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Nodule-Inducing Activity of Synthetic Sinorhizobium meliloti Nodulation Factors and Related Lipo-Chitooligosaccharides on Alfalfa. Importance of the Acyl Chain Structure1

Nathalie Demont-Caulet2, 3, Fabienne Maillet2, Denis Tailler, Jean-Claude Jacquinet, Jean-Claude Promé, Kyriacos C. Nicolaou, Georges Truchet, Jean-Marie Beau, and Jean Dénarié*

Institut de Pharmacologie et de Biologie Structurale, Centre National de la Recherche Scientifique (CNRS), 205 Route de Narbonne, 31077 Toulouse cedex, France (N.D.-C., J.-C.P.); Laboratoire de Biologie Moléculaire des Relations Plantes-Microorganismes, CNRS-Institut National de la Recherche Agronomique, B.P. 27, 31326 Castanet-Tolosan cedex, France (N.D.-C., F.M., G.T., J.D.); Laboratoire de Biochimie Structurale, Unité de Recherche Associée (URA)-CNRS 499, Université d'Orléans, B.P. 6759, 45067 Orléans cedex, France (D.T., J.-C.J., J.-M.B.); Department of Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, California 92037 (K.C.N.); and Laboratoire de Synthèse de Biomolécules, URA-CNRS 462, Institut de Chimie Moléculaire, Université Paris-Sud, 91405 Orsay cedex, France (J.-M.B.)

Sinorhizobium meliloti nodulation factors (NFs) elicit a number of symbiotic responses in alfalfa (Medicago sativa) roots. Using a semiquantitative nodulation assay, we have shown that chemically synthesized NFs trigger nodule formation in the same range of concentrations (down to 10-10 M) as natural NFs. The absence of O-sulfate or O-acetate substitutions resulted in a decrease in morphogenic activity of more than 100-fold and approximately 10-fold, respectively. To address the question of the influence of the structure of the N-acyl chain, we synthesized a series of sulfated tetrameric lipo-chitooligosaccharides (LCOs) having fatty acids of different lengths and with unsaturations either conjugated to the carbonyl group (2E) or located in the middle of the chain (9Z). A nonacylated, sulfated chitin tetramer was unable to elicit nodule formation. Acylation with short (C8) chains rendered the LCO active at 10-7 M. The optimal chain length was C16, with the C16-LCO being more than 10-fold more active than the C12- and C18-LCOs. Unsaturations were important, and the diunsaturated 2E,9Z LCO was more active than the monounsaturated LCOs. We discuss different hypotheses for the role of the acyl chain in NF perception.

1   This work was supported by grants from the Human Frontier Science Program (no. RG-372/92) and the European Communities BIOTECH program (no. PTP CT93-0400).
2   These two authors contributed equally to the paper.
3   Present address: Laboratoire de Biochimie Génétique Institut Jacques Monod-Centre National de la Recherche Scientifique, Université Paris 7, 2 Place Jussieu, 75251 Paris cedex 05, France.
*   Corresponding author; e-mail denarie{at}toulouse.inra.fr; fax 33-561-28-50-61.

Plant Physiol. (1999) 120: 83-92
Copyright Clearance Center:   0032-0889/99/120//10
© 1999 American Society of Plant Physiologists




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