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Glikoalkaloidy i saponiny - analityka, rola biologiczna, bezpieczeństwo żywności

Identyfikatory
Warianty tytułu
EN
Glycoalkaloids and saponins - analysis, biological role, food safety
Języki publikacji
PL
Abstrakty
PL
Glikoalkaloidy steroidowe to metabolity wtórne roślin psiankowatych, a zbliżone do nich strukturalnie saponiny to związki naturalne szeroko rozpowszechnione wśród roślin wyższych. Obie grupy związków mają interesujące właściwości biologiczne, ale też – chociaż ich toksyczność jest umiarkowana – w wyższych dawkach mogą wywoływać niekorzystne efekty zdrowotne. W artykule opisano wybrane substancje z obu grup, ich właściwości biologiczne oraz procedury analityczne stosowane w oznaczaniu tych istotnych składników żywności pochodzenia roślinnego.
EN
Steroidal glycoalkaloids are secondary metabolites produced by solanaceous plants, while structurally similar saponins are widely prevalent in higher plants. Both classes show many interesting biological activities. However, even if their toxicity is moderate, in high doses they may trigger some adverse effects. Selected glycoalkaloids and saponins, their biological properties and analytical procedures used for the determination of these important food components are briefly described in the article.
Rocznik
Tom
Strony
15--22
Opis fizyczny
Bibliogr. 53 poz., rys.
Twórcy
  • Katedra Analizy Środowiska, Wydział Chemii, Uniwersytet Gdański
Bibliografia
  • 1. Milner S.E., Brunton N.P., Jones P.W., O’Brien N.M., Collins S.G., Maguire A.R.: Bioactivities of glycoalkaloids and their aglycones from Solanum species. „Journal of Agricultural and Food Chemistry”, 2011, 59, 3454-3484.
  • 2. Price K.R., Johnson I.T., Fenwick G.R., Malinow M.R.: The chemistry and biological significance of saponins in foods and feedingstuffs. „CRC Critical Reviews in Food Science and Nutrition”, 1987, 26, 27-135.
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  • 5. Kozukue N., Yoon K.S., Byun G.I., Misoo S., Levin C.E., Friedman M.: Distribution of glycoalkaloids in potato tubers of 59 accessions of two wild and five cultivated Solanum species. „Journal of Agricultural and Food Chemistry”, 2008, 56, 11920-11928.
  • 6. Sinden S.L., Sanford L.L., Webb R.E.: Genetic and environmental control of potato glycoalkaloids. „American Potato Journal”, 1984, 61, 141-156.
  • 7. Friedman M.: Tomato glycoalkaloids: roles in the plant and in the diet. „Journal of Agricultural and Food Chemistry”, 2002, 50, 5751-5780.
  • 8. Choi S.H., Lee S.H., Kim H.J., Lee I.S., Kozukue N., Levin C.E., Friedman M.: Changes in free amino acid, phenolic, chlorophyll, carotenoid, and glycoalkaloid contents in tomatoes during 11 stages of growth and inhibition of cervical and lung human cancer cells by green tomato extract. „Journal of Agricultural and Food Chemistry”, 2010, 58, 7547-7556.
  • 9. Friedman M., Levin C.E.: Dehydrotomatine content in tomatoes. „Journal of Agricultural and Food Chemistry”, 1998, 46, 4571-4576.
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  • 18. Liu J., Kanetake S., Wu Y.H., Tam C., Cheng L.W., Land K.M., Friedman M.: Antiprotozoal effects of the tomato tetrasaccharide glycoalkaloid tomatine and the aglycone tomatidine on mucosal trichomonads. „Journal of Agricultural and Food Chemistry”, 2016, 64, 8806-8810.
  • 19. Fujiwara Y., Kiyota N., Tsurushima K., Yoshitomi M., Horlad H., Ikdea T., Nohara T., Takeya M., Nagai R.: Tomatidine, a tomato sapogenol, ameliorates hyperlipidemia and atherosclerosis in ApoEdeficient mice by inhibiting acyl-CoA:cholesterol acyl-transferase (ACAT). „Journal of Agricultural and Food Chemistry”, 2012, 60, 2472-2479.
