Skip to main content
SpringerLink
Log in

Structure, Stability and Color Variation of Natural Anthocyanins

  • Chapter
Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

Abstract

Anthocyanin is the general name applied to the glycosides of antho-cyanidin chromophores which are the origin of the red, violet, and blue colors found throughout the plant kingdom, such as the colors of petals, leaves and fruits. Only a few anthocyanidin nuclei have been found in spite of the great variety of plant colors. The major anthocyan- idins found in nature are pelargonidin, cyanidin, peonidin, delphinidin,

3,5-Diglucosides of common anthocyanins (anhydro base form). The name of the anthocyanidin is in parentheses. [From T. GOTO et al: Ann. New York Acad. Sci. 471, 155 (1986), with permission]

petunidin and malvidin (Fig. 1). The most common anthocyanins are 3-glucosides and 3,5-diglueosides of the anthocyanidins, but galactose, rhamnose, xylose and arabinose residues are also found. Many anthocyanins containing acylated sugar moieties are also known. The acyl groups are mostly derivatives of cinnamic acid such as p-coumaric, caffeic, and ferulic acid, but include some aliphatic acids such as malonic, succinic, and acetic acid as well.

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
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

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Abe, K., Y. Sakaino, J. Kakinuma, and H. Kakisawa: Structures of Anthocyanin Anhydro Bases. Nippon Kagaku Kaishi, 1197–1204 (1977).

    Google Scholar 

  2. Asen, S., and R.M. Horowitz: Apigenin 4′-0-β-D-glucoside 7-0-β-D-glucuronide: The Copigment in the Blue Pigment of Centaurea cyanus. Phytochem. 13, 1219-1223 (1974).

    CAS  Google Scholar 

  3. Asen, S., and L. Jurd: The Constitution of a Crystalline, Blue Cornflower Pigment. Phytochem. 6, 577-584 (1967).

    CAS  Google Scholar 

  4. Asen, S., K.H. Norris, and R.N. Stewart: Effect of pH and Concentration of the Anthocyanin-flavonol Co-pigment Complex on the Color of ‘Better Times’ Roses. J. Am. Soc. Hort. Sci. 96, 770–773 (1971).

    CAS  Google Scholar 

  5. Asen, S., R.N. Stewart, and K.H. Norris: Co-pigmentation Effect of Quercetin Glycosides on Absorption Characteristics of Cyanidin Glycosides and Color of Red Wing Azalea. Phytochem. 10, 171–175 (1971).

    CAS  Google Scholar 

  6. Asen, S., R.N. Stewart, and K.H. Norris: Co-pigmentation of Anthocyanins in Plant Tissues and its Effect on Color. Phytochem. 11, 1139–1144 (1972).

    CAS  Google Scholar 

  7. Asen, S., R.N. Stewart, and K.H. Norris: Anthocyanin, Flavonol Copigments, and pH Responsible for Larkspur Flower Color. Phytochem. 14, 2677–2682 (1975).

    CAS  Google Scholar 

  8. Asen, S., R.N. Stewart, and K.H. Norris: Anthocyanin and pH Involved in the Color of‘Heavenly Blue’ Morning Glory. Phytochem. 16, 1118–1119 (1977).

    CAS  Google Scholar 

  9. Asen, S., R.N. Stewart, K.H. Norris, and D.R. Hassie: A Stable Blue Non-metallic Co-pigment Complex of Delphanin and C-Glycosylflavones in Prof. Blaauw Iris. Phytochem. 9, 619–627 (1970).

    CAS  Google Scholar 

  10. Asen, S., N.W. Stuart, and H.W. Siegelman: Effect of Various Concentrations of Nitrogen, Phosphorus and Potassium on Sepal Color of Hydrangea macrophylla. Proc. Am. Soc. Hort. Sci. 73, 495–502 (1959).

    CAS  Google Scholar 

  11. Bayer, E. : Über den blauen Farbstoff der Kornblume I. Natürliche und synthetische Anthocyan-Metallkomplexe. Chem. Ber. 91, 1115–1122 (1958).

