Solamargine | CAS# 20311-51-7 | Biochemical

MedKoo Cat#: 573973 | Name: Solamargine

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Description:

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

Solamargine is a glycoalkaloid that has been found in S. lycocarpum and has anticancer activity. It decreases viability of H1650, H1975, PC-9, A549, and H1299 non-small cell lung cancer (NSCLC) cells. Solamargine increases ERK1/2 phosphorylation and decreases the expression of DNA methyltranferase 1 (DNMT1) in H1299 and A549 cells. It reduces tumor growth and increases ERK1/2 phosphorylation and reduces the expression of the prostaglandin E2 receptor, DNMT1, and c-Jun in tumor tissue.

Chemical Structure

Solamargine

CAS#20311-51-7

Theoretical Analysis

MedKoo Cat#: 573973

Name: Solamargine

CAS#: 20311-51-7

Chemical Formula: C45H73NO15

Exact Mass: 867.4980

Molecular Weight: 868.07

Elemental Analysis: C, 62.26; H, 8.48; N, 1.61; O, 27.65

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 weeks
10mg	USD 675.00	2 weeks
50mg	USD 1,450.00	2 Weeks

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Related CAS #

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Synonym

α-Solamargine, NSC 407810, Solamargine

IUPAC/Chemical Name

(2S,2'S,3R,3'R,4R,4'R,5R,5'R,6S,6'S)-6,6'-(((2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-(((4S,5'R,6aR,6bS,8aS,8bR,9S,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-yl)oxy)tetrahydro-2H-pyran-3,5-diyl)bis(oxy))bis(2-methyltetrahydro-2H-pyran-3,4,5-triol)

InChi Key

MBWUSSKCCUMJHO-ZGXDEBHDSA-N

InChi Code

InChI=1S/C45H73NO15/c1-19-9-14-45(46-17-19)20(2)30-28(61-45)16-27-25-8-7-23-15-24(10-12-43(23,5)26(25)11-13-44(27,30)6)57-42-39(60-41-36(53)34(51)32(49)22(4)56-41)37(54)38(29(18-47)58-42)59-40-35(52)33(50)31(48)21(3)55-40/h7,19-22,24-42,46-54H,8-18H2,1-6H3/t19-,20+,21+,22+,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

OC[C@H]([C@@H](O[C@@]1([H])[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O1)[C@H](O)[C@H]2O[C@@]3([H])[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O3)O[C@@]2([H])O[C@H](C4)CC[C@@]5(C)C4=CC[C@]6([H])[C@]5([H])CC[C@@]7(C)[C@@]6([H])C[C@@]8([H])[C@]7([H])[C@H](C)[C@]9(NC[C@H](C)CC9)O8

Appearance

Solid powder

Purity

>95% (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, 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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Solamargine at 6 µM reduces viability in various non-small cell lung cancer (NSCLC) cells (H1650, H1975, PC-9, A549, H1299). In H1299 and A549 cells, it increases ERK1/2 phosphorylation and decreases DNMT1 expression. In an A549 mouse xenograft model, a daily dose of solamargine at 8 mg/kg reduces tumor growth. In tumor tissue, solamargine increases ERK1/2 phosphorylation and decreases the expression of prostaglandin E2 receptor, DNMT1, and c-Jun.

In vitro activity:

The results of this study indicate that SM inhibited the viability and promoted the apoptosis of ACHN and 786-O cells, through a mechanism involving downregulation of p-STAT3 expression. Treatment of ACHN and 786-O cells with SM significantly enhanced the caspase-3, -8, and -9 activities. SM downregulated the expression of p-STAT3 and Bcl-2 but increased the expression of cleaved caspase-3, -8, -9 and Bax. Reference: Oncol Lett. 2023 Sep 28;26(5):493. https://pubmed.ncbi.nlm.nih.gov/37854861/

In vivo activity:

Solamargine may have therapeutic potential in cancer therapy with no apparent toxic effects. Solamargine, at doses of 5 or 10 mg/kg/day administered subcutaneously to male C57BL/6 mice for 5 days, decreased melanoma tumor size and frequency of mitoses in tumor tissue, indicative of a decrease in cell proliferation. There were no apparent signs of systemic toxicity, nephrotoxicity, and genotoxicity initiated by treatments either with solamargine alone or plant alkaloid incorporated into nanoparticles. Reference: J Toxicol Environ Health A. 2022 Feb 16;85(4):131-142. https://pubmed.ncbi.nlm.nih.gov/34612163/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	34.56
	DMSO	30.0	34.56
	Ethanol	30.0	34.56

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 868.07 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.

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. Huang S, Sun M, Ren Y, Luo T, Wang X, Weng G, Cen D. Solamargine induces apoptosis of human renal carcinoma cells via downregulating phosphorylated STAT3 expression. Oncol Lett. 2023 Sep 28;26(5):493. doi: 10.3892/ol.2023.14080. PMID: 37854861; PMCID: PMC10579987. 2. Qu X, Xie J, Zhang Y, Wang Z. Solamargine Alleviates Proliferation and Metastasis of Cervical Cancer Cells by Blocking the CXCL3-Mediated Erk Signaling Pathway. Evid Based Complement Alternat Med. 2022 Oct 29;2022:7634754. doi: 10.1155/2022/7634754. PMID: 36345403; PMCID: PMC9637034. 3. Ge J, Wang P, Ma H, Zhang J. Solamargine Inhibits Prostate Cancer Cell Growth and Enhances the Therapeutic Efficacy of Docetaxel via Akt Signaling. J Oncol. 2022 Mar 10;2022:9055954. doi: 10.1155/2022/9055954. PMID: 35310915; PMCID: PMC8930254. 4. Furtado RA, Ozelin SD, Ferreira NH, Miura BA, Almeida Junior S, Magalhães GM, Nassar EJ, Miranda MA, Bastos JK, Tavares DC. Antitumor activity of solamargine in mouse melanoma model: relevance to clinical safety. J Toxicol Environ Health A. 2022 Feb 16;85(4):131-142. doi: 10.1080/15287394.2021.1984348. Epub 2021 Oct 6. PMID: 34612163.

In vitro protocol:

In vivo protocol:

1. Ge J, Wang P, Ma H, Zhang J. Solamargine Inhibits Prostate Cancer Cell Growth and Enhances the Therapeutic Efficacy of Docetaxel via Akt Signaling. J Oncol. 2022 Mar 10;2022:9055954. doi: 10.1155/2022/9055954. PMID: 35310915; PMCID: PMC8930254. 2. Furtado RA, Ozelin SD, Ferreira NH, Miura BA, Almeida Junior S, Magalhães GM, Nassar EJ, Miranda MA, Bastos JK, Tavares DC. Antitumor activity of solamargine in mouse melanoma model: relevance to clinical safety. J Toxicol Environ Health A. 2022 Feb 16;85(4):131-142. doi: 10.1080/15287394.2021.1984348. Epub 2021 Oct 6. PMID: 34612163.

1. Chen, Y., Tang, Q., Xiao, Q., et al. Targeting EP4 downstream c-Jun through ERK1/2-mediated reduction of DNMT1 reveals novel mechanism of solamargine-inhibited growth of lung cancer cells. J. Cell. Mol. Med. 21(2), 222-233 (2017).