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  • 22. Choi S.H., Ahn J.B., Kozukue N., Kim H.J., Nishitani Y., Zhang L., Mizuno M., Levin C.E., Friedman M.: Structure−activity relationships of α-, β1-, γ-, and δ-tomatine and tomatidine against human breast (MDA-MB-231), gastric (KATO-III), and prostate (PC3) cancer cells. „Journal of Agricultural and Food Chemistry”, 2012, 60, 3891-3899.
  • 23. Lee K.R., Kozukue N., Han J.S., Park J.H., Chang E.Y., Baek E.J., Chang J.S., Friedman M.: Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells. „Journal of Agricultural and Food Chemistry”, 2004, 52, 2832-2839.
  • 24. Kim S.P., Nam S.H., Friedman M.: The tomato glycoalkaloid α-tomatine induces caspaseindependent cell death in mouse colon cancer CT-26 cells and transplanted tumors in mice. „Journal of Agricultural and Food Chemistry”, 2015, 63, 1142-1150.
  • 25. Friedman M., Levin C.E., Lee S.u., Kim H.J., Lee I.S., Byun J.O., Kozukue N.: Tomatine-containing green tomato extracts inhibit growth of human breast, colon, liver, and stomach cancer cells. „Journal of Agricultural and Food Chemistry”, 2009, 57, 5727-5733.
  • 26. Korchowiec B., Gorczyca M., Wojszko K., Janikowska M., Henry M., Rogalska E.: Impact of two different saponins on the organization of model lipid membranes. „Biochimca et Biophysica Acta”, 2015, 1848, 1963-1973.
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  • 28. Munafo J.P., Gianfagna T.J.: Antifungal activity and fungal metabolism of steroidal glycosides of easter lily (Lilium longiflorum Thunb.) by the plant pathogenic fungus, Botrytis cinerea. „Journal of Agricultural and Food Chemistry”, 2011, 59, 5945-5954.
  • 29. Johns T., Alonso J.G.: Glycoalkaloid change during the domestication of the potato, Solanum Section Petota. „Euphytica”, 1990, 50, 203-210.
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  • 31. Kozukue N., Han J.S., Lee K.R., Friedman M.: Dehydrotomatine and α-tomatine content in tomato fruits and vegetative plant tissues. „Journal of Agricultural and Food Chemistry”, 2004, 52, 2079-2083.
  • 32. Sánchez-Mata M.C., Yokoyama W.E., Hong Y.J., Prohens J.: α-Solasonine and α-solamargine contents of gboma (Solanum macrocarpon L.) and scarlet (Solanum aethiopicum L.) eggplants. „Journal of Agricultural and Food Chemistry”, 2010, 58, 5502-5508.
  • 33. Haliński Ł.P., Topolewska A., Rynkowska A., Mika A., Urasińska M., Czerski M., Stepnowski P.: Impact of plant domestication on selected nutrient and anti-nutrient compounds in Solanaceae with edible leaves (Solanum spp.). „Genetic Resources and Crop Evolution”, 2019, 66, 89-103.
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  • 37. Brown M.S., McDonald G.M., Friedman M.: Sampling leaves of young potato (Solanum tuberosum) plants for glycoalkaloid analysis. „Journal of Agricultural and Food Chemistry”, 1999, 47, 2331-2334.
  • 38. Friedman M., Kozukue N., Harden L.A.: Preparation and characterization of acid hydrolysis products of the tomato glycoalkaloid α-tomatine. „Journal of Agricultural and Food Chemistry”, 1998, 46, 2096-2101.
  • 39. Herb S.F., Fitzpatrick T.J., Osman S.F.: Separation of potato glycoalkaloids by gas chromatography. „Journal of Agricultural and Food Chemistry”, 1975, 23, 520-523.
