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Accumulation of phenolic acid conjugates and betacyanins, and changes in the activities of enzymes involved in feruloylglucose metabolism in cell-suspension cultures of Chenopodium rubrum L.

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Abstract

Cell-suspension cultures of Chenopodium rubrum accumulate various soluble secondary phenolic metabolites such as the hydroxybenzoic acid glycosides 4-hydroxybenzoic acid-β-glucoside, vanillic acid-β-glucoside, the hydroxycinnamic acid acylglycosides 1-O-(4-coumaroyl)-β-glucose, 1-O-feruloyl-β-glucose, 1-O-sinapoyl-β-glucose and 1-O-feruloyl-(β-1,2-glucuronosyl)-β-glucose, the hydroxycinnamic acid amide N-feruloylaspartate, and the betacyanins betanin, amaranthin and celosianin II. In addition, accumulation of the insoluble cell wall-bound hydroxycinnamic acids with ferulic acid as the major component occurs parallel to culture growth. The changes of three pivotal enzymatic activities, all O-transferases which are involved in the formation of the dominant ferulic acid conjugates, were determined. These are (i) uridine 5′-diphosphate(UDP)glucose-hydroxycinnamic acid O-glucosyltransferase (EC 2.4.1), (ii) UDP-glucuronic acid:1-O-hydroxycin-namoyl-β-glucose O-glucuronosyltransferase (EC 2.4.1) and (iii) 1-O-hydroxycinnamoyl-β-glucose:amaranthin O-hydroxycinnamoyltransferase (EC 2.3.1). The patterns of metabolite accumulation associated with these enzyme activities show that the hydroxycinnamic acid-glucose esters play a central role as metabolically active intermediates in the secondary metabolism of Ch. rubrum. Two cell lines of this culture (CH, CHN), differing in their betacyanin content, were compared with respect to this metabolism. A markedly higher total betacyanin content in the CHN line might possibly be the consequence of an increased supply of the key precursor for betalain biosynthesis, i.e. 3,4-dihydroxyphenylalanine (DOPA). In addition, the enhanced accumulation of celosianin II in the CHN line correlates well with a higher activity of the enzyme catalyzing the transfer of ferulic acid from 1-O-feruloyl-β-glucose to amaranthin.

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Abbreviations

CH line:

red-coloured betalain-producing cell-suspension cultures of Chenopodium rubrum (lower betacyanin content)

CHN line:

deep-red-coloured betalain-producing cell-suspension cultures of Ch. rubrum (higher betacyanin content), selected from CH line

DOPA:

3,4-dihydroxyphenylalanine

glucosyltransferase:

uridine 5′-diphosphate-glucose hydroxycinnamic acid O-glucosyltransferase (EC 2.4.1)

glucuronosyltransferase:

uridine 5′-diphosphate-glucuronic acid: 1-O-hydroxycinnamoyl-β-glucose O-glucuronosyltransferase (EC 2.4.1)

HPLC:

high-performance liquid chromatography

hydroxycinnamoyltransferase:

1-O-hydroxycinnamoyl-β-glucose:amaranthin O-hydroxycinnamoyltransferase (EC 2.3.1)

NMR:

nuclear magnetic resonance

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Authors and Affiliations

  1. Institut für Pharmazeutische Biologie der Technischen Universität Braunschweig, Mendelssohnstrasse 1, W-3300, Braunschweig, Germany

    Maria Bokern & Dieter Strack

  2. GBF — Gesellschaft für Biotechnologische Forschung, Mascheroder Weg 1, W-3300, Braunschweig, Germany

    Victor Wray

Authors
  1. Maria Bokern
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  2. Victor Wray
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  3. Dieter Strack
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Additional information

Support by the Deutsche Forschungsgemeinschaft and by the Fonds der Chemischen Industrie to D.S. is gratefully acknowledged. We thank Sabine Fehling for help in cell wall analyses and Heike Steingaß for optimization of enzyme assays. Our special thanks are due to Dr H. Harms (FAL, Braunschweig, FRG) and Dr J. Berlin (BBA, Braunschweig) for establishing and providing the CH and CHN lines, respectively, of the Chenopodium rubrum cell culture. We are grateful to Christel Kokoschka, H. Dirks and Inge Schweer (GBF, Braunschweig) for recording the NMR, FAB MS and EI MS data, respectively.

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Bokern, M., Wray, V. & Strack, D. Accumulation of phenolic acid conjugates and betacyanins, and changes in the activities of enzymes involved in feruloylglucose metabolism in cell-suspension cultures of Chenopodium rubrum L.. Planta 184, 261–270 (1991). https://doi.org/10.1007/BF00197956

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