chemicallytechFine Chemical TechnologiesТонкие химические технологии2410-65932686-7575MIREA – Russian Technological University (RTU MIREA).10.32362/2410-6593-2017-12-6-32-38chemicallytech-122Research ArticleCHEMISTRY AND TECHNOLOGY OF MEDICINAL COMPOUNDS AND BIOLOGICALLY ACTIVE SUBSTANCESХИМИЯ И ТЕХНОЛОГИЯ ЛЕКАРСТВЕННЫХ ПРЕПАРАТОВ И БИОЛОГИЧЕСКИ АКТИВНЫХ СОЕДИНЕНИЙOBTAINING RED CABBAGE ANTHOCYANIN COLORED ENCAPSULATED FORMS BY THE METHOD OF FREEZE-DRYINGПОЛУЧЕНИЕ РАЗНОЦВЕТНЫХ ИНКАПСУЛИРОВАННЫХ ФОРМ АНТОЦИАНОВ КРАСНОКОЧАННОЙ КАПУСТЫ МЕТОДОМ ЛИОФИЛЬНОЙ СУШКИКульченкоЯ. Ю.KulchenkoYa. Yu.

аспирант кафедры общей химии Института инженерных технологий и естественных наук

308015, Россия, Белгород, ул. Победы, 85

Postgraduate of General Chemistry Chair of Institute of Engineering Technologies and Natural Sciences

85, Pobeda str., Belgorod 308015, Russia

noemail@neicon.ruДейнекаВ. И.DeinekaV. I.

профессор кафедры общей химии Института инженерных технологий и естественных наук

308015, Россия, Белгород, ул. Победы, 85

a, Dr. Sc. (Chemistry), Professor of General Chemistry Chair of Institute of Engineering Technologies and Natural Sciences

85, Pobeda str., Belgorod 308015, Russia

deineka@bsu.edu.ruДейнекаЛ. А.DeinekaL. A.

доцент кафедры общей химии Института инженерных технологий и естественных наук

308015, Россия, Белгород, ул. Победы, 85

Ph. D. (Chemistry), Associate Professor of General Chemistry Chair of Institute of Engineering Technologies and Natural Sciences

85, Pobeda str., Belgorod 308015, Russia

noemail@neicon.ruБлиноваИ. П.BlinovaI. P.

доцент кафедры общей химии Института инженерных технологий и естественных наук

308015, Россия, Белгород, ул. Победы, 85

Ph. D. (Chemistry), Associate Professor of General Chemistry Chair of Institute of Engineering Technologies and Natural Sciences

85, Pobeda str., Belgorod 308015, Russia

noemail@neicon.ruБелгородский государственный национальный исследовательский университетРоссияBelgorod National Research UniversityRussian Federation2017281220171263238Copyright © Kulchenko Y.Y., Deineka V.I., Deineka L.A., Blinova I.P., 20172017Кульченко Я.Ю., Дейнека В.И., Дейнека Л.А., Блинова И.П.Kulchenko Y.Y., Deineka V.I., Deineka L.A., Blinova I.P.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://www.finechem-mirea.ru/jour/article/view/122

The method of reversed-phase HPLC with diode-array and mass-spectrometric detection was explored to determine the qualitative composition of red cabbage anthocyanins. Mono- and diacylated derivatives of cyanidin-3,5-diglycosides with a complex structure of the substituent in position were found, as well as non-esterified compounds. The acylation acids were paracoumaric, ferulic and sinapic. Quantitative analysis was performed according to a simplified spectrophotometric method: absorbance measurement at pH 4.5 was excluded. The measurement showed that the level of anthocyanins accumulation is as high as 0.100 g of anthocyanins per 100 g of raw plant material (as cyanidin-3-glucoside chloride equivalent). Analysis of electronic spectra of the extract at different pH revealed the existence of some basic structures with absorbance maxima shifted bathochromically as compared to the spectrum of flavylium structure. The existence of one basic form at pH 4.5 forced us to exclude absorbance measurement at pH 4.5 during quantitative anthocyanin determination. Thus, the possibility of obtaining some differently colored encapsulated forms was proved. Because of relative instability of non-flavylium forms of anthocyanins the freeze drying technique was used to prepare six differently colored forms of 3% anthocyanins encapsulated in maltodextrin. The decrease of anthocyanins contents at drying did not exceed 30%, while no statistically proved loss of anthocyanins was found at storage in a refrigerator during more than six months.

