title: Chemistry and anticarcinogenic mechanisms of glycoalkaloids produced by eggplants, potatoes, and tomatoes.
abstract: Inhibition of cancer can occur via apoptosis, a genetically directed process of cell self-destruction that involves numerous biomarkers and signaling pathways. Glycoalkaloids are nitrogen-containing secondary plant metabolites found in numerous Solanaceous plants including eggplants, potatoes, and tomatoes. Exposure of cancer cells to glycoalkaloids produced by eggplants (α-solamargine and α-solasonine), potatoes (α-chaconine and α-solanine), and tomatoes (α-tomatine) or their hydrolysis products (mono-, di-, and trisaccharide derivatives and the aglycones solasodine, solanidine, and tomatidine) inhibits the growth of the cells in culture (in vitro) as well as tumor growth in vivo. This overview comprehensively surveys and consolidates worldwide efforts to define the following aspects of these natural compounds: (a) their prevalence in the three foods; (b) their chemistry and structure-activity relationships; (c) the reported factors (biomarkers, signaling pathways) associated with apoptosis of bone, breast, cervical, colon, gastric, glioblastoma, leukemia, liver, lung, lymphoma, melanoma, pancreas, prostate, and squamous cell carcinoma cell lines in vitro and the in vivo inhibition of tumor formation and growth in fish and mice and in human skin cancers; and (d) future research needs. The described results may make it possible to better relate the structures of the active compounds to their health-promoting function, individually, in combination, and in food, and allow the consumer to select glycoalkaloid-containing food with the optimal content of nontoxic beneficial compounds. The described findings are expected to be a valuable record and resource for further investigation of the health benefits of food-related natural compounds.
authors.affiliation: Western Regional Research Center, Agricultural Research Service, United States Department Agriculture, Albany, California 94710, United States.
authors.forename: Mendel
authors.initials: M
authors.lastname: Friedman
mesh_terms: D000818:Animals; D016588:Anticarcinogenic Agents; D017209:Apoptosis / Q000187:drug effects; D045744:Cell Line, Tumor; D006801:Humans; D018551:Solanum lycopersicum / Q000378:metabolism*; D051379:Mice; D012991:Solanaceous Alkaloids / Q000096:biosynthesis / Q000737:chemistry* / Q000494:pharmacology*; D012992:Solanine / Q000031:analogs & derivatives / Q000494:pharmacology; D032323:Solanum melongena / Q000378:metabolism*; D011198:Solanum tuberosum / Q000378:metabolism*; D013329:Structure-Activity Relationship; D014053:Tomatine / Q000031:analogs & derivatives / Q000494:pharmacology
chemical_list: D016588:Anticarcinogenic Agents; D012991:Solanaceous Alkaloids; C514919:alpha-solanine; C484751:alpha-tomatine; D012992:Solanine; C011860:alpha-chaconine; D014053:Tomatine; C026608:alpha-solamargine
keywords: additive effects; analysis; biomarkers; cancer cell inhibition; chemistry; eggplants; glycoalkaloids; human health; immunostimulating effects; mechanisms; membrane disruptive effects; potatoes; research needs; signaling pathways; solanidine; solasodine; synergistic effects; tomatidine; tomatine-cholesterol affinity; tomatoes; tumor inhibition; α-chaconine; α-solamargine; α-solanine; α-solasonine; α-tomatine