alpha-Chaconine
alpha-Chaconine is found in potato. alpha-Chaconine is an alkaloid from Solanum chacoense and very many other Solanum species (Solanaceae). Alpha-chaconine has been shown to exhibit anti-angiogenic and anti-fungal functions
General
Type : Natural, Alkaloid, Glycoside
Chemical_Nomenclature : (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
Canonical SMILES : CC1CCC2C(C3C(N2C1)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)C)O)O)O)O)OC9C(C(C(C(O9)C)O)O)O)C)C)C
InChI : InChI=1S\/C45H73NO14\/c1-19-7-10-28-20(2)31-29(46(28)17-19)16-27-25-9-8-23-15-24(11-13-44(23,5)26(25)12-14-45(27,31)6)57-43-40(60-42-37(53)35(51)33(49)22(4)56-42)38(54)39(30(18-47)58-43)59-41-36(52)34(50)32(48)21(3)55-41\/h8,19-22,24-43,47-54H,7,9-18H2,1-6H3\/t19-,20+,21-,22-,24-,25+,26-,27-,28+,29-,30+,31-,32-,33-,34+,35+,36+,37+,38-,39+,40+,41-,42-,43+,44-,45-\/m0\/s1
InChIKey : TYNQWWGVEGFKRU-AJDPQWBVSA-N
Other name(s) : 5QOL0LIM81 || Chaconine || UNII-5QOL0LIM81 || CCRIS 6509 || BRN 0077396 || AC1L9DRN || CHEBI:10219 || 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))-
MW : 852.07
Formula : C45H73NO14
CAS_number : 20562-03-2
PubChem : 442971
UniChem : TYNQWWGVEGFKRU-AJDPQWBVSA-N
Wikipedia : Chaconine
Target
Families : alpha-Chaconine ligand of proteins in family
BCHE
References (14)
| Title : alpha-chaconine increases the sensitivity of HER2+ breast cancer cells to trastuzumab by targeting acetylcholinesterase - Hermawan_2025_Comput.Biol.Med_188_109809 |
| Author(s) : Hermawan A , Pamungkas Putri DD , Fatimah N , Rhamandana Putra IM , Lestari IA |
| Ref : Computers in Biology & Medicine , 188 :109809 , 2025 |
| Abstract : |
| PubMedSearch : Hermawan_2025_Comput.Biol.Med_188_109809 |
| PubMedID: 39955879 |
| Gene_locus related to this paper: human-DPP4 |
| Title : Gut microbiota gate host exposure to cholinesterase inhibitors from dietary Solanums - Liou_2025_bioRxiv__ |
| Author(s) : Liou CS , Louwies T , Iakiviak M , Rajniak J , Murugkar PP , Higginbottom SK , Weakley A , Meng X , Htet P , Cabrera AV , Jasper M , Dimas A , Schulman EA , Fischbach MA , Kashyap PC , Sattely ES |
| Ref : bioRxiv , : , 2025 |
| Abstract : |
| PubMedSearch : Liou_2025_bioRxiv__ |
| PubMedID: 41497638 |
| Title : Structural Impact of Steroidal Glycoalkaloids: Barrier Integrity, Permeability, Metabolism, and Uptake in Intestinal Cells - Keuter_2024_Mol.Nutr.Food.Res__e2300639 |
| Author(s) : Keuter L , Wolbeck A , Kasimir M , Schurmann L , Behrens M , Humpf HU |
| Ref : Mol Nutr Food Res , :e2300639 , 2024 |
| Abstract : |
| PubMedSearch : Keuter_2024_Mol.Nutr.Food.Res__e2300639 |
| PubMedID: 38389193 |
| Title : Risk assessment of glycoalkaloids in feed and food, in particular in potatoes and potato-derived products - Schrenk_2020_EFSA.J_18_e06222 |
| Author(s) : Schrenk D , Bignami M , Bodin L , Chipman JK , Del Mazo J , Hogstrand C , Hoogenboom LR , Leblanc JC , Nebbia CS , Nielsen E , Ntzani E , Petersen A , Sand S , Schwerdtle T , Vleminckx C , Wallace H , Brimer L , Cottrill B , Dusemund B , Mulder P , Vollmer G , Binaglia M , Ramos Bordajandi L , Riolo F , Roldan-Torres R , Grasl-Kraupp B |
| Ref : EFSA J , 18 :e06222 , 2020 |
| Abstract : |
| PubMedSearch : Schrenk_2020_EFSA.J_18_e06222 |
| PubMedID: 32788943 |
| Title : The Impact of Steroidal Glycoalkaloids on the Physiology of Phytophthora infestans, the Causative Agent of Potato Late Blight - Dahlin_2017_Mol.Plant.Microbe.Interact_30_531 |
