Solamargine CAS NO.20311-51-7

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General tips：For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging：1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition：Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Chemical Properties of Solamargine

Cas No.	20311-51-7
PubChem ID	73611	Appearance	White-beige powder
Formula	C45H73NO15	M.Wt	868.06
Type of Compound	Alkaloids	Storage	Desiccate at -20°C
Synonyms	Solamargin; δ-Solanigrine
Solubility	DMSO : ≥ 8.8 mg/mL (10.14 mM) *"≥" means soluble, but saturation unknown.
SMILES	CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)C)O)O)O)O)OC9C(C(C(C(O9)C)O)O)O)C)C)C)NC1
Standard InChIKey	MBWUSSKCCUMJHO-ZGXDEBHDSA-N
Standard InChI	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
General tips	For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging	1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment.
Shipping Condition	Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Solamargine

The herbs of Solanum nigrum L.

Biological Activity of Solamargine

Description	Solamargine has potential anti-trypanosomal, and anti-cancer activities; interactions between the glycoalkaloids solasonine and solamargine have inhibition of fungal growth. Solamargine significantly inhibits migration and invasion of HepG2 cells by down-regulating MMP-2 and MMP-9 expression and activity.
Targets	MMP(e.g.TIMP) | p53 | Bcl-2/Bax | Caspase | Antifection
In vitro	Solamargine inhibits migration and invasion of human hepatocellular carcinoma cells through down-regulation of matrix metalloproteinases 2 and 9 expression and activity.[Pubmed: 25819016] Toxicol In Vitro. 2015 Aug;29(5):893-900. Solamargine is a steroidal alkaloid glycoside isolated from Solanum nigrum. The aim of this study was to investigate the effects of Solamargine on tumor migration and invasion in aggressive human hepatocellular carcinoma cells. METHODS AND RESULTS: The MTT assay was used to assess the effects of Solamargine on the viability of HepG2 cells. Migration and invasion ability of HepG2 cells under Solamargine treatment were examined by a wound healing migration assay and Boyden chamber assay, respectively. Western blotting assays were used to detect the expression of MMP-2 and MMP-9 proteins and MMP-2 and MMP-9 activity were analyzed by gelatin zymography assay. Solamargine reduced HepG2 cell viability in a concentration-dependent manner. At 7.5μM Solamargine decreased cell viability by less than 20% in HepG2 cells. A wound healing migration assay and Boyden chamber invasion assay showed that Solamargine significantly inhibited in vitro migration and invasion of HepG2 cells. At the highest dose, Solamargine decreased cell migration and invasion by more than 70% and 72% in HepG2 cells, respectively. Western blotting and gelatin zymography results showed that Solamargine reduced expression and function of MMP-2 and MMP-9 proteins. CONCLUSIONS: In conclusion, the results showed that Solamargine significantly inhibits migration and invasion of HepG2 cells by down-regulating MMP-2 and MMP-9 expression and activity. In vitro trypanocidal activity of solamargine and extracts from Solanum palinacanthum and Solanum lycocarpum of Brazilian cerrado.[Pubmed: 24068082] An Acad Bras Cienc. 2013 Sep;85(3):903-7. METHODS AND RESULTS: The present investigation was to evaluate the potential trypanocidal activity of crude ethanolic extract of the fruits of Solanum palinacanthum, Solanum lycocarpum and the glycoalcaloid, Solamargine. S. palinacanthum and S. lycocarpum fruit powders were submitted to exhaustively extraction with 96% ethanol and Solamargine were isolated from the extract of S. palinacanthum. Both extracts and Solamargine were analysed for trypanocidal activity by using MTT colorimetric assay. Extracts of S. palinacanthum showed to be more active (IC50 = 175.9 μg.ml-1) than S. lycocarpum (IC50 = 194.7 μg.ml-1). Solamargine presented a strong activity (IC50 = 15.3 μg.ml-1), which can explain the better activity of the both extracts. Benznidazol (IC50 = 9.0 μg.ml-1) is the only drug used to treat Chagas' disease. CONCLUSIONS: These findings demonstrate for the first time that ethanol extracts obtained from both fruits of S. palinacanthum and S. lycocarpum and also Solamargine have a potential anti-trypanosomal activity. Interactions between the glycoalkaloids solasonine and solamargine in relation to inhibition of fungal growth.[Pubmed: 7765652] Phytochemistry. 1994 Nov;37(4):1007-11. Inhibition of mycelium development in Phoma medicaginis and Rhizoctonia solani by Solamargine and solasonine generally increased with increasing pH. P. medicaginis was the more susceptible species and Solamargine the more potent compound. Solasonine was inactive against R. solani over the tested pH range (5-8). Dose-response curves confirmed these differential effects. METHODS AND RESULTS: Solamargine caused 50% growth inhibition in P. medicaginis at 60 microM (at pH 7) whereas no other treatment achieved this effect at 100 microM. Combinations of 50 microM of each glycoalkaloid produced synergistic effects against both fungi, especially R. solani which was essentially unaffected by either compound, by significantly inhibited by a 1:1 mixture of the two. The magnitude of the synergism was not affected by a pH change between 6 and 7. Spore germination in Alternaria brassicicola was markedly inhibited by 100 microM Solamargine but unaffected by 100 microM solasonine or either compound at 50 microM. In P. medicaginis, neither glycoalkaloid was inhibitory up to 150 microM. CONCLUSIONS: In combination, the two compounds caused synergistic effects in both species, but to a much greater extent in A. brassicicola.

