EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

alpha-chaconine
beta-D-glucopyranoside, (3beta)-solanid-5-en-3-yl o-6-deoxy-alpha-l-mannopyranosyl-(1-2)-O-(6-deoxy-alpha-l-mannopyranosyl-(1-4))-

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CAS Number: 20562-03-2Picture of molecule3D/inchi
FDA UNII: 5QOL0LIM81
Beilstein Number:0077396
XlogP3-AA:1.80 (est)
Molecular Weight:852.07261000
Formula:C45 H73 N O14
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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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): 8.500 (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
a-Chaconine
Carbosynth
For experimental / research use only.
a-Chaconine
ExtraSynthese
For experimental / research use only.
alpha-Chaconine (HPLC) ≥98%
Glentham Life Sciences
a-Chaconine
 
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 19 mg/kg
LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Toxicology Letters. Vol. 3, Pg. 349, 1979.

intraperitoneal-rabbit LDLo 50 mg/kg
Research Communications in Chemical Pathology and Pharmacology. Vol. 12, Pg. 657, 1975.

intraperitoneal-rat LD50 84 mg/kg
BLOOD: HEMORRHAGE
Toxicology and Applied Pharmacology. Vol. 36, Pg. 227, 1976.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for alpha-chaconine usage levels up to:
 not for fragrance use.
 
Recommendation for alpha-chaconine flavor usage levels up to:
 not for flavor use.
 
Safety References:
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :104750
National Institute of Allergy and Infectious Diseases:Data
Chemidplus:0020562032
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):104750
Pubchem (sid):135060606
 
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
KEGG (GenomeNet):C10796
HMDB (The Human Metabolome Database):HMDB39353
FooDB:FDB018909
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
 potato flower
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 potato leaf
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 potato shoot
Search Trop Picture
 potato sprout
Search Trop Picture
 potato tissue culture
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 potato tuber
Search Trop Picture
 solanum chacoense
Search Trop Picture
 
Synonyms:
a-chaconine
beta-D-glucopyranoside, (3beta)-solanid-5-en-3-yl o-6-deoxy-alpha-l-mannopyranosyl-(1-2)-O-(6-deoxy-alpha-l-mannopyranosyl-(1-4))-
 

Articles:

