* Corresponding Author
Improvement of Bixin Carotenoid Stability through the Formation of M–bixin (M = Mg2+, Ca2+, Zn2+, and Se4+) Complex Compounds Based on Photodegradation Kinetic Studies
https://doi.org/10.22146/ijc.92098 Winda Rahmalia(1), Anis Shofiyani(2*), Yohana Sutiknyawati Kusuma Dewi(3), Fani Indriani(4), Alintianni Yolla Putri(5), Septiani Septiani(6)
(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Tanjungpura University, Jl. Prof. Dr. Hadari Nawawi, Pontianak 78124, Indonesia
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Tanjungpura University, Jl. Prof. Dr. Hadari Nawawi, Pontianak 78124, Indonesia
(3) Department of Food Technology, Faculty of Agriculture, Tanjungpura University, Jl. Prof. Dr. H. Hadari Nawawi, Pontianak 78124, Indonesia
(4) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Tanjungpura University, Jl. Prof. Dr. Hadari Nawawi, Pontianak 78124, Indonesia
(5) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Tanjungpura University, Jl. Prof. Dr. Hadari Nawawi, Pontianak 78124, Indonesia
(6) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Tanjungpura University, Jl. Prof. Dr. Hadari Nawawi, Pontianak 78124, Indonesia
(*) Corresponding Author
Abstract
Bixin is used in wide-ranging food applications but is susceptible to degradation by many factors, including light. This research aims to increase bixin photostability through metal complexation. Bixin was complexed with Mg2+, Ca2+, Zn2+, and Se4+. The synthesis process was carried out in deep eutectic solvent media. Metal-bixin complexes have been successfully synthesized, indicated by the change in retention factor and %III/II ratio values resulting from thin-layer chromatography and UV-vis spectrophotometer analysis, respectively. The Fourier transform infrared analysis showed the interaction between central metal ion with bixin ligand has occurred by hydroxyl and carbonyl groups of bixin, which was characterized by a decrease in the intensity of the absorption peak in wavenumber 3000–4000 cm−1 (for the –OH carboxylic group vibration) and the peak shift of metal-bixin complexes towards the larger compared to bixin in the range wavenumber 1600–1700 cm−1 (for C=O ester vibrations). First-order photodegradation kinetics studies showed that the metal-bixin complexes were more stable than pure bixin. Se-bixin was four times more stable than pure bixin. Complexation of bixin with metals was shown to be a potential method to increase the stability of bixin, especially against light exposure.
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[1] Miller, M.D., Steinmaus, C., Golub, M.S., Castorina, R., Thilakartne, R., Bradman, A., and Marty, M.A., 2022, Potential impacts of synthetic food dyes on activity and attention in children: A review of the human and animal evidence, Environ. Health, 21 (1), 45.
[2] Maoka, T., 2020, Carotenoids as natural functional pigments, J. Nat. Med., 74 (1), 1–6.
[3] Mezzomo, N., and Ferreira, S.R.S., 2016, Carotenoids functionality, sources, and processing by supercritical technology: A review, J. Chem., 2016 (1), 3164312.
[4] Hirko, B., and Getu, A., 2022, Bixa orellana (Annatto Bixa): A review on use, structure, extraction methods and analysis, J. Agron. Technol. Eng. Manage., 5 (1), 687–696.
[5] Islam, S., Rather, L.J., and Mohammad, F., 2016, Phytochemistry, biological activities and potential of annatto in natural colorant production for industrial applications - A review, J. Adv. Res., 7 (3), 499–514.
[6] Conte, L., Somacal, S., Nichelle, S.M., Rampelotto, C., Robalo, S.S., Roehrs, M., and Emanuelli, T., 2019, Short-term bixin supplementation of healthy subjects decreases the susceptibility of LDL to Cu2+-induced oxidation ex vivo, J. Nutr. Metab., 2019 (1), 9407069
[7] Bueno, A.M., Gonçalves, M.J., Barcellos, I.O., Souza, C.K., Carvalho, L.F., Ibsch, R.B.M., Warmling, B.R., and Bertoli, S.L., 2020, Colorimetric analysis of the stability of annatto dye in solution and its use in the dyeing of polyester fibers, Fibers Polym., 21 (1), 1–6.
[8] Kapoor, L., and Ramamoorthy, S., 2021, Strategies to meet the global demand for natural food colorant bixin: A multidisciplinary approach, J. Biotechnol., 338, 40–51.
[9] Tay-Agbozo, S., Street, S., and Kispert, L., 2018, The carotenoid bixin found to exhibit the highest measured carotenoid oxidation potential to date consistent with its practical protective use in cosmetics, drugs, and food, J. Photochem. Photobiol., B, 186, 1–8.
[10] Najar, S.V., Bobbio, F.O., and Bobbio, P.A., 1988, Effects of light, air, anti-oxidants, and pro-oxidants on annatto extracts (Bixa orellana), Food Chem., 29 (4), 283–289.
[11] de O Rios, A., Borsarelli, C.D., and Mercadante, A.Z., 2005, Thermal degradation kinetics of bixin in an aqueous model system, J. Agric. Food Chem., 53 (6), 2307–2311.