Protocol of Solamargine

Cell Research

Action of solamargine on human lung cancer cells--enhancement of the susceptibility of cancer cells to TNFs.[Pubmed: 15527763 ] Solamargine induces apoptosis associated with p53 transcription-dependent and transcription-independent pathways in human osteosarcoma U2OS cells.[Pubmed: 21163271] Antiproliferative activity of Solanum lycocarpum alkaloidic extract and their constituents, solamargine and solasonine, in tumor cell lines.[Pubmed: 23475509] J Nat Med. 2014 Jan;68(1):236-41. Natural products are some of the important sources of new anticancer drugs. The Brazilian flora is considered one of the most diverse in the word, although not many large-scale pharmacological and phytochemical studies have been conducted to date. METHODS AND RESULTS: With this in mind, in the present study we evaluated the antiproliferative activity of Solanum lycocarpum fruit glycoalkaloid extract (SL) and its major compounds, Solamargine (SM) and solasonine (SS), against different tumor cell lines: murine melanoma (B16F10), human colon carcinoma (HT29), human breast adenocarcinoma (MCF-7), human cervical adenocarcinoma (HeLa), human hepatocellular liver carcinoma (HepG2) and human glioblastoma (MO59J, U343 and U251). The antiproliferative activity was evaluated using XTT assay and results were expressed as IC50. The most pronounced antiproliferative activity was observed for SM, with IC50 values ranging from 4.58 to 18.23 μg/mL. The lowest IC50 values were observed against HepG2, being 9.60 μg/mL for SL, 4.58 μg/mL for SM and 6.01 μg/mL for SS. CONCLUSIONS: Thus, SL, SM and SS demonstrated antiproliferative activity against the tumor cell lines tested, and were most effective against the HepG2 cell line. Life Sci. 2011 Feb 14;88(7-8):314-21. Solamargine, a steroidal glycoalkaloid isolated from S. incanum, has been shown to induce apoptosis in several cancer cell lines. In this study, the involvement of p53 in the pro-apoptotic action of Solamargine was investigated in human osteosarcoma U2OS cells. METHODS AND RESULTS: The cytotoxicity of Solamargine was evaluated by MTT assay. Solamargine-induced apoptosis was evidenced by chromatin condensation, formation of apoptotic bodies and exposure of phosphatidylserine on the extracellular surface as revealed by DAPI nuclear staining, transmission electron microscopy and flow cytometry, respectively. mRNA expressions of p53 and Bax were investigated using real time-PCR. Western blot was used to examine the changes in the expression levels of p53, Bax, Bcl-2, caspase-3, caspase-9 and cytochrome c. Subcellular localization of p53 was verified by immunofluorescence staining and cell fractionation. Solamargine substantially reduced cell viability and induced apoptosis in osteosarcoma U2OS cells. In this connection, Solamargine increased the mRNA and protein expressions of p53 and Bax (a pro-apoptotic protein downstream to p53). The expression of Bcl-2 (an anti-apoptotic protein) was also reduced. Furthermore, Solamargine induced mitochondrial translocation of p53, loss of mitochondrial membrane potential, cytochrome c release and activation of caspase-9 and -3. p53-specific transcriptional inhibitor pifithrin-α or mitochondrial translocation inhibitor pifithrin-μ partially reversed Solamargine-induced apoptosis. CONCLUSIONS: Solamargine activates the mitochondria-mediated apoptotic pathway in U2OS cells via both p53 transcription-dependent and -independent mechanisms. This compound may merit further investigation as a potential therapeutic agent for the treatment of cancer. FEBS Lett. 2004 Nov 5;577(1-2):67-74. Solamargine (SM), isolated from Solanum incanum herb, displayed a superior cytotoxicity in four human lung cancer cell lines. METHODS AND RESULTS: The half-inhibitory concentrations (IC50), of the cell viability assay for H441, H520, H661 and H69 cells were 3, 6.7, 7.2 and 5.8 microM, respectively. SM-induced apoptosis of these cells by PS externalization in a dose-dependent manner and increased sub-G1 fraction were observed. Quenching of the expression of tumor necrosis factor receptors (TNFRs) during the progress of human lung carcinogenesis has been previously reported. SM may induce cell apoptosis via modulating the expression of TNFRs and their subsequent TRADD/FADD signal cascades. Subsequently, SM treatment increased the binding activities of TNF-alpha and TNF-beta to the lung cancers, and the intrinsic TNFs-resistant cancer cells became susceptible to TNF-alpha and -beta. In addition, SM caused release of cytochrome c, downregulation of anti-apoptotic Bcl-2 and Bcl-xL, increase of caspase-3 activity, and DNA fragmentation. CONCLUSIONS: Thus, SM could modulate the expressions of TNFRs and Bcl-2, and might be a potential anticancer agent for TNFs and Bcl-2 related resistance of human lung cancer cells.

