Anthocyanins: Natural pigments withantioxidant and therapeutic potential

Authors

  • Amany M Basuny Author
  • Shaker M Arafat Author

Keywords:

anthocyanins, arthritis, cancer, diabetes, flavonoids, pigments, polyphenols

Abstract

Anthocyanins are natural compounds, a member of the avonoid
groups of photochemistry, which participate in defense against the
harmful effects of ultraviolet radiation in plants and protect against
many oxidants. They represent a relatively small but diverse group
of avonoids in nature and are responsible for the attractive colors
ranging from red and purple to blue in many plants. The presence
of these dyes in owers and fruits appears to provide attraction for
pollination and aids in seed distribution, while also offering antiviral
and antimicrobial activities. Anthocyanins are polyphenols known
about their antioxidant activity, which may be responsible for some
of their biological effects, including preventing or reducing the risk
of cardiovascular disease, diabetes, arthritis, and cancer. However,
for such properties to be fully realized, their chemical stability and
bioavailability depend on several environmental and structural
factors. Understanding these factors is important for improving
the application of anthocyanins as natural, functional, and health-
promoting compounds in food and pharmaceutical industries.

References

Ames, B.N.; Shigenaga, M.K. and Hagen, T.M.(1993). Oxidants, antioxidants, and the degenerative diseases of aging. Proc. Natl. Acad. Sci., 90: 7915-7922.

Antolak, H.; Czyzowska, A.; Sakaˇc, M.; Mišan, A.; Ðuragi´c, O. and Kregiel, D. (2017). Phenolic compounds contained in little-known wild fruits as antiadhesive agents against the beverage-spoiling bacteria asaia spp. Molecules, 22: 1256.

Ariza, M. T.; Reboredo-Rodríguez, P.; Cervantes, L.; Soria, C.; Martínez-Ferri, E.; González-Barreiro, C.; Cancho-Grande, B.; Battino, M. and Simal-Gándara, J. (2018).Bioaccessibility and potential bioavailability of phenolic compounds from achenes as a new target for strawberry breeding programs. Food Chem., 248:155–165.

Bąkowska-Barczak, A. (2005). Acylated anthocyanins as stable, natural food colorants – A review. Pol J Food Nutr Sci., 14/55(2):107–116.

Barnard, H.; Dooley, A. N.; Areshian, G.; Gasparyan, B. and Faull, K. F. (2011).Chemical evidence for wine production around 4000 BCE in the Late Chalcolithic Near Eastern highlands. J. Archaeol Sci., 38(5):977–984.

Bridle, P. and Timberlake, C.F. (1997). Anthocyanins as natural food colours—selected aspects. Food Chem.,58 (1):103–109.

Byamukama, R.; Namukobe, J.; Jordheim, M.; Andersen, Ø.M. and Kiremire, B.T. (2011). Anthocyanins from ornamental flowers of red frangipani, plumeria rubra. Sci. Hortic., 129: 840–843.

Castañeda-Ovando, A.; de Lourdes Pacheco-Hernández, M.; Páez-Hernández, E.; Rodríguez, J. A. and Galán-Vidal, C. A. (2009).Chemical studies of anthocyanins: a review. Food Chem., 113(4):859– 871.

Cevallos-Casals, B.A. and Cisneros-Zevallos, L. (2003). Stoichiometric and kinetic studies of phenolic antioxidants from Andean purple corn and red-fleshed sweetpotato. J. Agric. Food Chem.,51(11):3313–3319.

Cisowska, A;. Wojnicz, D. and Hendrich, A.B. (2011). Anthocyanins as antimicrobial agents of natural plant origin. NatProd Commun.,6(1):149–156.

Costantino, L.; Albasini, A.; Rastelli, G. and Benvenuti, S. (1992). Activity of polyphenolic crude extracts as scavengers of superoxide radicals and inhibitors of xanthine oxidase. Planta Med., 58: 342-344.

Cushnie, T. P. T. and Lamb, A. J. (2005). Antimicrobial activity of flavonoids. Int J Antimicrob Agents., 26(5):343–356.

Dai, J. and Mumper, R. J.( 2010). Plant Phenolics: Extraction, Analysis and Their Antioxidant and Anticancer. PropertiesMolecules, 15 (10):7313-7352.

Diaconeasa, Z.; Leopold, L.; Rugina, D.; Ayvaz, H. and Socaciu, C. (2015). Antiproliferative and antioxidant propertie of anthocyanin rich extracts from blueberry and blackcurrant juice. Int. J. Mol. Sci., 16:2352–2365.

