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solasonine
b-D-galactopyranoside, (3b,22a,25R)-spirosol-5-en-3-yl O-6-deoxy-a-L-mannopyranosyl-(1->;2)-O-[b-D-glucopyranosyl-(1->3)]-

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CAS Number: 19121-58-5Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:242-826-6
FDA UNII: TR60638HXL
Nikkaji Web:J13.552F
XlogP3-AA:1.10 (est)
Molecular Weight:884.07101000
Formula:C45 H73 N O16
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Flash Point: 32.00 °F. TCC ( 0.00 °C. ) (est)
logP (o/w): 4.350 (est)
Soluble in:
 water, 0.9627 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Solasonine 98%
BOC Sciences
For experimental / research use only.
Solasonine
Carbosynth
For experimental / research use only.
Solasonine
Coompo
For experimental / research use only.
Solasonine from Plants ≥97%
Odor: characteristic
Use: Solasonine is a poisonous chemical compound. It is a glycoside of solasodine. Solasonine was one component of the unsuccessful experimental cancer drug candidate Coramsine. Two genetically diverse strains of Trypanosoma cruzi were tested in vitro for susceptibility to the solanum-derived triglycoside alkaloids solasonine and solamargine. Cytolytic assays were performed on epimastigotes (EMs) and bloodstream form trypomastigotes (BSFs) lifecycle stages by using serial dilutions of each alkaloid. Each alkaloid effectively lysed both lifecycle stages, although solasonine routinely required higher concentrations to induce similar results. EMs demonstrated greater resistance to cytolysis than BSFs at equal concentrations of either alkaloid. No significant resistance could be correlated to parasite strain. The reported synergistic cytolytic effects observed upon compounding solasonine and solamargine together were also tested. We failed to identify any cytolytic synergism in cultures of EMs or BSFs. The role of rhamnose-binding proteins (RBPs) in mediating cytolysis was investigated through competitive inhibition experiments. The addition of exogenous L: -rhamnose to the media failed to reduce parasite attrition independent of the parasite lifecycle stage. Based on these results, we suggest the mechanisms involved in cytolysis of T. cruzi by solasonine and solamargine are largely independent of rhamnose receptor-specific interactions. Experiments with solasonine at pH 6 and 8 suggest that the unprotonated form of the glycoalkaloids appears to be involved in the membrane effects. The nature of the carbohydrate side-chains of the steroidal glycosides governs relative potencies. The possible significance of the findings to food safety and plant physiology and possible application of the membrane assays to bacterial toxins are discussed.
Glentham Life Sciences
Solasonine
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 77300 ug/kg
Indian Journal of Experimental Biology. Vol. 15, Pg. 285, 1977.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for solasonine usage levels up to:
 not for fragrance use.
 
Recommendation for solasonine flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :119247
National Institute of Allergy and Infectious Diseases:Data
Chemidplus:0019121585
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):119247
Pubchem (sid):135033171
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C10824
HMDB (The Human Metabolome Database):Search
FooDB:FDB002456
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 eggplant
Search Trop Picture
 eggplant fruit
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 solanum aculeastrum
Search Trop Picture
 solanum nigrum
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Synonyms:
b-D-galactopyranoside, (3b,22a,25R)-spirosol-5-en-3-yl O-6-deoxy-a-L-mannopyranosyl-(1->;2)-O-[b-D-glucopyranosyl-(1->3)]-
 purapurine
 solamargine
 solanine-S
 

Articles:

