Skip to main content
SpringerLink
Log in

Introduction to Anthocyanins

  • Chapter
  • First Online:
Anthocyanins and Human Health: Biomolecular and therapeutic aspects

Part of the book series: SpringerBriefs in Food, Health, and Nutrition ((BRIEFSFOOD))

Abstract

Anthocyanins are secondary plant metabolites and are chemically di- or tri-hydroxy B-ring-substituted flavonoids containing a flavylium cation. These are focus of much attention these days due to their vibrant colors and immunity-boosting and health-promoting effects mainly in ameloriating various cholesterol-related and oxidation-induced diseases. All of these mentioned functions, effects and activities of anthocyanins are due to their unique structure. Anthocyanins being water-soluble pigments have high hydrogen bonding capacity. The OH groups on their sugar moieties, possible acyl groups and anthocyanindin imparts them hydrophilic characteristics. This chapter describes brief history of discovery of anthocyanins as well as detailed information on chemistry of anthocyanins. Various metabolites and intermediate products of anthocyanin metabolism and their chemistry have also been discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
eBook
USD 16.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 16.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Similar content being viewed by others

References

  1. Saad, B., & Said, O. (Eds.). (2011). Greco-Arab and Islamic herbal medicine: Traditional system, ethics, safety, efficacy, and regulatory issues. Hoboken: Wiley.

    Google Scholar 

  2. Saad, B. (2015). Integrating traditional Greco‐Arab and Islamic diet and herbal medicines in research and clinical practice. In I. Ramzan (Ed.), Phytotherapies: Efficacy, safety, and regulation (p. 142). Hoboken: Wiley.

    Chapter  Google Scholar 

  3. Saad, B. (2015). Greco-Arab and Islamic diet therapy: Tradition, research and practice. Arabian Journal of Medicinal and Aromatic Plants, 1, 1–24.

    Article  Google Scholar 

  4. Boyle, R. (2004). Experiments and considerations touching colours (1664). London: Henry Herringman.

    Google Scholar 

  5. Wheldale, M. (1916). Anthocyanic pigments of plants. Cambridge: Cambridge University Press.

    Google Scholar 

  6. Willstätter, R., & Everest, A. E. (1913). Untersuchungen über die Anthocyane. I. Über den Farbstoff der Kornblume. Justus Liebigs Annalen der Chemie, 401(2), 189–232.

    Article  Google Scholar 

  7. Willstätter, R., & Nolan, T. J. (1915). Untersuchungen über die Anthocyane. II. Über den Farbstoff der Rose. Justus Liebigs Annalen der Chemie, 408(1), 1–14.

    Article  Google Scholar 

  8. Shibata, K., Shibata, Y., & Kasiwagi, I. (1919). Studies on anthocyanins: Color variation in anthocyanins. Journal of the American Chemical Society, 41(2), 208–220.

    Article  CAS  Google Scholar 

  9. Landi, M., Tattini, M., & Gould, K. S. (2015). Multiple functional roles of anthocyanins in plant-environment interactions. Environmental and Experimental Botany, 119, 4–17.

    Article  CAS  Google Scholar 

  10. Lee, D., & Gould, K. (2002). Why leaves turn red pigments called anthocyanins probably protect leaves from light damage by direct shielding and by scavenging free radicals. American Scientist, 90(6), 524–528.

    Article  Google Scholar 

  11. Ghosh, D., & Konishi, T. (2007). Anthocyanins and anthocyanin-rich extracts: Role in diabetes and eye function. Asia Pacific Journal of Clinical Nutrition, 16(2), 200.

    CAS  Google Scholar 

  12. Oren-Shamir, M. (2009). Does anthocyanin degradation play a significant role in determining pigment concentration in plants? Plant Science, 177(4), 310–316.

    Article  CAS  Google Scholar 

  13. Delgado-Vargas, F., & Paredes-López, O. (2003). Anthocyanins and betalains. Natural Colorants for Food and Nutraceutical 167–219.

