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Identification of betanin degradation products

Identifizierung von Abbauprodukten des Betanin

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Zusammenfassung

Betanin-Lösungen wurden beim Erhitzen zu Betalaminsäure und 6-Hydroindol-2-carbonsäure-5-O-glykosid hydrolysiert. Die Reaktion wurde mit analytischer Hochdruckflüssigkeits-Chro-matographie (HPLC) überwacht. Die Produkte wurden durch präparative Phasenumkehr-HPLC oder Anionen-Austauscher-Sdulenchromatographie isoliert. Zum Nachweis der Abbauprodukte wurden Derivate der Betalaminsäure (Anilid, Semicarbazon, Kondensation Mitl-Prolin) und Cyclodopa-5-O-glykosid (Hexaacetat) hergestellt. Die Bildung eines decarboxylierten Betanins wurde auf Grund des gebildeten CO2, der chromatographischen Eigenschaften und der Lichtabsorption des decarboxylierten Produktes vorgeschlagen.

Summary

Betanin in solution, upon heating, was found to hydrolyze to betalamic acid and cyclodopa-5-O-glycoside. This reaction was monitored by an analytical high performance liquid chromatography (HPLC) method. The products were isolated by preparative reversed-phase HPLC or column chromatography using anion-exchange resins. Derivatives of betalamic acid (anilide, semicarbazone, condensation withl-proline) and cyclodopa-5-O-glycoside (hexaacetate) were prepared as evidence to support the identification of these decomposition compounds. Formation of decarboxylated betanin was proposed based on the identification of CO2, chromatographic properties and the light absorption characteristics of the decarboxylated product.

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References

  1. von Elbe JH, Pasch JH, Adams JP (1974) Betalaines as food colorants. Proc. IV Int. Congrss Food Sci and Technol Vol 1, p 485–492

    Google Scholar 

  2. Attoe EL, von Elbe JH (1982) Degradation kinetics of betanine in solutions as influenced by oxygen. J Agric Food Chem 30:708–712

    Google Scholar 

  3. Pasch JH, von Elbe JH (1979) Betanine stability in buffered solutions containing organic acids, metal cations, antioxidants, or sequestrants. J Food Sci 44:72–74

    Google Scholar 

  4. Saguy I (1979) Thermostability of red beet pigments (betanine and vulgaxanthine-I): Influence of pH and temperature. J Food Sci 4:1554–1555

    Google Scholar 

  5. Savolainen K, Kuusi T (1978) The stabilitiy properties of golden beet and red beet pigments: Influence of pH, temperature, and some stabilizers. Z Lebensm Unters Forsch 166:19–22

    Google Scholar 

  6. von Elbe JH, Maing IY, Amundson CH (1974) Color stability of betanin. J Food Sci 39:334–337

    Google Scholar 

  7. Wyler H, Dreiding AS (1962) Abbauprodukte des Betanidins. Helv Chim Acta 45:638–640

    Google Scholar 

  8. Kimler L (1972) Betalamic acid and other products of the biotransformation of L-dopa in betalain biogenesis. Ph. D. Thesis, University of Texas, Austin

    Google Scholar 

  9. Saguy I, Kopelman IJ, Mizrahi S (1978) Thermal kinetic degradation of betanin and betalamic acid. J Agric Food Chem 26:360–362

    Google Scholar 

  10. von Elbe JH, Schwartz SJ, Hildenbrand BE (1981) Loss and regeneration of betacyanin pigments during processing of red beets. J Food Sci 46:1713–1715

    Google Scholar 

  11. Adams JP, von Elbe JH (1977) Betanine separation and quantification by chromatography on gels. J Food Sci 43:410–414

    Google Scholar 

  12. Schwartz SJ, von Elbe JH (1980) Quantitative determination of individual betacyanin pigments by high-performance liquid chromatography. J Agric Food Chem 28:540–543

    Google Scholar 

  13. Wilcox ME, Wyler H, Mabry TJ, Dreiding AS (1965) Die Struktur des Betanins. Helv Chim Acta 48:252–258

    Google Scholar 

  14. Kimler L, Larson RA, Messenger L, Moore JB, Mabry TJ (1971) Betalamic acid, a new naturally occurring pigment. Chem Commun 1329–1330

  15. Wilcox ME, Wyler H, Dreiding AS (1965) Derivate der Betalaminsdure. Helv Chim Acta 48:1922–1926

    Google Scholar 

  16. Büchi G, Fliri H, Shapiro R (1978) Synthesis of betalaines. J Org Chem 43:4765–4769

    Google Scholar 

  17. Piattelli M, Minale L, Prota G (1964) Isolation, structure and absolute configuration of indicaxanthin. Tetrahedron 20:2325–2329

    Google Scholar 

  18. Piattelli M, Minale L (1964) Pigments of Centrospermae II. Distribution of betacyanins. Phytochem 3:547–557

    Google Scholar 

  19. Sciuto S, Oriente G, Piattelli M (1972) Betanidin glucosylation inOpuntia dellenii. Phytochem 11:2259–2262

    Google Scholar 

  20. Wyler H (1972) Biogenesis of betalaines. Physiol Chemie 35:126–127

    Google Scholar 

  21. Miller HE, Rösler H, Wohlpart A, Wyler H, Wilcox ME, Frohofer H, Mabry TJ, Dreiding AS (1968) Biogenese der Betalaine. Biotransformation von Dopa und Tyrosin in den Betalaminsäu-reteil des Betanins. Helv Chim Acta 51:1470–1474

    Google Scholar 

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Authors and Affiliations

  1. Department of Food Science, University of Wisconsin-Madison, WI 53706, Madison, USA

    Steven J. Schwartz & Joachim H. von Elbe

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  1. Steven J. Schwartz
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  2. Joachim H. von Elbe
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Additional information

This research was supported by the College of Agricultural and Life Sciences, University of Wisconsin-Madison

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Schwartz, S.J., von Elbe, J.H. Identification of betanin degradation products. Z Lebensm Unters Forch 176, 448–453 (1983). https://doi.org/10.1007/BF01042560

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  • DOI: https://doi.org/10.1007/BF01042560

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