Complexation and Colour Stability of Anthocyanins from the Extracts of Java Plum Fruits (Syzygium cumini) with Selected Metal Cations (Al3+, Fe3+, and Ca2+) at Various pHs
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Keywords:
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Anthocyanins, Java Plum, Syzygium cumini, Complexation
Abstract
Anthocyanins are highly coloured polyphenols, a class of flavonoids, which are natural, non-toxic, and water-soluble compounds. Because of that, anthocyanins have been used in numerous applications, such as natural colorants for foods, beverages, and textiles. However, anthocyanins have some drawbacks regarding their stability towards temperature, pH, and light, leading to degradation. One method to improve anthocyanins’ stability can be achieved through a complexation reaction of anthocyanins with metal cations. Thus, this study aimed to investigate the stability and colour profiles of anthocyanins extracted from Java Plum fruits (Syzygium cumini) complexed with Al3+, Fe3+, and Ca2+ ions in pH 1-12. Previously, anthocyanins from Java Plum fruits have been identified by LC-MS as cyanidin-3-O-glucoside ([M]+, m/z 449.3), delphinidin-3-O-glucoside ([M]+, m/z 465.3), and petunidin O-glucoside ([M]+, m/z 479.3). The ATR FTIR was also performed to confirm the functional group of anthocyanins. The colour of each solution at different pH was evaluated by UV-Vis Spectrophotometer at 200-800 nm. Complexation of anthocyanins with Al3+, Fe3+, and Ca2+ ions showed various colours at different pHs. The complexation of anthocyanins with Al3+ at pH 4-5 developed a blue colour. The intensity of the blue colour increases with an increase in Al3+ ion concentration. This investigation showed the potential application of anthocyanin-metal chelation for the textile industry due to the range of colour produced. Furthermore, the complexation of anthocyanins to produce blue colour can be an alternative in food industries as this colour is difficult to obtain in acidic pH.
References
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Becerril, R., C. Nerín, and F. Silva (2021). Bring Some Colour to Your Package: Freshness Indicators Based on Anthocyanin Extracts. Trends in Food Science and Technology, 111; 495–505.
Dangles, O. and J.-A. Fenger (2018). The Chemical Reactivity of Anthocyanins and Its Consequences in Food Science and Nutrition. Molecules, 23(8); 1–23.
Estévez, L., N. Otero, and R. A. Mosquera (2011). Molecular Structure of Cyanidin Metal Complexes: Al(III) Versus Mg(II). Theoretical Chemistry Accounts, 128(4); 485–495.
Jeyaram, S. and T. Geethakrishnan (2020). Vibrational Spectroscopic, Linear and Nonlinear Optical Characteristics of Anthocyanin Extracted From Blueberry. Results in Optics, 1; 100010.
Klisurova, D., I. Petrova, M. Ognyanov, Y. Georgiev, M. Kratchanova, and P. Denev (2019). Co-Pigmentation of Black Chokeberry (Aronia melanocarpa) Anthocyanins With Phenolic Co-Pigments and Herbal Extracts. Food Chemistry, 279; 162–170.
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León-Carmona, J. R., A. Galano, and J. R. Alvarez-Idaboy (2016). Deprotonation Routes of Anthocyanidins in Aqueous Solution, pK a Values, and Speciation Under Physiological Conditions. RSC Advances, 6(58); 53421–53429.
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Li, D., P. Wang, Y. Luo, M. Zhao, and F. Chen (2017). Health Benefits of Anthocyanins and Molecular Mechanisms: Update From Recent Decade. Critical Reviews in Food Science and Nutrition, 57(8); 1729–1741.
Li, X. D., J. Li, M. Wang, and H. Jiang (2016). Copigmentation Effects and Thermal Degradation Kinetics of Purple Sweet Potato Anthocyanins with Metal Ions and Sugars. Applied Biological Chemistry, 59(1); 15–24.
Mannino, G., C. Gentile, A. Ertani, G. Serio, and C. M. Bertea (2021). Anthocyanins: Biosynthesis, Distribution, Ecological Role, and Use of Biostimulants to Increase Their Content in Plant Foods—A Review. Agriculture (Switzerland), 11(3); 1–25.
Marpaung, A. and K. Tjahjadi (2020). The Analysis of Monomeric Anthocyanin by pH Differential Method is not Appropriate for Certain Anthocyanins. In Proceedings of the 16th ASEAN Food Conference (16th AFC 2019), pages 26–30.
