MedKoo Cat#: 592696 | Name: Solasonine

Description:

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

Solasonine is weakly anti-fungal.

Chemical Structure

Solasonine
Solasonine
CAS#19121-58-5

Theoretical Analysis

MedKoo Cat#: 592696

Name: Solasonine

CAS#: 19121-58-5

Chemical Formula: C45H73NO16

Exact Mass: 883.4929

Molecular Weight: 884.07

Elemental Analysis: C, 61.14; H, 8.32; N, 1.58; O, 28.96

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Solasonine; NSC 82149; NSC82149; NSC82149
IUPAC/Chemical Name
beta-D-Galactopyranoside, (3beta,22alpha,25R)-spirosol-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(beta-D-glucopyranosyl-(1-3))- (9CI)
InChi Key
QCTMYNGDIBTNSK-XEAAVONHSA-N
InChi Code
InChI=1S/C45H73NO16/c1-19-8-13-45(46-16-19)20(2)30-27(62-45)15-26-24-7-6-22-14-23(9-11-43(22,4)25(24)10-12-44(26,30)5)57-42-39(61-40-36(54)34(52)31(49)21(3)56-40)38(33(51)29(18-48)59-42)60-41-37(55)35(53)32(50)28(17-47)58-41/h6,19-21,23-42,46-55H,7-18H2,1-5H3/t19-,20+,21+,23+,24-,25+,26+,27+,28-,29-,30+,31+,32-,33+,34-,35+,36-,37-,38+,39-,40+,41+,42-,43+,44+,45-/m1/s1
SMILES Code
C[C@@H]1CC[C@]2(O[C@H]3C[C@H]4[C@@H]5CC=C6C[C@@H](O[C@@H]7O[C@@H]([C@@H]([C@@H]([C@H]7O[C@@H]8O[C@H]([C@@H]([C@H]([C@H]8O)O)O)C)O[C@@H]9O[C@@H]([C@H]([C@@H]([C@H]9O)O)O)CO)O)CO)CC[C@@]6([C@H]5CC[C@@]4([C@H]3[C@@H]2C)C)C)NC1
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
>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