Einbond, L.S.; Reynertson, K.A.; Luo, X.D.;Basile, M.J. and Kenelli E.J. (2004).Anthocyanin antioxidants from edible fruits. Food Chem., 84: 23-28.

Feng, R.; Ni, H.M.;Wang, S.Y.; Tourkova, I.L.; Shurin, M.R.; Harada, H. and Yin, X.M. (2007). Cyanidin-3-rutinoside, a natural polyphenol antioxidant, selectively kills leukemic cells by induction of oxidative stress. J. Biol. Chem., 282: 13468–13476.

Fiander, H. and Schneider, H. (2000). Dietary ortho phenols that induce glutathione S-transferase and increase the resistance of cells to hydrogen peroxide are potential cancer chemopreventives that act by two mechanisms: the alleviation of oxidative stress and the detoxification of mutagenic xenobiotics. Cancer Lett.,156:117-124.

Garzón, G. A.; Manns, D. C.; Riedl, K.; Schwartz, S. J. and Padilla-Zakour, O. ( 2015). Identification of phenolic compounds in petals of nasturtium flowers (tropaeolum majus) by high-performance liquid chromatography coupled to mass spectrometry and determination of oxygen radical absorbance capacity (orac). J. Agric. Food Chem., 63: 1803–1811.

Goupy, P.; Vian, M.A.; Chemat, F. and Caris-Veyrat, C. (2013). Identification and quantification of flavonols, anthocyanins and lutein diesters in tepals of crocus sativus by ultra performance liquid chromatography coupled to diode array and ion trap mass spectrometry detections. Ind. Crop. Prod., 44: 496–510.

Grajeda-Iglesias, C.; Salas, E.; Barouh, N.; Barea, B. and Figueroa-Espinoza, M.C. (2017). Lipophilization and ms characterization of the main anthocyanins purified from hibiscus flowers. Food Chem., 230: 189–194.

Grotewold, E. (2006). The genetics and biochemistry of floral pigments. Annu Rev. Plant Biol., 57: 761-780.

Hämäläinen, M.; Nieminen, R.; Vuorela, P.; Heinonen, M. and Moilanen, E. (2007). Anti-Inflammatory effects of flavonoids: genistein, kaempferol, quercetin, and daidzein inhibit STAT-1 and NF-κB activations, whereas flavone, isorhamnetin, naringenin, and pelargonidin inhibit only NF-κB activation along with their inhibitory effect on iNOS expression and NO production in activated macrophages. Mediators Inflamm. 10.1155/2007 /45673.

Hashimoto, M.; Suzuki, T. and Iwashina, T. (2011). New acylated anthocyanins and other flavonoids from the red flowers clematis cultivars. Sage J., 61:1631–1636.

Havsteen, B. (1983).Flavonoids, a class of natural products of high pharmacological potency. Biochem. Pharmacol., 32:1141-1148.

He, F.; Mu, L.; G-Liang, Y.; Na-Na L.; Qiu-Hong, P.; Wang ,J.; Reeves, M. J. and Chang-Qing, D.(2010). Biosynthesis of anthocyanins and their regulation in colored grapes.Molecules, 15 (12):9057-9091.

He, J. and Giusti, M.M. (2010). Anthocyanins: natural colorants with health-promoting properties. Annu Rev Food Sci Technol., 1:163–187.

Heinonen, I. M.; Meyer, A.S. and Frankel, E.N.(1998). Antioxidant activity of berry phenolics on human low-density lipoprotein and liposome oxidation. J. Agric. Food Chem., 46: 4107-4112

Hou, D.X.; Yanagita, T.; Uto, T.; Masuzaki, S. and Fujii, M. (2005). Anthocyanidins inhibit cyclooxygenase-2 expression in LPS-evoked macrophages: structure-activity relationship and molecular mechanism involved. Biochem. Pharmacol., 70:417-425.

Jaakola, L. (2013). New insights into the regulation of anthocyanin biosynthesis in fruits. Trends Plant Sci.,18(9):477–483.

Jaakola, L.; Määttä, K.; Pirttilä, A.M.; Törrönen, R.; Kärenlampi, S. and Hohtola, A. (2002). Expression of genes involved in anthocyanin biosynthesis in relation to anthocyanin, proanthocyanidin, and flavonol levels during bilberry fruit development. Plant Physiol., 130: 729-739.

Jayaprakasam, B.; Vareed, S. K.; Olson, L. K.; Nair, M.G. (2005). Insulin secretion by bioactive anthocyanins and anthocyanidins present in fruits. J Agric Food Chem., 53 (1):28–31.