Mendoza, J., N. Basílio, F. Pina, T. Kondo, and K. Yoshida (2018). Rationalizing the Color in Heavenly Blue Anthocyanin: A Complete Kinetic and Thermodynamic Study. Journal of Physical Chemistry B, 122(19); 4982–4992.
Moriya, C., T. Hosoya, S. Agawa, Y. Sugiyama, I. Kozone, K. Shin-Ya, N. Terahara, and S. Kumazawa (2015). New Acylated Anthocyanins from Purple Yam and Their Antioxidant Activity. Bioscience, Biotechnology and Biochemistry, 79(9); 1484–1492.
Muche, B. M., R. A. Speers, and H. P. V. Rupasinghe (2018). Storage Temperature Impacts on Anthocyanins Degradation, Color Changes and Haze Development in Juice of “Merlot” and “Ruby” Grapes (Vitis vinifera). Frontiers in Nutrition, 5; 1–9.
Ndiaye, K., C. Kane, O. B. K. Cisse, N. Ayessou, and C. M. Diop (2021). Monitoring of Anthocyanins and Colour in Electrochemically Processed Hibiscus sabdariffa Juice. Food and Nutrition Sciences, 12(11); 1073–1087.
Oladzadabbasabadi, N., A. Mohammadi Nafchi, M. Ghasemlou, F. Ariffin, Z. Singh, and A. A. Al-Hassan (2022). Natural Anthocyanins: Sources, Extraction, Characterization, and Suitability for Smart Packaging. Food Packaging and Shelf Life, 33; 100872.
Olivas-Aguirre, F. J., J. Rodrigo-García, N. D. R. Martínez-Ruiz, A. I. Cárdenas-Robles, S. O. Mendoza-Díaz, E. Álvarez Parrilla, G. A. González-Aguilar, L. A. De La Rosa, A. Ramos-Jiménez, and A. Wall-Medrano (2016). Cyanidin-3-O-glucoside: Physical-chemistry, Foodomics and Health Effects. Molecules, 21(9); 1–30.
Patras, A., N. P. Brunton, C. O’Donnell, and B. K. Tiwari (2010). Effect of Thermal Processing on Anthocyanin Stability in Foods; Mechanisms and Kinetics of Degradation. Trends in Food Science and Technology, 21(1); 3–11.
Sandoval-Ramírez, B. A., U. Catalán, S. Fernández-Castillejo, L. Rubió, A. Maciá, and R. Solá (2018). Anthocyanin Tissue Bioavailability in Animals: Possible Implications for Human Health. A Systematic Review. Journal of Agricultural and Food Chemistry, 66(44); 11531–11543.
Sigurdson, G. T. and M. M. Giusti (2014). Bathochromic and Hyperchromic Effects of Aluminum Salt Complexation by Anthocyanins from Edible Sources for Blue Color Development. Journal of Agricultural and Food Chemistry, 62(29); 6955–6965.
Sigurdson, G. T., R. J. Robbins, T. M. Collins, and M. M. Giusti (2016). Evaluating the Role of Metal Ions in the Bathochromic and Hyperchromic Responses of Cyanidin Derivatives in Acidic and Alkaline pH. Food Chemistry, 208; 26–34.
Sigurdson, G. T., R. J. Robbins, T. M. Collins, and M. M. Giusti (2017). Spectral and Colorimetric Characteristics of Metal Chelates of Acylated Cyanidin Derivatives. Food Chemistry, 221; 1088–1095.
Sinela, A., N. Rawat, C. Mertz, N. Achir, H. Fulcrand, and M. Dornier (2017). Anthocyanins Degradation During Storage of Hibiscus sabdariffa Extract and Evolution of its Degradation Products. Food Chemistry, 214; 234–241.
Sipahli, S., V. Mohanlall, and J. J. Mellem (2017). Stability and Degradation Kinetics of Crude Anthocyanin Extracts from H. sabdariffa. Food Science and Technology (Campinas), 37(2); 209–215.
Swer, T. L., C. Mukhim, K. Bashir, and K. Chauhan (2018). Optimization of Enzyme Aided Extraction of Anthocyanins from Prunus nepalensis L. LWT - Food Science and Technology, 91; 382–390.
Tachibana, N., Y. Kimura, and T. Ohno (2014). Examination of Molecular Mechanism for the Enhanced Thermal Stability of Anthocyanins by Metal Cations and Polysaccharides. Food Chemistry, 143; 452–458.