[12] Hu, W., Liu, D., Su, S., Ren, L., Ren, H., Wei, L., Yue, S., Xie, Q., Zhang, Z., Wang, Z., Yang, N., Wu, L., Deng, J., Qi, Y., and Fu, P., 2021, Photochemical degradation of organic matter in the atmosphere, Adv. Sustainable Syst., 5 (11), 2100027.
[13] De Marco, R., Vieira, A.M.S., Ugri, M.C.A., Monteiro, A.R.G., and Bergamasco, R.C., 2013, Microencapsulation of annatto seed extract: Stability and application, Chem. Eng. Trans., 32, 1777–1782.
[14] Kohno, Y., Asai, S., Shibata, M., Fukuhara, C., Maeda, Y., Tomita, Y., and Kobayashi, K., 2014, Improved photostability of hydrophobic natural dye incorporated in organo-modified hydrotalcite, J. Phys. Chem. Solids, 75 (8), 945–950.
[15] de Sousa Lobato, K.B., Paese, K., Forgearini, J.C., Guterres, S.S., Jablonski, A., and de Oliveira Rios, A., 2015, Evaluation of the stability of bixin in nanocapsules in model systems of photosensitization and heating, LWT-Food Sci. Technol., 60 (1), 8–14.
[16] Marcolino, V.A., Zanin, G.M., Durrant, L.R., Benassi, M.D.T., and Matioli, G., 2011, Interaction of curcumin and bixin with β-cyclodextrin: Complexation methods, stability, and applications in food, J. Agric. Food Chem., 59 (7), 3348–3357.
[17] Rao, M.P., Manjunath, K., Bhagawati, S.T., and Thippeswami, B.S., 2014, Bixin loaded solid lipid nanoparticles for enhanced hepatoprotection - Preparation, characterization and in vivo evaluation, Int. J. Pharm., 473 (1-2), 485–492.
[18] Pérez-Monterroza, E.J., Chaux-Gutiérrez, A.M., Franco, C.M.L., and Nicoletti, V.R., 2018, Encapsulation of bixin with high amylose starch as affected by temperature and whey protein, Food Biophys., 13 (4), 343–352.
[19] Cortez, R., Luna-Vital, D.A., Margulis, D., and Gonzalez de Mejia, E., 2017, Natural pigments: Stabilization methods of anthocyanins for food applications, Compr. Rev. Food Sci. Food Saf., 16, 180–198.
[20] Rahmalia, W., Septiani, S., Naselia, U.A., Usman, T., Silalahi, I.H., and Mouloungui, Z., 2021, Performance improvements of bixin and metal-bixin complexes sensitized solar cells by 1-methyl-3-propylimidazolium iodide in electrolyte system, Indones. J. Chem., 21 (3), 669–678.
[21] Maresz, K., 2015, Proper calcium use: Vitamin K2 as a promotor of bone and cardiovascular health, Integr. Med., 14 (1), 34–39.
[22] Vannucci, L., Fossi, C., Quattrini, S., Guasti, L., Pampaloni, B., Gronchi, G., Giusti, F., Romagnoli, C., Cianferotti, L., Marcucci, G., and Brandi, M.L., 2018, Calcium intake in bone health: A focus on calcium-rich mineral waters, Nutrients, 10 (12), 1930.
[23] Al Alawi, A.M., Majoni, S.W., and Falhammar, H., 2018, Magnesium and human health: Perspectives and research directions, Int. J. Endocrinol., 2018 (1), 9041694.
[24] Sangeetha, V.J, Dutta, S., Moses, J.A., and Anandharamakrishnan, C., 2022, Zinc nutrition and human health: Overview and implications, eFood, 3 (5), e17.
[25] Abu Jamra, S.R., Komatsu, C.G., Barbosa, F., Roxo-Junior, P., and Navarro, A.M., 2023, Proposal to screen for zinc and selenium in patients with IgA deficiency, Nutrients, 15 (9), 2145.
[26] Oyagbemi, A.A., Ajibade, T.O., Aboua, Y.G., Gbadamosi, I.T., Adedapo, A.D.A., Aro, A.O., Adejumobi, O.A., Thamahane-Katengua, E., Omobowale, T.O., Falayi, O.O., Oyagbemi, T.O., Ogunpolu, B.S., Hassan, F.O., Ogunmiluyi, I.O., Ola-Davies, O.E., Saba, A.B., Adedapo, A.A., Nkadimeng, S.M., McGaw, L.J., Kayoka-Kabongo, P.N., Oguntibeju, O.O., and Yakubu, M.A., 2021, Potential health benefits of zinc supplementation for the management of COVID-19 pandemic, J. Food Biochem., 45 (2), e13604.
[27] Rahmalia, W., Shofiyani, A., Dewi, Y.S.K., and Septiani, S., 2022, Simple green routes for metal-bixin complexes synthesis using glycerol-based deep eutectic solvent, Indones. J. Chem., 22 (6), 1759–1767.
