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Solasonine

$214

  • Brand : BIOFRON

  • Catalogue Number : BD-P0582

  • Specification : 98.0%(HPLC)

  • CAS number : 19121-58-5

  • Formula : C45H73NO16

  • Molecular Weight : 884.06

  • PUBCHEM ID : 73410

  • Volume : 25mg

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Catalogue Number

BD-P0582

Analysis Method

Specification

98.0%(HPLC)

Storage

-20℃

Molecular Weight

884.06

Appearance

Powder

Botanical Source

This product is isolated and purified from the herbs of Solanum nigrum L.

Structure Type

Category

SMILES

CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)C)O)O)O)C)C)C)NC1

Synonyms

α-Solasonine/PURAPURIN/Solasoonine/Purapurine/SOLANINE S/Solanine-S/SOLASONIN/(3β,22α,25R)-Spirosol-5-en-3-yl 6-deoxy-α-L-mannopyranosyl-(1->2)-[β-D-glucopyranosyl-(1->;3)]-β-D-galactopyranoside/SOLASODAMINE/(3b,22a,25R)-Spirosol-5-en-3-yl O-6-Deoxy-a-L-mannopyranosyl(1®2)-O-[b-D-glucopyranosyl(1®3)]-b-D-galactopyranoside/β-D-Galactopyranoside, (3β,22α,25R)-spirosol-5-en-3-yl O-6-deoxy-α-L-mannopyranosyl-(1->2)-O-[β-D-glucopyranosyl-(1->3)]-/UNII:TR60638HXL/SOLANCARPIN

IUPAC Name

Applications

In vitro leishmanicidal and cytotoxic activities of the glycoalkaloids from Solanum lycocarpum (Solanaceae) fruits.[Pubmed: 23576350]Chem Biodivers. 2013 Apr;10(4):642-8. Leishmaniasis is an infection caused by a protozoan parasite of the genus Leishmania and is the second most prevalent parasitic protozoal disease after malaria in the world. METHODS AND RESULTS: We report the in vitro leishmanicidal activity on promastigote forms of Leishmania amazonensis and cytotoxicity, using LLCMK2 cells, of the glycoalkaloids from the fruits of Solanum lycocarpum, determined by colorimetric methods. The alkaloidic extract was obtained by acid-base extraction; solamargine and Solasonine were isolated by silica-gel chromatography, followed by reversed-phase HPLC final purification. The alkaloidic extract, solamargine, Solasonine, as well as the equimolar mixture of the glycoalkaloids solamargine and Solasonine displayed leishmanicidal activity against promastigote forms of L. amazonensis, whereas the aglycone solasodine was inactive. After 24 and 72 h of incubation, most of the samples showed lower cytotoxicities (IC50 6.5 to 124 μM) as compared to leishmanicidal activity (IC50 1.1 to 23.6 μM). The equimolar mixture solamargine/Solasonine was the most active with an IC50 value of 1.1 μM, after 72 h. Likewise, solamargine was the most active after 24 h with an IC50 value of 14.4 μM, both in comparison with the positive control amphotericin B.

Density

1.4±0.1 g/cm3

Solubility

Methanol

Flash Point

Boiling Point

Melting Point

301-303℃

InChl

InChl Key

QCTMYNGDIBTNSK-LFRCBARCSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:19121-58-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

27754442

Abstract

The major obstacle limiting the efficacy of current Smoothened (Smo) inhibitors is the primary and acquired resistance mainly caused by Smo mutations and Gli amplification. In this context, developing Hh inhibitors targeting Gli, the final effector of this signaling pathway, may combat the resistance. In this study we found that solasonine, a natural glycoalkaloid compound, significantly inhibited the hedgehog (Hh) pathway activity. Meanwhile, solasonine may obviously inhibit the alkaline phosphatase (ALP) activity in C3H10T1/2 cells, concomitantly with reductions of the mRNA expression of Gli1 and Ptch1. However, we found that solasonine exhibited no effect on the transcriptional factors activities provoked by TNF-α and PGE2, thus suggesting its selectivity against Hh pathway activity. Furthermore, we identified that solasonine inhibited the Hh pathway activity by acting on its transcriptional factor Gli using a series of complementary data. We also observed that solasonine obviously inhibited the Gli-luciferase activity provoked by ectopic expression of Smo mutants which may cause the resistance to the current Smo inhibitors. Our study suggests that solasonine may significantly inhibit the Hh pathway activity by acting on Gli, therefore indicating the possibility to use solasonine as a lead compound to develop anticancer drugs for combating the resistance of current Smo inhibitors.