Preparing Stock Solutions of Solamargine

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	1.152 mL	5.76 mL	11.5199 mL	23.0399 mL	28.7999 mL
5 mM	0.2304 mL	1.152 mL	2.304 mL	4.608 mL	5.76 mL
10 mM	0.1152 mL	0.576 mL	1.152 mL	2.304 mL	2.88 mL
50 mM	0.023 mL	0.1152 mL	0.2304 mL	0.4608 mL	0.576 mL
100 mM	0.0115 mL	0.0576 mL	0.1152 mL	0.2304 mL	0.288 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

References on Solamargine

Interactions between the glycoalkaloids solasonine and solamargine in relation to inhibition of fungal growth.[Pubmed:7765652]

Phytochemistry. 1994 Nov;37(4):1007-11.

Inhibition of mycelium development in Phoma medicaginis and Rhizoctonia solani by Solamargine and solasonine generally increased with increasing pH. P. medicaginis was the more susceptible species and Solamargine the more potent compound. Solasonine was inactive against R. solani over the tested pH range (5-8). Dose-response curves confirmed these differential effects. Solamargine caused 50% growth inhibition in P. medicaginis at 60 microM (at pH 7) whereas no other treatment achieved this effect at 100 microM. Combinations of 50 microM of each glycoalkaloid produced synergistic effects against both fungi, especially R. solani which was essentially unaffected by either compound, by significantly inhibited by a 1:1 mixture of the two. The magnitude of the synergism was not affected by a pH change between 6 and 7. Spore germination in Alternaria brassicicola was markedly inhibited by 100 microM Solamargine but unaffected by 100 microM solasonine or either compound at 50 microM. In P. medicaginis, neither glycoalkaloid was inhibitory up to 150 microM. In combination, the two compounds caused synergistic effects in both species, but to a much greater extent in A. brassicicola.

