhuang YW, Wu CE, Zhou JY, Chen X, Wu J, Jiang S, Peng HY, Zou X, Liu JY, Wu DP, Gong T, Qi MH, Xue T, Liu SL, Cai H. Solasodine inhibits human colorectal cancer cells through suppression of the AKT/glycogen synthase kinase-3β/β-catenin pathway. Cancer Sci. 2017 Nov;108(11):2248-2264. doi: 10.1111/cas.13354. Epub 2017 Sep 14. PMID: 28803443; PMCID: PMC5666038. 3. Su K, Yao X, Guo C, Qian C, Wang Y, Ma X, Wang X, Yang Y. Solasodine suppresses the metastasis of gastric cancer through claudin-2 via the AMPK/STAT3/NF-κB pathway. Chem Biol Interact. 2023 Jul 1;379:110520. doi: 10.1016/j.cbi.2023.110520. Epub 2023 Apr 28. PMID: 37121296. 4. Arora P, Nainwal LM, Gupta G, Singh SK, Chellappan DK, Oliver BG, Dua K. Orally administered solasodine, a steroidal glycoalkaloid, suppresses ovalbumin-induced exaggerated Th2-immune response in rat model of bronchial asthma. Chem Biol Interact. 2022 Oct 1;366:110138. doi: 10.1016/j.cbi.2022.110138. Epub 2022 Sep 6. PMID: 36084726.

In vitro protocol:

In vivo protocol:

1. Su K, Yao X, Guo C, Qian C, Wang Y, Ma X, Wang X, Yang Y. Solasodine suppresses the metastasis of gastric cancer through claudin-2 via the AMPK/STAT3/NF-κB pathway. Chem Biol Interact. 2023 Jul 1;379:110520. doi: 10.1016/j.cbi.2023.110520. Epub 2023 Apr 28. PMID: 37121296. 2. Arora P, Nainwal LM, Gupta G, Singh SK, Chellappan DK, Oliver BG, Dua K. Orally administered solasodine, a steroidal glycoalkaloid, suppresses ovalbumin-induced exaggerated Th2-immune response in rat model of bronchial asthma. Chem Biol Interact. 2022 Oct 1;366:110138. doi: 10.1016/j.cbi.2022.110138. Epub 2022 Sep 6. PMID: 36084726.

