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Anthocyanins

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Natural Products

Abstract

Anthocyanins are a group of plant phenolics characterized by their blue-orange-red color. They have a double interest as plant constituents, one technological, since they can not only be used as natural colorants in the food industry but also can interact with other plant components influencing the final characteristics of the processed product, and the other is related to their implications on human health as they can be considered functional ingredients and have shown themselves as potential targets for the pharmacological industry.

This chapter summarizes the existing literature in this area: from anthocyanin occurrence and phytochemistry to their biosynthesis, biological activities, and an overview of the biotechnological approaches that are in use at present.

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Abbreviations

AATs:

Anthocyanin acyltransferases

ACE:

Angiotensin-converting enzyme

CHS:

Chalcone synthase

DFR:

Dihydroflavonol 4-reductase

F3′H:

Flavonoid 3′-hydroxylase

FLS:

Flavonol synthase

MCP-1:

Monocyte chemoattractant protein 1

ROS:

Reactive oxygen species

TNF-α:

Tumor necrosis factor-α

TRAP:

Thrombin receptor-activating peptide

VEGF:

Vascular endothelial growth factor

References

  1. Mazza G, Miniati E (1993) Anthocyanins in fruits, vegetables, and grains. CRC Press, Boca Raton

    Google Scholar 

  2. Strack D, Wray V (1993) The anthocyanins. In: Harborne JB (ed) The flavonoids: advances in research since 1986. Chapman & Hall, London, p 1

    Google Scholar 

  3. Delgado-Vargas F, Jiménez AR, Paredez-López Q (2000) Natural pigments: Carotenoids, anthocyanins, and betalains - Characteristics, biosynthesis, processing, and stability. Crit Rev Food Sci Nutr 40:173

    Article  CAS  Google Scholar 

  4. Wang H, Cao G, Prior RL (1997) Oxygen radical absorbing capacity of anthocyanins. J Agric Food Chem 45:304

    Article  CAS  Google Scholar 

  5. Clifford MN (2000) Anthocyanins - nature, occurrence and dietary burden. J Sci Food Agric 80:1063

    Article  CAS  Google Scholar 

  6. de Pascual-Teresa S, Moreno DA, García-Viguera C (2010) Flavanols and Anthocyanins in cardiovascular health: a review of current evidence. Int J Mol Sci 11:1679

    Article  Google Scholar 

  7. Jackman RL, Yada RY, Tung MA, Speers RA (1987) Anthocyanins as food colorants-a review. J Food Biochem 11:201

    Article  CAS  Google Scholar 

  8. Francis FJ (1989) Food colorants-Anthocyanins. Crit Rev Food Sci Nutr 28:273

    Article  CAS  Google Scholar 

  9. Timberlake CF, Bridle P (1966) Effects of substituents on the ionization of flavylium salts and anthocyanins and their reactions with sulfur dioxide. Chem Ind 1965 4:1097–1102

    Google Scholar 

  10. Mazza G, Brouillard R (1990) The mechanism of copigmentation of anthocyanins in aqueous-solutions. Phytochemistry 29:1097

    Article  CAS  Google Scholar 

  11. Maccarone E, Maccarrone A, Rapisarda P (1985) Stabilization of anthocyanins of blood orange fruit juice. J Food Sci 50:901

    Article  CAS  Google Scholar 

  12. Maccarone E, Maccarrone A, Rapisarda P (1987) Color stabilization of orange fruit juice by tannic acid. Int J Food Sci Technol 22:153

    Google Scholar 

  13. Teh LS, Francis FJ (1988) Stability of anthocyanins from zebrina pendula and ipomoea tricolor in a model beverage. J Food Sci 53:1580

    Article  CAS  Google Scholar 

  14. Xiong SY, Melton LD, Easteal AJ, Siew D (2006) Stability and antioxidant activity of black currant anthocyanins in solution and encapsulated in glucan gel. J Agric Food Chem 54:6201