Solamargine induces apoptosis associated with p53 transcription-dependent and transcription-independent pathways in human osteosarcoma U2OS cells.[Pubmed:21163271]

Life Sci. 2011 Feb 14;88(7-8):314-21.

AIMS: Solamargine, a steroidal glycoalkaloid isolated from S. incanum, has been shown to induce apoptosis in several cancer cell lines. In this study, the involvement of p53 in the pro-apoptotic action of Solamargine was investigated in human osteosarcoma U2OS cells. MAIN METHODS: The cytotoxicity of Solamargine was evaluated by MTT assay. Solamargine-induced apoptosis was evidenced by chromatin condensation, formation of apoptotic bodies and exposure of phosphatidylserine on the extracellular surface as revealed by DAPI nuclear staining, transmission electron microscopy and flow cytometry, respectively. mRNA expressions of p53 and Bax were investigated using real time-PCR. Western blot was used to examine the changes in the expression levels of p53, Bax, Bcl-2, caspase-3, caspase-9 and cytochrome c. Subcellular localization of p53 was verified by immunofluorescence staining and cell fractionation. KEY FINDINGS: Solamargine substantially reduced cell viability and induced apoptosis in osteosarcoma U2OS cells. In this connection, Solamargine increased the mRNA and protein expressions of p53 and Bax (a pro-apoptotic protein downstream to p53). The expression of Bcl-2 (an anti-apoptotic protein) was also reduced. Furthermore, Solamargine induced mitochondrial translocation of p53, loss of mitochondrial membrane potential, cytochrome c release and activation of caspase-9 and -3. p53-specific transcriptional inhibitor pifithrin-alpha or mitochondrial translocation inhibitor pifithrin-mu partially reversed Solamargine-induced apoptosis. SIGNIFICANCE: Solamargine activates the mitochondria-mediated apoptotic pathway in U2OS cells via both p53 transcription-dependent and -independent mechanisms. This compound may merit further investigation as a potential therapeutic agent for the treatment of cancer.

Antiproliferative activity of Solanum lycocarpum alkaloidic extract and their constituents, solamargine and solasonine, in tumor cell lines.[Pubmed:23475509]

J Nat Med. 2014 Jan;68(1):236-41.

Natural products are some of the important sources of new anticancer drugs. The Brazilian flora is considered one of the most diverse in the word, although not many large-scale pharmacological and phytochemical studies have been conducted to date. With this in mind, in the present study we evaluated the antiproliferative activity of Solanum lycocarpum fruit glycoalkaloid extract (SL) and its major compounds, Solamargine (SM) and solasonine (SS), against different tumor cell lines: murine melanoma (B16F10), human colon carcinoma (HT29), human breast adenocarcinoma (MCF-7), human cervical adenocarcinoma (HeLa), human hepatocellular liver carcinoma (HepG2) and human glioblastoma (MO59J, U343 and U251). The antiproliferative activity was evaluated using XTT assay and results were expressed as IC50. The most pronounced antiproliferative activity was observed for SM, with IC50 values ranging from 4.58 to 18.23 mug/mL. The lowest IC50 values were observed against HepG2, being 9.60 mug/mL for SL, 4.58 mug/mL for SM and 6.01 mug/mL for SS. Thus, SL, SM and SS demonstrated antiproliferative activity against the tumor cell lines tested, and were most effective against the HepG2 cell line.

Solamargine inhibits migration and invasion of human hepatocellular carcinoma cells through down-regulation of matrix metalloproteinases 2 and 9 expression and activity.[Pubmed:25819016]

Toxicol In Vitro. 2015 Aug;29(5):893-900.