Tavares, I. M. d. C., E. S. Lago-Vanzela, L. P. G. Rebello, A. M. Ramos, S. Gómez-Alonso, E. García-Romero, R. Da Silva, and I. Hermosín-Gutiérrez (2016). Comprehensive Study of the Phenolic Composition of the Edible Parts of Jambolan Fruit (Syzygium cumini (L.) Skeels). Food Research International, 82; 1–13.
Teng, H., Y. Mi, H. Cao, and L. Chen (2022). Enzymatic Acylation of Raspberry Anthocyanin: Evaluations on Its Stability and Oxidative Stress Prevention. Food Chemistry, 372; 130766.
Wathon, M. H., N. Beaumont, M. Benohoud, R. S. Blackburn, and C. M. Rayner (2019). Extraction of Anthocyanins from Aronia melanocarpa Skin Waste as a Sustainable Source of Natural Colorants. Coloration Technology, 135(1); 5–16.
Wathon, M. H., E. Susilowati, and S. R. D. Ariani (2023a). Anthocyanins from Java Plum Fruits (cumini) and Their Stability in Various pHs. Journal of Biomimetics, Biomaterials and Biomedical Engineering, 62; 51–61.
Wathon, M. H., E. Susilowati, and S. R. D. A. Ariani (2023b). pH-Sensitive Strips Based on Cellulose and Anthocyanins from Dried Java Plum Fruits (Syzygium cumini). Jurnal Kimia Dan Pendidikan Kimia, 8(1); 1–12.
Yang, L., K. S. Wen, X. Ruan, Y. X. Zhao, F. Wei, and Q. Wang (2018). Response of Plant Secondary Metabolites to Environmental Factors. Molecules, 23(4); 1–26.
Zhang, K., T. S. Huang, H. Yan, X. Hu, and T. Ren (2020a). Novel pH-Sensitive Films Based on Starch/Polyvinyl Alcohol and Food Anthocyanins as a Visual Indicator of Shrimp Deterioration. International Journal of Biological Macromolecules, 145; 768–776.
Zhang, Z., J. Li, L. Fan, and Z. Duan (2020b). Effect of Organic Acid on Cyanidin-3-O-glucoside Oxidation Mediated by Iron in Model Chinese Bayberry Wine. Food Chemistry, 310; 125980.
Alappat, B. and J. Alappat (2020). Anthocyanin Pigments: Beyond Aesthetics. Molecules, 25(23); 5500.
Alisaac, A., M. Alsahag, M. Alshareef, R. M. Snari, M. Alhasani, H. M. Abumelha, and N. M. El-Metwaly (2022). Development of Smart Cotton Fabrics Immobilized With Anthocyanin and Potassium Alum for Colorimetric Detection of Bacteria. Inorganic Chemistry Communications, 145; 110023.
Araújo, P., N. Basílio, J. Azevedo, A. Fernandes, N. Mateus, F. Pina, V. de Freitas, and J. Oliveira (2018). Colour Modulation of Blue Anthocyanin-Derivatives: Lignosulfonates as a Tool To Improve the Water Solubility of Natural Blue Dyes. Dyes and Pigments, 153; 150–159.
Becerril, R., C. Nerín, and F. Silva (2021). Bring Some Colour to Your Package: Freshness Indicators Based on Anthocyanin Extracts. Trends in Food Science and Technology, 111; 495–505.
Dangles, O. and J.-A. Fenger (2018). The Chemical Reactivity of Anthocyanins and Its Consequences in Food Science and Nutrition. Molecules, 23(8); 1–23.
Estévez, L., N. Otero, and R. A. Mosquera (2011). Molecular Structure of Cyanidin Metal Complexes: Al(III) Versus Mg(II). Theoretical Chemistry Accounts, 128(4); 485–495.
Jeyaram, S. and T. Geethakrishnan (2020). Vibrational Spectroscopic, Linear and Nonlinear Optical Characteristics of Anthocyanin Extracted From Blueberry. Results in Optics, 1; 100010.
Klisurova, D., I. Petrova, M. Ognyanov, Y. Georgiev, M. Kratchanova, and P. Denev (2019). Co-Pigmentation of Black Chokeberry (Aronia melanocarpa) Anthocyanins With Phenolic Co-Pigments and Herbal Extracts. Food Chemistry, 279; 162–170.
Klotz, K., W. Weistenhöfer, F. Neff, A. Hartwig, C. Van Thriel, and H. Drexler (2017). The Health Effects of Aluminum Exposure. Deutsches Arzteblatt International, 114(39); 653–659.
