Synthesis, (1→3)-β-D-glucanase-binding ability, and phytoalexin-elicitor activity of a mixture of 3,4-epoxybutyl (1→3)-β-D-oligoglucosides

Autor: Man-Xi Liu, Xin-Ya Mei, Gang-Liang Huang
Rok vydání: 2004
Předmět:
Zdroj: Carbohydrate Research. 339:1453-1457
ISSN: 0008-6215
Popis: We describe a approach for the synthesis of a mixture of 3,4-epoxybutyl (1 → 3)-β- D -oligoglucosides. The particular (1 → 3)-β- D -glucan isolated from the cell walls of Saccharomyces cerevisiae was recovered from the aqueous medium as water-insoluble particles by the spray drying (GS) method, and it was characterized by FTIR spectroscopy. The acid-solubilized (1 → 3)-β- D -oligoglucosides were prepared by partial acid hydrolysis of glucan particles, which were qualitatively analyzed by fluorophore-assisted carbohydrate electrophoresis (FACE). The peracetylated 3-butenyl (1 → 3)-β- D -oligoglucosides were synthesized by treating peracetylated (1 → 3)-β- D -oligoglucosides with the 3-butenyl alcohols and a Lewis acid (SnCl4) catalyst. Epoxidation of the peracetylated 3-butenyl oligoglucosides took place with m-chloroperoxybenzoic acid (m-CPBA). NaOMe in dry methanol was used for the deacetylation of the blocked derivatives, to give the 3,4-epoxybutyl (1 → 3)-β- D -oligoglucoside mixture in an overall yield of 21%. The sample was analyzed by positive-ion electrospray ionization mass spectrometry (ESIMS). In a 3,4-epoxybutyl (1 → 3)-β- D -oligoglucoside-binding (1 → 3)-β- D -glucanase assay, we found that the (1 → 3)-β- D -glucanase was obviously inactivated by the 3,4-epoxybutyl (1 → 3)-β- D -oligoglucosides. At the same time, we found the 3,4-epoxybutyl (1 → 3)-β- D -oligoglucoside mixture was more active as compared to the underivatized oligoglucoside mixture in eliciting phytoalexin accumulation in tobacco cotyledon tissue. Furthermore, it could be kept for a longer time than a (1 → 3)-β- D -oligoglucoside mixture, which indicated it is much more stable than (1 → 3)-β- D -oligoglucosides.
Databáze: OpenAIRE
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