  • 40. Laurila J., Laakso I., Vaananen T., Kuronen P., Huopalahti, R., Pehu E.: Determination of solanidine- and tomatidine-type glycoalkaloid aglycons by gas chromatography/mass spectrometry. „Journal of Agricultural and Food Chemistry”, 1999, 47, 2738-2742.
  • 41. Carman Jr. A.S., Kuan S.S., Ware G.M., Francis Jr. O.J., Kirschenheuter, G.P.: Rapid highperformance liquid chromatographic determination of the potato glycoalkaloids α-solanine and α-chaconine. „Journal of Agricultural and Food Chemistry”, 1986, 34, 279-282.
  • 42. Eanes R.C., Tek N., Kirsoy O., Frary A., Doganlar S., Almeida A.E.: Development of practical HPLC methods for the separation and determination of eggplant steroidal glycoalkaloids and their aglycones. „Journal of Liquid Chromatography & Related Technologies”, 2008, 31, 984-1000.
  • 43. Bushway R.J., Perkins L.B., Paradis L.R., Vanderpan S.: High-performance liquid chromatographic determination of the tomato glycoalkaloid, tomatine, in green and red tomatoes. „Journal of Agricultural and Food Chemistry”, 1994, 42, 2824-2829.
  • 44. Keukens E.A., Hop M.E.C.M., Jongen W.M.F.: Rapid high-performance liquid chromatographic method for the quantification of α-tomatine in tomato. „Journal of Agricultural and Food Chemistry”, 1994, 42, 2475-2477.
  • 45. Friedman M., Levin C.E., McDonald G.M.: α-Tomatine determination in tomatoes by HPLC using pulsed amperometric detection. „Journal of Agricultural and Food Chemistry”, 1994, 42, 1959-1964.
  • 46. Friedman M., Levin C.E.: α-Tomatine content in tomato and tomato products determined by HPLC with pulsed amperometric detection. „Journal of Agricultural and Food Chemistry”, 1995, 43, 1507-1511.
  • 47. Shakya R., Navarre D.A.: LC-MS analysis of solanidane glycoalkaloid diversity among tubers of four wild potato species and three cultivars (Solanum tuberosum). „Journal of Agricultural and Food Chemistry”, 2008, 56, 6949-6958.
  • 48. Cataldi T.R.I., Lelario F., Bufo S.A.: Analysis of tomato glycoalkaloids by liquid chromatography coupled with electrospray ionization tandem mass spectrometry. „Rapid Communications in Mass Spectrometry”, 2005, 19, 3103-3110.
  • 49. Han P., Wang Z., Lavoir A.V., Michel T., Seassau A., Zheng W., Niu C., Desneux N.: Increased water salinity applied to tomato plants accelerates the development of the leaf miner Tuta absoluta through bottom-up effects. „Scientific Reports”, 2016, 6, 32403.
  • 50. Iijima Y., Watanabe B., Sasaki R., Takenada M., Ono H., Sakurai N., Umemoto N., Suzuki H., Shibata D., Aoki K.: Steroidal glycoalkaloid profiling and structures of glycoalkaloids in wild tomato fruit. „Phytochemistry”, 2013, 95, 145-157.
  • 51. Abell D.C., Sporns P.: Rapid quantitation of potato glycoalkaloids by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. „Journal of Agricultural and Food Chemistry”, 1996, 44, 2292-2296.
  • 52. Ha M., Kwak J.H., Kim Y., Zee O.P.: Direct analysis for the distribution of toxic glycoalkaloids in potato tuber tissue using matrix-assisted laser desorption/ionization mass spectrometric imaging. „Food Chemistry”, 2012, 133, 1155-1162.
  • 53. Friedman M., Bautista F.F., Stanker L.H., Larkin K.A.: Analysis of potato glycoalkaloids by a new ELISA kit. „Journal of Agricultural and Food Chemistry”, 1998, 46, 5097-5102
Uwagi
PL
Opracowanie rekordu w ramach umowy 509/P-DUN/2018 ze środków MNiSW przeznaczonych na działalność upowszechniającą naukę (2019).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-ae0dc364-ad9b-4491-8cb7-927afa5f0245
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