Jia, N.; Shu, Q.Y.; Wang, L.S.; Du, H.; Xu, Y. J. and Liu, Z. A. (2008). Analysis of petal anthocyanins to investigate coloration mechanism in herbaceous peony cultivars. Sci. Hortic., 117: 167–173.

Jing, P.(2006). Purple corn anthocyanins: chemical structure, chemopreventive activity and structure/function relationships. PhD thesis, The Ohio State University, 5-90.

Kähkönen, M. P. and Heinonen, M. (2003). Antioxidant activity of anthocyanins and their aglycons. J. Agric. Food Chem., 51: 628-633.

Katsumoto, Y.; Fukuchi-Mizutani, M.; Fukui, Y.; Brugliera, F.; Holton, T. A.; Karan, M.; Nakamura, N .; Yonekura-Sakakibara, K.; Togami, J.; Pigeaire, A.; Guo-Qing, T.; Nehra, N. S.; Chin-Yi, L. Dyson, B. K.; Tsuda, S.; Ashikari, T.; Kusumi, T. G.; Mason, J. and Tanaka, Y. (2007). Engineering of the rose flavonoid biosynthetic pathway successfully generated blue hued flowers accumulating delphinidin. Plant Cell Physiol., 48(11):1589–1600.

Kay C. (2004). Analysis of the bioactivity, metabolism, and pharmacokinetics of anthocyanins in humans. PhD thesis. University of Guelph, Ontario, Canada, 1-9.

Kazuma, K.; Kogawa, K.; Noda, N.; Kato, N. and Suzuki, M. (2004). Identification of delphinidin 3-o-(6”-o-malonyl)-beta-glucoside-3’-o-beta-glucoside, a postulated intermediate in the biosynthesis of ternatin c5 in the blue petals of clitoria ternatea (butterfly pea). Chem. Biodivers., 1: 1762–1770.

Koca, I. and Karadeniz, B.(2009). Antioxidant properties of blackberry and blueberry fruits grown in the Black Sea region of Turkey. Sci.Hort., 121: 447-450.

Kong, J. M.; Chia, L. S.; Goh, N. K.; Chia, T.F. and Brouillard, R. (2003). Analysis and biological activities of anthocyanins .Phytoche., 64: 923-933.

Lee, J.; Finn, C.E. and Wrolstad, R.E. (2004).Comparison of anthocyanin pigment and ather phenolic compounds of Vaccinium membranaceum and Vaccinium ovatum native to the Pacific Northwest of North America. J. Agric. Food. Chem., 52: 7039-7044.

Marhuenda, J.; Alemán, M. D.; Gironés-Vilaplana, A.; Pérez, A.; Caravaca, G.; Figueroa, F.; Mulero, J. and Zafrilla, P. (2016).Phenolic composition, antioxidant activity, and in vitro availability of four different berries. J. Chem., 1–7.

Mattila, P.H.; Hellström, J.; Karhu, S.; Pihlava, J.-M. and Veteläinen, M. (2016). High variability in flavonoid contents and composition between different north-european currant (ribes spp.) varieties. Food Chem., 204:14–20.

Mazza, G. and Francis, F. J. (1995). Anthocyanins in grapes and grape products. Crit Rev Food Sci Nutr.,35 (4):341–371.

Miyake, S.; Takahashi, N.; Sasaki. M.; Kobayashi, S.; Tsubota, K. and Ozawa, Y. (2012). Vision preservation during retinal inflammation by anthocyaninrich bilberry extract: cellular and molecular mechanism. Lab Invest., 92(1):102–109.

Mortensen, A. (2006). Carotenoids and other pigments as natural colorants. Pure Appl. Chem., 78 (8): 1477–1491.

Moyer, R.A.; , K.E.; Finn, C.E.; Frei, B. and Wrolstad, R.E. (2002).Anthocyanins, phenolics, and antioxidant capacity in diverse small fruits: Vaccinium, Rubus, and Ribes. J. Agric. Food Chem., 50: 519-525.

Muselík, J.; García-Alonso, M.; Martín-López, M.P.; Žemlička, M. and Rivas-Gonzalo, J.C. (2007). Measurement of antioxidant activity of wine catechins, procyanidins, anthocyanins and pyranoanthocyanins. Int. J. Mol. Sci., 8: 797-809.

Nair, V.; Bang, W.Y.; Schreckinger, E.; Andarwulan, N. and Cisneros-Zevallos, L. (2015). Protective role of ternatin anthocyanins and quercetin glycosides from butterfly pea (clitoria ternatea leguminosae) blue flower petals against lipopolysaccharide (lps) induced inflammation in macrophage cells. J. Agric. Food Chem., 63: 6355–6365.

