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Substrate promiscuity of a rosmarinic acid synthase from lavender (Lavandula angustifolia L.)

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Abstract

One of the most common types of modification of secondary metabolites is the acylation of oxygen- and nitrogen-containing substrates to produce esters and amides, respectively. Among the known acyltransferases, the members of the plant BAHD family are capable of acylating a wide variety of substrates. Two full-length acyltransferase cDNAs (LaAT1 and 2) were isolated from lavender flowers (Lavandula angustifolia L.) by reverse transcriptase-PCR using degenerate primers based on BAHD sequences. Recombinant LaAT1 exhibited a broad substrate tolerance accepting (hydroxy)cinnamoyl-CoAs as acyl donors and not only tyramine, tryptamine, phenylethylamine and anthranilic acid but also shikimic acid and 4-hydroxyphenyllactic acid as acceptors. Thus, LaLT1 forms esters and amides like its phylogenetic neighbors. In planta LaAT1 might be involved in the biosynthesis of rosmarinic acid, the ester of caffeic acid and 3,4-dihydroxyphenyllactic acid, a major constituent of lavender flowers. LaAT2 is one of three members of clade VI with unknown function.

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Abbreviations

4CL:

(Hydroxy)cinnamic acid:CoA ligase

BAHD:

Family of acyltransferases named after the first four biochemically characterized enzymes

DTT:

Dithiothreitol

GC–MS:

Gas chromatography mass spectrometry

GST:

Glutathion S-transferase

HCAA:

Hydroxycinnamic acid amides

HPLC-ESI-MSn :

High-performance liquid chromatography electrospray ionization mass spectrometry

IPTG:

Isopropyl-β-d-thiogalactopyranoside

RACE:

Rapid amplification of cDNA ends

RT-PCR:

Reverse transcriptase polymerase chain reaction

SDS-PAGE:

Sodium dodecylsulphate polyacrylamide gel electrophoresis

THT:

Tyramine N-(hydroxycinnamoyl) transferase

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Acknowledgments

We thank Till Beuerle (Institute for Pharmaceutical Biology, Technical University Braunschweig, Braunschweig, Germany) and Eran Pichersky (Department of Molecular, Cellular and Developmental Biology, University of Michigan, Ann Arbor, USA) for providing the (hydroxy)cinnamic acid:CoA ligase gene. The financial support by Degussa is gratefully acknowledged.

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Author notes

  1. Christian Landmann

    Present address: CMC Development, Analytical Development, Merck Serono, Frankfurter Str. 250, 64293, Darmstadt, Germany

Authors and Affiliations

  1. Biotechnology of Natural Products, Technische Universitaet Muenchen, Liesel-Beckmann-Str. 1, 85354, Freising, Germany

    Christian Landmann, Stefanie Hücherig, Barbara Fink, Thomas Hoffmann, Daniela Dittlein & Wilfried Schwab

  2. Department of Ecology and Evolutionary Biology, University of Toronto, 25 Willcocks St, Toronto, ON, M5S 3B2, Canada

    Heather A. Coiner

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  1. Christian Landmann
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Corresponding author

Correspondence to Wilfried Schwab.

Additional information

The nucleotide sequences reported in this article have been deposited in the GenBank database under Accession Nos. DQ886904 (LaAT1) and DQ886905 (LaAT2).

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Landmann, C., Hücherig, S., Fink, B. et al. Substrate promiscuity of a rosmarinic acid synthase from lavender (Lavandula angustifolia L.). Planta 234, 305–320 (2011). https://doi.org/10.1007/s00425-011-1400-5

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