    CAS  Google Scholar 

  12. Bayer, E. : Complex formation and Flower Colors. Angew. Chem. Internat. Edit. 5, 791–798 (1966).

    CAS  Google Scholar 

  13. Birkofer, L., C. Kaiser, M. Donike, and W. Koch: Konstitution von Acyl-antho- cyanen. Z. Naturforsch. 20b, 424–426 (1965).

    CAS  Google Scholar 

  14. Birkofer, L., C. Kaiser, W. Koch, M. Donike, and D. Wolf: Acylierte Anthocyane II. cis-trans-Isomerie bei Acyl-Anthocyanen. Z. Naturforsch. 18b, 631–634 (1963).

    CAS  Google Scholar 

  15. Bloom, M., and T.A. Geissman: Malonic acid: the Acyl Moiety of the Minulus leteus Anthocyanin. Phytochem. 12, 2005-2006 (1973).

    CAS  Google Scholar 

  16. Bridle, P., R.S.T. Loeffler, C.F. Timberlake, and R. Self: Cyanidin 3-Malonylglu- coside in Cichorium intybus. Phytochem. 23, 2968–2969 (1984).

    CAS  Google Scholar 

  17. Brouillard, R.: Origin of the Exceptional Colour Stability of the Zebrina Anthocyanin. Phytochem. 20, 143–145 (1981).

    CAS  Google Scholar 

  18. Brouillard, R.: Chemical Structure of Anthocyanins. In: Anthocyanins as Food Colors, Chapter 1, pp 1–40, Academic Press, New York, 1982.

    Google Scholar 

  19. Brouillard, R. : The in vivo Expression of Anthocyanin Colour in Plants. Phytochem. 22, 1311–1323 (1983).

    CAS  Google Scholar 

  20. Brouillard, R., and B. Delaporte: Chemistry of Anthocyanin Pigments. 2. Kinetic and Thermodynamic Study of Proton Transfer, Hydration, and Tautomeric Reactions of Malvidin 3-Glucoside. J. Am. Chem. Soc. 99, 8461–8468 (1977).

    CAS  Google Scholar 

  21. Brouillard, R., and J.-E. Dubois: Mechanism of the Structural Transformations of Anthocyanins in Acidic Media. J. Am. Chem. Soc. 99, 1359–1364 (1977).

    CAS  Google Scholar 

  22. Brouillard, R., G.A. Iacobucci, and J.G. Sweeny: Chemistry of Anthocyanin Pigments. 9. Uv-Visible Spectrophotometric Determination of the Acidity Constants of Apigeninidin and Three Related 3-Deoxyflavylium Salts. J. Am. Chem. Soc. 104, 7585–7590 (1982).

    CAS  Google Scholar 

  23. Cheminât, A., and R. Brouillard: PMR Investigation of 3-0-(β-D-glucosyl)malvi- din. Structural Transformation in Aqueous Solutions. Tetrahedron Lett. 27, 4457–4460 (1986).

    Google Scholar 

  24. Chen, L.-J., and G. Hrazdina: Structural Aspects of Anthocyanin-flavonoid Complex Formation and its Role in Plant Color. Phytochem. 20, 297–303 (1981).

    CAS  Google Scholar 

  25. Cornuz, G., H. Wyler, and J. Lauter wein: Pelargonidin 3-malonylsophoroside from the Red Iceland Poppy, Papaver nudicaule. Phytochem. 20, 1461–1462 (1981).

    CAS  Google Scholar 

  26. Everest, A.E., and A.J. Hall: Anthocyanins and Anthocyanidins IV. Observations on: (a) Anthocyan Colors in Flowers, and (b) The Formation of Anthocyans in Plants. Proc. Roy. Soc. London 92B, 150–162 (1921).

    Google Scholar 

  27. Goto, T., T. Hoshino, and M. Ohba: Stabilization Effect of Neutral Salts on Anthocyanins, Flavylium Salts, Anhydro Bases and Genuine Anthocyanins. Agric. Biol. Chem. 40, 1593–1596 (1976).

    CAS  Google Scholar 

  28. Goto, T., T. Hoshino, and S. Takase: 20th Symposium on the Chemistry of Natural Products. Symposium Papers pp 59–66 (1976).