Nikkhah, E.; Khayami, M. and Heidari, R.(2008). In vitro screening for antioxidant activity and cancer suppressive effect on blackberry (Morus nigra). Iran. J. Canc. Prevent., 1: 167-172.

Nørbæk, R. and Kondo, T. (1999). Further anthocyanins from flowers of crocus antalyensis (iridaceae). Phytochemistry, 50: 325–328.

Park, K. I.; Hoshino, A.; Saito, N. and Tatsuzawa, F. (2014). Anthocyanins in the flowers of ipomoea tricolor cav. (convolvulaceae). Biochem. Syst. Ecol., 54: 15–18

Pergola, C.; Rossi, A.; Dugo, P.; Cuzzocrea, S. and Sautebin, L.(2006). Inhibition of nitric oxide biosynthesis by anthocyanin fraction of blackberry extract. Nitric Oxide, 15: 30-39.

Phippen, W .B. and Simon, J. E. (1998). Anthocyanins in basil (ocimum basilicum l.). J. Agric. Food Chem., 46:1734–1738.

Pojer, E.; Mattivi, F.; Johnson, D.; Stockley, C.S. (2013).The case for anthocyanin consumption to promote human health: a review. Compr Rev. Food Sci. Food Saf., 12 (5):483–508.

Prior, R.L.; Cao, G.; Martin, A..; Sofic, E.; McEwen, J.; O'Brien, C.; Lischner, N.; Ehlenfeldt, M.; Kalt, W.; Krewer, G.and Mainland, C.M.(1998). Antioxidant capacity as influenced by total phenolic and anthocyanin content, maturity, and variety of Vaccinium species. J. Agric. Food. Chem., 46: 2686-2693.

Robinson, G.M. and Robinson, R. (1932).A survey of anthocyanins. II. Biochemical J., 6(5):1647.

Sang, J.; Ma, Q. and Li, C. q. (2017). Development and validation of green chromatography for the determination of anthocyanins in haskap berry, mulberry and blackberry. Anal. Methods, 9: 2535–2545.

Seeram, N.P.; Momin, R.A.; Nair, M.G.and Bourquin, L. D. (2001). Cyclooxygenase inhibitory and antioxidant cyanidin glycosides in cherries and berries. Phytomedicin,8(5):362–369.

Slimestad, R. and Solheim, H. (2002). Anthocyanins from black currants (Ribes nigrum L.). J. Agric. Food Chem., 50(11):3228–3231.

Solomon, A.; Golubowicz, S.; Yablowicz, Z.; Grossman, S.; Bergman, M.; Gottlieb, H.E.; Altman, A.; Kerem, Z. and Flaishman, M. A.(2006). Antioxidant activities and anthocyanin content of fresh fruits of common fig (Ficus carica L.). J. Agric. Food Chem., 54: 7717-7723.

Steed, L. E. and Truong V. D. (2008). Anthocyanin content, antioxidant activity, and selected physical properties of flowable purple-fleshed sweet potato purees. J. Food Sci., 73: 215-221.

Szymanowska, U.; Zlotek, U.; Karas, M. and Baraniak, B. (2015). Anti-inflammatory and antioxidative activity of anthocyanins from purple basil leaves induced by selected abiotic elicitors. Food Chem., 172:71–77.

Tanaka, Y.; Matsuoka, M.; Yamanoto, N.; Ohashi, Y.; Kano-Murakami, Y. and Ozeki, Y. (1989a). Structure and characterization of a cDNA clone for phenylalanine ammonia-lyase from cut-injured roots of sweet potato. Plant physiol., 90: 1403-1407.

Tanaka, Y.; Tsuda, S. and Kusumi, T. (1998b). Metabolic engineering to modify flower color. Plant Cell Physiol., 39 (11):1119–1126.

Tomas, M.; Toydemir, G.; Boyacioglu, D.; Hall, R.; Beekwilder, J. and Capanoglu, E. (2015).The effects of juice processing on black mulberry antioxidants. Food Chem., 186:277–284.

Tsuda, T.; Horio, F.; Uchida, K.; Aoki, H. and Osawa, T. (2003). Dietary cyanidin 3- O-β-D-glucoside rich purple corn color prevents obesity and ameliorates hyperglycemia in mice. J. Nutr., 133(7):2125–2130.

Turner, M. K. (2009). Anthocyanins increase antioxidant enzyme activity in HT-29 adenocarcinoma cells. MsC thesis. Athens, Georgia, USA.

