5-Tomatine

Other common phytoalexins in food materials are pisatin, cinnamylphenols, glyceolin, phaseolin [13401 -40-6] (14), and 5-deoxykieritol in peas, beans, soybeans, and lima beans viniferin in grapes momilactones and ory2alexins in rice a-tomatine in tomato lubimen in eggplant and capsidiol in green peppers. 

Defago G and Kern H (1983), Induction of Fusarium solani mutants insensitive to tomatine, their pathogenicity and aggressiveness to tomato fruits and pea plants ,... 

Defago G, Kern H and Sedlar L (1983), Genetic analysis of tomatine insensitivity, sterol content and pathogenicity for green tomato fruits in mutants of Fusarium solani, Physiol Mol Plant Pathol, 22, 39-43. 

Leonardi C, Ambrosino P, Esposito F and Fogliano V. 2000. Antioxidative activity and carotenoid and tomatine contents in different typologies of fresh consumption tomatoes. J Agric Food Chem 48(10) 4723-4727. 

Fig. 2.1 Strucnires of some common saponins. The strucnires of some of the saponins described in the text are shown, including aescin from horse chesnut, avenacin A-1 and avenacoside A from oat, and a-tomatine from tomato. The glucose molecule enclosed in square brackets in the structure of avenacoside A highlights the glucose moiety that is cleaved off by hydrolysis by glycosidases in disrupted oat leaf tissue, leading to the fungitoxic 26-desglucosyl avenacoside A. Redrawn from [94]...

Although tomatinases from different fungal sources share the same substrate, they cleave different sugar moieties from a-tomatine. For example, tomatinases of S. lycopersici [55] and V. albo-atrum [62] remove the terminal P-l,2-linked glucose molecule, while that from B. cinerea removes the terminal P-l,3-linked xylose [67], On the other hand, F. oxysporum sp. lycopersici [63, 64], F. solani [66], and... 

Steel CC, Drysdale RB (1988) Electrolyte leakage from plant and fungal tissues and dismption of liposome membranes by a-tomatine. Phytochemistry 27 1025... 

Stine KJ et al (2006) Interaction of the glycoalkaloid tomatine with DMPC and sterol mono-layers studied by surface pressure measurements and brewster angle microscopy. J Physical Chem B 110 22220... 

SchonbeckE, SchlosserE (1976) Preformed substances as potential protectants. In Heitefuss, R, WiUiams, PH (eds) Physiological plant pathology. Springer, Berlin, pp. 653-678 Pegg GE, Woodward S (1986) Synthesis and metabohsm of a-tomatine in tomato isoUnes in relation to resistance to Verticillium albo-atrum. Mol Plant Microbe Interact 28 187 Eord JE et al (1977) The detoxification of a-tomatine by Fusarium oxysporum f.sp. lycopersici. Phytochemistry 16 544... 

Lairini K, Ruiz-Rubio M (1998) Detoxification of a-tomatine by Fusarium solani. Mycol Res... 

Weltring KM et al (1998) Metabohsm of the tomato saponin a-tomatine by Gibberella pulicaris. Phytochemistry 48 1321... 

The Indians of the Peruvian Altiplano eat potatoes with a dip of clay and a mustard-like herb. They say the clay removes the bitter taste and prevents stomach pains or vomiting after eating large amounts of potatoes. The people who eat clay intend detoxication. This may explain how Indians started to utilize and domesticate wild potatoes. Indeed, experiments have shown that four different types of edible clay adsorb the glycoalkaloid tomatine under simulated... 

Kozukue, N. Han, J.-S. Lee, K.-R. Friedman, M. Dehydrotomatine and a-Tomatine Content in Tomato Fruits and Vegetative Plant Tissues. J. Agric. Food Chem. 2004, 52, 2079-2083. 

Steroid alkaloids Solanaceae Liliaceae Solanum tuberosum Lycopersicon esculentum Veratrum album Solanidine Tomatine Jervine Cyclop amine Cycloposine Protoveratrine A Protoveratrine B... 

Ma, R. and Fontaine, T. D. 1948. In vitro antibiotic activity of crystalline tomatine towards Candida albicans. Antagonistic effect of rutin anquercitin. Archives of Biochemistry and Biophysics, 16 399 02. 

Thennopsine 34 Thiazolidines 58 Tinctorine 165, 201 Tomatidine 10, 146, 201, 209 Tomatine 27, 42 Tramadol 169 Trialkylpyrazine 44 Tricycbc alkaloids 88, 100, 101 Tricycbc gephyrotoxins 58 Tricycbc qninolizidine alkaloids 100 Triptonine 108, 110 Triptonine B 110 Trispheridine 36... 

Fig. 1A-C. Examples of different classes of saponins A the triterpenoid saponin avenacin A-1 from roots of Avena spp B the steroidal saponin gracillin, from Costus speciosus C the steroidal glycoalkaloid a-tomatine from tomato (Lycopersicon spp.)...

These considerations suggest the possibility of developing high-tomatine potatoes for safety and health-promoting qualities (Friedman et al., 2007 Kozukue et al., 2008). 

Friedman, M., Fitch, T. E., Yokoyama, W. E. (2000b). Lowering of plasma LDL cholesterol in hamsters by the tomato glycoalkaloid tomatine. Food Chem. Toxicol., 38, 549-553. 

Friedman, M., McQuistan, T., Hendricks, J. D., Pereira, C., Bailey, G. S. (2007). Protective effect of dietary tomatine against dibenzo[a,l]pyrene (DBP)-induced liver and stomach tumors in rainbow trout. Mol. Nutr. Food Res., 51,1485-1491. 

Kozukue, N., Friedman, M. (2003). Tomatine, chlorophyll, p-carotene and lycopene content in tomatoes during growth and maturation. J. Sci. Food Agric., 83, 195-200. 

Figure 14.3 Potato glycoalkaloids. (a) is tomatine, a spirosolane and (b) solanine, a solanidane.

A key question that cannot be answered using cell culture assays is whether dietary GAs can have similar effects. Importantly, evidence that dietary tomatine is effective against cancer was shown in a feeding study using rainbow trout, in which reduced tumor incidence was found in tomatine-fed trout (Friedman et al., 2007). Tomatidine has potential as a chemosensitizing... 

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