Solamargine is a steroidal alkaloid glycoside isolated from Solanum nigrum. The aim of this study was to investigate the effects of Solamargine on tumor migration and invasion in aggressive human hepatocellular carcinoma cells. The MTT assay was used to assess the effects of Solamargine on the viability of HepG2 cells. Migration and invasion ability of HepG2 cells under Solamargine treatment were examined by a wound healing migration assay and Boyden chamber assay, respectively. Western blotting assays were used to detect the expression of MMP-2 and MMP-9 proteins and MMP-2 and MMP-9 activity were analyzed by gelatin zymography assay. Solamargine reduced HepG2 cell viability in a concentration-dependent manner. At 7.5muM Solamargine decreased cell viability by less than 20% in HepG2 cells. A wound healing migration assay and Boyden chamber invasion assay showed that Solamargine significantly inhibited in vitro migration and invasion of HepG2 cells. At the highest dose, Solamargine decreased cell migration and invasion by more than 70% and 72% in HepG2 cells, respectively. Western blotting and gelatin zymography results showed that Solamargine reduced expression and function of MMP-2 and MMP-9 proteins. In conclusion, the results showed that Solamargine significantly inhibits migration and invasion of HepG2 cells by down-regulating MMP-2 and MMP-9 expression and activity.

In vitro trypanocidal activity of solamargine and extracts from Solanum palinacanthum and Solanum lycocarpum of Brazilian cerrado.[Pubmed:24068082]

An Acad Bras Cienc. 2013 Sep;85(3):903-7.

The present investigation was to evaluate the potential trypanocidal activity of crude ethanolic extract of the fruits of Solanum palinacanthum, Solanum lycocarpum and the glycoalcaloid, Solamargine. S. palinacanthum and S. lycocarpum fruit powders were submitted to exhaustively extraction with 96% ethanol and Solamargine were isolated from the extract of S. palinacanthum. Both extracts and Solamargine were analysed for trypanocidal activity by using MTT colorimetric assay. Extracts of S. palinacanthum showed to be more active (IC50 = 175.9 microg.ml-1) than S. lycocarpum (IC50 = 194.7 microg.ml-1). Solamargine presented a strong activity (IC50 = 15.3 microg.ml-1), which can explain the better activity of the both extracts. Benznidazol (IC50 = 9.0 microg.ml-1) is the only drug used to treat Chagas' disease. These findings demonstrate for the first time that ethanol extracts obtained from both fruits of S. palinacanthum and S. lycocarpum and also Solamargine have a potential anti-trypanosomal activity.

Action of solamargine on human lung cancer cells--enhancement of the susceptibility of cancer cells to TNFs.[Pubmed:15527763]

FEBS Lett. 2004 Nov 5;577(1-2):67-74.

Solamargine (SM), isolated from Solanum incanum herb, displayed a superior cytotoxicity in four human lung cancer cell lines. The half-inhibitory concentrations (IC50), of the cell viability assay for H441, H520, H661 and H69 cells were 3, 6.7, 7.2 and 5.8 microM, respectively. SM-induced apoptosis of these cells by PS externalization in a dose-dependent manner and increased sub-G1 fraction were observed. Quenching of the expression of tumor necrosis factor receptors (TNFRs) during the progress of human lung carcinogenesis has been previously reported. SM may induce cell apoptosis via modulating the expression of TNFRs and their subsequent TRADD/FADD signal cascades. Subsequently, SM treatment increased the binding activities of TNF-alpha and TNF-beta to the lung cancers, and the intrinsic TNFs-resistant cancer cells became susceptible to TNF-alpha and -beta. In addition, SM caused release of cytochrome c, downregulation of anti-apoptotic Bcl-2 and Bcl-xL, increase of caspase-3 activity, and DNA fragmentation. Thus, SM could modulate the expressions of TNFRs and Bcl-2, and might be a potential anticancer agent for TNFs and Bcl-2 related resistance of human lung cancer cells.

Description

Solamargine, a derivative from the steroidal solasodine in Solanum species, exhibits anticancer activities in numerous types of cancer. Solamargine induces non-selective cytotoxicity and P-glycoprotein inhibition. Solamargine significantly inhibits migration and invasion of HepG2 cells by down-regulating MMP-2 and MMP-9 expression and activity.

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