Tomatine does not have a single well-defined biological target. It forms complexes with membrane sterols such as cholesterol, disrupting membrane integrity and triggering apoptosis, oxidative stress, growth inhibition, and antifungal or anticancer cellular responses. α-Tomatine activates phosphotyrosine kinase and monomeric G-protein signaling pathways, leading to Ca2+ elevation and ROS burst in fungal cells.

The neuroblastoma cell line (SH-SY5Y), non-small lung cancer cell line (A549), and tomatine suspension cell line (AGS) had IC50 values of 2 μM, 1.6 μM, and 1.1 μM, respectively [1].
In vitro, tomatine exhibits antifungal, antibacterial, and anticancer activities. It is active against a panel of 19 plant pathogenic fungi with EC50 values of 13–912 µM. Tomatine inhibits the growth of breast adenocarcinoma cells and promotes nuclear apoptosis-inducing factor (AIF) upregulation in neuroblastoma cells. It exhibits strong antifungal and antibacterial properties by disrupting cell membranes.

In vivo, tomatine has been studied for its anticancer, antifungal, and anti-inflammatory activities. It exhibits antifungal activity against plant pathogens and has been used as an antiproliferative agent in the suppression of breast adenocarcinoma cells. Tomatine also modulates cholesterol metabolism and immune responses and has been shown to induce neurotoxicity in a RIP1 kinase- and caspase-independent manner.

In vitro enzyme/receptor binding assays for tomatine measure its ability to form complexes with sterols such as cholesterol. The compound's antifungal activity is assessed by determining EC50 values against plant pathogenic fungi. Its effects on cell membrane integrity and apoptosis are evaluated in cell-based assays.

In vitro cell-based assays for tomatine use cancer cell lines such as breast adenocarcinoma cells and neuroblastoma cells. Cells are treated with serial dilutions of the compound, and cell viability is measured using MTT or other assays. Apoptosis is assessed by measuring nuclear AIF upregulation and caspase activity. Antifungal activity is assessed by measuring growth inhibition of fungal cultures.

In vivo animal models for tomatine include models of cancer and fungal infections. The compound is administered via appropriate routes, and its effects on tumor growth, fungal burden, and disease progression are evaluated. Tomatine has been studied for its neurotoxic effects in animal models.

α-Tomatine has a molecular formula of C50H83NO21 and a molecular weight of 1034.2 g/mol. It is soluble in DMSO and methanol and has a melting point of >250°C (dec.). The compound is also known as Lycopersicin and is used as a reference substance. It is stored under appropriate conditions for research use.

Interactions
Tomatine reduced the growth-enhancing effect of indole-3-acetic acid by 10⁻⁴ moles.
The toxicity profile of tomatine includes neurotoxic effects in certain models. The compound induces neurotoxicity in a RIP1 kinase- and caspase-independent manner and promotes nuclear AIF upregulation. Tomatine is for research use only and is not approved for clinical use. Appropriate safety precautions should be taken during handling.

[1]. Neurotoxicity of the steroidal alkaloids tomatine and tomatidine is RIP1 kinase- and caspase-independent and involves the eIF2α branch of the endoplasmic reticulum. J Steroid Biochem Mol Biol. 2017 Jul;171:178-186.

Tomatine is a steroidal alkaloid, a derivative of tomatine, with its 3-hydroxyl group linked to a tetrasaccharide of tomato. Tomatine is a tetrasaccharide composed of two D-glucose units, one D-xylose unit, and one D-galactose unit. Tomatine can be used as an immune adjuvant, phytotoxicant, and antifungal agent. It is a steroidal alkaloid, a tetrasaccharide derivative, an alkaloid antibiotic, a glycoside, and a glycosidic alkaloid. Its function is related to tomatine. Tomatine has been reported in potatoes (Solanum tuberosum), nightshade plants, and other organisms with relevant data. Tomatine is an alkaloid found in extracts from wild tomato leaves. Studies have found that it can inhibit the growth of various fungi and bacteria. It can be used as a precipitant for steroidal compounds. (Excerpt from Merck Index, 11th edition)

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Mechanism of Action
We tested the cardiotonic activity of six glycosidic alkaloids and one glycosidone, and compared them with K-tropin using isolated frog hearts. The order of potency in descending order is as follows: K-tropin > tomatine > α-carboxine > α-solanine > α-solanine > demicin > styracin > β-carboxine > solanine. Cardiotonic activity is directly related to the number of sugars in the glycosidic alkaloid molecules, which share common glycosidic aglycones. Removing one or more sugar residues from the α-tomatine molecule significantly reduces its antifungal activity. Although partial hydrolysis of α-tomatine has little effect on its surfactant properties, it does disrupt the alkaloid's ability to form complexes with cholesterol.

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Therapeutic Uses
Antifungal agent; anti-infective agent; indicator and reagent
Experimental Uses: Intramuscular injection of 1-10 mg/kg or oral administration of 15-30 mg/kg tomatine in intact rats dose-dependently inhibits carrageenan-induced paw edema. The inhibitory effect of the intramuscular dose of 10 mg/kg lasts for 24 hours. Administration of 5-10 mg/kg tomatine daily for 7 consecutive days to intact rats dose-dependently inhibited granulation tissue formation induced by subcutaneous implantation of carrageenan-impregnated cotton balls.
Tomatine is a natural glycoalkaloid found in tomato plants with anti-inflammatory, fungicidal, antimicrobial, and insecticidal properties. It exhibits amphipathic properties and forms complexes with sterols, influencing membrane integrity. Tomatine is used as an antiproliferative agent in the suppression of breast adenocarcinoma cells and is also known as α-Tomatine. The compound is intended for laboratory research use only.

C50H83NO21

1034.2

1033.545

17406-45-0

28523

White to off-white solid powder

1.5±0.1 g/cm3

300-305ºC

1.638

2.22

13

22

11

72

1840

31

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

REJLGAUYTKNVJM-SGXCCWNXSA-N

InChI=1S/C50H83NO21/c1-20-7-12-50(51-15-20)21(2)32-28(72-50)14-26-24-6-5-22-13-23(8-10-48(22,3)25(24)9-11-49(26,32)4)65-45-40(63)37(60)41(31(18-54)68-45)69-47-43(71-46-39(62)36(59)34(57)29(16-52)66-46)42(35(58)30(17-53)67-47)70-44-38(61)33(56)27(55)19-64-44/h20-47,51-63H,5-19H2,1-4H3/t20-,21-,22-,23-,24+,25-,26-,27+,28-,29+,30+,31+,32-,33-,34+,35+,36-,37+,38+,39+,40+,41-,42-,43+,44-,45+,46-,47-,48-,49-,50-/m0/s1

(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

NSC 234440; Lycopersicin; Tomatine

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~100 mg/mL (~96.69 mM)

Solubility in Formulation 1: ≥ 2.08 mg/mL (2.01 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.08 mg/mL (2.01 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (2.01 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)