    Article  CAS  Google Scholar 

  15. Robert P, Gorena T, Romero N, Sepulveda E, Chavez J, Saenz C (2010) Encapsulation of polyphenols and anthocyanins from pomegranate (Punica granatum) by spray drying. Int J Food Sci Technol 22:153

    Google Scholar 

  16. Brouillard R (1982) Chemical structure of anthocyanins. In: Markakis P (ed) Anthocyanins as food colors. Academic, New York

    Google Scholar 

  17. Small CJ, Pecket RC (1982) The ultrastructure of anthocyanoplats in red cabbage. Planta 154:97

    Article  Google Scholar 

  18. Escribano-Bailón MT, Santos-Buelga C, Rivas-Gonzalo JC (2004) Anthocyanins in cereals. J Cromatogr A 1054:129

    Google Scholar 

  19. Kong JM, Chia LS, Goh NK, Chia TF, Brouillard R (2003) Analysis and biological activities of anthocyanins. Phytochemistry 64:923

    Article  CAS  Google Scholar 

  20. Petroni K, Tonelli C (2011) Recent advances on the regulation of anthocyanin synthesis in reproductive organs. Plant Sci 181:219

    Article  CAS  Google Scholar 

  21. Montefiori M, Espley RV, Stevenson D, Cooney J, Datson PM, Saiz A, Atkinson RG, Hellens RP, Allan AC (2011) Identification and characterisation of F3GT1 and F3GGT1, two glycosyltransferases responsible for anthocyanin biosynthesis in red-fleshed kiwifruit (Actinidia chinensis). Plant J 65:106

    Article  CAS  Google Scholar 

  22. Campos-Vargas R, Saltveit ME (2002) Involvement of putative chemical wound signals in the induction of phenolic metabolism in wounded lettuce. Physiol Plant 114:73

    Article  CAS  Google Scholar 

  23. Toguri T, Umemoto N, Kobayashi O, Ohtani T (1993) Activation of anthocyanin synthesis genes by white light in eggplant hypocotyl tissues, and identification of an inducible P450 cDNA. Plant Mol Biol 23:933

    Article  CAS  Google Scholar 

  24. Hodges DM, Nozzolillo C (1996) Anthocyanin and anthocyanoplast content of cruciferous seedlings subjected to mineral nutrient deficiencies. J Plant Physiol 147:749–754

    Article  CAS  Google Scholar 

  25. García-Alonso M, Rimbach G, Rivas-Gonzalo JC, de Pascual-Teresa S (2004) Antioxidant and cellular activities of anthocyanins and their corresponding vitisins A - Studies in platelets, monocytes, and human endothelial cells. J Agric Food Chem 52:3378

    Article  Google Scholar 

  26. Oak MH, Bedoui JE, Madeira SV, Chalupsky K, Schini-Kerth VB (2006) Delphinidin and cyanidin inhibit PDGF(AB)-induced VEGF release in vascular smooth muscle cells by preventing activation of p38 MAPK and JNK. Br J Pharmacol 149:283

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  28. Rechner AR, Kroner C (2005) Anthocyanins and colonic metabolites of dietary polyphenols inhibit platelet function. Thromb Res 116:327

    Article  CAS  Google Scholar 

  29. Bell DR, Gochenaur K (2006) Direct vasoactive and vasoprotective properties of anthocyanin-rich extracts. J Appl Physiol 100:1164

    Article  CAS  Google Scholar 

  30. Xia M, Ling W, Zhu H, Wang Q, Ma J, Hou M, Tang Z, Li L, Ye Q (2007) Anthocyanin prevents CD40-activated proinflammatory signaling in endothelial cells by regulating cholesterol distribution. Arterioscler Thromb Vasc Biol 27:519–524

    Article  CAS  Google Scholar 

  31. Hidalgo M, Martín-Santamaría S, Recio I, Sanchez-Moreno C, de Pascual-Teresa B, Rimbach G, de Pascual-Teresa S (2011) Potential anti-inflammatory, anti-adhesive, anti/estrogenic, and angiotensin-converting enzyme inhibitory activities of anthocyanins and their gut metabolites. Genes Nutr 7:295–306