    Google Scholar 

  29. Goto, T., T. Hoshino, and S. Takase: A Proposed Structure of Commelinin, a Sky-blue Anthocyanin Complex Obtained from the Flower Petals of Commelina. Tetrahedron Lett. 2905–2908 (1979).

    Google Scholar 

  30. Goto, T., H. Imagawa, and T. Kondo: Heavenly Blue Anthocyanin III. Structure of Bis-deacyl Heavenly Blue Anthocyanin, a Controlled Alkaline Hydrolysis Product of Heavenly Blue Anthocyanin. Heterocycles 17, 355–358 (1982).

    CAS  Google Scholar 

  31. Goto, T., T. Kondo, H. Imagawa, and I. Miura: Heavenly Blue Anthocyanin II. Trans -4-O-(6-trans-3-0-(β-D-glucopyranosyl)caffeyl)-β-D-glucopyranosyl)caffeic Acid, a Novel Component in Heavenly Blue Anthocyanin. Tetrahedron Lett. 22, 3213–3216(1981).

    CAS  Google Scholar 

  32. Goto, T., T. Kondo, H. Imagawa, S. Takase, M. Atobe, and I. Miura: Structure Confirmation of Tris-Deacyl Heavenly Blue Anthocyanin obtained from Flower of Morning Glory “Heavenly Blue” Chemistry Lett. 883–886 (1981).

    Google Scholar 

  33. Goto, T., T. Kondo, H. Tamura, H. Imagawa, A. Iino, and K. Takeda: Structure of Gentiodelphin, an Acylated Anthocyanin Isolated from Gentiana makinoi, That Is Stable in Dilute Aqueous Solution. Tetrahedron Lett. 23, 3695–3698 (1982).

    CAS  Google Scholar 

  34. Goto, T., T. Kondo, H. Tamura, and K. Kawahori: Structure of Platyconin, a Diacylated Anthocyanin Isolated from the Chinese Bellflower Platycodon grandi-florum. Tetrahedron Lett. 24, 2181–2184 (1983).

    CAS  Google Scholar 

  35. Goto, T., T. Kondo, H. Tamura, and S. Takase: Structure of Malonylawobanin, the Real Anthocyanin Present in Blue-Colored Flower Petals of Commelina communis. Tetrahedron Lett. 24, 4863–4866 (1983).

    CAS  Google Scholar 

  36. Goto, T., T. Kondo, T. Kawai, and H. Tamura: Structure of Cinerarin, a Tetraacy- lated Anthocyanin Isolated from the Blue Garden Cineraria, Senecio cruentus. Tetrahedron Lett. 25, 6021–6024 (1984).

    CAS  Google Scholar 

  37. Goto, T., S. Takase, and T. Kondo: PMR Spectra of Natural Acylated Anthocyanins. Determination of Stereostructure of Awobanin, Shisonin and Violanin. Tetrahedron Lett. 2413–2416 (1978).

    Google Scholar 

  38. Goto, T., H. Tamura, T. Kawai, T. Hoshino, N. Harada, and T. Kondo: Chemistry of Metalloanthoeyanins. Annals New York Acad. Sci. 47, 155–173 (1986).

    Google Scholar 

  39. Goto, T., H. Tamura, and T. Kondo: Unpublished.

    Google Scholar 

  40. Harborne, J.B.: Spectral Methods of Characterizing Anthocyanins. Biochem. J. 70, 22–28 (1958).

    CAS  Google Scholar 

  41. Harborne, J.B.: Plant Polyphenols-XI. The Structure of Acylated Anthocyanins. Phytochem. 3, 151–160 (1964).

    CAS  Google Scholar 

  42. Harborne, J.B.: Flavonoids: Distribution and Contribution to Plant Colour. In: T.W. Goodwin (ed.) Chemistry and Biochemistry of Plant Pigments, Chapter 9, pp 247–267. Academic Press, New York, 1965.

    Google Scholar 

  43. Harborne, J.B. : Comparative Biochemistry of the Flavonoids. Academic Press, London, 1967.

    Google Scholar 

  44. Harborne, J.B., and M. Boardley: The Widespread Occurrence in Nature of Anthocyanins as Zwitterions. Z. Naturforsch. 40c, 305–308 (1985).