В работе методом обращенно-фазовой ВЭЖХ с диодно-матричным и масс-спектрометрическим детектированием определен качественный состав антоцианов краснокочанной капусты: он включает моно- и диацилированные производные 3,5-диглюкозидов цианидина со сложным строением заместителя в положении 3. Количественный анализ упрощенным (в работе объяснена причина отказа от дифференциального метода) спектрофотометрическим методом показал, что уровень накопления антоцианов составляет порядка 0.100 г антоцианов на 100 г растительного материала (в пересчете на цианидин-3-глюкозида хлорид). На основе анализа электронных спектров экстракта при различных рН установлено образование четырех разноокрашенных структур антоцианов. Описаны процедуры экстракции, частичной очистки и получения разноцветных окрашенных форм методом лиофильной сушки. Получены 6 образцов инкапсулированных в мальтодекстрин форм различной окраски с высокой устойчивостью при хранении в морозильной камере.

краснокочанная капустаантоцианывлияние рНразноцветные инкапсулированные формылиофильная сушкаобращенно-фазовая ВЭЖХred cabbageanthocyaninseffect of рНcolored encapsulated formslyophilic dryingreversed-phase HPLCReferencesMiguel M.G. Anthocyanins: Antioxidant and/or anti-inflammatory activities // J. Appl. Pharm. Sci. 2011. V. 1. № 6. P. 7-15.Miguel M.G. Anthocyanins: Antioxidant and/or anti-inflammatory activities // J. Appl. Pharm. Sci. 2011. V. 1. № 6. P. 7-15.Mazza G. Anthocyanins and heart health // Ann. Ist. Super Sanità. 2007. V. 43. № 4. P. 369-374.Mazza G. Anthocyanins and heart health // Ann. Ist. Super Sanità. 2007. V. 43. № 4. P. 369–374.Taylor C. Wallace Anthocyanins in Cardiovascular Disease // Adv. Nutr. 2011. V. 2. P. 1-7.Taylor C. Wallace Anthocyanins in Cardiovascular Disease // Adv. Nutr. 2011. V. 2. P. 1–7.Francis F.J. A new group of food colorants // Trends Food Sci. Technol. 1992. V. 31. P. 27-30.Francis F.J. A new group of food colorants // Trends Food Sci. Technol. 1992. V. 31. P. 27–30.Brouillard R., Lang J. The hemiacetal - cischalcone equilibrium of malvin, a natural anthocyanin // Can. J. Chem. 1990. V. 68. № 5. P. 755-761.Brouillard R., Lang J. The hemiacetal – cischalcone equilibrium of malvin, a natural anthocyanin // Can. J. Chem. 1990. V. 68. № 5. P. 755–761.Silva V.O., Freitas A.A., Maçanita A.L., Quina F.H. Chemistry and photochemistry of natural plant pigments: the anthocyanins // J. Phys. Org. Chem. 2016. V. 29. № 11. P. 594-599.Silva V.O., Freitas A.A., Maçanita A.L., Quina F.H. Chemistry and photochemistry of natural plant pigments: the anthocyanins // J. Phys. Org. Chem. 2016. V. 29. № 11. P. 594–599.Lee J., Durst R.W., Wrolstad R.E. Determination of Total Monomeric Anthocyanin Pigment Content of Fruit Juices, Beverages, Natural Colorants, and Wines by the pH Differential Method: Collaborative Study // J. AOAC Internat. 2005. V. 88. № 5. P. 1269-1278.Lee J., Durst R.W., Wrolstad R.E. Determination of Total Monomeric Anthocyanin Pigment Content of Fruit Juices, Beverages, Natural Colorants, and Wines by the pH Differential Method: Collaborative Study // J. AOAC Internat. 