Semi-synthesis of red beet betacyanin ethyl-esters by esterification

• Autorzy: Tuwalska D. , Starzak K. , Szot D. , Wybraniec S. , Winterhalter P. , Jerz G.
• Języki publikacji: EN

Abstrakty

EN

Red beet pigments recovered from Beta vulgaris L. (Chenopodiaceae), mainly consist of purple betacyanins, such as 15R/15S-betanin. Currently,this pigment class is intensively investigated in respect of stability in food systems. Quite popular is the use of red beet extracts in dairy products such as yoghurts, and ice-creams. So far, there are no issues of toxicity using these natural pigments in food – so they seem to be a very good alternative to replace synthetic dyes which had been frequently discussed for negative side-effects to human health. Betacyanins, the glycosidation products of betanidin are very polar and therefore water soluble pigments, which are biosynthetically derived from condensation of cyclo-DOPA and betalamic acid. The significant polarity of betacyanins requires the use of ion-pair reagents such as trifluoro-acetic acid (TFA) or other homologue fluorinated additives under standard separation conditions on larger scale in spiral coil countercurrent chromatography (spCCC). In our synthetic experiment, the polarity of the natural betacyanins was reduced. This omitted the use of toxic per-fluoro ion-pair reagents. The three carboxylic groups of the betanin pigment backbone were the target functional groups of the derivatisation. In semi-synthesis, fortified red beet pigment extract was esterified with water-free ethanolic hydrogen chloride solution. The reaction was carried out at ambient temperature (7 days) to yield a mixture of betacyanin mono-, di- and tri-ethyl-esters, and their epimeric forms, as well as the respective betanidin-ethyl-esters. The time course of the reaction mixture was monitored by analytical C18-HPLC with ESI-DAD-MS/MS detection. The detected molecular weights of the pigments confirmed the presence of expected products. To the best of our knowledge, the presence of betalains containing ethyl-ester groups in biological samples have not been studied before.

Słowa kluczowe

EN

betacyanin ethyl-esters; betalains; betacyanins; betanin; betanidin; esterification

PL

estry etylowe; betalainy; betacyjaniny; betanina; betanidyna; estryfikacja

• Wydawca: Foundation for Young Scientists
• Czasopismo: Challenges of Modern Technology
• Rocznik: 2014
• Tom: Vol. 5, no. 3
• Strony: 27--31
• Opis fizyczny: Bibliogr. 11 poz., rys., tab., wykr.

Twórcy

autor

Tuwalska D.

• Department of Analytical Chemistry, Institute C-1, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. Warszawska 24, Cracow 31-155, Poland

autor

Starzak K.

• Department of Analytical Chemistry, Institute C-1, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. Warszawska 24, Cracow 31-155, Poland

autor

Szot D.

• Department of Analytical Chemistry, Institute C-1, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. Warszawska 24, Cracow 31-155, Poland

autor

Wybraniec S.

• Department of Analytical Chemistry, Institute C-1, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. Warszawska 24, Cracow 31-155, Poland

autor

Winterhalter P.

• Institute of Food Chemistry, Technische Universität Braunschweig, Braunschweig, Germany

autor

Jerz G.

• Institute of Food Chemistry, Technische Universität Braunschweig, Braunschweig, Germany

Bibliografia

• [1] Chethana S., Nayak C.A., and K.S.M.S. Raghavarao. “Aqueous two phase extraction for purificationand concentration of betalains”. Journal of Food Engineering, 81 (2007): 679-687.
• [2] Strack, D., Vogt, T., and W. Schliemann. “Recent advances in betalain research”. Phytochemistry 62 (2003): 247-269.
• [3] Delgado-Vargaz F., Jimenez A. R., and O; Paredes-Lopez. “Natural Pigments: Carotenoids, Anthocyanins, and Betalains – Characteristics, Biosynthesis, Processing, and Stability”. Critical Reviews in Food Science and Nutrition 40(3) (2000): 173-289.
• [4] Xiao-Hong Han, Zhao-Jian Gao, and Xing-Guo Xiao. “Enzymes and genes involved in the betalain biosynthesis in higher plants”. African Journal of Biotechnology 8 (24), (2009): 6735- 6744.
• [5] Mousumi Biswas, Satyahari Dey, and Sen Ramkrishna. “Betalains from Amranthus tricolor L.”. Journal of Pharmacognosy and Phytochemistry 1(5) (2013): 87-95.
• [6] Jerz G., Skotzki T., Fiege K., Winterhalter P., and S. Wybraniec. “Separation of betalains from berries of Phytolacca americana by ion-pair high-speed counter-current chromatography”. Journal of Chromatography A 1190 (2008): 63-73.
• [7] Wybraniec S., Jerz G., Gebers N., and P. Winterhalter. “Ion-pair high-speed countercurrent chromatography in fractionation of a high-molecular weight variation of acyl-oligosaccharide linked betacyanins from purple bracts of Bougainvillea glabra”. Journal of Chromatography B 878 (2010): 538-550.
• [8] Piattelli M., Minale L., and R.A. Nicolaus. “Pigments of Centrospermae. V. Betaxanthins from Mirabilis jalapa L.”. Phytochemistry 4 (1965): 817-823.
• [9] Wybraniec S. “Retetion of methylated betanidin esters in RPHPLC”. 5th International symposium on Separation Science & 5th AACI (June 27-29, 2007): Slovak Republik.
• [10] Wiliams J.R.. Myers K.E., Owens M.M., and M.A. Bonne, “Food quality indicator”. Patent No. US 2006/00570022 A1.
• [11] Azeredo H.M.C. “Betalain: properties, sources, applications, and stability – a review”. International Journal of Food Science and Technology 44 (2009), 2365–2376.