    CAS  Google Scholar 

  45. Harper, K.A.: Structure Changes of Flavylium Salts. J. Biol. Chem. Biothechnol. 23, 261–271 (1973).

    CAS  Google Scholar 

  46. Hayashi, K., Y. Abe, and S. Mitsui: Blue Anthocyanin from the Flowers of Commelina, the Crystallization and Some Properties Thereof. Studies on Anthocyanins XXX. Proc. Japan Acad. 34, 373–378 (1958).

    CAS  Google Scholar 

  47. Hayashi, K., N. Saito, and K. Mitsui: Anthocyanins (XXIV) Metallic Components in Newly Crystallized Specimens of Bayer’s Protocyanin, a Blue Metallo-Antho- cyanin from the Cornflower. Proc. Japan Acad. 37, 393–397 (1961).

    CAS  Google Scholar 

  48. Hayashi, K., and K. Takeda: Further Purification and Component Analysis of Commelinin Showing the Presence of Magnesium in This Blue Complex Molecule. Studies on Anthocyanins LXII. Proc. Japan Acad. 46, 535–540 (1970).

    CAS  Google Scholar 

  49. Hoshino, T., U. Matsumoto, and T. Goto: Evidences of the Self-association of Anthocyanins I. Circular Dichroism of Cyanin Anhydrobase. Tetrahedron Lett. 21, 1751–1754 (1980).

    CAS  Google Scholar 

  50. Hoshino, T., U. Matsumoto, and T. Goto: The Stabilizing Effect of the Acyl Group on the Co-pigmentation of Acylated Anthocyanins with C-Glucosylflavones. Phytochem. 19, 663–667 (1980).

    CAS  Google Scholar 

  51. Hoshino, T., U. Matsumoto, and T. Goto: Self-association of Some Anthocyanins in Neutral Aqueous Solution. Phytochem. 20, 1971–1976 (1981).

    CAS  Google Scholar 

  52. Hoshino, T., U. Matsumoto, T. Goto, and N. Harada: Evidence for the Self- association of Anthocyanins IV. PMR Spectroscopic Evidence for the Vertical Stacking of Anthocyanin Molecules. Tetrahedron Lett. 23, 433–436 (1982).

    CAS  Google Scholar 

  53. Hoshino, T., U. Matsumoto, N. Harada, and T. Goto: Chiral Exciton Coupled Stacking of Anthochanins : Interpretation of the Origin of Anomalous CD Induced by Anthocyanin Association. Tetrahedron Lett. 22, 3621–3624 (1981).

    CAS  Google Scholar 

  54. Hrazdina, G.: Anthocyanins. In: J.B. Harborne and T. Mabry (ed.), The Flavonoids, Chapter 3, pp 135–186, Chapman & Hall, London, 1982.

    Google Scholar 

  55. Hrazdina, G., H. Iredale, and L.R. Mattick: Anthocyanin Composition of Brassica oleracea cv. Red Danish. Phytochem. 16, 297–299 (1977).

    CAS  Google Scholar 

  56. Iacobucci, G., and J.G. Sweeny: The Chemistry of Anthocyanins, Anthocyanidins and Related Flavylium Salts, (review) Tetrahedron 39, 3005–3038 (1983).

    CAS  Google Scholar 

  57. Idaka, E., Y. Ohashi, T. Ogawa, T. Kondo, and T. Goto: Structure of Zebrinin, a Novel Acylated Anthocyanin Isolated From Zebrina pendula. Tetrahedron Lett., 28, 1901–1904 (1987).

    CAS  Google Scholar 

  58. Imbert, M.P., C.E. Seaforth, and D.B. Williams: Anthocyanin Pigments of the Sweet Potato, Ipomoea batatas. Proc. Am. Soc. Hort. Sci. 88, 481–485 (1966).

    CAS  Google Scholar 

  59. Ishikura, N., and S. Hayashida: Kaempferol Glycosides in the Seedcoat of Ophiopogon jaburan (Kunth) Lodd. Agric. Biol. Chem. 43, 1923–1926 (1979).

