Abstract
Anthocyanins are glycosylated derivatives of anthocyanidins, whose hydroxyl groups are occasionally acylated with organic acids. The effect of anthocyanin composition on their stability under in vitro gastrointestinal digestion was investigated. Black soybean had all glycosylated anthocyanins with monosaccharide, grape contained glycosylated anthocyanins with disaccharide (23%) and acylated anthocyanins bound with two sugars (77%), and purple sweet potato had all acylated anthocyanins bound with three sugars. The order of total anthocyanins content was purple sweet potato, grape, and black soybean. Gastric digestion did not significantly decrease anthocyanins content in three samples, while intestinal digestion resulted in the significant decrease of total anthocyanins content in black soybean (40%), grape (45%), and purple sweet potato (25%). This indicates that the degree of glycosylation and acylation of anthocyanins affects their stability under the gastrointestinal conditions. Phenolic acids derived from anthocyanin degradation increased total phenolic content as well as ABTS radical scavenging activity.
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References
Bermúdez-Soto MJ, Tomás-Barberán FA. Evaluation of commercial red fruit juice concentrates as ingredients for antioxidant functional juices. European Food Research and Technology. 219: 133-141 (2004)
Bouayed J, Hoffmann L, Bohn T. Total phenolics, flavonoids, anthocyanins and antioxidant activity following simulated gastro-intestinal digestion and dialysis of apple varieties: Bioaccessibility and potential uptake. Food Chemistry. 128: 14-21 (2011)
Boyer J, Brown D, Liu RH. In vitro digestion and lactase treatment influence uptake of quercetin and quercetin glucoside by the Caco-2 cell monolayer. Nutrition Journal. 4 :1-15 (2005)
Braga ARC, Murador DC, de Souza Mesquita LM, de Rosso VV. Bioavailability of anthocyanins: gaps in knowledge, challenges and future research. Journal of Food Composition and Analysis. 68: 31-40 (2018)
Bronnum-Hansen K, Flink JM. Anthocyanin colourants from elderberry (Sambucus nigra L.) 2. Process considerations for production of freeze dried product. International Journal of Food Science and Technology. 20 :713-723 (1985)
Choi SJ. The difference of anthocyanin pigment composition and colour expression in fruit skin of several grape cultivars. Korean Journal of Food Preservation. 17: 847-852 (2010)
Choung MG, Baek IY, Kang ST, Han WY, Shin DC, Moon HP, Kang KH. Isolation and determination of anthocyanins in seed coats of black soybean (Glycine max (L.) Merr.). Journal of Agricultural and Food Chemistry. 49: 5848-5851 (2001)
Correa-Betanzo J, Allen-Vercoe E, McDonald J, Schroeter K, Corredig M, Paliyath G. Stability and biological activity of wild blueberry (Vaccinium angustifolium) polyphenols during simulated in vitro gastrointestinal digestion. Food Chemistry. 165: 522-531 (2014)
De la Cruz AA, Hilbert G, Rivière C, Mengin V, Ollat N, Bordenave L, Decroocq S, Delaunay J-C, Delrot S, Mérillon J-M, Monti J-P, Gomès E, Richard T. Anthocyanin identification and composition of wild Vitis spp. accessions by using LC–MS and LC–NMR. Analytica Chimica Acta. 732: 145-152 (2012)
Dudonné S, Vitrac X, Coutiére P, Woillez M, Mérillon JM. Comparative study of antioxidant properties and total phenolic content of 30 plant extracts of industrial interest using DPPH, ABTS, FRAP, SOD, and ORAC assays. Journal of Agricultural and Food Chemistry. 57: 1768-1774 (2009)
Escribano-Bailón MT, Santos-Buelga C, Rivas-Gonzalo JC. Anthocyanins in cereals. Journal of Chromatography A. 1054: 129-141 (2004)
Fossen T, Cabrita L, Andersen OM. Colour and stability of pure anthocyanins influenced by pH including the alkaline region. Food Chemistry. 63: 435-440 (1998)
Gil-Izquierdo A, Gil MI, Ferreres F, Tomás-Barberán FA. In vitro availability of flavonoids and other phenolics in orange juice. Journal of Agricultural and Food Chemistry. 49: 1035-1041 (2001)
Goto T, Kondo T, Tamura H, Kawahori K, Hattori H. Structure of platyconin, a diacylated anthocyanin isolated from the Chinese bell-flower Platycodon grandiflorum. Tetrahedron Letters. 24: 2181-2184 (1983)
Hong KH, Koh E. Effects of cooking methods on anthocyanins and total phenolics in purple-fleshed sweet potato. Journal of Food Processing and Preservation. 40: 1054-1063 (2016)
Kamonpatana K, Failla ML, Kumar PS, Giusti MM. Anthocyanin structure determines susceptibility to microbial degradation and bioavailability to the buccal mucosa. Journal of Agricultural and Food Chemistry. 62: 6903-6910 (2014)
Kim HW, Kim JB, Cho SM, Chung MN, Lee YM, Chu SM, Che JH, Kim SN, Kim SY, Cho YS, Kim JH, Park HJ, Lee DJ. Anthocyanin changes in the Korean purple-fleshed sweet potato, Shinzami, as affected by steaming and baking. Food Chemistry. 130: 966-972 (2012)
Lee J, Durst RW, Wrolstad RE. Determination of total monomeric anthocyanin pigment content of fruit juices, beverages, natural colorants, and wines by the pH differential method: Collaborative study. Journal of AOAC International. 88: 1269-1278 (2005)
Lee JH, Kang NS, Shin S-O, Shin S-H, Lim S-G, Suh D-Y, Baek I-Y, Park K-Y, Ha TJ. Characterisation of anthocyanins in the black soybean (Glycine max L.) by HPLC-DAD-ESI/MS analysis. Food Chemistry. 112: 226-231 (2009)