Lee, S. G., T. M. Vance, T. G. Nam, D. H. Kim, S. I. Koo, and O. K. Chun (2016). Evaluation of pH Differential and HPLC Methods Expressed as Cyanidin-3-Glucoside Equivalent for Measuring the Total Anthocyanin Contents of Berries. Journal of Food Measurement and Characterization, 10(3); 562–568.
León-Carmona, J. R., A. Galano, and J. R. Alvarez-Idaboy (2016). Deprotonation Routes of Anthocyanidins in Aqueous Solution, pK a Values, and Speciation Under Physiological Conditions. RSC Advances, 6(58); 53421–53429.
Lestario, L. N., L. R. Howard, C. Brownmiller, N. B. Stebbins, R. Liyanage, and J. O. Lay, Jr (2017). Changes in Polyphenolics During Maturation of Java Plum (Syzygium cumini Lam.). Food Research International, 100; 385–391.
Li, D., P. Wang, Y. Luo, M. Zhao, and F. Chen (2017). Health Benefits of Anthocyanins and Molecular Mechanisms: Update From Recent Decade. Critical Reviews in Food Science and Nutrition, 57(8); 1729–1741.
Li, X. D., J. Li, M. Wang, and H. Jiang (2016). Copigmentation Effects and Thermal Degradation Kinetics of Purple Sweet Potato Anthocyanins with Metal Ions and Sugars. Applied Biological Chemistry, 59(1); 15–24.
Mannino, G., C. Gentile, A. Ertani, G. Serio, and C. M. Bertea (2021). Anthocyanins: Biosynthesis, Distribution, Ecological Role, and Use of Biostimulants to Increase Their Content in Plant Foods—A Review. Agriculture (Switzerland), 11(3); 1–25.
Marpaung, A. and K. Tjahjadi (2020). The Analysis of Monomeric Anthocyanin by pH Differential Method is not Appropriate for Certain Anthocyanins. In Proceedings of the 16th ASEAN Food Conference (16th AFC 2019), pages 26–30.
Mendoza, J., N. Basílio, F. Pina, T. Kondo, and K. Yoshida (2018). Rationalizing the Color in Heavenly Blue Anthocyanin: A Complete Kinetic and Thermodynamic Study. Journal of Physical Chemistry B, 122(19); 4982–4992.
Moriya, C., T. Hosoya, S. Agawa, Y. Sugiyama, I. Kozone, K. Shin-Ya, N. Terahara, and S. Kumazawa (2015). New Acylated Anthocyanins from Purple Yam and Their Antioxidant Activity. Bioscience, Biotechnology and Biochemistry, 79(9); 1484–1492.
Muche, B. M., R. A. Speers, and H. P. V. Rupasinghe (2018). Storage Temperature Impacts on Anthocyanins Degradation, Color Changes and Haze Development in Juice of “Merlot” and “Ruby” Grapes (Vitis vinifera). Frontiers in Nutrition, 5; 1–9.
Ndiaye, K., C. Kane, O. B. K. Cisse, N. Ayessou, and C. M. Diop (2021). Monitoring of Anthocyanins and Colour in Electrochemically Processed Hibiscus sabdariffa Juice. Food and Nutrition Sciences, 12(11); 1073–1087.
Oladzadabbasabadi, N., A. Mohammadi Nafchi, M. Ghasemlou, F. Ariffin, Z. Singh, and A. A. Al-Hassan (2022). Natural Anthocyanins: Sources, Extraction, Characterization, and Suitability for Smart Packaging. Food Packaging and Shelf Life, 33; 100872.
Olivas-Aguirre, F. J., J. Rodrigo-García, N. D. R. Martínez-Ruiz, A. I. Cárdenas-Robles, S. O. Mendoza-Díaz, E. Álvarez Parrilla, G. A. González-Aguilar, L. A. De La Rosa, A. Ramos-Jiménez, and A. Wall-Medrano (2016). Cyanidin-3-O-glucoside: Physical-chemistry, Foodomics and Health Effects. Molecules, 21(9); 1–30.
Patras, A., N. P. Brunton, C. O’Donnell, and B. K. Tiwari (2010). Effect of Thermal Processing on Anthocyanin Stability in Foods; Mechanisms and Kinetics of Degradation. Trends in Food Science and Technology, 21(1); 3–11.
Sandoval-Ramírez, B. A., U. Catalán, S. Fernández-Castillejo, L. Rubió, A. Maciá, and R. Solá (2018). Anthocyanin Tissue Bioavailability in Animals: Possible Implications for Human Health. A Systematic Review. Journal of Agricultural and Food Chemistry, 66(44); 11531–11543.