Preparing Stock Solutions

The following data is based on the product molecular weight 884.07 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
1: Huang W, Wang Y, Zhu H, Wu Y, Xie X, Wang D. [Solasonine-induced Apoptosis in Lung Cancer Cell Line H446 and Its Mechanism]. Zhongguo Fei Ai Za Zhi. 2015 Jul;18(7):416-21. doi: 10.3779/j.issn.1009-3419.2015.07.05. Chinese. PubMed PMID: 26182866; PubMed Central PMCID: PMC6000244. 2: Chen Y, Zhang S, Chen D, Zhou M, Zheng J, Xiang Z. An UPLC-MS/MS method for determination of solasonine in rat plasma and its application of a pharmacokinetic and bioavailability study. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Mar 15;985:1-5. doi: 10.1016/j.jchromb.2015.01.017. Epub 2015 Jan 23. PubMed PMID: 25645955. 3: Yang J, Huang W, Tan W. Solasonine, A Natural Glycoalkaloid Compound, Inhibits Gli-Mediated Transcriptional Activity. Molecules. 2016 Oct 14;21(10). pii: E1364. PubMed PMID: 27754442. 4: Munari CC, de Oliveira PF, Campos JC, Martins Sde P, Da Costa JC, Bastos JK, Tavares DC. Antiproliferative activity of Solanum lycocarpum alkaloidic extract and their constituents, solamargine and solasonine, in tumor cell lines. J Nat Med. 2014 Jan;68(1):236-41. doi: 10.1007/s11418-013-0757-0. Epub 2013 Mar 10. PubMed PMID: 23475509. 5: Sánchez-Mata MC, Yokoyama WE, Hong YJ, Prohens J. Alpha-solasonine and alpha-solamargine contents of gboma (Solanum macrocarpon L.) and scarlet (Solanum aethiopicum L.) eggplants. J Agric Food Chem. 2010 May 12;58(9):5502-8. doi: 10.1021/jf100709g. PubMed PMID: 20397650. 6: Hall CA, Hobby T, Cipollini M. Efficacy and mechanisms of alpha-solasonine-and alpha-solamargine-induced cytolysis on two strains of Trypanosoma cruzi. J Chem Ecol. 2006 Nov;32(11):2405-16. PubMed PMID: 17001530. 7: Lezama-Dávila CM, McChesney JD, Bastos JK, Miranda MA, Tiossi RF, da Costa Jde C, Bentley MV, Gaitan-Puch SE, Isaac-Márquez AP. A New Antileishmanial Preparation of Combined Solamargine and Solasonine Heals Cutaneous Leishmaniasis through Different Immunochemical Pathways. Antimicrob Agents Chemother. 2016 Apr 22;60(5):2732-8. doi: 10.1128/AAC.02804-15. Print 2016 May. PubMed PMID: 26883711; PubMed Central PMCID: PMC4862480. 8: Fewell AM, Roddick JG, Weissenberg M. Interactions between the glycoalkaloids solasonine and solamargine in relation to inhibition of fungal growth. Phytochemistry. 1994 Nov;37(4):1007-11. PubMed PMID: 7765652. 9: Friedman M. Chemistry and anticarcinogenic mechanisms of glycoalkaloids produced by eggplants, potatoes, and tomatoes. J Agric Food Chem. 2015 Apr 8;63(13):3323-37. doi: 10.1021/acs.jafc.5b00818. Epub 2015 Mar 30. Review. PubMed PMID: 25821990. 10: Cavlovic P, Mankotia M, Pantazopoulos P, Scott PM. Liquid chromatographic determination of alpha-solasonine in frozen green peas as an indicator of the presence of nightshade berries. J AOAC Int. 2003 Jul-Aug;86(4):759-63. PubMed PMID: 14509436. 11: Blankemeyer JT, McWilliams ML, Rayburn JR, Weissenberg M, Friedman M. Developmental toxicology of solamargine and solasonine glycoalkaloids in frog embryos. Food Chem Toxicol. 1998 May;36(5):383-9. PubMed PMID: 9662413. 12: Regerat F, Pourrat H. [Isolation of solasonine from glucoalkaloid mixtures by fungal fermentation.]. Planta Med. 1981 Nov;43(11):280-4. German. PubMed PMID: 17402045. 13: Basu A, Lahiri SC. Some pharmacological actions of solasonine. Indian J Exp Biol. 1977 Apr;15(4):285-9. PubMed PMID: 914337. 14: Abreu Miranda M, Tiossi RF, da Silva MR, Rodrigues KC, Kuehn CC, Rodrigues Oliveira LG, Albuquerque S, McChesney JD, Lezama-Davila CM, Isaac-Marquez AP, Kenupp Bastos J. In vitro leishmanicidal and cytotoxic activities of the glycoalkaloids from Solanum lycocarpum (Solanaceae) fruits. Chem Biodivers. 2013 Apr;10(4):642-8. doi: 10.1002/cbdv.201200063. PubMed PMID: 23576350. 15: Tiossi RF, Da Costa JC, Miranda MA, Praça FS, McChesney JD, Bentley MV, Bastos JK. In vitro and in vivo evaluation of the delivery of topical formulations containing glycoalkaloids of Solanum lycocarpum fruits. Eur J Pharm Biopharm. 2014 Sep;88(1):28-33. doi: 10.1016/j.ejpb.2014.01.010. Epub 2014 Feb 6. PubMed PMID: 24509413. 16: Wang X, Zou S, Lan YL, Xing JS, Lan XQ, Zhang B. Solasonine inhibits glioma growth through anti-inflammatory pathways. Am J Transl Res. 2017 Sep 15;9(9):3977-3989. eCollection 2017. PubMed PMID: 28979674; PubMed Central PMCID: PMC5622243. 17: Miranda MA, Magalhães LG, Tiossi RF, Kuehn CC, Oliveira LG, Rodrigues V, McChesney JD, Bastos JK. Evaluation of the schistosomicidal activity of the steroidal alkaloids from Solanum lycocarpum fruits. Parasitol Res. 2012 Jul;111(1):257-62. doi: 10.1007/s00436-012-2827-8. Epub 2012 Jan 27. PubMed PMID: 22281548. 18: Roddick JG, Weissenberg M, Leonard AL. Membrane disruption and enzyme inhibition by naturally-occurring and modified chacotriose-containing Solanum steroidal glycoalkaloids. Phytochemistry. 2001 Mar;56(6):603-10. PubMed PMID: 11281138. 19: Mayank, Jaitak V. Molecular docking study of natural alkaloids as multi-targeted hedgehog pathway inhibitors in cancer stem cell therapy. Comput Biol Chem. 2016 Jun;62:145-54. doi: 10.1016/j.compbiolchem.2015.08.001. Epub 2015 Aug 6. PubMed PMID: 26278973. 20: Jared JJ, Murungi LK, Wesonga J, Torto B. Steroidal glycoalkaloids: chemical defence of edible African nightshades against the tomato red spider mite, Tetranychus evansi (Acari: Tetranychidae). Pest Manag Sci. 2016 Apr;72(4):828-36. doi: 10.1002/ps.4100. Epub 2015 Sep 28. PubMed PMID: 26299255.