Skip to main content
SpringerLink
Log in

Flavonoid glycosides and hydroxycinnamic acid esters of blackcurrants (Ribes nigrum)

Phenolics of Fruits 9

Flavonoidglykoside und Hydroxyzimtsäure-Ester der Schwarzen Johannisbeeren (Ribes nigrum)

9. Mitteilung über phenolische Inhaltsstoffe des Obstes

  • Original Papers
  • Published:
Zeitschrift für Lebensmittel-Untersuchung und Forschung Aims and scope Submit manuscript

Zusammenfassung

Aus den reifen Beeren der Schwarzen Johannisbeeren (Ribes nigrum „Silvergieters Schwarze”) wurden Myricetin-3-β-d-glucopyranosid, Rutin und Isoquercitrin als Hauptflavonolglykoside kristallin gewonnen. Dünnschichtchromatographisch wurde das Vorkommen der 3-Rutinoside und 3-Glucoside des Cyanidins und Delphinidins bestätigt. Freie Flavonoid-Aglykone treten jedoch in frischen Beeren nicht auf. Die hauptsächliche auf Papier- und Cellulose Dünnschichtchromatogrammen unter Ultraviolettlicht blau fluorescierende Verbindung wurde als 1-O-Caffeyl-β-d-glucopyranose charakterisiert. Daneben wurden 1-O-Ferulyl- und 1-O-p-Cumaryl-β-d-glucopyranose isoliert. Zuckerester der Hydroxyzimtsäuren sind bisher offensichtlich in Schwarzen Johannisbeeren noch nicht aufgefunden worden.

Summary

The major flavonol glycosides of ripe blackcurrants (Ribes nigrum cv. Silvergieters Schwarze), myricetin 3-β-d-glucopyranoside, rutin, and isoquercitrin, have been isolated in crystalline form. Analysis by thin-layer chromatography confirmed the occurrence of the 3-rutinosides and 3-glucosides of cyanidin and delphinidin. No free flavonoid aglycones could, however, be detected in the fresh berries. The major constituent fluorescing blue under ultraviolet light on paper and cellulose thin-layer chromatograms, was isolated and characterized as 1O-caffeyl-β-d-glucopyranose. Also isolated were 1-O-ferulyl-and 1-O-p-coumaryl-β-d-glucopyranose. The occurrence of hydroxycinnamyl-d-glucoses in black-currants does not appear to have been recognized previously.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

References

  1. Robinson, G. H., Robinson, R.: Biochem. J.25, 1687 (1931)

    Google Scholar 

  2. Pollard, A.: Nature (Lond.)150, 490 (1942)

    Google Scholar 

  3. Kühnau, J.: Klin. Wschr.27, 249 (1949)

    Google Scholar 

  4. Williams, B. L., Ice, C. H., Wender, S. H.: J. Amer. Chem. Soc.74, 4566 (1952)

    Google Scholar 

  5. Fouassin, A.: Rev. Ferment.11, 173 (1956)

    Google Scholar 

  6. Schinz, H., Seidel, C. F.: Helv. Chim. Acta40, 1839 (1957)

    Google Scholar 

  7. Kajanne, P., Stén, M.: Suomen KemistilehtiB 31, 149 (1958)

    Google Scholar 

  8. Gleisberg, W., Aumann, H.: Gartenbauwissenschaft23, 512 (1958)

    Google Scholar 

  9. Herrmann, K.: Z. Lebensm. Unters.-Forsch.108, 152 (1958)

    Google Scholar 

  10. Chandler, B. V., Harper, K. A.: Nature (Lond.)181, 131 (1958)

    Google Scholar 

  11. Mehlitz, A., Matzick, B.: Ind. Obst-Gemüseverwert.43, 171 (1958)

    Google Scholar 

  12. Mehlitz, A., Drews, H.: Ind. Obst-Gemüseverwert.45, 174 (1960)

    Google Scholar 

  13. Reichel, L., Reichwald, W.: Naturwissenschaften47, 41 (1960)

    Google Scholar 

  14. Gleisberg, W., Aumann, H.: Gartenbauwissenschaft25, 1 (1960)

    Google Scholar 

  15. Ayres, A. D., Charley, V. L. S., Swindells, R.: Food Proc. Pack.30, 413 (1961)

    Google Scholar 

  16. Chandler, B. V., Harper, K. A.: Austral. J. Chem.15, 114 (1962)

    Google Scholar 

  17. Harborne, J. B., Hall, E.: Phytochemistry3, 453 (1964)

    Google Scholar 

  18. Samarodova-Bianki, G. B.: Biokhimiya30, 248 (1965)

    Google Scholar 

  19. Blundstone, H. A. W., Crean, D. E. C.: The pigments of red fruits. Report of Fruit and Veg. Pres. Res. Assoc., Chipping Campden 1966

