1.0 2010-04-08 22:10:08 UTC 2025-11-18 23:36:00 UTC FDB012367 Tomatine Tomatine is a mildly toxic glycoalkaloid or glycospirosolane (steroidal alkaloids whose structure contains a spirosolane skeleton) found in the stems and leaves of tomato plants as well as in the fruit of unripened (green) tomatoes (up to 500 mg/kg). Red, ripe tomatoes have somewhat reduced amounts of tomatine. A toxic dose of tomatine for an adult human would appear to require the consumption of at least 500 g of tomato leaves in one sitting (“Toxic Plants of North America” (Iowa State University Press, 2001)). Tomatine is known to have fungicidal and antimicrobial properties and is likely produced by tomato plants as a defense against bacteria, fungi, viruses, and insects (PMID: 19514731). Some microbes produce an enzyme called tomatinase which can degrade tomatine, rendering it ineffective as an antimicrobial (PMID: 18835993).Tomatine has historically been used as a reagent in analytical chemistry for precipitating cholesterol from solution (PMID: 4362143). When lab animals ingest tomatine, essentially all of it passes through the animal unabsorbed. Tomatine apparently binds to cholesterol in the digestive tract, and the largely insoluble combination is excreted — ridding the body of both the alkaloid and cholesterol. Experiments with hamsters have shown that both tomatine-rich green tomatoes and purified tomatine can substantially lower the levels of undesirable LDL cholesterol while maintaining normal levels of HDL (PMID: 10942315). Experiments with high-tomatine green tomato extracts were recently shown to strongly inhibit the growth of a number of human cancer cell lines including breast (MCF-7), colon (HT-29), gastric (AGS), and hepatoma (liver) (HepG2), as well as normal human liver cells (PMID: 19514731). Other studies have found that purified tomatine is an outstanding immunoadjuvant capable of stimulating potent antigen-specific humoral and cellular immune responses that contribute to protection against malaria, Francisella tularensis and regression of experimental tumors (PMID: 15193398). &alpha;-tomatine a-Tomatine A''-tomatidine alpha -Tomatine Alpha-tomatine Lycopersicin Tomatidine, glycoside Tomatin Tomatine C50H83NO21 1034.1881 1033.545758723 2-[(2-{[4,5-dihydroxy-2-(hydroxymethyl)-6-{5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidine]oxy}oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol 2-[(2-{[4,5-dihydroxy-2-(hydroxymethyl)-6-{5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidine]oxy}oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol 17406-45-0 CC1C2C(CC3C4CCC5CC(CCC5(C)C4CCC23C)OC2OC(CO)C(OC3OC(CO)C(O)C(OC4OCC(O)C(O)C4O)C3OC3OC(CO)C(O)C(O)C3O)C(O)C2O)OC11CCC(C)CN1 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 REJLGAUYTKNVJM-UHFFFAOYSA-N belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative. Steroidal saponins Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Steroidal glycosides Aliphatic heteropolycyclic compounds Acetals Alkaloids and derivatives Azacyclic compounds Azaspirodecane derivatives Azasteroids and derivatives Dialkylamines Diterpene glycosides Diterpenoids Hemiaminals Hydrocarbon derivatives O-glycosyl compounds Oligosaccharides Organopnictogen compounds Oxacyclic compounds Oxanes Piperidines Polyols Primary alcohols Secondary alcohols Spirosolanes and derivatives Tetrahydrofurans Acetal Alcohol Aliphatic heteropolycyclic compound Alkaloid or derivatives Amine Azacycle Azaspirodecane Azasteroid Diterpene glycoside Diterpenoid Glycosyl compound Hemiaminal Hydrocarbon derivative O-glycosyl compound Oligosaccharide Organic nitrogen compound Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Oxane Piperidine Polyol Primary alcohol Secondary alcohol Secondary aliphatic amine Secondary amine Spirosolane skeleton Steroidal alkaloid Steroidal saponin Terpene glycoside Tetrahydrofuran logp -0.14 ALOGPS logs -2.78 ALOGPS solubility 1.71e+00 g/l ALOGPS melting_point Mp 263-267° dec. logp -1.4 ChemAxon pka_strongest_acidic 11.78 ChemAxon pka_strongest_basic 9.54 ChemAxon iupac 2-[(2-{[4,5-dihydroxy-2-(hydroxymethyl)-6-{5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidine]oxy}oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol ChemAxon average_mass 1034.1881 ChemAxon mono_mass 1033.545758723 ChemAxon smiles CC1C2C(CC3C4CCC5CC(CCC5(C)C4CCC23C)OC2OC(CO)C(OC3OC(CO)C(O)C(OC4OCC(O)C(O)C4O)C3OC3OC(CO)C(O)C(O)C3O)C(O)C2O)OC11CCC(C)CN1 ChemAxon formula C50H83NO21 ChemAxon inchi 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 ChemAxon inchikey REJLGAUYTKNVJM-UHFFFAOYSA-N ChemAxon polar_surface_area 337.86 ChemAxon refractivity 244.79 ChemAxon polarizability 110.87 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 22 ChemAxon donor_count 13 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 7925 Specdb::MsMs 7926 Specdb::MsMs 7927 Specdb::MsMs 14597 Specdb::MsMs 14598 Specdb::MsMs 14599 Specdb::MsMs 2238764 Specdb::MsMs 2466722 Specdb::MsMs 2466723 Specdb::MsMs 2466724 Specdb::MsMs 2496224 Specdb::MsMs 2496225 Specdb::MsMs 2496226 Specdb::NmrOneD 124438 Specdb::NmrOneD 124439 Specdb::NmrOneD 124440 Specdb::NmrOneD 124441 Specdb::NmrOneD 124442 Specdb::NmrOneD 124443 Specdb::NmrOneD 124444 Specdb::NmrOneD 124445 Specdb::NmrOneD 124446 Specdb::NmrOneD 124447 Specdb::NmrOneD 124448 Specdb::NmrOneD 124449 Specdb::NmrOneD 124450 Specdb::NmrOneD 124451 Specdb::NmrOneD 124452 Specdb::NmrOneD 124453 Specdb::NmrOneD 124454 Specdb::NmrOneD 124455 Specdb::NmrOneD 124456 Specdb::NmrOneD 124457 HMDB34103 9630 #<Reference:0x000055ce305b0398> #<Reference:0x000055ce305b0118> #<Reference:0x000055ce305afee8> #<Reference:0x000055ce305afc68> #<Reference:0x000055ce305afab0> #<Reference:0x000055ce305af8f8> Cherry tomato Type 1 specific Solanum lycopersicum var. cerasiforme 195583 Fruit juice Type 2 specific Garden tomato Type 1 specific Solanum lycopersicum 4081 Garden tomato (var.) Type 1 specific Solanum lycopersicum var. lycopersicum 397755 0.7 0.7 0.7 mg/100 g Ketchup Type 2 specific Potato Type 1 specific Solanum tuberosum 4113 Anti bacterial 145 A substance that kills or slows the growth of bacteria. Anti-inflammatory 370 A substance that reduces or suppresses inflammation. Fungicide 940 A substance used to destroy fungal pests. Immunostimulant 1032 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity. Molluscicide 1113 A substance used to destroy pests of the phylum Mollusca. Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.