    Google Scholar 

  32. Lazzè MC, Pizzala R, Perucca P, Cazzalini O, Savio M, Forti L, Vannini V, Bianchi L (2006) Anthocyanidins decrease endothelin-1 production and increase endothelial nitric oxide synthase in human endothelial cells. Mol Nutr Food Res 50:44

    Article  Google Scholar 

  33. Kamei H, Hashimoto Y, Koide T, Kojima T, Hasegawa M (1998) Inhibition of cell growth in culture by quinones. Cancer Biother Radiopharm 13:447

    Article  CAS  Google Scholar 

  34. Shih PH, Yeh CT, Yen GC (2005) Effects of anthocyanidin on the inhibition of proliferation and induction of apoptosis in human gastric adenocarcinoma cells. Food Chem Toxicol 43:1557

    Article  CAS  Google Scholar 

  35. Hagiwara A, Miyashita K, Nakanishi T, Sano M, Tamano S, Kadota T, Koda T, Nakamura M, Imaida K, Ito N, Shirai T (2001) Pronounced inhibition by a natural anthocyanin, purple corn color, of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)associated colorectal carcinogenesis in male F344 rats pretreated with 1,2-dimethylhydrazine. Cancer Lett 171:17

    Article  CAS  Google Scholar 

  36. Liu M, Li XQ, Weber C, Lee CY, Brown J, Liu RH (2002) Antioxidant and anti proliferative activities of raspberries. J Agric Food Chem 50:2926

    Article  CAS  Google Scholar 

  37. Marko D, Puppel N, Tjaden Z (2004) The substitution pattern of anthocyanidins affects different cellular signaling cascades regulating cell proliferation. Mol Nutr Food Res 48:318–332

    Article  CAS  Google Scholar 

  38. Fimognari C, Berti F, Nüsse M, Cantelli-Forti G, Hrelia P (2004) Induction of apoptosis in two human leukemia cell lines as well as differentiation in human promyelocytic cells by cyanidin-3-O-beta-glucopyranoside. Biochem Pharmacol 67:2047

    Article  CAS  Google Scholar 

  39. Liu Z, Schwimer J, Liu D, Greenway FL, Anthony CT, Woltering EA (2005) Black raspberry extract and fractions contain angiogenesis inhibitors. J Agric Food Chem 53:3909

    Article  CAS  Google Scholar 

  40. Smith SH, Tate PL, Huang G, Magee JB, Meepagala KM, Wedge DE, Larcom LL (2004) Antimutagenic activity of berry extracts. J Med Food 7:450

    Article  Google Scholar 

  41. Sarma AD, Sharma R (1999) Anthocyanin-DNA copigmentation complex: mutual protection against oxidative damage. Phytochemistry 52:1313

    Article  CAS  Google Scholar 

  42. Jayaprakasam B, Vareed SK, Olson LK, Nair MG (2005) Insulin secretion by bioactive anthocyanins and anthocyanidins present in fruits. J Agric Food Chem 53:28

    Article  CAS  Google Scholar 

  43. Scazzocchio B, Varì R, Filesi C, D’Archivio M, Santangelo C, Giovannini C, Iacovelli A, Silecchia G, Li Volti G, Galvano F, Masella R (2011) Cyanidin-3-O-beta-glucoside and protocatechuic acid exert insulin-like effects by upregulating PPAR gamma activity in human omental adipocytes. Diabetes 60:2234

    Article  CAS  Google Scholar 

  44. Adisakwattana S, Yibchok-Anun S, Charoenlertkul P, Wongsasiripat N (2011) Cyanidin-3-rutinoside alleviates postprandial hyperglycemia and its synergism with acarbose by inhibition of intestinal alpha-glucosidase. J Clin Biochem Nutr 49:36

    Article  CAS  Google Scholar 

  45. Canter PH, Ernst E (2004) Anthocyanosides of Vaccinium myrtillus (bilberry) for night vision--a systematic review of placebo-controlled trials. Surv Ophthalmol 49:38

