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))-

CAS: 20562-03-2 C45 H73 N O14 MW: 852.07261000

Identification

Namealpha-chaconine
CAS Number20562-03-2
FDA UNII5QOL0LIM81
Molecular FormulaC45 H73 N O14
Molecular Weight852.07261000
Beilstein0077396

Regulatory

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)

No sensory data available

Safety Information

Oral/Parenteral Toxicityintraperitoneal-mouse LD50 19 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for alpha-chaconine usage levels up tonot for fragrance use.
Recommendation for alpha-chaconine flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

potato flower potato leaf potato shoot potato sprout potato tissue culture potato tuber solanum chacoense

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))- 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.