tomatine

Also known as alpha-tomatine, lycopersicin, A''-Tomatidine, (3beta,5alpha,22beta,25S)-spirosolan-3-yl O-beta-D-glucopyranosyl-(1->2)-O-(beta-D-xylopyranosyl)-(1->3)-O-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranoside, Tomatin

Tomatine (sometimes called tomatin or lycopersicin) is a glycoalkaloid, found in the stems and leaves of tomato plants, and in the fruits at much lower concentrations. Chemically pure tomatine is a white crystalline solid at standard temperature and pressure.

Chemical data

Formula: C50H83NO21
Molecular weight: 1034.2 g/mol
IUPAC name: (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-yl]oxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES: C[C@H]1CC[C@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@@H]6[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)CO)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)C)C)C)NC1
InChIKey: REJLGAUYTKNVJM-SGXCCWNXSA-N
XLogP: -0.7
Polar surface area: 338 Å²
H-bond donors: 13
H-bond acceptors: 22
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

430 papers

Alpha-tomatine and the two sides of the same coin: An anti-nutritional glycoalkaloid with potential in human health.Food chemistry · 2022
Tomatine as a versatile adjuvant boosts mRNA vaccine responses.Materials today. Bio · 2025
Current Advances in the Biosynthesis, Metabolism, and Transcriptional Regulation of α-Tomatine in Tomato.Plants (Basel, Switzerland) · 2023
The steroidal alkaloids α-tomatine and tomatidine: Panorama of their mode of action and pharmacological properties.Steroids · 2021
α-Tomatine gradient across artificial roots recreates the recruitment of tomato root-associated Sphingobium.Plant direct · 2023

via PubMed

Wikidata facts

Mass: 1033.546

Show 7 more facts

found in taxon: tomato
chemical formula: C₅₀H₈₃NO₂₁
isomeric SMILES: C[C@H]1CC[C@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@@H]6[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)CO)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)C)C)C)NC1
canonical SMILES: CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)OC9C(C(C(CO9)O)O)O)OC2C(C(C(C(O2)CO)O)O)O)O)O)C)C)C)NC1
subject has role: antifungal
Commons category: Tomatine
has characteristic: bitterness

Sources (2)

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~9 min read

Encyclopedic overview

11 sections

Contents

History
Structure and biosynthesis
Mechanism of action
Membrane disruption
Inhibition of acetylcholinesterase
Metabolism
Uses
Toxicity
See also
References
External links

Tomatine is sometimes confused with the glycoalkaloid solanine.

Excerpted from Wikipedia’s “tomatine” article, available under the CC BY-SA 4.0 licence.

Gallery (3)

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