    CAS  Google Scholar 

  60. Ishikura, N., and M. Shimizu: Studies on the Flower Color of Morning Glory I. Anthocyanins and Some Concomitant Phenolics in the Blue Petals of Ipomoea ruburo-coerulea Hook, “Heavenly Blue” Kumamoto J. Sci. Biol. 12, 41–70 (1975).

    CAS  Google Scholar 

  61. Ishikura, N., and U. Takahama: Notes on the Anthocyanidin Types and Metals in Blue Flowers and Fruits. Kumamoto J. Sci. Biol. 11, 13–17 (1972).

    CAS  Google Scholar 

  62. Ishikura, N., and E. Yamamoto: Some Factors Involved in the Blue Color of ‘Heavenly Blue’ Morning Glory Flowers (in Japanese). Nippon Nogeikagaku Kaishi 54, 637–643 (1980).

    CAS  Google Scholar 

  63. Ishikura, N., and K. Yoshitama: Anthocyanin-Flavonol Co-pigmentation in Blue Seed Coats of Ophiopogon jaburan. J. Plant Physiol. 115, 171–175 (1984).

    CAS  Google Scholar 

  64. Jurd, L. : Anthocyanins and Related Compounds. I. Structural Transformations of Flavylium Salts in Acidic Solutions. J. Org. Chem. 28, 987–991 (1963).

    CAS  Google Scholar 

  65. Jurd, L., and T.A. Geissman: Anthocyanins and Related Compounds. II. Structure Transformations of Some Anhydro Bases. J. Org. Chem. 28, 2394–2397 (1968).

    Google Scholar 

  66. Karrer, P., and R. Widmer: Pflanzenfarbstoffe VIII. Ueber die Konstitution des Monardaeins. Helv. Chim. Acta 11, 837–842 (1928).

    CAS  Google Scholar 

  67. Karrer, P., and R. Widmer: Zur Konstitution des Monardaeins und Salvianins. XII. Mitteilung über Pflanzenfarbstoffe. Helv. Chim. Acta 12, 292–295 (1929).

    CAS  Google Scholar 

  68. Kondo, T., T. Kawai, H. Tamura, and T. Goto: Structure Determination of Heavenly Blue Anthocyanin, a Complex Monomeric Anthocyanin from the Morning Glory Ipomoea tricolor, by Means of the Negative NOE Method. Tetrahedron Lett., 28, 2273–2276 (1987).

    CAS  Google Scholar 

  69. Kondo, T., Y. Nakane, H. Tamura, T. Goto, and G.H. Eugster: Structure of Monardaein, a bis-Malonylated Anthocyanin Isolated from Golden Balm, Monarda didyma. Tetrahedron Lett. 26, 5879–5882 (1985).

    CAS  Google Scholar 

  70. Kondo, T., H. Tamura, S. Takase, and T. Goto: Complete Stereostructure Determination of Natural Acylated Anthocyanins, Violanin, Awobanin and Malonylawobanin by 1H-NMR. Nippon Kagaku Kaishi 1571–1578 (1986).

    Google Scholar 

  71. Kuroda, C.: The Colouring Matter of “Awobana” Parti. Proc. Imp. Acad. 7, 61–63 (1931).

    CAS  Google Scholar 

  72. Kuroda, C.: The Colouring Matter of “Awobana” Part II. Proc. Imp. Acad. 9, 94–96 (1933).

    CAS  Google Scholar 

  73. Kuroda, C.: The Colouring Matter of “Awobana” Part III. Proc. Imp. Acad. 11, 238–239 (1935).

    CAS  Google Scholar 

  74. Kuroda, C. : The Constitution of Awobanin and Awobanol, the Colouring Matter of Awobana and its Copigment. Bull. Chem. Soc. Japan 11, 265–270 (1936).

    CAS  Google Scholar 

  75. McClelland, R.A., and S. Gedge: Hydration of the Flavylium Ion. J. Am. Chem. Soc. 102, 5838–5848 (1980).

    CAS  Google Scholar 

  76. Mitsui, S., K. Hayashi, and S. Hattori: Further Studies on Commelinin, a Crystalline Blue Metalloanthocyanin from the Flowers of Commelina. Studies on Anthocyanins XXXI. Proc. Japan Acad. 35, 169–174 (1959).