    Article  Google Scholar 

  46. Fursova AZh, Gesarevich OG, Gonchar AM, Trofimova NA, Kolosova NG (2005) Dietary supplementation with bilberry extract prevents macular degeneration and cataracts in senesce-accelerated OXYS rats. Adv Gerontol 16:76

    Google Scholar 

  47. Lee J, Lee HK, Kim CY, Hong YJ, Choe CM, You TW, Seong GJ (2005) Purified high-dose anthocyanoside oligomer administration improves nocturnal vision and clinical symptoms in myopia subjects. Br J Nutr 93:895

    Article  CAS  Google Scholar 

  48. Liu Y, Song X, Han Y, Zhou F, Zhang D, Ji B, Hu J, Lv Y, Cai S, Wei Y, Gao F, Jia X (2011) Identification of anthocyanin components of wild chinese blueberries and amelioration of light-induced retinal damage in pigmented rabbit using whole berries. J Agric Food Chem 59:356

    Article  CAS  Google Scholar 

  49. Puupponen-Pimiä R, Nohynek L, Hartmann-Schmidlin S, Kähkönen M, Heinonen M, Määttä-Riihinen K, Oksman-Caldentey KM (2005) Bioactive berry compounds - novel tools against human pathogens. J Appl Microbiol 98:991

    Article  Google Scholar 

  50. Nohynek LJ, Alakomi HL, Kähkönen MP, Heinonen M, Helander IM, Oksman-Caldentey KM, Puupponen-Pimiä RH (2006) Berry phenolics: Antimicrobial properties and mechanisms of action against severe human pathogens. Nutr Cancer 54:18

    Article  CAS  Google Scholar 

  51. Knox YM, Suzutani T, Yosida I, Azuma M (2003) Anti-influenza virus activity of crude extract of Ribes nigrum L. Phytother Res 17:120

    Article  Google Scholar 

  52. Suzutani T, Ogasawara M, Yoshida I, Azuma M, Knox YM (2003) Anti-influenza virus activity of crude extract of Ribes nigrum L.. Phytother Res 17:609

    Article  Google Scholar 

  53. Joseph JA, Denisova NA, Arendash G, Gordon M, Diamond D, Shukitt-Hale B, Morgan D (2003) Blueberry supplementation enhances signaling and prevents behavioral deficits in an Alzheimer disease model. Nutr Neurosci 6:153

    Article  CAS  Google Scholar 

  54. Ke Z, Liu Y, Wang X, Fan Z, Chen G, Xu M, Bower KA, Frank JA, Ou X, Shi X, Luo J (2011) Cyanidin-3-glucoside ameliorates ethanol neurotoxicity in the developing brain. J Neurosci Res 89:1676

    Article  CAS  Google Scholar 

  55. Meyer P, Heidmann I, Forkmann G, Saedler H (1987) A new petunia flower color generated by transformation of a mutant with a maize gene. Nature 330:677

    Article  CAS  Google Scholar 

  56. Katsumoto Y, Fukuchi-Mizutani M, Fukui Y, Brugliera F, Holton TA, Karan M, Nakamura N, Yonekura-Sakakibara K, Togami J, Pigeaire A, Tao GQ, Nehra NS, Lu CY, Dyson BK, Tsuda S, Ashikari T, Kusumi T, Mason JG, Tanaka Y (2007) Engineering of the rose flavonoid biosynthetic pathway successfully generated blue-hued flowers accumulating delphinidin. Plant Cell Physiol 48:1589

    Article  CAS  Google Scholar 

  57. Dao TT, Linthorst HJ, Verpoorte R (2011) Chalcone synthase and its functions in plant resistance. Phytochem Rev 10:397

    Article  CAS  Google Scholar 

  58. Shimada Y, Nakano-Shimada R, Ohbayashi M, Okinaka Y, Kiyokawa S, Kikuchi Y (1999) Expression of chimeric P450 genes encoding flavonoid-3′,5′-hydroxylase in transgenic tobacco and petunia plants. FEBS Lett 461:241