    Google Scholar 

  14. Chalker Scott, L. (1999). Environmental significance of anthocyanins in plant stress responses. Photochemistry and Photobiology, 70(1), 1–9.

    Article  CAS  Google Scholar 

  15. Da Costa, C. T., Horton, D., & Margolis, S. A. (2000). Analysis of anthocyanins in foods by liquid chromatography, liquid chromatography-mass spectrometry and capillary electrophoresis. Journal of Chromatography A, 881(1), 403–410.

    Article  Google Scholar 

  16. Strack, D., Steglich, W., & Wray, V. (1993). Betalains. Methods in Plant Biochemistry, 8, 421–450.

    CAS  Google Scholar 

  17. Bkowska-Barczak, A. (2005). Acylated anthocyanins as stable, natural food colorants – A review. Polish Journal of Food and Nutrition Sciences, 14, 107–116.

    Google Scholar 

  18. Valls, J., Millán, S., Martí, M. P., Borràs, E., & Arola, L. (2009). Advanced separation methods of food anthocyanins, isoflavones and flavanols. Journal of Chromatography A, 1216(43), 7143–7172.

    Article  CAS  Google Scholar 

  19. Stintzing, F. C., & Carle, R. (2004). Functional properties of anthocyanins and betalains in plants, food, and in human nutrition. Trends in Food Science and Technology, 15(1), 19–38.

    Article  CAS  Google Scholar 

  20. Kong, J. M., Chia, L. S., Goh, N. K., Chia, T. F., & Brouillard, R. (2003). Analysis and biological activities of anthocyanins. Phytochemistry, 64(5), 923–933.

    Article  CAS  Google Scholar 

  21. Andersen, Ø. M., Fossen, T., Torskangerpoll, K., Fossen, A., & Hauge, U. (2004). Anthocyanin from strawberry (Fragaria ananassa) with the novel aglycone, 5-carboxypyranopelargonidin. Phytochemistry, 65(4), 405–410.

    Article  CAS  Google Scholar 

  22. Rentzsch, M., Schwarz, M., & Winterhalter, P. (2007). Pyranoanthocyanins – An overview on structures, occurrence, and pathways of formation. Trends in Food Science and Technology, 18(10), 526–534.

    Article  CAS  Google Scholar 

  23. Castañeda-Ovando, A., Pacheco-Hernández, M., Páez-Hernández, M. E., Rodríguez, J. A., & Galán-Vidal, C. (2009). Chemical studies of anthocyanins: A review. Food Chemistry, 113(4), 859–871.

    Article  Google Scholar 

  24. Pozo-Bayón, M. A., Monagas, M., Polo, M. C., & Gómez-Cordovés, C. (2004). Occurrence of pyranoanthocyanins in sparkling wines manufactured with red grape varieties. Journal of Agricultural and Food Chemistry, 52(5), 1300–1306.

    Article  Google Scholar 

  25. Monagas, M., Bartolomé, B., & Gómez-Cordovés, C. (2005). Evolution of polyphenols in red wines from Vitis vinifera L. during aging in the bottle. European Food Research and Technology, 220(3–4), 331–340.

    Article  CAS  Google Scholar 

  26. Bakker, J., & Timberlake, C. F. (1997). Isolation, identification, and characterization of new color-stable anthocyanins occurring in some red wines. Journal of Agricultural and Food Chemistry, 45(1), 35–43.

    Article  CAS  Google Scholar 

  27. Romero, C., & Bakker, J. (1999). Interactions between grape anthocyanins and pyruvic acid, with effect of pH and acid concentration on anthocyanin composition and color in model solutions. Journal of Agricultural and Food Chemistry, 47(8), 3130–3139.

    Article  CAS  Google Scholar 

  28. Lu, Y., Foo, L. Y., & Sun, Y. (2002). New pyranoanthocyanins from blackcurrant seeds. Tetrahedron Letters, 43(41), 7341–7344.

