Synthesis, immunological activities, and scavenging ability toward superoxide anion of (1→3)-β-D-pentaglucoside and its epoxyalkyl derivatives

The epoxyalkyl (1 -> 3)-p-D-pentaglucosides 2 and 3 were synthesized in order by acetylation, glycosidation, oxidation, and deacetylation of 1. The immunological activities (superoxide anion production activity, phagocytic activity, and lymphocyte proliferation) and scavenging ability toward superoxide anion of (1 -> 3)-beta-D-pentaglucoside (1) and its epoxyalkyl derivatives (2 and 3) were investigated. Superoxide anion released from human blood monocytes was measured by the reduction of ferricytochrome c. Phagocytosis by peritoneal macrophages was detected through a teal ingesting that measured the chicken red blood cells (CRBC). Lymphocyte proliferation was determined by the MTT method. The scavenging ability of 1, 2, and 3 toward superoxide anions was evaluated by means of chemiluminescence (CL). The results showed that 2 and 3 had a little higher immunological activity and scavenging ability toward superoxide anion than 1, which indicated that the reducing end of the oligoglucosides was quite important for maximum biological activity. (c) 2005 Elsevier Ltd. All rights reserved.