[28] Rahmalia, W., Prayitno, D.I., Adhitiyawarman, A., Septiani, S., 2023, Sintesis dan uji fotostabilitas kompleks Zn(II)-astaxanthin, J. Ris. Kim., 14 (1), 52–60.
[29] Mehta, A.A., Behera, L.K., Tandel, M.B., Jadeja, D.B., and Vashi, B.G., 2015, Efficacy of different oils used for the extraction of annatto color from the seeds of Bixa orellana L., J. Appl. Nat. Sci., 7 (2), 828–831.
[30] Chuyen, H.V., and Eun, J.B., 2021, Effects of different extraction methods on the extraction yield, degradation of bixin and formation of harmful volatile compounds in the extracts from annatto seeds, Food Res., 5 (6), 42–48.
[31] Oliveira, S.S.C., Sarmento, E.S., Marinho, V.H., Pereira, R.R., Fonseca, L.P., and Ferreira, I.M., 2022, Green extraction of annatto seed oily extract and its use as a pharmaceutical material for the production of lipid nanoparticles, Molecules, 27 (16), 5187.
[32] Dew, Y.S.K., Putri, D.M., Fadly, D., and Rahmalia, W., 2023, Innovation of goat's milk soft candy with annatto extract (Bixa Orellana L.) as natural colorant and antioxidant, Indones. Food Sci. Technol. J., 7 (1), 9–16.
[33] David, S.L.J., Julián, G.C.C., Liliana, V.S.C., Ayala-Aponte, A.A., and Liliana, S.C., 2022, Kinetics and bixine extraction time from achiote (Bixa Orellana L.), J. Food Sci. Technol., 59 (3), 1239–1246.
[34] Rahmalia, W., Fabre, J.F., Usman, T., and Mouloungui, Z., 2014, Aprotic solvents effect on the UV-visible absorption spectra of bixin, Spectrochim. Acta, Part A, 131, 455–460.
[35] Adusei-Gyamfi, J., Ouddane, B., Rietveld, L., Cornard, J.P., and Criquet, J., 2019, Natural organic matter-cations complexation and its impact on water treatment: A critical review, Water Res., 160, 130–147.
[36] Dudev, T., Cheshmedzhieva, D., Dimitrova, R., Dorkov, P., and Pantcheva, I., 2020, Factors governing the competition between group IA and IB cations for monensin A: A DFT/PCM study, RSC Adv., 10 (10), 5734–5741.
[37] Rodriguez-Amaya, D.B., 2001, A Guide to Carotenoid Analysis in Foods, ILSI Press, One Thomas Circle, N.W., Washington, D.C., US.
[38] Montenegro, M.A., Nazareno, M.A., Durantini, E.N., and Borsarelli, C.D., 2002, Singlet molecular oxygen quenching ability of carotenoids in a reverse-micelle membrane mimetic system, Photochem. Photobiol., 75 (4), 353–361.
[39] Rahmalia, W., Fabre, J.F., and Mouloungui, Z., 2015, Effects of cyclohexane/acetone ratio on bixin extraction yield by accelerated solvent extraction method, Procedia Chem., 14, 455–464.
[40] Tayyari, S.F., Vakili, M., Nekoei, A.R., Rahemi, H., and Wang, Y.A., 2007, Vibrational assignment and structure of trifluorobenzoylacetone: A density functional theoretical study, Spectrochim. Acta, Part A, 66 (3), 626–636.
[41] Zheng, H., Zhong, B., Wang, Q., Li, W., Chen, J., Liu, L., and Liu, T., 2023, ZnO-doped metal-organic frameworks nanoparticles: antibacterial activity and mechanisms, Int. J. Mol. Sci., 24 (15), 12238.
[42] Abe, K., Katano, S., and Ohta, K., 2018, Microwave-assisted synthesis of phthalocyanine metal complexes: Relationship between yield and maximum temperature reached by microwave irradiation, J. Jpn. Pet. Inst., 61 (2), 140–149.
[43] Singha, A., and Bag, B.G., 2019, Bixin extraction from annatto seed (Bixa orellana) using ethyl acetate, Int. J. Environ. Technol. Sci., 7, 253–259.
[44] Ahmad, I., Ahmed, S., Anwar, Z., Sheraz, M.A., and Sikorski, M., 2016, Photostability and photostabilization of drugs and drug products, Int. J. Photoenergy, 2016 (1), 8135608.
[45] Semitsoglou-Tsiapou, S., Meador, T.B., Peng, B., and Aluwihare, L., 2022, Photochemical (UV–vis/H2O2) degradation of carotenoids: Kinetics and molecular end products, Chemosphere, 286, 131697.
[46] Groeneveld, I., Kanelli, M., Ariese, F., and van Bommel, M.R., 2023, Parameters that affect the photodegradation of dyes and pigments in solution and on a substrate – An overview, Dyes and Pigm., 210, 110999.
[47] Muthaiah, S., Bhatia, A., and Kannan, M., 2019, “Stability of Metal Complexes” in Stability and Applications of Coordination Compounds, IntechOpen, Rijeka, Croatia.
DOI: https://doi.org/10.22146/ijc.92098
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