KEYWORDS

Gli resistance; hedgehog; solasonine.

Title

Solasonine, A Natural Glycoalkaloid Compound, Inhibits Gli-Mediated Transcriptional Activity

Author

Jun Yang 1 , Wenjing Huang 2 , Wenfu Tan 3

Publish date

2016 Oct 14

PMID

28867954

Abstract

Eggplant (Solanum melongena L.) is one of the most consumed vegetables in the world. The eggplant glycoalkaloids (GAs) are toxic secondary metabolites that may have detrimental effects on human health, particularly if the magnitudes of GAs are higher than the recommended food safety level (200 mg per kg of fresh mass). In this study, the content of solasonine compound and the expression patterns of solasodine galactosyltransferase (SGT1) gene were assessed in different tissues (mature leaves, flower buds, young, mature, and physiologically ripe fruits) of two Iranian eggplant genotypes (D1 and J10) under field conditions. The maximum mass fraction of solasonine in D1 was detected in flower buds (135.63 µg/g), followed by leaf (113.29 µg/g), physiologically ripe fruit (74.74 µg/g), young fruit (61.33 µg/g), and mature fruit (21.55 µg/g). Comparing both genotypes, the genotype of bitter fruits (J10) contained higher mass fraction of solasonine, as one of the main factors for producing bitter flavour of the plant. Regarding the expression profiles of SGT1, in both genotypes, the activity of the gene was increased nearly parallel with the concentration of solasonine. In the J10 genotype, transcript level of the gene was significantly higher than the genotype of sweet fruits (D1). Although both D1 and J10 genotypes are possibly recommendable for human food consumption, D1 is more suitable for daily diet.

KEYWORDS

Gli resistance; hedgehog; solasonine.

Title

Evaluation of Solasonine Content and Expression Patterns of SGT1 Gene in Different Tissues of Two Iranian Eggplant ( Solanum melongena L.) Genotypes

Author

Evaluation of Solasonine Content and Expression Patterns of SGT1 Gene in Different Tissues of Two Iranian Eggplant ( Solanum melongena L.) Genotypes

Publish date

2017 Jun 1

PMID

30628118

Abstract

Liver cancer, of which human hepatocellular carcinoma (HCC) is the most common type, represents the second most common cause of death from cancer worldwide. To date, treatments remain mostly ineffective and efforts are made to discover new molecules or therapeutic strategies against HCC. Mortalin, an hsp70 chaperone protein, is overexpressed in various cancer, including HCC. Mortalin sequesters p53 into the cytoplasm, thereby inhibiting its translocation to the nucleus and consequently, its cellular functions. Inhibition of mortalin-p53 interactions, which should activate the apoptotic process and the subsequent cell death, has thus been proposed as an anticancer strategy. In silico screening of a database of 354 natural compounds identified solasonine, a steroidal glycoalkaloid from Solanaceae, as a potent inhibitor of p53-mortalin interactions. Pharmacological studies confirmed that solasonine was able to inhibit efficiently mortalin-p53 interaction in HCC HepG2 cell line that expresses both mortalin and p53. This resulted in p53 translocation to the nucleus. Solasonine-induced apoptosis and cell death of HCC cell lines either expressing p53 (HepG2) or not (Hep3b), indicating that apoptotic activities of solasonine can be mediated not only through p53-dependent but also p53-independent pathways. The cytotoxic effects of solasonine correlated in part with its apoptotic properties and differed in the two HCC cell lines, being reversed by pifithrin-α, an inhibitor of p53 functions, in HepG2 cells but not in Hep3b cells. Nonapoptotic cell death was also observed, notably in Hep3b cells.

KEYWORDS

apoptosis; cell death; hepatocellular carcinoma; in silico screening; mortalin-p53 inhibitor; solasonine.

Title

In Silico Analysis of the Binding Properties of Solasonine to Mortalin and p53, and in Vitro Pharmacological Studies of Its Apoptotic and Cytotoxic Effects on Human HepG2 and Hep3b Hepatocellular Carcinoma Cells

Author

Minh Quan Pham 1 2 , Thi Hoai Van Tran 2 3 4 , Quoc Long Pham 2 , Jean Edouard Gairin 1

Publish date

2019 Aug