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Sinapate esters in brassicaceous plants: biochemistry, molecular biology, evolution and metabolic engineering

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Abstract

Brassicaceous plants are characterized by a pronounced metabolic flux toward sinapate, produced by the shikimate/phenylpropanoid pathway, which is converted into a broad spectrum of O-ester conjugates. The abundant sinapate esters in Brassica napus and Arabidopsis thaliana reflect a well-known metabolic network, including UDP-glucose:sinapate glucosyltransferase (SGT), sinapoylglucose:choline sinapoyltransferase (SCT), sinapoylglucose:l-malate sinapoyltransferase (SMT) and sinapoylcholine (sinapine) esterase (SCE). 1-O-Sinapoylglucose, produced by SGT during seed development, is converted to sinapine by SCT and hydrolyzed by SCE in germinating seeds. The released sinapate feeds via sinapoylglucose into the biosynthesis of sinapoylmalate in the seedlings catalyzed by SMT. Sinapoylmalate is involved in protecting the leaves against the deleterious effects of UV-B radiation. Sinapine might function as storage vehicle for ready supply of choline for phosphatidylcholine biosynthesis in young seedlings. The antinutritive character of sinapine and related sinapate esters hamper the use of the valuable seed protein of the oilseed crop B. napus for animal feed and human nutrition. Due to limited variation in seed sinapine content within the assortment of B. napus cultivars, low sinapine lines cannot be generated by conventional breeding giving rise to genetic engineering of sinapate ester metabolism as a promising means. In this article we review the progress made throughout the last decade in identification of genes involved in sinapate ester metabolism and characterization of the encoded enzymes. Based on gene structures and enzyme recruitment, evolution of sinapate ester metabolism is discussed. Strategies of targeted metabolic engineering, designed to generate low-sinapate ester lines of B. napus, are evaluated.

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Abbreviations

SCE:

Sinapoylcholine (sinapine) esterase

SCPL:

Serine carboxy peptidase-like

SCT:

Sinapoylglucose:choline sinapoyltransferase

SGT:

UDP-glucose:sinapate glucosyltransferase

SMT:

Sinapoylglucose:l-malate sinapoyltransferase

UGT:

UDP-dependent glycosyltransferase

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Acknowledgments

Work in our laboratory reviewed in this article was supported by the Bundesministerium für Bildung und Forschung (BMBF) within the research projects “Napus 2000—Healthy Food from Transgenic Rape Seeds” and “YelLowSin Rapeseed: Functional Genomics Approaches for the Development of Yellow-Seeded, Low Sinapine Oilseed Rape/Canola (Brassica napus)”, as well as by the German Science Foundation (DFG; Bonn, Germany) within the priority program 1152, “Evolution of Metabolic Diversity” (EvoMet) and individual research grants provided by the DFG.

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  1. Interdisciplinary Center for Crop Plant Research (IZN), Martin Luther University Halle-Wittenberg, Hoher Weg 8, 06120, Halle (Saale), Germany

    Carsten Milkowski

  2. Department of Secondary Metabolism, Leibniz Institute of Plant Biochemistry (IPB), Weinberg 3, 06120, Halle (Saale), Germany

    Dieter Strack

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  1. Carsten Milkowski
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Correspondence to Carsten Milkowski or Dieter Strack.

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Milkowski, C., Strack, D. Sinapate esters in brassicaceous plants: biochemistry, molecular biology, evolution and metabolic engineering. Planta 232, 19–35 (2010). https://doi.org/10.1007/s00425-010-1168-z

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