| Author(s) : Dahlin P , Muller MC , Ekengren S , McKee LS , Bulone V |
| Ref : Mol Plant Microbe Interact , 30 :531 , 2017 |
| Abstract : |
| PubMedSearch : Dahlin_2017_Mol.Plant.Microbe.Interact_30_531 |
| PubMedID: 28510502 |
| Title : Detection of glycoalkaloids using disposable biosensors based on genetically modified enzymes - Espinoza_2014_Anal.Biochem_457_85 |
| Author(s) : Espinoza MA , Istamboulie G , Chira A , Noguer T , Stoytcheva M , Marty JL |
| Ref : Analytical Biochemistry , 457 :85 , 2014 |
| Abstract : |
| PubMedSearch : Espinoza_2014_Anal.Biochem_457_85 |
| PubMedID: 24747413 |
| Title : Acute toxicity of high doses of the glycoalkaloids, alpha-solanine and alpha-chaconine, in the Syrian Golden hamster - Langkilde_2008_J.Agric.Food.Chem_56_8753 |
| Author(s) : Langkilde S , Schroder M , Stewart D , Meyer O , Conner S , Davies H , Poulsen M |
| Ref : Journal of Agricultural and Food Chemistry , 56 :8753 , 2008 |
| Abstract : |
| PubMedSearch : Langkilde_2008_J.Agric.Food.Chem_56_8753 |
| PubMedID: 18710251 |
| Title : [Study of the interaction of main potato glycoalkaloids in inhibition of immobilized butyryl cholinesterase] - Arkhypova_2006_Ukr.Biokhim.Zh.(1999)_78_155 |
| Author(s) : Arkhypova VM , Dziadevych SV , Jaffrezic-Renault N , Martelet C , Soldatkin OP |
| Ref : Ukr Biokhim Zh (1999) , 78 :155 , 2006 |
| Abstract : |
| PubMedSearch : Arkhypova_2006_Ukr.Biokhim.Zh.(1999)_78_155 |
| PubMedID: 17290795 |
| Title : A novel enzyme biosensor for steroidal glycoalkaloids detection based on pH-sensitive field effect transistors - Korpan_2002_Bioelectrochemistry_55_9 |
| Author(s) : Korpan YI , Volotovsky VV , Martelet C , Jaffrezic-Renault N , Nazarenko EA , El'skaya AV , Soldatkin AP |
| Ref : Bioelectrochemistry , 55 :9 , 2002 |
| Abstract : |
| PubMedSearch : Korpan_2002_Bioelectrochemistry_55_9 |
| PubMedID: 11786329 |
| Title : Membrane disruption and enzyme inhibition by naturally-occurring and modified chacotriose-containing Solanum steroidal glycoalkaloids - Roddick_2001_Phytochemistry_56_603 |
| Author(s) : Roddick JG , Weissenberg M , Leonard AL |
| Ref : Phytochemistry , 56 :603 , 2001 |
| Abstract : |
| PubMedSearch : Roddick_2001_Phytochemistry_56_603 |
| PubMedID: 11281138 |
| Title : Cholinesterase inhibition by potato glycoalkaloids slows mivacurium metabolism - McGehee_2000_Anesthesiology_93_510 |
| Author(s) : McGehee DS , Krasowski MD , Fung DL , Wilson B , Gronert GA , Moss J |
| Ref : Anesthesiology , 93 :510 , 2000 |
| Abstract : |
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| PubMedID: 10910502 |
| Title : Inhibition of human plasma and serum butyrylcholinesterase (EC 3.1.1.8) by alpha-chaconine and alpha-solanine - Nigg_1996_Fundam.Appl.Toxicol_33_272 |
| Author(s) : Nigg HN , Ramos LE , Graham EM , Sterling J , Brown S , Cornell JA |
| Ref : Fundamental & Applied Toxicology , 33 :272 , 1996 |
| Abstract : |
| PubMedSearch : Nigg_1996_Fundam.Appl.Toxicol_33_272 |
| PubMedID: 8921346 |
| Title : Natural pesticides and bioactive components in foods - Beier_1990_Rev.Environ.Contam.Toxicol_113_47 |
| Author(s) : Beier RC |
| Ref : Rev Environ Contam Toxicol , 113 :47 , 1990 |
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| PubMedID: 2404325 |
| Title : Differential inhibition of the serum cholinesterase phenotypes by solanine and solanidine - |
| Author(s) : Harris H , Whittaker M |
| Ref : Annals of Human Genetics , 26 :73 , 1962 |
| PubMedID: 13904837 |