Sigurdson, G. T. and M. M. Giusti (2014). Bathochromic and Hyperchromic Effects of Aluminum Salt Complexation by Anthocyanins from Edible Sources for Blue Color Development. Journal of Agricultural and Food Chemistry, 62(29); 6955–6965.
Sigurdson, G. T., R. J. Robbins, T. M. Collins, and M. M. Giusti (2016). Evaluating the Role of Metal Ions in the Bathochromic and Hyperchromic Responses of Cyanidin Derivatives in Acidic and Alkaline pH. Food Chemistry, 208; 26–34.
Sigurdson, G. T., R. J. Robbins, T. M. Collins, and M. M. Giusti (2017). Spectral and Colorimetric Characteristics of Metal Chelates of Acylated Cyanidin Derivatives. Food Chemistry, 221; 1088–1095.
Sinela, A., N. Rawat, C. Mertz, N. Achir, H. Fulcrand, and M. Dornier (2017). Anthocyanins Degradation During Storage of Hibiscus sabdariffa Extract and Evolution of its Degradation Products. Food Chemistry, 214; 234–241.
Sipahli, S., V. Mohanlall, and J. J. Mellem (2017). Stability and Degradation Kinetics of Crude Anthocyanin Extracts from H. sabdariffa. Food Science and Technology (Campinas), 37(2); 209–215.
Swer, T. L., C. Mukhim, K. Bashir, and K. Chauhan (2018). Optimization of Enzyme Aided Extraction of Anthocyanins from Prunus nepalensis L. LWT - Food Science and Technology, 91; 382–390.
Tachibana, N., Y. Kimura, and T. Ohno (2014). Examination of Molecular Mechanism for the Enhanced Thermal Stability of Anthocyanins by Metal Cations and Polysaccharides. Food Chemistry, 143; 452–458.
Tavares, I. M. d. C., E. S. Lago-Vanzela, L. P. G. Rebello, A. M. Ramos, S. Gómez-Alonso, E. García-Romero, R. Da Silva, and I. Hermosín-Gutiérrez (2016). Comprehensive Study of the Phenolic Composition of the Edible Parts of Jambolan Fruit (Syzygium cumini (L.) Skeels). Food Research International, 82; 1–13.
Teng, H., Y. Mi, H. Cao, and L. Chen (2022). Enzymatic Acylation of Raspberry Anthocyanin: Evaluations on Its Stability and Oxidative Stress Prevention. Food Chemistry, 372; 130766.
Wathon, M. H., N. Beaumont, M. Benohoud, R. S. Blackburn, and C. M. Rayner (2019). Extraction of Anthocyanins from Aronia melanocarpa Skin Waste as a Sustainable Source of Natural Colorants. Coloration Technology, 135(1); 5–16.
Wathon, M. H., E. Susilowati, and S. R. D. Ariani (2023a). Anthocyanins from Java Plum Fruits (cumini) and Their Stability in Various pHs. Journal of Biomimetics, Biomaterials and Biomedical Engineering, 62; 51–61.
Wathon, M. H., E. Susilowati, and S. R. D. A. Ariani (2023b). pH-Sensitive Strips Based on Cellulose and Anthocyanins from Dried Java Plum Fruits (Syzygium cumini). Jurnal Kimia Dan Pendidikan Kimia, 8(1); 1–12.
Yang, L., K. S. Wen, X. Ruan, Y. X. Zhao, F. Wei, and Q. Wang (2018). Response of Plant Secondary Metabolites to Environmental Factors. Molecules, 23(4); 1–26.
Zhang, K., T. S. Huang, H. Yan, X. Hu, and T. Ren (2020a). Novel pH-Sensitive Films Based on Starch/Polyvinyl Alcohol and Food Anthocyanins as a Visual Indicator of Shrimp Deterioration. International Journal of Biological Macromolecules, 145; 768–776.
Zhang, Z., J. Li, L. Fan, and Z. Duan (2020b). Effect of Organic Acid on Cyanidin-3-O-glucoside Oxidation Mediated by Iron in Model Chinese Bayberry Wine. Food Chemistry, 310; 125980.
Authors
Wathon, M. H., Susilowati, E. ., Ariani, S. R. D. ., & Sari, L. . (2025). Complexation and Colour Stability of Anthocyanins from the Extracts of Java Plum Fruits (Syzygium cumini) with Selected Metal Cations (Al3+, Fe3+, and Ca2+) at Various pHs. Science and Technology Indonesia, 10(1), 43–55. https://doi.org/10.26554/sti.2025.10.1.43-55
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