PubMed:[Determination of alpha-solanine, alpha-chaconine and solanidine in plasma and urine by ultra-performance liquid chromatography-triple quadrupole mass spectrometry].
PubMed:Sterol side chain reductase 2 is a key enzyme in the biosynthesis of cholesterol, the common precursor of toxic steroidal glycoalkaloids in potato.
PubMed:Detection of glycoalkaloids using disposable biosensors based on genetically modified enzymes.
PubMed:Effect of genotype and environment on the glycoalkaloid content of rare, heritage, and commercial potato varieties.
PubMed:Ultrasonic extraction of steroidal alkaloids from potato peel waste.
PubMed:Conversion of exogenous cholesterol into glycoalkaloids in potato shoots, using two methods for sterol solubilisation.
PubMed:Electrochemical determination of glycoalkaloids using a carbon nanotubes-phenylboronic acid modified glassy carbon electrode.
PubMed:Allelic variation in genes contributing to glycoalkaloid biosynthesis in a diploid interspecific population of potato.
PubMed:Synergistic cytotoxicity induced by α-solanine and α-chaconine.
PubMed:Glycoalkaloid and calystegine levels in table potato cultivars subjected to wounding, light, and heat treatments.
PubMed:Solanidine isolation from Solanum tuberosum by centrifugal partition chromatography.
PubMed:Review of the inhibition of biological activities of food-related selected toxins by natural compounds.
PubMed:Anti-inflammatory properties of potato glycoalkaloids in stimulated Jurkat and Raw 264.7 mouse macrophages.
PubMed:Effect of peeling and three cooking methods on the content of selected phytochemicals in potato tubers with various colour of flesh.
PubMed:Guatemalan potato moth Tecia solanivora distinguish odour profiles from qualitatively different potatoes Solanum tuberosum L.
PubMed:Preparative separation of glycoalkaloids α-solanine and α-chaconine by centrifugal partition chromatography.
PubMed:Polyphenol and glycoalkaloid contents in potato cultivars grown in Luxembourg.
PubMed:Compositional and toxicological analysis of a GM potato line with reduced α-solanine content--a 90-day feeding study in the Syrian Golden hamster.
PubMed:Glycoalkaloids (α-chaconine and α-solanine) contents of selected Pakistani potato cultivars and their dietary intake assessment.
PubMed:Induction of potato steroidal glycoalkaloid biosynthetic pathway by overexpression of cDNA encoding primary metabolism HMG-CoA reductase and squalene synthase.
PubMed:Development of a liquid chromatography-tandem mass spectrometric method for the simultaneous determination of tropane alkaloids and glycoalkaloids in crops.
PubMed:Glycoalkaloid content in pet food by UPLC-tandem mass spectrometry.
PubMed:Elucidation of the mass fragmentation pathways of potato glycoalkaloids and aglycons using Orbitrap mass spectrometry.
PubMed:The bioactive compounds alpha-chaconine and gallic acid in potato extracts decrease survival and induce apoptosis in LNCaP and PC3 prostate cancer cells.
PubMed:alpha-Chaconine inhibits angiogenesis in vitro by reducing matrix metalloproteinase-2.
PubMed:Naturally occurring glycoalkaloids in potatoes aggravate intestinal inflammation in two mouse models of inflammatory bowel disease.
PubMed:Composition of phenolic compounds and glycoalkaloids alpha-solanine and alpha-chaconine during commercial potato processing.
PubMed:Glycoalkaloids as biomarkers for recognition of cultivated, wild, and somatic hybrids of potato.
PubMed:Degradation of the potato glycoalkaloids--alpha-solanine and alpha-chaconine in groundwater.
PubMed:Probabilistic modelling of exposure doses and implications for health risk characterization: glycoalkaloids from potatoes.
PubMed:Fate of toxic potato glycoalkaloids in a potato field.
PubMed:A 28-day repeat dose toxicity study of steroidal glycoalkaloids, alpha-solanine and alpha-chaconine in the Syrian Golden hamster.
PubMed:Modification of the health-promoting value of potato tubers field grown under drought stress: emphasis on dietary antioxidant and glycoalkaloid contents in five native andean cultivars (Solanum tuberosum L.).
PubMed:Distribution of glycoalkaloids in potato tubers of 59 accessions of two wild and five cultivated Solanum species.
PubMed:PI3K/AKT, JNK, and ERK pathways are not crucial for the induction of cholesterol biosynthesis gene transcription in intestinal epithelial cells following treatment with the potato glycoalkaloid alpha-chaconine.
PubMed:Acute toxicity of high doses of the glycoalkaloids, alpha-solanine and alpha-chaconine, in the Syrian Golden hamster.
PubMed:A human dietary risk assessment associated with glycoalkaloid responses of potato to Colorado potato beetle defoliation.
PubMed:A major QTL and an SSR marker associated with glycoalkaloid content in potato tubers from Solanum tuberosum x S. sparsipilum located on chromosome I.
PubMed:Potato glycoalkaloids in soil-optimising liquid chromatography-time-of-flight mass spectrometry for quantitative studies.
PubMed:Alpha-chaconine-reduced metastasis involves a PI3K/Akt signaling pathway with downregulation of NF-kappaB in human lung adenocarcinoma A549 cells.
PubMed:Differential gene expression in intestinal epithelial cells induced by single and mixtures of potato glycoalkaloids.
PubMed:Potato steroidal glycoalkaloid levels and the expression of key isoprenoid metabolic genes.
PubMed:[Survey of glycoalkaloids content in the various potatoes].