  20. Koch, J., Haase-Sajak, E.: Z. Lebensm. Unters.-Forsch.131, 347 (1967)

    Google Scholar 

  21. Demina, T. G.: Rast. Resur4, 88 (1968); cf. Chem. Abstracts69, 16829 (1968)

    Google Scholar 

  22. Morton, A. D.: J. Food Technol.3, 269 (1968)

    Google Scholar 

  23. Berger, W.-G.: Catechine und deren Abbauprodukte in Weintrauben, Trestern, Essigweinen und daraus hergestellten Essigen. Nachweis der Verfälschung von Essigweinen durch Trester-und Nachweine, p. 84. Diss. Techn. Univ. Hannover 1971

  24. Wildanger, W., Herrmann, K.: Z. Lebensm. Unters.-Forsch.151, 103 (1973)

    Google Scholar 

  25. Stöhr, H., Herrmann, K.: Z. Lebensm. Unters.-Forsch.159, 31 (1975)

    Google Scholar 

  26. Le Lous, J., Majoie, B., Morinière, J.-L., Wulfert, E.: Ann. Pharm. Fr.33, 393 (1975)

    Google Scholar 

  27. Starke, H., Herrmann, K.: Z. Lebensm. Unters.-Forsch.161, 131 (1976)

    Google Scholar 

  28. Bacharach, A. L., Coates, M. E.: Biochem. J.38, 5 (1944)

    Google Scholar 

  29. Roux, D. G., Maihs, E.: J. Chromatog.4, 65 (1960)

    Google Scholar 

  30. Partridge, S. M.: Nature (Lond.)164, 443 (1949)

    Google Scholar 

  31. Koeppen, B. H., Roux, D. G., Smit, C. J. B.: Biochem. J.82, 507 (1962)

    Google Scholar 

  32. Mabry, T. J., Markham, K. R., Thomas, M. B.: The systematic identification of flavonoids. Berlin-Heidelberg-New York: Springer 1970

    Google Scholar 

  33. Birkofer, L., Kaiser, C., Nouvertné, W., Thomas, U.: Z. Naturforsch.166, 249 (1961)

    Google Scholar 

  34. Harborne, J. B., Corner, J. J.: Biochem. J.81, 242 (1961)

    Google Scholar 

  35. Birkofer, L., Kaiser, C., Hillges, B., Becker, F.:Liebigs Ann. Chem.725, 196 (1969)

    Google Scholar 

  36. Simonyan, A. V., Litvinenko, V. I., Shinkarenko, A. L.: Khim. Prir. Soedin.-Chem. Nat. Compounds (USSR)8, 383 Russ., 372 Eng. (1972)

    Google Scholar 

  37. Maier, V. P., Metzler, D. M., Huber, A. F.: Biochem. Biophys. Res. Comm.14, 124 (1964)

    Google Scholar 

  38. Harborne, J. B., Williams, C. A.: In: Harborne, J. B., Mabry, T. J., Mabry, H. The flavonoids, p. 427. London: Chapman and Hall 1975

    Google Scholar 

  39. Sotnikova, O. M., Litvinenko, V.I.: Khim. Prir. Soedin.-Chem. Nat. Compounds (USSR)4, 50 Russ., 42 Eng. (1968)

    Google Scholar 

  40. Soboleva, V. A., Chagovets, R. K.: Khim. Prir. Soedin.-Chem. Nat. Compounds (USSR)7, 528 Russ., 509 Eng. (1971)

    Google Scholar 

  41. Medvedeva, S. A., Tyukavkina, N. A., Ivanova, S. Z.: Khim. Prir. Soedin.-Chem. Nat. Compounds (USSR)8, 800 Russ., 781 Eng. (1972)

    Google Scholar 

  42. Chumbalov, T. K., Omurkamzinova, V. B.: Khim. Prir. Soedin.-Chem. Nat. Compounds (USSR)11, 424 Russ., 438 Eng. (1975)

    Google Scholar 

Download references

Author information

Author notes

  1. Brian H. Koeppen

    Present address: Department of Food Science, University of Stellenbosch, 7600, Republic of South Africa

Authors and Affiliations

  1. Chair of Food Chemistry, Technical University of Hannover, Wunstorfer Str. 14, D-3000, Hannover 91, Bundesrepublik Deutschland

    Brian H. Koeppen & Karl Herrmann

Authors
  1. Brian H. Koeppen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Karl Herrmann
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Koeppen, B.H., Herrmann, K. Flavonoid glycosides and hydroxycinnamic acid esters of blackcurrants (Ribes nigrum). Z Lebensm Unters Forch 164, 263–268 (1977). https://doi.org/10.1007/BF01147302

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01147302

Keywords

Search

Navigation