Abstract
Protein preparations from cell-suspension cultures of an Afghan cultivar of Daucus carota (carrot) catalyzed the formation of acylated anthocyanins from a cyanidin triglycoside isolated from the carrot cultures using (1-O-sinapoyl-, 1-O-feruloyl-) and 1-O-(p-coumaroyl)-β-glucose as acyl donors. The enzyme activities can be classified as 1-O-hydroxycinnamoyl-β-glucose: cyanidin 3-O-(2″-O-xylosyl-6″-O-glucosylgalactoside) 6‴-O-hydroxycinnamoyltransferases (EC 2.3.1.-).
Similar content being viewed by others
Abbreviations
- HCA:
-
hydroxycinnamic acid
- HPLC-MS:
-
high-performance liquid chromatography — mass spectrometry
References
Albach, R.F., Kepner, R.E., Webb, A.D. (1965) Structures of acylated anthocyanin pigments in Vitis vinifera variety Tinta Pinheira. Identification of anthocyanidin, sugar, and acid moieties. J. Food Sci. 30, 69–76
Barz, W., Köster, J., Weltring, K.-M., Strack, D. (1985) Recent advances in the metabolism of phenolic compounds in plants and animals. Annu. Proc. Phytochem. Soc. 25, 307–347
Bokern, M., Strack, D. (1988) Synthesis of hydroxycinnamic acid esters of betacyanins via 1-O-acylglucosides of hydroxycinnamic acids by protein preparations from cell suspension cultures of Chenopodium rubrum and petals of Lampranthus sociorum. Planta 174, 101–105
Bokern, M., Wray, V., Strack, D. (1991) Accumulation of phenolic acid conjugates and betacyanins, and changes in the activities of enzymes involved in feruloylglucose metabolism in cellsuspension cultures of Chenopodium rubrum L. Planta 184, 261–270
Bradford, M.M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248–254
Brouillard, R. (1983) The in vivo expression of anthocyanin colour in plants. Phytochemistry 22, 1311–1323
Bruins, A.P., Covey, T.R., Henion, J.D. (1987) Ion spray interface for combined liquid chromatography/atmospheric pressure ionization mass spectrometry. Anal. Chem. 59, 2642–2646
Gläßgen, W.E., Wray, V., Strack, D., Metzger, J.W., Seitz, H.U. Anthocyanins from cell suspension cultures of Daucus carota. Phytochemistry, in press
Gleitz, J., Seitz, H.U. (1989) Induction of chalcone synthase in cell suspension cultures of carrot (Daucus carota L. ssp. sativus) by ultraviolet light: evidence for two different forms of chalcone synthase. Planta 179, 323–330
Goto, T., Kondo, T. (1991) Struktur und molekulare Stapelung von Anthocyanen-Variation der Blütenfarben. Angew. Chem. 103, 17–33
Halaweish, F.T., Dougall, D.K. (1990) Sinapoyl glucose synthesis by extracts of wild carrot cell cultures. Plant Sci. 71, 179–184
Harborne, J.B. (1967) Comparative biochemistry of the flavonoids. Academic Press, London
Harborne, J.B., Mayer, A.M., Bar-Nun, N. (1983) Identification of the major anthocyanin of carrot cells in tissue culture as cyanidin 3-(sinapoylxylosylglucosylgalactoside). Z. Naturforsch. 38c, 1055–1056
Heller, W., Forkmann, G. (1988) Biosynthesis. In: The flavonoids: advances in research since 1980, pp. 399–425, Harborne, J.B., ed. Chapman and Hall, London
Hopp, W. Seitz, H.U. (1987) The uptake of acylated anthocyanin into isolated vacuoles from a cell suspension culture of Daucus carota. Planta 170, 74–85
Kamsteeg, J., Van Brederode, J., Hommels, C.H., Van Nigtevecht, G. (1980) Identification, properties and genetic control of hydroxycinnamoyl-coenzyme A: anthocyanidin 3-rhamnosyl(1→6)glucoside 4‴-hydroxycinnamoyl transferase isolated from petals of Silene dioica. Biochem. Physiol. Pflanz. 175, 403–411
Matern, U., Reichenbach, C., Heller, W. (1986) Efficient uptake of flavonoids into parsley (Petroselinum hortense) vacuoles requires acylated glycosides. Planta 167, 183–189
Noé, W., Langebartels, C., Seitz, H.U. (1980) Anthocyanin accumulation and PAL-activity in a suspension culture of Daucus carota L. Inhibition by 1-α-aminooxy-β-phenylpropionic acid and t-cinnamic acid. Planta 149, 283–287
Saylor, M.H., Mansell, R.L. (1977) Hydroxycinnamoyl: coenzyme A transferase involved in the biosynthesis of kaempferol-3-(p- coumaroyl triglucoside) in Pisum sativum Z. Naturforsch. 32c, 765–768
Stöckigt, J., Zenk, M.H. (1975) Chemical syntheses and properties of hydroxycinnamoyl-coenzyme A derivatives. Z. Naturforsch. 30c, 352–358
Strack, D., Knogge, W., Dahlbender, B. (1983) Enzymatic synthesis of sinapine from 1-O-sinapoyl-β-d-glocose and choline by a cell-free system from developing seeds of red radish (Raphanus sativus L. var. sativus). Z. Naturforsch. 38c, 21–27
Strack, D., Gross, W., Heilemann, J., Keller, H., Ohm, S. (1988) Enzymic synthesis of hydroxycinnamic acid esters of glucaric acid and hydroaromatic acids from the respective 1-O-hydroxycinnamoylglucoside and hydroxycinnamoyl-coenzyme A thioester as acyldonors with a protein preparation from Cestrum elegans leaves. Z. Naturforsch. 43c, 32–36
Teusch, M., Forkmann, G., Seyffert, W. (1987) Genetic control of hydroxycinnamoyl-coenzyme A: anthocyanidin 3-glycosidehydroxycinnamoyltransferase from petals of Matthiola incana. Phytochemistry 26, 991–994
Villegas, R.J.A., Kojima, M. (1986) Purification and characterization of hydroxycinnamoyl d-glucose quinate hydroxycinnamoyl transferase in the root of sweet potato, Ipomoea batatas LAM. J. Biol. Chem. 261, 8729–8733
Zenk, M.H. (1979) Recent work on cinnamoyl CoA derivatives. In: Recent advances in phytochemistry, vol. 12, pp. 139–176, Swain, T., Harborne, J.B., Van Sumere, C.F., eds. Plenum Press, New York London
Author information
Authors and Affiliations
Additional information
The authors wish to express their thanks to Dr. D. Strack and his co-workers (Technische Universität, Braunschweig, FRG) for kindly providing us with the 1-O-acylglucosides and for many helpful discussions. The HPLC-MS was performed with the excellent help of Dr. J.W. Metzger (Universität Tübingen, FRG). The technical assistance of J. Madlung is gratefully acknowledged. We are also grateful to Dr. F. Constabel (Plant Biotechnology Institute, Saskatoon, Canada) for critical reading of the English manuscript. This work was supported by a fellowship (LGFG) of the Land Baden-Württemberg and by the Deutsche Forschungsgemeinschaft.
Rights and permissions
About this article
Cite this article
Edgar Gläßgen, W., Ulrich Seitz, H. Acylation of anthocyanins with hydroxycinnamic acids via 1-O-acylglucosides by protein preparations from cell cultures of Daucus carota L.. Planta 186, 582–585 (1992). https://doi.org/10.1007/BF00198039
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00198039