Sulfonation and anticoagulant activity of fungal exocellular β-(1→6)-d-glucan (lasiodiplodan)

An exocellular β-(1→6)-d-glucan (lasiodiplodan) produced by a strain of Lasiodiplodia theobromae (MMLR) grown on sucrose was derivatized by sulfonation to promote anticoagulant activity. The structural features of the sulfonated β-(1→6)-d-glucan were investigated by UV-vis, FT-IR and 13C NMR spectroscopy, and the anticoagulant activity was investigated by the classical coagulation assays APTT, PT and TT using heparin as standard. The content of sulfur and degree of substitution of the sulfonated glucan was 11.73% and 0.95, respectively. UV spectroscopy showed a band at 261 nm due to the unsaturated bond formed in the sulfonation reaction. Results of FT-IR and 13C NMR indicated that sulfonyl groups were inserted on the polysaccharide. The sulfonated β-(1→6)-d-glucan presented anticoagulant activity as demonstrated by the increase in dose dependence of APTT and TT, and these actions most likely occurred because of the inserted sulfonate groups on the polysaccharide. The lasiodiplodan did not inhibit the coagulation tests. © 2012 Elsevier Ltd.

Keywords

β-(1→6)-d-Glucan, Anticoagulant activity, Lasiodiplodan, Lasiodiplodia theobromae, Sulfonation, Anticoagulant activities, Coagulation assays, Coagulation tests, D-glucan, Degree of substitution, Dose dependences, Most likely, Structural feature, Sulfonate groups, Sulfonyl groups, Unsaturated bonds, Coagulation, Nuclear magnetic resonance spectroscopy, Sugar (sucrose), Ultraviolet spectroscopy, anticoagulant agent, antithrombin, beta 1,6 glucan, beta glucan, beta-1,6-glucan, heparin, sucrose, sulfonic acid derivative, thrombin, water, Ascomycetes, blood clotting test, chemistry, drug antagonism, growth, development and aging, human, solubility, Anticoagulants, Antithrombins, Ascomycota, beta-Glucans, Blood Coagulation Tests, Heparin, Humans, Solubility, Sucrose, Sulfonic Acids, Thrombin, Water