    CAS  Google Scholar 

  77. Mitsui, S., K. Hayashi, and S. Hattori: Crystallization and Properties of Commelinin, a Blue Metallo-anthocyanin from Commelina. (Studies on Anthocyanins XXXI) (in Japanese). Bot. Mag. Tokyo 72, 853–854 (1959).

    Google Scholar 

  78. Nilsson, E.: Studies of Flavylium Compounds. Chemica Scripta 4, 49–55 (1973).

    CAS  Google Scholar 

  79. Ootani, S. : Chemico-genetical Studies on the Flower Colors and Pigment Components in Wild and Cultivated Pansies, with Special Regard to their Inter-varietal Relationship. Rep. Inst, for Breeding Res., Tokyo Univ. Agric., Supplement 1–72 (1973).

    Google Scholar 

  80. Osawa, Y. : Copigmentation of Anthocyanins. In: P. Markakis (ed.), Anthocyanins as Food Colors, Chapter 2, pp 41–68. Academic Press, New York, 1982.

    Google Scholar 

  81. Osawa, Y., M. Koizumi, and N. Saito: Zone Electrophoretic Investigation of Anthocyanins. Phytochem. 10, 1591–1593 (1971).

    CAS  Google Scholar 

  82. Pomilio, A.B., and J.F. Sproviero: Complex Anthocyanins From Ipomoea congesta. Phytochem. 11, 2323–2326 (1972).

    CAS  Google Scholar 

  83. Robinson, G.M., and R. Robinson: CLXXXII. A Survey of Anthocyanins. I. Bio-chem. J. 25, 1687–1705 (1931).

    CAS  Google Scholar 

  84. Robinson, R., and G.M. Robinson: The Colloid Chemistry of Leaf and Flower Pigments and the Precursors of the Anthocyanins. J. Am. Chem. Soc. 61, 1605–1606 (1939).

    CAS  Google Scholar 

  85. Saito, N., K. Abe, T. Honda, C.F. Timberlake, and P. Bridle: Acylated Delphinidin Glucosides and Flavonols from Clitoria ternatea. Phytochem. 24, 1583–1586 (1985).

    CAS  Google Scholar 

  86. Saito, N., Y. Osawa, and K. Hayashi: Platyconin, a New Acylated Anthocyanin in Chinese Bell-Flower, Platycodon grandiflorum. Phytochem. 10, 445–447 (1971).

    CAS  Google Scholar 

  87. Saito, N., K. Ueno, and K. Takeda: The Crystallographic Study of Commelinin, a Blue Metalloanthocyanin, and Its Reconstituted Analogues by the X-ray Diffraction Method. Meijigakuin Daigaku Ippankyoiku Fuzokukenkyusho Kiyo No 10, 63–81 (1986).

    Google Scholar 

  88. Saito, N., Y. Osawa, and K. Hayashi: Isolation of a Blue-Violet Pigment from the Flowers of Platycodon grandiflorum. Bot. Mag. Tokyo 85, 105–110 (1972).

    CAS  Google Scholar 

  89. Saito, N., C.F. Timberlake, O.G. Tucknott, and I.A.S. Lewis: Fast Atom Bombardment Mass Spectrometry of the Anthocyanins Violanin and Platyconin. Phytochem. 22, 1007–1009 (1983).

    CAS  Google Scholar 

  90. Scheffeldt, P., and G. Hrazdina: Co-pigmentation of Anthocyanins under Physiological Conditions. J. Food Science 43, 517–520 (1978).

    CAS  Google Scholar 

  91. Shibata, K., Y. Shibata, and I. Kasiwagi: Studies on Anthocyanin. Color Variation in Anthocyanins. J. Am. Chem. Soc. 41, 208–220 (1919).

    CAS  Google Scholar 

  92. Singleton, V.L. : Common Plant Phenols Other than Anthocyanins, Contributions to Coloration and Discoloration. In: C.O. Chichester (ed.) The Chemistry of Plant Pigments, pp 143–191. Academic Press, New York, 1972.

