Anthocyanin Complex: Characterization and Cytotoxicity Studies
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Anthocyanin Complex: Characterization and Cytotoxicity Studies

Authors: Sucharat Limsitthichaikoon, Kedsarin Saodaeng, Aroonsri Priprem, Teerasak Damrongrungruang

Abstract:

Complexation of anthocyanins to mimic natural copigmentation process was investigated. Cyanidin-rich extracts from Zea mays L. ceritina Kulesh. and delphinidin-rich extracts from Clitoria ternatea L. were used to form 4 anthocyanin complexes, AC1, AC2, AC3 and AC4, in the presence of several polyphenols and a trace metal. Characterizations of the ACs were conducted by UV, FTIR, DSC/TGA and morphological observations. Bathochromic shifts of the UV spectra of 4 formulas of ACs were observed at peak wavelengths of about 510-620 nm by 10 nm suggesting complex formation. FTIR spectra of the ACs indicate shifts of peaks from 1,733 cm-1 to 1,696 cm-1 indicating interactions and a decrease in the peak areas within the wavenumber of 3,400-3,500 cm-1 indicating changes in hydrogen bonding. Thermal analysis of all of the ACs suggests increases in melting temperature after complexation. AC with the highest melting temperature was morphologically observed by SEM and TEM to be crystal-like particles within a range of 50 to 200 nm. Particle size analysis of the AC by laser diffraction gave a range of 50-600 nm, indicating aggregation. This AC was shown to have no cytotoxic effect on cultured HGEPp0.5 and HGF (all p> 0.05) by MTT. Therefore, complexation of anthocyanins was simple and self-assembly process, potentially resulting in nanosized particles of anthocyanin complex.

Keywords: Anthocyanins, complexation, purple corn cops, butterfly pea, physicochemical characteristics, cytotoxicity.

Digital Object Identifier (DOI): doi.org/10.5281/zenodo.1099068

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References:


