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The signal molecule lysophosphatidylcholine in Eschscholzia californica is rapidly metabolized by reacylation

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Abstract

In cultured cells of California poppy (Eschscholzia californica), lysophosphatidylcholine (LPC) triggers a signal path that finally induces alkaloid biosynthesis. LPC is transiently generated by elicitor-activated phospholipase A2 of the plasma membrane. Externally added LPC is rapidly acylated by a membrane-bound enzyme that shows the highest specific activity in the purified plasma membrane. The fatty acid incorporated into the sn-2 position of LPC is preferentially linoleic (18:2), which is the most abundant acyl component in the PC species of Eschscholzia cells, but a minor component of the pool of free fatty acids. The fatty acid at the sn-1 position of LPC is less important for substrate specificity. The capacity of LPC acylation by intact cells or isolated plasma membranes by far exceeds the rate of LPC generation by activated phospholipase A2 and is not limited by the availability of acyl donors. Metabolites other than phosphatidylcholine (PC) were not significantly produced from labeled LPC within 20 min, indicating that lysophospholipases are not significantly contributing to the short-time metabolism of LPC. It is concluded that reacylation to PC is the dominating process in the detoxication of LPC and ensures the transient character of its steady state concentrations, even at maximum phospholipase A2 activities.

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Abbreviations

PC:

Phosphatidlycholine

LPC:

Lysophosphatidylcholine

BODIPY® FL-sn1-C11-LPC:

2-decanoyl-1-(O-(11-(4,4-difluoro-5,7-dimethyl-4-bora-3a,4a-diaza-s-indacene-3-propionyl)amino)undecyl)-sn-glycero-3-phosphocholine

bis-BODIPY® FL-C11-PC:

1,2-bis-(4,4-difluoro-5,7-dimethyl-4-bora-3a,4a-diaza-s-indacene-3-undecanoyl)-sn-glycero-3-phosphocholine

MALDI-TOF MS:

Matrix-assisted laser-desorption time-of-flight mass spectrometry

HPTLC:

High performance thin layer chromatography

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Acknowledgments

The work was suported by the Deutsche Forschungsgemeinschaft (Forschergruppe Zellspezialisierung). The help of Dr. Michael Heinze, this laboratory, with the PLA2 assay, and of Dr. Angelica Schierhorn, Max Planck Arbeitsgruppe ‘Enzymatik der Proteinfaltung’, Halle, with the MS analysis of phospholipids, is gratefully acknowledged. We are also grateful for the expert technical assistance by Gabriele Danders and Kathrin Thomasch.

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  1. Fakultät Biowissenschaften, Institut für Pharmazie, Bereich Pharmazeutische Biologie und Pharmakologie, Abteilung Molekulare Zellbiologie, Martin-Luther-Universität Halle-Wittenberg, Kurt-Mothes-Str. 3, 06120, Halle, Germany

    Wieland Schwartze & Werner Roos

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  1. Wieland Schwartze
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  2. Werner Roos
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Correspondence to Werner Roos.

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Schwartze, W., Roos, W. The signal molecule lysophosphatidylcholine in Eschscholzia californica is rapidly metabolized by reacylation. Planta 229, 183–191 (2008). https://doi.org/10.1007/s00425-008-0819-9

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  • DOI: https://doi.org/10.1007/s00425-008-0819-9

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