Basic information
- CAS
20562-03-2- Standard SMILES
C[C@H]1CC[C@@H]2[C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC=C6C[C@@H](O[C@@H]7O[C@H](CO)[C@@H](O[C@@H]8O[C@@H](C)[C@H](O)[C@@H](O)[C@H]8O)[C@H](O)[C@H]7O[C@@H]7O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O)CC[C@]6(C)[C@H]5CC[C@]34C)N2C1- InChIKey
TYNQWWGVEGFKRU-AJDPQWBVSA-N- Molecular formula
- C45H73NO14
- Average molar mass
- 852.1 g/mol
- Monoisotopic mass
- 851.503106
Overview
Alpha-Chaconine is a glycoalkaloid and a steroid saponin.
Names & identifiers
- Preferred name
- Alpha-Chaconine
- IUPAC
- (2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
- English name
- α-Chaconine
- Molecular formula
- C45H73NO14
- Molecular weight
- 852.06
Names & synonyms
alpha-Chaconine20562-03-25QOL0LIM81DTXSID501016601(2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol(2S,3R,4R,5R,6S)-2-((2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-(((1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-yl)oxy)-5-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl)oxy-6-methyloxane-3,4,5-triolRefChem:111118DTXCID301474794(2S,3R,4R,5R,6S)-2-((2R,3R,4S,5S,6R)-4-hydroxy-2-(hydroxymethyl)-6-(((1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-yl)oxy)-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl)oxy-6-methyloxane-3,4,5-triol2-((4-hydroxy-2-(hydroxymethyl)-6-((10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-yl)oxy)-5-((3,4,5-trihydroxy-6-methyloxan-2-yl)oxy)oxan-3-yl)oxy)-6-methyloxane-3,4,5-triol
Properties
Computed structural properties
- XLogP
- 1.8
- Topological polar surface area
- 220 Ų
- Hydrogen bond donors
- 8
- Hydrogen bond acceptors
- 15
- Rotatable bonds
- 7
- Heavy atoms
- 60
- Formal charge
- 0
- Complexity
- 1,570
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Solanidines and alkaloid derivatives [ST0115]
Physicochemical properties
- Melting point
- 228 · 228-236 °C
- Density
- 1.37 · 1.37±0.1 g/cm3(Predicted)
- storage temp.
- 20 °C · −20°C
- solubility
- 10 mg/mL, · pyridine: 10 mg/mL, clear, very faintly yellow
- form
- Solid
- pka
- 12 · 12+-.0.70(Predicted)
- color
- White to Off-White
- Stability
- Hygroscopic
- LogP
- 8.5 · 8.500 (est)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 5 QOL0LIM81 · 5QOL0LIM81
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Warning
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H361 (95.2%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory InformationRegulation (EC) No 178/2002 (amended)
Hazard Classes and CategoriesRepr. 2 (95.2%)
Toxicology
Toxicity Summary
The European Commission asked EFSA for a scientific opinion on the risks for animal and human health related to the presence of glycoalkaloids (GAs) in feed and food. Their risk assessment covers edible parts of potato plants and other food plants containing GAs, in particular, tomato and aubergine. The acute toxic effects of potato GAs (α-solanine and α-chaconine) in humans include gastrointestinal symptoms such as nausea, vomiting and diarrhoea. In humans, no evidence of health problems associated with repeated or long-term intake of GAs via potatoes has been identified. For tomato and aubergine GAs, the risk to human health could not be characterised due to the lack of occurrence data and the limited toxicity data. For horses, farm and companion animals, no risk characterisation for potato GAs could be performed due to insufficient data on occurrence in feed and on potential adverse effects of GAs in these species.
Alpha-Chaconine has inhibitory effect on lung adenocarcinoma cell metastasis in vitro. Alpha-chaconine could inhibit phosphorylation of c-Jun N-terminal kinase (JNK) and Akt, whereas it did not affected phosphorylation of extracellular signal regulating kinase (ERK) and p38. In addition, alpha-chaconine significantly decreased the nuclear level of nuclear factor kappa B (NF-_B) and the binding ability of NF-_B. Therefore, alpha-chaconine inhibited A549 cell metastasis by a reduction of matrix metalloproteinase-2 (MMP-2) and matrix metalloproteinase-9 (MMP-9) activities involving suppression of phosphoinositide 3-kinase/Akt/NF-_B (PI3K/Akt/NF-_B) signaling pathway. Alpha-chaconine has exhibited its antiproliferative and apoptotic effects on the growth of cancer cells originating from human skin, liver, prostate, breast, and colon. In addition to the cytotoxicity in various cancer cells, R-chaconine induces significant cytotoxicity in Chang, normal human liver cells. (A15417)
Chemistry & industry
Pharmacology
Mechanism of Action
The adverse effects of glycoalkaloids (GAs) may be due to their ability to complex with membrane 3β‐hydroxy sterols, thereby causing disruption and loss of integrity of cell membranes. After oral exposure, these effects may affect the mucosa of the gastrointestinal tract and cause the symptoms observed in intoxicated humans such as nausea, vomiting and diarrhoea. GAs inhibit acetylcholinesterase (AChE) and serum butyrylcholinesterase (BuChE) by a reversible, competitive mode of action. The relative potency of inhibition of α‐solanine and α‐chaconine appears to be similar. The aglycones exert weak or no inhibitory effects. The excess of acetylcholine at the neuronal and neuromuscular junctions upon inhibition of the enzymes might also contribute to the symptoms shown for intoxications with GAs.
Absorption, Distribution and Excretion
Chaconine was poorly absorbed from the gastrointestinal tract and rapidly excreted in feces when administered orally to rats. Intraperitoneal administration of low doses resulted in urinary and fecal excretion of metabolites, and probably involved biliary excretion. High intraperitoneal doses depressed fecal and urinary elimination, and resulted in accumulation in various tissues. The major metabolite appeared to be the aglycone, solanidine. Alpha-chaconine is very similar to alpha-solanine in its elimination and distribution in rats.
The potato glycoalkaloids (GAs), α‐solanine and α‐chaconine, show a relatively low oral bioavailability, with differences between species. Hamsters exhibit higher absorption and slower excretion rates for both substances compared to rats. The metabolic profiles of potato GAs in experimental animals could not be characterised due to the limited information. In humans, α‐solanine and α‐chaconine are systemically absorbed following ingestion, and relatively long serum half‐lives were reported. The blood clearance of the respective aglycone solanidine appears to be slow, and levels of solanidine were regularly detected in the blood of human volunteers. This suggests hydrolysis of GAs. No further information is available on metabolism and excretion of potato GAs in humans.
Uses & manufacturing
Uses
Related reactions
0 records
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Compound notes
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