[1] E. Pojer, F. Mattivi, D. Johnson, C. S. Stockley, “The Case for Anthocyanin Consumption to Promote Human Health: A Review” Compr.Rev. Food Sci. F. vol. 12, pp. 483, 2013.
[2] M. Shiono, N. Matsugaki, K. Takeda, “Phytochemistry: structure of the blue cornflower pigment” Nature vol. 436, pp. 791, 2005.
[3] Y. Zhu et al., “Anti-inflammatory effect of purified dietary anthocyanin in adults with hypercholesterolemia: A randomized controlled trial” Nutr. Metab. Cardiovasc. Dis. vol. 23, pp. 843, 2013.
[4] J. Y. Choi et al., “Analysis and tentative structure elucidation of new anthocyanins in fruit peel of Vitiscoignetiae Pulliat (meoru) using LCMS/ MS: Contribution to the overall antioxidant activity” J. Sep. Sci. vol. 33, pp. 1192, 2010.
[5] C. Ubeda et al., “Employment of different processes for the production of strawberry vinegars: Effects on antioxidant activity, total phenols and monomeric anthocyanins” LWT - Food Sci. Technol. vol. 52, pp. 139, 2013.
[6] S. C. Thomasset, University of Leicester (2008).
[7] L. C. Vasconcelos, M. C. Sampaio, F. C. Sampaio, J. S. Higino, “Use of Punicagranatum as an antifungal agent against candidosis associated with denture stomatitis” Mycoses vol. 46, pp. 192, 2003.
[8] A. Cisowska, D. Wojnicz, A. Hendrich, “Anthocyanins as antimicrobial agents of natural plant origin.” Nat. Prod. Commun.vol. 6, pp. 149, 2011.
[9] Z. Yang, Y. Han, Z. Gu, G. Fan, Z. Chen, “Thermal degradation kinetics of aqueous anthocyanins and visual color of purple corn (Zea mays L.) cob” Innov. Food Sci. Emerg. Technol. vol. 9, pp. 341, 2008.
[10] Z. Yang, W. Zhai, “Identification and antioxidant activity of anthocyanins extracted from the seed and cob of purple corn (Zea mays L.)”Innov. Food Sci. Emerg. Technol. vol. 11, pp. 169, 2010.
[11] K. Kazuma, N. Noda, M. Suzuki, “Flavonoid composition related to petal color in different lines of Clitoria ternatea” Phytochemistry vol. 64, pp. 1133, 2003.
[12] M. Ponec, “In vitro cultured human skin cells as alternatives to animals for skin irritancy screening” Int.J.Cosmet.Sci. vol. 14, pp. 245, 1992.
[13] R. K. Ward, A. W. Hubbard, H. Sulley, M. J. Garle, R. H. Clothier, “ Human keratinocyte cultures in an in vitro approach for the assessment of surfactant-induced irritation” Toxicol.in Vitro vol. 12, pp. 163, 1998.
[14] H. Wang et al., “Antioxidant and anti-inflammatory activities of anthocyanins and their aglycon, cyanidin, from tart cherries” J. Nat.Prod.vol. 62, pp. 294, 1999.
[15] I. T. Nizamutdinova et al., “Anthocyanins from black soybean seed coats preferentially Inhibit TNF-α-mediated Induction of VCAM-1 over ICAM-1 through the regulation of GATAs and IRF-1” J. Agri. Food Chem.vol. 57, pp. 7324, 2009.
[16] F. Afaq et al., “Delphinidin, an anthocyanidin in pigmented fruits and vegetables, protects human HaCa T keratinocytes and mouse skin against UVB-mediated oxidative stress and apoptosis” J. Invest. Dermatol. vol. 127, pp. 222, 2007.
[17] D. X. Hou, X. Tong, N. Terahara, D. Luo, M. Fujii, “Delphinidin 3- sambubioside, a Hibiscus anthocyanin, induces apoptosis in human leukemia cells through reactive oxygen species-mediated mitochondrial pathway” Arch. Biochem. Biophys. vol. 440 pp. 101, 2005.
[18] P.H. Shih, C.T. Yeh, G.C. Yen, “Anthocyanins induce the activation of phase II enzymes through the antioxidant response element pathway against oxidative stress-induced apoptosis” J. Agri. Food Chem.vol. 55, pp. 9427, 2007.
[19] K. Tsoyi et al., “Protective effect of anthocyanins from black soybean seed coats on uvb-induced apoptotic cell death in vitro and in vivo” J. Agri. Food Chem.vol. 56, pp. 10600, 2008.
[20] S. R. Mallery et al., “Formulation and in-vitro and in-vivo evaluation of a mucoadhesive gel containing freeze dried black raspberries: implications for oral cancer chemoprevention” Pharm. Res. vol. 24, pp. 728, 2007.
[21] B. S. Shumway et al., “Effects of a topically applied bioadhesive berry gel on loss of heterozygosity indices in premalignant oral lesions” Clin. Cancer Res. vol. 14, pp. 2421, 2008.
[22] R. Boulton, “The copigmentation of anthocyanins and its role in the color of red wine: a critical review” Am. J. Enol. Vitic. vol. 52, pp. 67, 2001.
[23] Y. Osawa, Copigmentation of anthocyanins. In: anthocyanins as food colors. P. Markakis, Ed., (Academic Press Inc., New York, 1982).
[24] M. Rein, University of Helsinki (2005).
[25] M. S. Starr, F. J. Francis, “Effect of metallic ions on color and pigment content of cranberry juice cocktail” J. Food Sci. vol. 38, pp. 1043, 1974.
[26] J. Sun, X. Cao, W. Bai, X. Liao, X. Hu, “Comparative analyses of copigmentation of cyanidin 3-glucoside and cyanidin 3-sophoroside from red raspberry fruits” Food Chem. vol. 120, pp. 1131, 2010.
[27] C. H. Brenes, D. D. Pozo-Insfran, S. T. Talcott, “Stability of copigmented anthocyanins and ascorbic acid in a grape juice model system” J. Agri. Food Chem. vol. 53, pp. 49, 2005.
[28] E. F. Gris, E. A. Ferreira, L. D. Falca˜o, M. T. Bordignon-Luiz, “Caffeic acid copigmentation of anthocyanins from Cabernet Sauvignon grape extracts in model systems” Food Chem. vol. 100, pp. 1289, 2007.
[29] M. Kopjar, V. Piližota, “Copigmentation effect of phenolic compounds on red currant juice anthocyanins during storage” Croatian J. Food Sci. Technol.vol. 1, pp. 16, 2009.
[30] S. Kunsági-Máté, E. Ortmann, L. Kollár, K. Szabó, M. P. Nikfardjam, “Effect of ferrous and ferric ions on copigmentation in model solutions” J. Mol. Struct. vol. 891, pp. 471, 2008.
[31] C. Zhang, Y. Ma, X. Zhao, J. Mu, “Influence of copigmentation on stability of anthocyanins from purple potato peel in both liquid state and solid state” J. Agri. Food Chem.vol. 57, pp. 9503, 2009.
[32] K. Torskangerpoll, Ø. M. Andersen, “Colour stability of anthocyanins in aqueous solutions at various pH values” Food Chem. vol. 89, pp. 427, 2005.
[33] M. A. Eskan, G. Hajishengallis, D. F. Kinane, “Differential activation of human gingival epithelial cells and monocytes by porphyromonasgingivalis fimbriae” Infect. Immun. vol. 75, pp. 892, 2007.
[34] A. Beklen, T. Sorsa, Y. T. Konttinen, “Toll-like receptors 2 and 5 in human gingival epithelial cells co-operate with T-cell cytokine interleukin-17” Oral Microbiol. Immunol. vol. 24, pp. 38, 2009.
[35] J. I. Gallin, R. Snyderman, D. T. Fearon, B. F. Haynes, C. Nathan, Inflammation: Basic Principles and Clinical Correlates.(Lippincott Williams & Wilkins, Philadelphia, ed. 3, 1999).
[36] T. Ara et al., “Human gingival fibroblasts are critical in sustaining inflammation in periodontal disease” J. Periodontal Res. vol. 44, pp. 21, 2009.
[37] S. Singhabutta, 200 types of Thai herbal activities by SountareeSinghabutta. (Koon, Bangkok, 1993).
[38] B. Khampaenjiraroch, A. Priprem, K. Lertrat, T. Damrongrungruang, “Rapid HPLC of cyanidin and delphinidin of an anthocyanin complex exposed to human gingival epithelial cells” Appl. Mech. Mater.vol. 563, pp. 403, 2014.
[39] G. T. Sigurdson, M. M. Giusti, “Bathochromic and hyperchromic effects of aluminum salt complexation by anthocyanins from edible sources for blue color development” J. Agri. Food Chem.vol. 62, pp. 6955, 2014.
[40] C. A. Sims, J. R. Morris, “Effect of acetaldehyde and Tannins on the color and chemical age of red muscadine (vitisrotundifolia) wine” Enol. Vitic. vol. 37, pp. 163, 1986.