PubMed:In vitro and in vivo evaluation of the delivery of topical formulations containing glycoalkaloids of Solanum lycocarpum fruits.
PubMed:Purification, antitumor activity in vitro of steroidal glycoalkaloids from black nightshade (Solanum nigrum L.).
PubMed:In vitro leishmanicidal and cytotoxic activities of the glycoalkaloids from Solanum lycocarpum (Solanaceae) fruits.
PubMed:Antiproliferative activity of Solanum lycocarpum alkaloidic extract and their constituents, solamargine and solasonine, in tumor cell lines.
PubMed:Biosynthesis of steroidal alkaloids in Solanaceae plants: involvement of an aldehyde intermediate during C-26 amination.
PubMed:A Validated Reverse Phase HPLC Analytical Method for Quantitation of Glycoalkaloids in Solanum lycocarpum and Its Extracts.
PubMed:Antihepatitis B virus constituents of Solanum erianthum.
PubMed:Evaluation of the schistosomicidal activity of the steroidal alkaloids from Solanum lycocarpum fruits.
PubMed:[Simultaneous determination of three steroidal alkaloids from Solanum Nigrum by RP-HPLC].
PubMed:Antimutagenic potential of Solanum lycocarpum against induction of chromosomal aberrations in V79 cells and micronuclei in mice by doxorubicin.
PubMed:Simultaneous determination of three steroidal glycoalkaloids in Solanum xanthocarpum by high performance thin layer chromatography.
PubMed:In vivo antimalarial activities of glycoalkaloids isolated from Solanaceae plants.
PubMed:Effects of glycoalkaloids from Solanum plants on cucumber root growth.
PubMed:Characterization of health-related compounds in eggplant (Solanum melongena L.) lines derived from introgression of allied species.
PubMed:Alpha-solasonine and alpha-solamargine contents of gboma (Solanum macrocarpon L.) and scarlet (Solanum aethiopicum L.) eggplants.
PubMed:pH-Zone-refining centrifugal partition chromatography for preparative isolation and purification of steroidal glycoalkaloids from Solanum xanthocarpum.
PubMed:Solanaceous steroidal glycoalkaloids and poisoning by Solanum torvum, the normally edible susumber berry.
PubMed:Phytochemical study of Solanum lycocarpum (St. Hil) unripe fruit and its effects on rat gestation.
PubMed:Structures of steroidal alkaloid oligoglycosides, robeneosides A and B, and antidiabetogenic constituents from the Brazilian medicinal plant Solanum lycocarpum.
PubMed:Efficacy and mechanisms of alpha-solasonine-and alpha-solamargine-induced cytolysis on two strains of Trypanosoma cruzi.
PubMed:Rats exposed to Solanum lycocarpum fruit in utero and during lactation: neurochemical, behavioral and histopathological effects.
PubMed:Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells.
PubMed:Liquid chromatographic determination of alpha-solasonine in frozen green peas as an indicator of the presence of nightshade berries.
PubMed:Monitoring changes in anthocyanin and steroid alkaloid glycoside content in lines of transgenic potato plants using liquid chromatography/mass spectrometry.
PubMed:Effect of feeding solanidine, solasodine and tomatidine to non-pregnant and pregnant mice.
PubMed:Effects of naturally occurring glucosides, solasodine glucosides, ginsenosides and parishin derivatives on multidrug resistance of lymphoma cells and leukocyte functions.
PubMed:Membrane disruption and enzyme inhibition by naturally-occurring and modified chacotriose-containing Solanum steroidal glycoalkaloids.
PubMed:Absence of interceptive effect in rats treated with Solanum lycocarpum (St. Hil).
PubMed:Developmental toxicology of solamargine and solasonine glycoalkaloids in frog embryos.
PubMed:Inhibition of Trypanosoma cruzi growth in vitro by Solanum alkaloids: a comparison with ketoconazole.
PubMed:The effect of some Solanum steroidal alkaloids and glycoalkaloids on larvae of the red flour beetle, Tribolium castaneum, and the tobacco hornworm, Manduca sexta.
PubMed:Steroidal alkaloid glycosides from Solanum suaveolens.
PubMed:Steroid alkaloid glycosides from Solanum coccineum.
PubMed:Feeding of potato, tomato and eggplant alkaloids affects food consumption and body and liver weights in mice.
PubMed:Solasodine glycosides of Solanum unguiculatum (A.) Rich.
PubMed:Steroid alkaloid glycosides from Solanum robustum.
PubMed:Production of monoclonal antibodies and development of an ELISA for solamargine.
PubMed:Interactions between the glycoalkaloids solasonine and solamargine in relation to inhibition of fungal growth.
PubMed:1H- and 13C-nmr assignments and structural determination of a novel glycoalkaloid from Solanum platanifolium.
PubMed:Analysis of glycoalkaloids from potato shoots and tomatoes by four-sector tandem mass spectrometry with scanning-array detection: comparison of positive ion and negative ion methods.
PubMed:Isolation of steroidal glycoalkaloids from Solanum incanum by two countercurrent chromatographic methods.
PubMed:Solasodine glycosides. Selective cytotoxicity for cancer cells and inhibition of cytotoxicity by rhamnose in mice with sarcoma 180.
PubMed:HPLC of Glycoalkaloids from Solanum sodomaeum.
PubMed:The inactivation of herpes simplex virus by some Solanaceae glycoalkaloids.
PubMed:Molluscicidal steroid glycoalkaloids possessing stereoisomeric spirosolane structures.
PubMed:[Isolation of solasonine from glucoalkaloid mixtures by fungal fermentation.].
PubMed:Some pharmacological actions of solasonine.
 
Notes:
solasonine is weakly anti-fungal.
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