solanine

Also known as α-solanine, alpha-solanine

Solanine is a glycoalkaloid poison found in species of the nightshade family within the genus Solanum, such as the potato (Solanum tuberosum). It can occur naturally in any part of the plant, including the leaves, fruit, and tubers. Solanine has pesticidal properties, and it is one of the plant's natural defenses. Solanine was first isolated in 1820 from the berries of the European black nightshade (Solanum nigrum), after which it was named. It belongs to the chemical family of saponins.

Chemical data

Formula: C45H73NO15
Molecular weight: 868.1 g/mol
IUPAC name: (2R,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-[[(1S,2S,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]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
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(CCC(C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O[C@@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O)C)C)C
InChIKey: ZGVSETXHNHBTRK-WWELWOLRSA-N
XLogP: 1.8
Polar surface area: 241 Å²
H-bond donors: 9
H-bond acceptors: 16
Formal charge: 0

via PubChem

Research

521 papers

Network pharmacology-based strategy to investigate the effect and mechanism of α-solanine against glioma.BMC complementary medicine and therapies · 2023
Solanine poisoning.British medical journal · 1979
Alpha Solanine: A Novel Natural Bioactive Molecule with Anticancer Effects in Multiple Human Malignancies.Nutrition and cancer · 2021
Toxicology of solanine: an overview.Veterinary and human toxicology · 1983
Updated aspects of alpha-Solanine as a potential anticancer agent: Mechanistic insights and future directions.Food science & nutrition · 2024

via PubMed

Wikidata facts

Mass: 867.4980206359999

Show 4 more facts

canonical SMILES: CC1CCC2C(C3C(N2C1)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)C)O)O)O)C)C)C
chemical formula: C₄₅H₇₃NO₁₅
Commons category: Solanine
isomeric 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](O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[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@@]43C)N2C1

Sources (3)

via Wikidata · CC0

~15 min read

Article

18 sections

Contents

Solanine poisoning
Symptoms
Correlation with birth defects
Livestock poisoning
Mechanism of action
Biosynthesis
Safety
Suggested limits on consumption of solanine
Storage of potatoes
Effects of cooking on solanine levels
Recorded human poisonings
In potatoes
In other plants
{{vanchor|In tomatoes}}
In popular culture
See also
References
External links

{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464404882 | Name = α-Solanine | ImageFile = Solanine.svg | ImageSize = 250px | ImageFile2 = Solanine_3d_structure.png | ImageSize2 = | IUPACName = Solanid-5-en-3β-yl α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-galactopyranoside | SystematicName = (2S,3R,4R,5R,6S)-2-{[(2R,3R,4S,5S,6R)-5-Hydroxy-6-(hydroxymethyl)-2-{[(2S,4aR,4bS,6aS,6bR,7S,7aR,10S,12aS,13aS,13bS)-4a,6a,7,10-tetramethyl-2,3,4,4a,4b,5,6,6a,6b,7,7a,8,9,10,11,12a,13,13a,13b,14-icosahydro-1H-naphtho[2′,1′:4,5]indeno[1,2-b]indolizin-2-yl]oxy}-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol | OtherNames = α-Solanine; Solanin; Solatunine | Section1=

|Section2=