Van de Velde, F.; Grace, M.H.; Esposito, D.; Pirovani, M.É. and Lila, M. A. (2016). Quantitative comparison of phytochemical profile, antioxidant, and anti-inflammatory properties of blackberry fruits adapted to argentina. J. Food Compos. Anal., 47: 82–91.

Veberic, R.; Slatnar, A.; Bizjak, J.; Stampar, F. and Mikulic-Petkovsek, M. ( 2015). Anthocyanin composition of different wild and cultivated berry species. Lwt Food Sci. Technol., 60:509–517.

Wang, H.; Nair, M.G.; Strasburg, G.M.; Chang, Y.; Booren, A.M.; Gray, J.I. and DeWitt, D.L.(1999). Antioxidant and anti-inflammatory activities of anthocyanins and their aglycon, cyanidin, from tart cherries. J. Nat. Prod., 62: 294–296.

Wang, H.;Cao, G.and Prior, R.L.(1997). Oxygen radical absorbing capacity of anthocyanins. J. Agric. Food Chem., 45: 304-309.

Wang, L.S.; Hecht, S.S.; Carmella, S.G.; Yu, N.; Larue, B.; Henry, C.; McIntyre, C.; Rocha, C.; Lechner, J. F. and Stoner, G. D.(2009). Anthocyanins in black raspberries prevent esophageal tumors in rats. Cancer Prev. Res., 2(1):84–93.

Wang, Q.; Han, P.; Zhang, M.; Xia, M.; Zhu, H.; Ma, J.; Hou, M.; Tang, Z. and Ling, W.(2007). Supplementation of black rice pigment fraction improves antioxidant and anti-inflammatory status in patients with coronary heart disease. Asia Pac. J. Clin. Nutr., 16: 1295-1301.

Wang, Q.; Xia, M.; Liu, C.; Guo, H.; Ye, Q.; Hu, Y.; Zhang, Y.; Hou, M.; Zhu, H.; Ma, J. and Ling, W.(2008). Cyanidin-3-O-α-glucoside inhibits iNOS and COX-2 expression by inducing liver X receptor alpha activation in THP-1 macrophages. Life Sci., 83: 176-184.

Wang, S.Y. and Lin, H.S. (2000). Antioxidant activity in fruits and leaves of blackberry, raspberry, and strawberry varies with cultivar and developmental stage. J. Agric. Food Chem., 48: 140-146.

Wang. S.Y. and Jiao, H. (2000). Scavenging capacity of berry crops on superoxide radicals, hydrogen peroxide, hydroxyl radicals, and singlet oxygen. J. Agri. Food Chem., 48: 5677-5684.

Winkel-Shirley, B. (2002). Biosynthesis of flavonoids and effects of stress. Curr Opinion Plant Biol., 5: 218-223.

Xia, X.; Ling, W.; Ma, J.; Xia, M.; Hou, M.; Wang, Q.; Zhu, H. and Tang, Z. (2006). An anthocyanin-rich extract from black rice enhances atherosclerotic plaque sta

bilization in apolipoprotein E-deficient mice. J. Nutr., 136: 2220-2225.

Xie, R.; Zheng, L.; He, S.; Zheng, Y. and Deng, L. (2014). Anthocyanin biosynthesis in fruit tree crops: Genes and their regulation. Afr. J. Biotechnol .,10: 19890-19897.

Yabuya, T.; Nakamura, M.; Iwashina, T.; Yamaguchi, M. and Takehara, T. (1997). Anthocyanin-flavone copigmentation in bluish purple flowers of Japanese garden iris (Iris ensata Thunb.). Euphytica.,98(3):163–167.

Yao, L.H.; Jiang, Y.M.; Shi, J.; Toma´s-Barbera´n, F.A.; Datta, N.; Singanusong, R. and Chen, S.S. (2004). Flavonoids in food and their health benefits. Plant Foods Hum. Nutr., 59: 113–122.

Zheng ,W. and Wang, S.Y. (2003).Oxygen radical absorbing capacity of phenolics in blueberries, cranberries, chokeberries, and lingonberries. J. Agric. Food Chem. ,51: 502-509.

Published

2025-09-20

Issue

Section

Articles

How to Cite

Basuny, A. M., & Arafat, S. M. (2025). Anthocyanins: Natural pigments withantioxidant and therapeutic potential. Transnational Journal of Agriculture, Environment and Sustainability, 1(1). https://journals.novapexpublishers.com/sustainable-agriculture/article/view/12

Most read articles by the same author(s)