PubMed:Induction of the cholesterol biosynthesis pathway in differentiated Caco-2 cells by the potato glycoalkaloid alpha-chaconine.
PubMed:Effect of carbohydrates on the production of thaxtomin A by Streptomyces acidiscabies.
PubMed:[Study of the interaction of main potato glycoalkaloids in inhibition of immobilized butyryl cholinesterase].
PubMed:Potato glycosterol rhamnosyltransferase, the terminal step in triose side-chain biosynthesis.
PubMed:[Kinetic properties of butyrylcholinesterases immobilised on pH-sensitive field-effect transistor surface and inhibitory action of steroidal glycoalkaloids on these enzymes].
PubMed:Potato glycoalkaloids and metabolites: roles in the plant and in the diet.
PubMed:Alpha-chaconine, a potato glycoalkaloid, induces apoptosis of HT-29 human colon cancer cells through caspase-3 activation and inhibition of ERK 1/2 phosphorylation.
PubMed:The primary in vivo steroidal alkaloid glucosyltransferase from potato.
PubMed:Hydrolysis of the potato glycoalkaloid alpha-chaconine by filamentous fungi.
PubMed:Simple and sensitive method for determination of glycoalkaloids in potato tubers by high-performance liquid chromatography with chemiluminescence detection.
PubMed:Anticarcinogenic effects of glycoalkaloids from potatoes against human cervical, liver, lymphoma, and stomach cancer cells.
PubMed:[Contents and its change during storage of alpha-solanine and alpha-chaconine in potatoes].
PubMed:Potato glycoalkaloids and adverse effects in humans: an ascending dose study.
PubMed:Comparison of rapid liquid chromatography-electrospray ionization-tandem mass spectrometry methods for determination of glycoalkaloids in transgenic field-grown potatoes.
PubMed:Effects of steroidal glycoalkaloids from potatoes (Solanum tuberosum) on in vitro bovine embryo development.
PubMed:Analysis of biologically active compounds in potatoes (Solanum tuberosum), tomatoes (Lycopersicon esculentum), and jimson weed (Datura stramonium) seeds.
PubMed:Effect of selenate supplementation on glycoalkaloid content of potato (Solanum tuberosum L.).
PubMed:Enrichment of the glycoalkaloids alpha-solanine and alpha-chaconine from potato juice by adsorptive bubble separation using a pH gradient.
PubMed:Colorado potato beetle toxins revisited: evidence the beetle does not sequester host plant glycoalkaloids.
PubMed:Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells.
PubMed:Determination of potato glycoalkaloids using high-pressure liquid chromatography-electrospray ionisation/mass spectrometry.
PubMed:Potato glycoalkaloids: true safety or false sense of security?
PubMed:Development and optimisation of biosensors based on pH-sensitive field effect transistors and cholinesterases for sensitive detection of solanaceous glycoalkaloids.
PubMed:Glycoalkaloid and calystegine contents of eight potato cultivars.
PubMed:Evaluation of glycoalkaloids in tubers of genetically modified virus Y-resistant potato plants (var. Désirée) by non-aqueous capillary electrophoresis coupled with electrospray ionization mass spectrometry (NACE-ESI-MS).
PubMed:[Glycoalkaloids in potatoes].
PubMed:Monitoring changes in anthocyanin and steroid alkaloid glycoside content in lines of transgenic potato plants using liquid chromatography/mass spectrometry.
PubMed:ADP ribosylation factor regulates metabolism and antioxidant capacity of transgenic potato tubers.
PubMed:Potato glycoalkaloids adversely affect intestinal permeability and aggravate inflammatory bowel disease.
PubMed:Effect of feeding solanidine, solasodine and tomatidine to non-pregnant and pregnant mice.
PubMed:Glycoalkaloid content and chemical composition of potatoes improved with nonconventional breeding approaches.
PubMed:A novel enzyme biosensor for steroidal glycoalkaloids detection based on pH-sensitive field effect transistors.
PubMed:Comparative Responses of Globodera rostochiensis and G. pallida to Hatching Chemicals.
PubMed:Practical and highly regio- and stereoselective synthesis of 2-substituted dihydropyridines and piperidines: application to the synthesis of (-)-coniine.
PubMed:Effect of light exposure on the glycoalkaloid content of Solanum phureja tubers.
PubMed:Glycoalkaloids in potato tubers grown under controlled environments.
PubMed:Synthesis of peracetylated chacotriose.
PubMed:Synergism between the potato glycoalkaloids alpha-chaconine and alpha-solanine in inhibition of snail feeding.
PubMed:Immunoaffinity sample purification and MALDI-TOF MS analysis of alpha-Solanine and alpha-chaconine in serum.
PubMed:Tracer studies on the incorporation of [2-14C]-DL-mevalonate into chlorophylls a and b, alpha-chaconine, and alpha-solanine of potato sprouts.
PubMed:High-performance thin-layer chromatographic determination of potato glycoalkaloids.
PubMed:Determination of alpha-solanine and alpha-chaconine in potatoes by high-performance thin-layer chromatography/densitometry.
PubMed:The folic acid analogue methotrexate protects frog embryo cell membranes against damage by the potato glycoalkaloid alpha-chaconine.
PubMed:Cholinesterase inhibition by potato glycoalkaloids slows mivacurium metabolism.
PubMed:High-performance liquid chromatographic determination of the glycoalkaloids alpha-solanine and alpha-chaconine in 12 commercial varieties of Mexican potato.
PubMed:Determination of potato glycoalkaloids using a liposome immunomigration, liquid-phase competition immunoassay.
PubMed:Sampling leaves of young potato (Solanum tuberosum) plants for glycoalkaloid analysis.