    Article  CAS  Google Scholar 

  29. Fulcrand, H., Montserrat, D., Erika, S., & Véronique, C. (2006). Phenolic reactions during winemaking and aging. American Journal of Enology and Viticulture, 57(3), 289–297.

    CAS  Google Scholar 

  30. Bakker, J., & Timberlake, C. F. (1985). The distribution of anthocyanins in grape skin extracts of port wine cultivars as determined by high performance liquid chromatography. Journal of the Science of Food and Agriculture, 36(12), 1315–1324.

    Article  CAS  Google Scholar 

  31. Mateus, N., Oliveira, J., Haettich-Motta, M., & de Freitas, V. (2004). New family of bluish pyranoanthocyanins. BioMed Research International, 2004(5), 299–305.

    Google Scholar 

  32. de Freitas, V., & Mateus, N. (2011). Formation of pyranoanthocyanins in red wines: A new and diverse class of anthocyanin derivatives. Analytical and Bioanalytical Chemistry, 401(5), 1463–1473.

    Article  Google Scholar 

  33. Schwarz, M., Wabnitz, T. C., & Winterhalter, P. (2003). Pathway leading to the formation of anthocyanin-vinylphenol adducts and related pigments in red wines. Journal of Agricultural and Food Chemistry, 51(12), 3682–3687.

    Article  CAS  Google Scholar 

  34. Mateus, N., Pascual-Teresa, S., Rivas-Gonzalo, J. C., Santos-Buelga, C., & Victor de Freitas, V. D. (2002). Structural diversity of anthocyanin-derived pigments in port wines. Food Chemistry, 76(3), 335–342.

    Article  CAS  Google Scholar 

  35. Gómez-Alonso, S., Collins, V. J., Vauzour, D., Rodríguez-Mateos, A., Corona, G., & Spencer, J. P. E. (2012). Inhibition of colon adenocarcinoma cell proliferation by flavonols is linked to a G2/M cell cycle block and reduction in cyclin D1 expression. Food Chemistry, 130(3), 493–500.

    Article  Google Scholar 

  36. He, F., Liang, N. N., Mu, L., Pan, Q. H., Wang, J., & Reeves, M. J. (2012). Anthocyanins and their variation in red wines I. Monomeric anthocyanins and their color expression. Molecules, 17(2), 1571–1601.

    Article  CAS  Google Scholar 

  37. Schwarz, M., Jerz, G., & Winterhalter, P. (2015). Isolation and structure of Pinotin A, a new anthocyanin derivative from Pinotage wine. VITIS-Journal of Grapevine Research, 42(2), 105.

    Google Scholar 

  38. Fossen, T., & Andersen, Ø. M. (2003). Anthocyanins from red onion, (Allium cepa) with novel aglycone. Phytochemistry, 62(8), 1217–1220.

    Google Scholar 

  39. Lu, Y., & Foo, L. Y. (2001). Unusual anthocyanin reaction with acetone leading to pyranoanthocyanin formation. Tetrahedron Letters, 42(7), 1371–1373.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Shaheed Benazir Bhutto University, Sheringal, Pakistan

    Muhammad Riaz Ph.D.

  2. The Patent Office, Karachi, Pakistan

    Muhammad Zia-Ul-Haq Ph.D.

  3. Al-Qasemi Academic College, Baga Algharbiya, Israel

    Bashar Saad Ph.D.

  4. Arab American University Jenin, Jenin, Palestine

    Bashar Saad Ph.D.

Authors
  1. Muhammad Riaz Ph.D.
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Muhammad Zia-Ul-Haq Ph.D.
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Bashar Saad Ph.D.
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 2016 The Authors

About this chapter

Cite this chapter

Riaz, M., Zia-Ul-Haq, M., Saad, B. (2016). Introduction to Anthocyanins. In: Anthocyanins and Human Health: Biomolecular and therapeutic aspects. SpringerBriefs in Food, Health, and Nutrition. Springer, Cham. https://doi.org/10.1007/978-3-319-26456-1_2

Download citation

Publish with us

Policies and ethics

Search

Navigation