    Article  CAS  Google Scholar 

  59. Boase MR, Lewis DH, Davies KM, Marshall GB, Patel D, Schwinn KE, Deroles SC (2010) Isolation and antisense suppression of flavonoid 3′,5′-hydroxylase modifies flower pigments and colour in cyclamen. BMC Plant Biol 10:107

    Article  Google Scholar 

  60. Aida R, Yoshida K, Kondo T, Kishimoto S, Shibata M (2000) Copigmentation gives bluer flowers on transgenic torenia plants with the antisense dihydroflavonol-4-reductase gene. Plant Sci 160:49

    Article  CAS  Google Scholar 

  61. Winkel-Shirley B (2001) Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology, and biotechnology. Plant Physiol 126:485

    Article  CAS  Google Scholar 

  62. Lloyd AM, Walbot V, Davis RW (1992) Arabidopsis and nicotiana anthocyanin production activated by maize regulator-r and regulator-C1. Science 258:1773

    Article  CAS  Google Scholar 

  63. Bovy A, de Vos R, Kemper M, Schijlen E, Almenar Pertejo M, Muir S, Collins G, Robinson S, Verhoeyen M, Hughes S, Santos-Buelga C, van Tunen A (2002) High-flavonol tomatoes resulting from the heterologous expression of the maize transcription factor genes LC and C1. Plant Cell 14:2509

    Article  CAS  Google Scholar 

  64. Quattrocchio F, Verweij W, Kroon A, Spelt C, Mol J, Koes R (2006) Plant Cell 18:1274

    Article  CAS  Google Scholar 

  65. Treutter D (2006) PH4 of petunia is an R2R3 MYB protein that activates vacuolar acidification through interactions with basic-helix-loop-helix transcription factors of the anthocyanin pathway. Environ Chem Let 4:147

    Article  CAS  Google Scholar 

  66. McKown R, Kuroki G, Warren G (1996) Cold responses of Arabidopsis mutants impaired in freezing tolerance. J Exp Bot 47:1919

    Article  CAS  Google Scholar 

  67. Lukaszewicz M, Matysiak-Kata I, Skala J, Fecka I, Cisowski W, Szopa J (2004) Antioxidant capacity manipulation in transgenic potato tuber by changes in phenolic compounds content. J Agric Food Chem 52:1526

    Article  CAS  Google Scholar 

  68. Jones CM, Mes P, Myers JR (2003) Characterization and inheritance of the Anthocyanin fruit (Aft) tomato. J Hered 94:449

    Article  CAS  Google Scholar 

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Author information

Authors and Affiliations

  1. Department of Metabolism and Nutrition, Institute of Food Science, Food Technology and Nutrition (ICTAN), CSIC, Madrid, 28040, Spain

    Dr. Sonia de Pascual-Teresa

  2. Department of Characterization, Quality and Security, Institute of Food Science, Food Technology and Nutrition (ICTAN), CSIC, Madrid, 28040, Spain

    Maria Teresa Sanchez-Ballesta

  3. Department of Food Science and Technology, Centro de Edafología y Biología Aplicada del Segura (CEBAS), CSIC, Murcia, 30100, Spain

    Cristina García-Viguera

Authors
  1. Dr. Sonia de Pascual-Teresa
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  2. Maria Teresa Sanchez-Ballesta
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  3. Cristina García-Viguera
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Corresponding author

Correspondence to Sonia de Pascual-Teresa .

Editor information

Editors and Affiliations

  1. Botany Department, M.L. Sukhadia University, Durga Nursery Road, Udaipur, 313001, Rajasthan, India

    Kishan Gopal Ramawat

  2. Institute of Vine and Wine Sciences, Biological-Active Plant Substances Study, University of Bordeaux, 210 Chemin de Leysotte CS 50008, Villenave d'Ornon, 33882, France

    Jean-Michel Mérillon

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de Pascual-Teresa, S., Sanchez-Ballesta, M.T., García-Viguera, C. (2013). Anthocyanins. In: Ramawat, K., Mérillon, JM. (eds) Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-22144-6_59

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