PubMed:Photo-induced synthesis of tomatidenol-based glycoalkaloids in Solanum phureja tubers.
PubMed:Comparison of commercial solid-phase extraction sorbents for the sample preparation of potato glycoalkaloids.
PubMed:Inheritance of morphological characters and glycoalkaloids in potatoes of somatic hybrids between dihaploid Solanum acauleand tetraploid Solanum tuberosum.
PubMed:Amelioration by glucose-6-phosphate and NADP of potato glycoalkaloid inhibition in cell, enzyme and liposome assays.
PubMed:Inhibition of Trypanosoma cruzi growth in vitro by Solanum alkaloids: a comparison with ketoconazole.
PubMed:Liquid chromatographic determination of the glycoalkaloids alpha-solanine and alpha-chaconine in potato tubers: NMKL Interlaboratory Study. Nordic Committee on Food Analysis.
PubMed:Synthesis of gamma-chaconine and gamma-solanine are catalyzed in potato by two separate glycosyltransferases: UDP-glucose:solanidine glucosyltransferase and UDP-galactose:solanidine galactosyltransferase.
PubMed:Inhibition of human plasma and serum butyrylcholinesterase (EC 3.1.1.8) by alpha-chaconine and alpha-solanine.
PubMed:A Point Mutation of Acetylcholinesterase Associated with Azinphosmethyl Resistance and Reduced Fitness in Colorado Potato Beetle
PubMed:A study of the toxic hazard that might be associated with the consumption of green potato tops.
PubMed:Effects of saponins and glycoalkaloids on the permeability and viability of mammalian intestinal cells and on the integrity of tissue preparations in vitro.
PubMed:Feeding of potato, tomato and eggplant alkaloids affects food consumption and body and liver weights in mice.
PubMed:Glycoalkaloids selectively permeabilize cholesterol containing biomembranes.
PubMed:Induction of terata in hamsters by solanidane alkaloids derived from Solanum tuberosum.
PubMed:Comparison of high- and low-energy collision-induced dissociation tandem mass spectrometry in the analysis of glycoalkaloids and their aglycons.
PubMed:Steroidal glycoalkaloids in Andean potatoes.
PubMed:Molecular basis of glycoalkaloid induced membrane disruption.
PubMed:Protective effects of glucose-6-phosphate and NADP against alpha-chaconine-induced developmental toxicity in Xenopus embryos.
PubMed:Synergistic interaction of glycoalkaloids alpha-chaconine and alpha-solanine on developmental toxicity in Xenopus embryos.
PubMed:The glycoalkaloids: naturally of interest (but a hot potato?).
PubMed:A preliminary assessment of the toxic and mutagenic potential of steroidal alkaloids in transgenic mice.
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:Steroidal alkaloid toxicity to fish embryos.
PubMed:[Teratogenic effect of potato glycoalkaloids].
PubMed:Dual specificity of sterol-mediated glycoalkaloid induced membrane disruption.
PubMed:Absence of genotoxicity of potato alkaloids alpha-chaconine, alpha-solanine and solanidine in the Ames Salmonella and adult and foetal erythrocyte micronucleus assays.
PubMed:Studies of embryotoxicity and the incidence of external malformations after continuous intravenous infusion of alpha-chaconine in pregnant rats.
PubMed:Glycoalkaloid and nitrate content of potatoes as affected by method of selenium application.
PubMed:Determination of potato glycoalkaloids and their aglycone in blood serum by high-performance liquid chromatography. Application to pharmacokinetic studies in humans.
PubMed:Inhibition of insect acetylcholinesterase by the potato glycoalkaloid alpha-chaconine.
PubMed:Developmental toxicology of potato alkaloids in the frog embryo teratogenesis assay--Xenopus (FETAX).
PubMed:Hepatic ornithine decarboxylase induction by potato glycoalkaloids in rats.
PubMed:Comparison of solanaceous glycoalkaloids-evoked Ca(2+) influx in different types of cultured cells.
PubMed:Natural pesticides and bioactive components in foods.
PubMed:Extending the detection limit of the TDx fluorescence polarization immunoassay for benzoylecgonine in urine.
PubMed:Synergistic interaction between potato glycoalkaloidsα-solanine andα-chaconine in relation to destabilization of cell membranes: Ecological implications.
PubMed:Utilization of potatoes in bioregenerative life support systems.
PubMed:The inactivation of herpes simplex virus by some Solanaceae glycoalkaloids.
PubMed:Steroidal glycoalkaloid content of potato, tomato and their somatic hybrids.
PubMed:Neural-tube defects produced in Syrian hamsters by potato glycoalkaloids.
PubMed:Subcellular distribution of alpha-chaconine in mouse hepatocytes.
PubMed:High-performance liquid chromatographic separation of potato glycoalkaloids using a radially compressed amino column.
PubMed:Naturally occurring toxic alkaloids in foods.
PubMed:Potato glycoalkaloids.
PubMed:Excretion of alpha-chaconine-3H, a steroidal glycoalkaloid from Solanum tuberosum L. and its metabolites in hamsters.
PubMed:An outbreak of suspected solanine poisoning in schoolboys: Examinations of criteria of solanine poisoning.
PubMed:Positive inotropic action of Solanaceae glycoalkaloids.
PubMed:Excretion, distribution and metabolic fate of 3H-alpha-chaconine.
PubMed:Pharmacology and toxicology of chaconine and tomatine.
PubMed:Nematicidal Activity of alpha -Chaconine: Effect of Hydrogen-ion Concentration.
 
Notes:
glycoside of solanidine. Alkaloid from Solanum chacoense and very many other Solanum spp. (Solanaceae)
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