1: Sharma T, Airao V, Panara N, Vaishnav D, Ranpariya V, Sheth N, Parmar S. Solasodine protects rat brain against ischemia/reperfusion injury through its antioxidant activity. Eur J Pharmacol. 2014 Feb 15;725:40-6. doi: 10.1016/j.ejphar.2014.01.005. Epub 2014 Jan 17. PubMed PMID: 24444441. 2: Ma J, Ding X, Sun C, Lin C, An X, Lin G, Yang X, Wang X. Development and validation a liquid chromatography mass spectrometry for determination of solasodine in rat plasma and its application to a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Jul 15;963:24-8. doi: 10.1016/j.jchromb.2014.05.031. Epub 2014 May 23. PubMed PMID: 24922600. 3: Li Y, Chang W, Zhang M, Ying Z, Lou H. Natural product solasodine-3-O-β-D-glucopyranoside inhibits the virulence factors of Candida albicans. FEMS Yeast Res. 2015 Sep;15(6). pii: fov060. doi: 10.1093/femsyr/fov060. Epub 2015 Jul 9. PubMed PMID: 26162798. 4: Chauhan K, Sheth N, Ranpariya V, Parmar S. Anticonvulsant activity of solasodine isolated from Solanum sisymbriifolium fruits in rodents. Pharm Biol. 2011 Feb;49(2):194-9. doi: 10.3109/13880209.2010.508499. Epub 2010 Nov 9. PubMed PMID: 21062107. 5: Manrique-Moreno M, Londoño-Londoño J, Jemioła-Rzemińska M, Strzałka K, Villena F, Avello M, Suwalsky M. Structural effects of the Solanum steroids solasodine, diosgenin and solanine on human erythrocytes and molecular models of eukaryotic membranes. Biochim Biophys Acta. 2014 Jan;1838(1 Pt B):266-77. doi: 10.1016/j.bbamem.2013.08.003. Epub 2013 Aug 14. PubMed PMID: 23954587. 6: Lecanu L, Hashim AI, McCourty A, Giscos-Douriez I, Dinca I, Yao W, Vicini S, Szabo G, Erdélyi F, Greeson J, Papadopoulos V. The naturally occurring steroid solasodine induces neurogenesis in vitro and in vivo. Neuroscience. 2011 Jun 2;183:251-64. doi: 10.1016/j.neuroscience.2011.03.042. Epub 2011 Apr 7. PubMed PMID: 21496476. 7: Thongchai W, Liawruangrath B, Liawruangrath S. Sequential injection analysis with lab-at-valve (SI-LAV) for the determination of solasodine in Solanum species. Talanta. 2010 Apr 15;81(1-2):565-71. doi: 10.1016/j.talanta.2009.12.044. Epub 2010 Jan 4. PubMed PMID: 20188963. 8: Cui CZ, Wen XS, Cui M, Gao J, Sun B, Lou HX. Synthesis of solasodine glycoside derivatives and evaluation of their cytotoxic effects on human cancer cells. Drug Discov Ther. 2012 Feb;6(1):9-17. PubMed PMID: 22460423. 9: Cham BE, Chase TR. Solasodine rhamnosyl glycosides cause apoptosis in cancer cells. Do they also prime the immune system resulting in long-term protection against cancer? Planta Med. 2012 Mar;78(4):349-53. doi: 10.1055/s-0031-1298149. Epub 2012 Jan 13. PubMed PMID: 22399274. 10: Bhatnagar P, Bhatnagar M, Nath AK, Sharma DR. Production of solasodine by Solanum laciniatum using plant tissue culture technique. Indian J Exp Biol. 2004 Oct;42(10):1020-3. PubMed PMID: 15511009. 11: Friedman M, Henika PR, Mackey BE. Effect of feeding solanidine, solasodine and tomatidine to non-pregnant and pregnant mice. Food Chem Toxicol. 2003 Jan;41(1):61-71. PubMed PMID: 12453729. 12: Bhat MA, Ahmad S, Aslam J, Mujib A, Mahmooduzzfar. Salinity stress enhances production of solasodine in Solanum nigrum L. Chem Pharm Bull (Tokyo). 2008 Jan;56(1):17-21. PubMed PMID: 18175968. 13: Kou Y, Koag MC, Cheun Y, Shin A, Lee S. Application of hypoiodite-mediated aminyl radical cyclization to synthesis of solasodine acetate. Steroids. 2012 Sep;77(11):1069-74. doi: 10.1016/j.steroids.2012.05.002. Epub 2012 May 11. PubMed PMID: 22583912. 14: Putalun W, Taura F, Qing W, Matsushita H, Tanaka H, Shoyama Y. Anti-solasodine glycoside single-chain Fv antibody stimulates biosynthesis of solasodine glycoside in plants. Plant Cell Rep. 2003 Dec;22(5):344-9. Epub 2003 Sep 20. PubMed PMID: 14504907. 15: Zhang D, Tao L, Zhao H, Yuan H, Lan M. A functional drug delivery platform for targeting and imaging cancer cells based on Pluronic F127. J Biomater Sci Polym Ed. 2015;26(8):468-82. doi: 10.1080/09205063.2015.1030136. Epub 2015 Apr 8. PubMed PMID: 25780935. 16: Trivedi PD, Patel BC, Rathnam S, Pundarikakshudu K. A validated liquid chromatographic method for estimation of solasodine in various Solanum species and market formulations. J AOAC Int. 2006 Nov-Dec;89(6):1519-23. PubMed PMID: 17225596. 17: Kulcsár-Gergely J. The effect of solasodine on the body temperature. Arzneimittelforschung. 1976;26(1):55-7. PubMed PMID: 947178. 18: Dixit VP, Gupta RS, Gupta S. Antifertility plant products: testicular cell population dynamicsfollowing solasodine (C27H43O2N) administration in rhesus monkey (Macaca mulatta). Andrologia. 1989 Nov-Dec;21(6):542-6. PubMed PMID: 2619100. 19: Zhuang YW, Wu CE, Zhou JY, Chen X, Wu J, Jiang S, Peng HY, Zou X, Liu JY, Wu DP, Gong T, Qi MH, Xue T, Liu SL, Cai H. Solasodine inhibits human colorectal cancer cells through suppression of the AKT/glycogen synthase kinase-3β/β-catenin pathway. Cancer Sci. 2017 Nov;108(11):2248-2264. doi: 10.1111/cas.13354. Epub 2017 Sep 14. PubMed PMID: 28803443; PubMed Central PMCID: PMC5666038. 20: Paczkowski C, Kalinowska M, Wojciechowski ZA. UDP-glucose:solasodine glucosyltransferase from eggplant (Solanum melongena L.) leaves: partial purification and characterization. Acta Biochim Pol. 1997;44(1):43-53. PubMed PMID: 9241353.

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