Leon A, Robertson A, Robinson R, Seshadri TR. Experiments on the synthesis of anthocyanins Part VII. The four isomeric β-glucosides of pelargonidin chloride. Journal of the Chemical Society. 2672–2701 (1931)
Lingua MS, Wunderlin DA, Baroni MV. Effect of simulated digestion on the phenolic components of red grapes and their corresponding wines. Journal of Functional Foods. 44: 86-94 (2018)
McDougall GJ, Dobson P, Smith P, Blake A, Stewart D. Assessing potential bioavailability of raspberry anthocyanins using an in vitro digestion system. Journal of Agricultural and Food Chemistry. 53: 5896-5904 (2005)
McDougall GJ, Fyffe S, Dobson P, Stewart D. Anthocyanins from red cabbage – stability to simulated gastrointestinal digestion. Phytochemistry. 68: 1285-1294 (2007)
Oh YS, Lee JH, Yoon SH, Oh CH, Choi DS, Choe E, Jung MY. Characterization and quantification of anthocyanins in grape juices obtained from the grapes cultivated in Korea by HPLC/DAD, HPLC/MS, and HPLC/MS/MS. Journal of Food Science. 73: C378-C389 (2008)
Pérez-Vicente A, Gil-Izquierdo A, García-Viguera C. In vitro gastrointestinal digestion study of pomegranate juice phenolic compounds, anthocyanins, and vitamin C. Journal of Agricultural and Food Chemistry. 50: 2308-2312 (2002)
Podsędek A, Redzynia M, Klewicka E, Koziołkiewicz M. Matrix effects on the stability and antioxidant activity of red cabbage anthocyanins under simulated gastrointestinal digestion. BioMed Research International. 2014: 1-11 (2014)
Ryu D, Koh E. Application of response surface methodology to acidified water extraction of black soybeans for improving anthocyanin content, total phenols content and antioxidant activity. Food Chemistry. 260-266 (2018)
Ryu D, Park H-M, Koh E. Effects of Solid-Liquid Ratio, Time, and Temperature on Water Extraction of Anthocyanin from Campbell Early Grape. Food Analytical Methods. 13: 637-646 (2020)
Ryu D, Sung Y, Hong J, Koh E. Cellular uptake of anthocyanins extracted from black soybean, grape, and purple sweet potato using INT-407 cells. Food Science and Biotechnology. 30: 1383-1391 (2021)
Sabraoui T, Khider T, Nasser B, Eddoha R, Moujahid A, Benbachir M, Essamadi A. Determination of punicalagins content, metal chelating, and antioxidant properties of edible pomegranate (Punica granatum L) peels and seeds grown in Morocco. International Journal of Food Science. 2020: 1-8 (2020)
Šaponjac VT, Gironés-Vilaplana A, Djilas S, Mena P, Ćetković G, Moreno DA, Čanadanović-Brunet J, Vulić J, Stajćić S, Krunić M. Anthocyanin profiles and biological properties of cranberry (Rubus spp.) press residues. Journal of the Science of Food and Agriculture. 94: 2393-2400 (2013)
Shi J, Gong J, Liu J, Wu X, Zhang Y. Antioxidant capacity of extract from edible flowers of Prunus mume in China and its active components. LWT-Food Science and Technology. 42: 477-482 (2009)
Singleton VL, Rossi JA. Colorimetry of total phenolics with phosphomolybdic-phosphotungstic acid reagents. American Journal of Enology and Viticulture. 16: 144-158 (1965)
Sun D, Huang S, Cai S, Cao J, Han P. Digestion property and synergistic effect on biological activity of purple rice (Oryza sativa L.). Food Research International. 78: 114-123 (2015)
Valdez JC, Bolling BW. Anthocyanins and intestinal barrier function: A review. Journal of Food Bioactives. 5:18-30.
Wang S, Amigo-Benavent M, Mateos R, Bravo L, Sarriá B. Effects of in vitro digestion and storage on the phenolic content and antioxidant capacity of a red grape pomace. International Journal of Food Science and Nutrition. 68: 188-200 (2017)
Woodward GM, Needs PW, Kay CD. Anthocyanin-derived phenolic acids form glucuronides following simulated gastrointestinal digestion and microsomal glucuronidation. Molecular Nutrition & Food Research. 55: 378-386 (2011)
Yang ZW, Tang CE, Zhang JL, Zhou Q, Zhang ZC. Stability and antioxidant activity of anthocyanins from purple sweet potato (Ipomoea batatas L. cultivar Eshu No. 8) subjected to simulated in vitro gastrointestinal digestion. International Journal of Food Science & Technology. 54: 2604-2614 (2019)
Zhoa L, Li S, Zhao L, Zhu Y, Hao T. Antioxidant activities and major bioactive components of consecutive extracts from blue honeysuckle (Lonicera caerulea L.) cultivated in China. Journal of Food Biochemistry. 39: 653-662 (2015)
Zhao CL, Yu YQ, Chen ZJ, Wen GS, Wei FG, Zheng Q, Wang CD, Xiao XL. Stability-increasing effects of anthocyanin glycosyl acylation. Food Chemistry. 214: 119-128 (2017)
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This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (2017R1D1A1B03028841).
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Eunmi Koh and Dayeon Ryu declared that there is no conflict of interest.
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Ryu, D., Koh, E. Stability assessment of anthocyanins from black soybean, grape, and purple sweet potato under in vitro gastrointestinal digestion. Food Sci Biotechnol 31, 1053–1062 (2022). https://doi.org/10.1007/s10068-022-01071-6
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DOI: https://doi.org/10.1007/s10068-022-01071-6