Nodule-inducing activity of synthetic Sinorhizobium meliloti nodulation factors and related lipo-chitooligosaccharides on alfalfa. Importance of the acyl chain structure
N. Demont-caulet et al., Nodule-inducing activity of synthetic Sinorhizobium meliloti nodulation factors and related lipo-chitooligosaccharides on alfalfa. Importance of the acyl chain structure, PLANT PHYSL, 120(1), 1999, pp. 83-92
Sinorhizobium meliloti nodulation factors (NFs) elicit a number of symbioti
c responses in alfalfa (Medicago sativa) roots. Using a semiquantitative no
dulation assay, we have shown that chemically synthesized NFs trigger nodul
e formation in the same range of concentrations (down to 10(-10) M) as natu
ral 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 struct
ure of the N-acyl chain, we synthesized a series of sulfated tetrameric lip
o-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 wa
s unable to elicit nodule formation. Acylation with short (C8) chains rende
red 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. Uns
aturations 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.