    Google Scholar 

  93. Sommers, T.C., and M.E. Evans: Grape Pigment Phenomena: Interpretation of Major Colour Losses During Vinification. J. Sci. Food Agric. 30, 623–633 (1979).

    Google Scholar 

  94. Sulyok, G., and A. Laszlo-Bencsik : Cyanidin 3-(6-succinylglucoside)-5-glucoside from Flowers of Seven Centaurea Species. Phytochem. 24, 1121–1122 (1985).

    CAS  Google Scholar 

  95. Sweeny, J.G., M.M. Wilkinson, and G.A. Iacobucci: Effect of Flavonoid Sulfonates on the Photobleaching of Anthocyanins in Acid Solution. J. Agric. Food. Chem. 29, 563–567 (1981).

    CAS  Google Scholar 

  96. Takeda, K. : Metallo-anthocyanins II. Further Experiments of Synthesizing Crystalline Blue Metallo-anthocyanins Using Various Kinds of Bivalent Metals. Proc. Japan Acad. 53, Ser. B, 257–261 (1977).

    Google Scholar 

  97. Takeda, K., T. Fujii, and M. Iida: Magnesium in the Blue Pigment Complex Commelinin. Phytochem. 23, 879–881 (1984).

    CAS  Google Scholar 

  98. Takeda, K., and K. Hayashi: Oxidative Degradation of Acylated Anthocyanins Showing the Presence of Organic Acid-sugar Linkage in the 3-Position of Anthocyanidins; Experiments on Ensatin, Awobanin, and Shisonin. Studies on Anthocyanins XLIII. Proc. Japan Acad. 40, 510–515 (1964).

    CAS  Google Scholar 

  99. Takeda, K., and K. Hayashi: Metallo-anthocyanins I. Reconstruction of Commelinin from Its Components, Awobanin, Flavocommelin and Magnesium. Proc. Japan Acad. 53, Ser B, 1–5 (1977).

    Google Scholar 

  100. Takeda, K., R. Kubota, and C. Yagioka: Copigments in the Blueing of Sepal Colour of Hydrangea macrophylla. Phytochem. 24, 1207–1209 (1985); K. Takeda, M. Kariuda, and H. Itoi: Blueing of Sepal Colour of Hydrangea macrophylla. Phytochem. 24, 2251–2254 (1985).

    CAS  Google Scholar 

  101. Takeda, K., S. Mitsui, and K. Hayashi: Structure of a New Flavonoid in the Blue Complex Molecule of Commelinin. Studies on Anthocyanins LIV. Bot. Mag. Tokyo 79, 578–587 (1966).

    CAS  Google Scholar 

  102. Takeda, K., N. Saito, and K. Hayashi: Further Experiments on the Structure of Genuine Anthocyanins. Studies on Anthocyanins LIX. Proc. Japan Acad. 44, 352–357 (1968).

    CAS  Google Scholar 

  103. Takeda, K., and S. Tominaga: The Anthocyanin in Blue Flowers of Centaurea cyanus. Bot. Mag. Tokyo 96, 359–363 (1983).

    CAS  Google Scholar 

  104. Tamura, H., T. Kondo, and T. Goto: The Composition of Commelinin, a Highly Associated Metalloanthocyanin Present in the Blue Flower Petals of Commelina communis. Tetrahedron Lett. 27, 1801–1804 (1986).

    CAS  Google Scholar 

  105. Tamura, H., T. Kondo, Y. Kato, and T. Goto: Structure of Succinyl Anthocyanin and a Malonyl Flavone, Two Constituents of the Complex Blue Pigment of Cornflower Centaurea cyanus. Tetrahedron Lett. 24, 5749–5752 (1983).

    CAS  Google Scholar 

  106. Tanchev, S.S., and C.F. Timberlake: The Anthocyanins of Red Cabbage (Brassica oleracea). Phytochem. 8, 1825–1827 (1969).