2005. V. 88. № 5. P. 1269–1278.Saito N., Tatsuzawa F., Toki K., Shinoda K., Shigihara A., Honda T. The blue anthocyanin pigments from the blue flowers of Heliophila coronopifolia L. (Brassicaceae) // Phytochem. 2011. V. 72. № 17. P. 2219-2229.Saito N., Tatsuzawa F., Toki K., Shinoda K., Shigihara A., Honda T. The blue anthocyanin pigments from the blue flowers of Heliophila coronopifolia L. (Brassicaceae) // Phytochem. 2011. V. 72. № 17. P. 2219–2229.Bloor S.J. Deep blue anthocyanins from blue Dianella berries// Phytochem. 2001. V. 58. № 6. P. 923-927.Bloor S.J. Deep blue anthocyanins from blue Dianella berries// Phytochem. 2001. V. 58. № 6. P. 923–927.Yoshida K, Mori M, Kondo T. Blue flower color development by anthocyanins: from chemical structure to cell physiology // Nat Prod Rep. 2009. V. 26. № 7. P. 884-915.Yoshida K, Mori M, Kondo T. Blue flower color development by anthocyanins: from chemical structure to cell physiology // Nat Prod Rep. 2009. V. 26. № 7. P. 884–915.Robbins R.J., Christopher Johnson J., Collins T.M., Ahmadiani N., Monica Giusti M. Natural blue anthocyanin-containing colorants: WO 2014152478 A2 Mars, Incorporated, The Ohio State Univsity. Filled 14.03.2014. Date of Patent 25.09.2014.Robbins R.J., Christopher Johnson J., Collins T.M., Ahmadiani N., Monica Giusti M. Natural blue anthocyanin-containing colorants: WO 2014152478 A2 Mars, Incorporated, The Ohio State Univsity. Filled 14.03.2014. Date of Patent 25.09.2014.Wiczkowski W., Szawara-Nowak D., Topolska J. Red cabbage anthocyanins: Profile, isolation, identification, and antioxidant activity // Food Res. Internat. 2013. V. 51. P. 303-309.Wiczkowski W., Szawara-Nowak D., Topolska J. Red cabbage anthocyanins: Profile, isolation, identification, and antioxidant activity // Food Res. Internat. 2013. V. 51. P. 303–309.Ahmadiani N., Robbins R.J., Collins T.M., Giusti M.M. Anthocyanins contents, profiles, and color characteristics of red cabbage extracts from different cultivars and maturity stages // J Agric Food Chem. 2014. V. 62. №. 30. P. 7524-7531.Ahmadiani N., Robbins R.J., Collins T.M., Giusti M.M. Anthocyanins contents, profiles, and color characteristics of red cabbage extracts from different cultivars and maturity stages // J Agric Food Chem. 2014. V. 62. №. 30. P. 7524–7531.Дейнека Л.А., Блинова И.П., Кульченко Я.И., Озер П.С., Саенко И.И., Дейнека В.И. Сохранность и переход между формами антоцианов в растворах // Успехи современного естествознания. 2016. №2. С. 16-20.Deineka L.A., Blinova I.P., Kulchenko Ya.Yu., Ozer P.S., Saenko I.I., Deineka V.I. Stability and interconversions between anthocyanin forms in solutions // Uspekhi sovremennogo estestvoznaniya (Advances in Current Natural Science). 2016. № 2. С. 16–20. (in Russ.).Pina F. Thermodynamics and kinetics of favylium salts // J. Chem. Soc., Faraday Trans. 1998. V. 94. № 15. P. 2109-2116.Pina F. Thermodynamics and kinetics of favylium salts // J. Chem. Soc., Faraday Trans. 1998. V. 94. № 15. P. 2109–2116.

The authors declare that there are no conflicts of interest present.