Comparison of the structures and elicitor activities of a synthetic and a mycelial-wall-derived hexa(beta-D-glucopyranosyl)-D-glucitol.

Abstract

The elicitor activity and structural characteristics of chemically synthesized hepta- and octa-beta-D-glucopyranosides were compared with the same properties of an elicitor-active mycelial-wall-derived hexa(beta-D-glucopyranosyl)-D-glucitol. The specific elicitor activities, retention times on reversed-phase liquid chromatography columns, glycosyl-linkage compositions, 1H NMR analyses, and glycosyl-sequence analyses of the synthetic and mycelial-wall-derived hexa(beta-D-glucopyranosyl)-D-glucitols were indistinguishable. This work provided conclusive proof that elicitor activity was associated with the structure proposed (Sharp, J. K., McNeil, M., and Albersheim, P. (1984) J. Biol. Chem. 259, 11321-11336) for the elicitor-active mycelial-wall-derived hexa(beta-D-glucopyranosyl)-D-glucitol.