    CAS  Google Scholar 

  107. Timberlake, C.F.: Anthocyanins—Occurrence, Extraction and Chemistry. Food Chem. 5, 69–80 (1980).

    CAS  Google Scholar 

  108. Timberlake, C.F. : Anthocyanins in Fruits and Vegetables. In: J. Friend, and M.J.C. Rhodes (ed.), Recent Advances in the Biochemistry of Fruit and Vegetables, Chapter 12, pp 221–247. Academic Press, New York, 1981–1982.

    Google Scholar 

  109. Timberlake, C.F., and P. Bridle: Spectral Studies of Anthocyanin and Anthocyanidin Equilibria in Aqueous Solution. Nature 212, 158–159 (1966).

    CAS  Google Scholar 

  110. Timberlake, C.F., and P. Bridle: The Anthocyanins. In: J.B. Harborne, T.J. Mabry, and H. Mabry (ed.), The Flavonoids, Chapter 5, pp 215–266. Chapman & Hall, London, 1975.

    Google Scholar 

  111. Timberlake, C.F., and P. Bridle: Anthocyanins. In: J. Walford (ed.), Developments in Food Colours — 1, Chapter 5, pp 115–150. Applied Science Publ., London, 1980.

    Google Scholar 

  112. Watanabe, S., S. Sakamura, and Y. Obata: The Structure of Acylated Anthocyanins in Eggplant and Perilla, and the Position of Acylation. Agric. Biol. Chem. 30, 420–422 (1966).

    CAS  Google Scholar 

  113. Williams, M., and G. Hrazdina: Anthocyanins as Food Colorants: Effect of pH on the Formation of Anthocyanin-Rutin Complexes. J. Food Science 44, 66–68 (1979).

    CAS  Google Scholar 

  114. Willstätter, R., and E.K. Bolton: Untersuchungen über die Anthocyane; XI. Über das Anthocyan der rotblühenden Salviaarten. Liebigs Ann. Chem. 412, 113–137 (1917).

    Google Scholar 

  115. Willstätter, R., and A.E. Everest: Untersuchungen über die Anthocyane I. Über den Farbstoff der Kornblume. Liebigs Ann. Chem. 401, 189–232 (1913).

    Google Scholar 

  116. Yazaki, Y.: Co-pigmentation and the Color Change with Age in Petals of Fuchsia hybrida. Bot. Mag. Tokyo 89, 45–57 (1976).

    CAS  Google Scholar 

  117. Yazaki, Y., and K. Hayashi: Analysis of Flower Colors in Fuchsia hybrida in Reference to the Concept of Co-pigmentation. Studies on Anthocyanins. LVI. Proc. Japan Acad. 43, 316–321 (1967).

    CAS  Google Scholar 

  118. Yoshitama, K.: An Acylated Delphinidin 3-Rutinoside-5, 3′, 5′-triglucoside from Lobelia erinus. Phytochem. 16, 1857–1858 (1977).

    CAS  Google Scholar 

  119. Yoshitama, K. : Blue and Purple Anthocyanins Isolated from the Flowers of Tradescantia reflexa. Bot. Mag. Tokyo 91, 207–212 (1978).

    CAS  Google Scholar 

  120. Yoshitama, K., and K. Hayashi: Concerning the Structure of Cinerarin, a Blue Anthocyanin From Garden Cineraria. Studies on Anthocyanins, LXVI. Bot. Mag. Tokyo 87, 33–40 (1974).

    CAS  Google Scholar 

  121. Yoshitama, K., K. Hayashi, K. Abe, and H. Kakisawa: Further Evidence for the Glycoside Structure of Cinerarin. Studies on Anthocyanins, LXVII. Bot. Mag. Tokyo 88, 213–217 (1975).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Laboratory of Organic Chemistry, Faculty of Agriculture, Nagoya University, Chikusa, Nagoya, Japan

    T. Goto

Authors
  1. T. Goto
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 1987 Springer-Verlag/Wien

About this chapter

Cite this chapter

Goto, T. (1987). Structure, Stability and Color Variation of Natural Anthocyanins. In: Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 52. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8906-1_3

Download citation

  • DOI: https://doi.org/10.1007/978-3-7091-8906-1_3

  • Publisher Name: Springer, Vienna

  • Print ISBN: 978-3-7091-8908-5

  • Online ISBN: 978-3-7091-8906-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation