Glikoalkaloidy i saponiny - analityka, rola biologiczna, bezpieczeństwo żywności

Haliński, Łukasz

Artykuł - szczegóły

Tytuł artykułu

Glikoalkaloidy i saponiny - analityka, rola biologiczna, bezpieczeństwo żywności

Autorzy

Haliński Łukasz

Identyfikatory

Warianty tytułu

Glycoalkaloids and saponins - analysis, biological role, food safety

Języki publikacji

Abstrakty

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.

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.

Słowa kluczowe

glikoalkaloidy steroidowe saponiny aglikon bezpieczeństwo żywności analiza chemiczna

steroidal glycoalkaloids saponins aglycon food safety chemical analysis

Wydawca

ELAMED Media Group

Czasopismo

Laboratorium - Przegląd Ogólnopolski

Rocznik

2019

Tom

nr 4

Strony

15--22

Opis fizyczny

Bibliogr. 53 poz., rys.

Twórcy

autor

Haliński Łukasz

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.
3. Lásztity R., Hidvégi M., Bata A.: Saponins in foods. „Food Reviews International”, 1998, 14, 371-390.
4. Friedman M.: Potato glycoalkaloids and metabolites: roles in the plant and in the diet. „Journal of Agricultural and Food Chemistry”, 2006, 54, 8655-8681.
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.
10. Ono H., Kozuka D., Chiba Y., Horigane A., Isshiki K.: Structure and cytotoxicity of dehydrotomatine, a minor component of tomato glycoalkaloids. „Journal of Agricultural and Food Chemistry”, 1997, 45, 3743-3746.
11. Thagun C., Imanishi S., Kudo T. et al.: Jasmonate-responsive ERF transcription factors regulate steroidal glycoalkaloid biosynthesis in tomato. „Plant & Cell Physiology”, 2016, 57, 961-975.
12. Al Sinani S.S.S., Eltayeb E.A.: The steroidal glycoalkaloids solamargine and solasonine in Solanum plants. „South African Journal of Botany”, 2017, 112, 253–269.
13. Fenwick D.E., Oakenfull D.: Saponin content of food plants and some prepared food. „Journal of the Science of Food and Agriculture”, 1983, 34, 186-191.
14. Milgate J., Roberts D.C.K.: The nutritional & biological significance of saponins. „Nutritional Research”, 1995, 15, 1223-1249.
15. Güntner C., González A., Dos Reis R., González G., Vázquez A., Ferreira F., Moyna P.: Effect of Solanum glycoalkaloids on potato aphid Macrosiphum euphorbiae. „Journal of Chemical Ecology”, 1997, 23, 1651-1659.
16. Rial C., Gómez E., Varela R.M., Molinillo J.M.G., Macías F.A.: Ecological relevance of the major allelochemicals in Lycopersicon esculentum roots and exudates. „Journal of Agricultural and Food Chemistry”, 2018, 66, 4638-4644.
17. Blankemeyer J.T., McWilliams M.L., Rayburn J.R., Weissenberg M., Friedman M.: Developmental toxicology of solamargine and solasonine glycoalkaloids in frog embryos. „Food and Chemical Toxicology”, 1998, 36, 383-389.
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.
20. Friedman M.: Anticarcinogenic, cardioprotective, and other health benefits of tomato compounds lycopene, α-tomatine, and tomatidine in pure form and in fresh and processed tomatoes. „Journal of Agricultural and Food Chemistry”, 2013, 61, 9534-9550.
21. Friedman M.: Chemistry and anticarcinogenic mechanisms of glycoalkaloids produced by eggplants, potatoes, and tomatoes. „Journal of Agricultural and Food Chemistry”, 2015, 63, 3323-3337.
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.
27. Sidhu G.S., Oakenfull D.G.: A mechanism for the hypocholesterolaemic activity of saponins. „British Journal of Nutrition”, 1986, 55, 643-649.
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.
30. Friedman M., Dao L.: Distribution of glycoalkaloids in potato plants and commercial potato products. „Journal of Agricultural and Food Chemistry”, 1992, 40, 419-423.
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.
34. Güçlü-Üstündag Ö., Mazza G.: Saponins: properties, applications and processing. „Critical Reviews in Food Science and Nutrition”, 2007, 47, 231-258.
35. Cheok C.Y., Salman H.A.K., Sulaiman R.: Extraction and quantification of saponins: a review. „Food Research International”, 2014, 59, 16-40.
36. Negi J.S., Singh P., Pant G.J.N., Rawat M.S.M.: High-performance liquid chromatography analysis of plant saponins: an update 2005-2010. „Pharmacognosy Review”, 2011, 5, 155-158.
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

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