α-chaconine
Sign in to saveα-Chaconine is a steroidal glycoalkaloid that occurs in plants of the family Solanaceae. It is a natural toxicant produced in green potatoes and gives the potato a bitter taste. Tubers produce this glycoalkaloid in response to stress, providing the plant with insecticidal and fungicidal properties. It belongs to the chemical family of saponins. Since it causes physiological effects on individual organism, chaconine is considered to be a defensive allelochemical. Solanine, a related substance also found in potatoes, has similar properties.
Wikidata facts
- Mass
- 851.503106
Show 4 more facts
- chemical formula
- C₄₅H₇₃NO₁₄
- 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
- isomeric SMILES
- C[C@H]1CC[C@@H]2[C@H]([C@H]3[C@@H](N2C1)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)O)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O)C)C)C
- Commons category
- Chaconine
Sources (2)
via Wikidata · CC0
~7 min read
Article
14 sectionsContents
- Symptoms and treatment
- Toxicity
- Difference from solanine
- Structural difference
- Difference in toxicity
- Ratio of ɑ-chaconine to ɑ-solanine in potato
- Research on glycoalkaloids
- Controlling the amount of steroidal glycoalkaloids in potatoes
- Level of glycoalkaloids
- Treating poisons in potato
- Attempts to make toxin-free potato
- See also
- References
- External links
{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 437977784 | ImageFile = Chaconine.svg | ImageSize = | ImageFile2 = File:Chaconine1.png | ImageCaption2 = 3D model of chaconine using MolView | IUPACName = Solanid-5-en-3β-yl α--rhamnopyranosyl-(1→2)-[α--rhamnopyranosyl-(1→4)]-β--glucopyranoside | SystematicName = (2S,2′S,3R,3′R,4R,4′R,5R,5′R,6S,6′S)-2,2′-{[(2R,3S,4S,5R,6R)-4-Hydroxy-2-(hydroxymethyl)-6-{[(2S,4aR,4bS,6aS,6bR,7S,7aR,10S,12aS,13aS,13bS)-4a,6a,7,10-tetramethyl-1,3,4,4a,4b,5,6,6a,6b,7,7a,8,9,10,11,12a,13,13a,13b,14-icosahydro-2H-naphtho[2′,1′:4,5]indeno[1,2-b]indolizin-2-yl]oxy}oxane-3,5-diyl]bis(oxy)}bis(6-methyloxane-3,4,5-triol) | OtherNames = α-Chaconine, Chaconine | Section1 = | Section2 = | Section3 = }} α-Chaconine is a steroidal glycoalkaloid that occurs in plants of the family Solanaceae. It is a natural toxicant produced in green potatoes and gives the potato a bitter taste. Tubers produce this glycoalkaloid in response to stress, providing the plant with insecticidal and fungicidal properties. It belongs to the chemical family of saponins. Since it causes physiological effects on individual organism, chaconine is considered to be a defensive allelochemical. Solanine, a related substance also found in potatoes, has similar properties.
== Symptoms and treatment == Symptoms resemble those seen following solanine ingestion including abdominal pain, diarrhea, and headache.