Structure-activity relationships of oligo-β-glucoside elicitors of phytoalexin accumulation in soybean

Abstract

The abilities of a family of chemically synthesized oligo-β-glucosides, ranging in size from hexamer to decamer, to induce phytoalexin accumulation in soybean cotyledons were investigated to determine which structural elements of the oligoglucosides are important for their biological activity. The results of the biological assays established that the following structural motif is necessary for the oligo-β-glucosides to have high elicitor activity: Glcβ(1→6)Glcβ(1→6)Glcβ(1→6)Glcβ(1→6)-R Glcβ(1→3)⌋ Glcβ(1→3)⌋ The branched trisaccharide at the nonreducing end of the oligoglucosides was found to be essential for maximum elicitor activity. Substitution of either the nonreducing terminal backbone glucosyl residue or the side-chain glucosyl residue closest to the nonreducing end with glucosaminyl or N-acetylglucosaminyl residues reduced the elicitor activity of the oligoglucosides between 10-fold and 10,000-fold. Elicitor activity was also reduced 1000-fold if the two side-chain glucosyl residues were attached to adjacent backbone glucosyl residues rather than to glucosyl residues separated by an unbranched residue. In contrast, modifications of the reducing terminal glucosyl residue of an elicitor-active hepta-β-glucoside by conjugation with tyramine and subsequent iodination had no significant effect on the elicitor activity of the hepta-β-glucoside. These results demonstrate that oligo-β-glucosides must have a specific structure to trigger the signal transduction pathway, which ultimately leads to the de novo synthesis of phytoalexins in soybean.