Application of amylomaltase for the synthesis of salicin-alpha-glucosides as efficient anticoagulant and anti-inflammatory agents

作者：Rudeekulthamrong Prakarn; Kaulpiboon Jarunee^*

来源：Carbohydrate Research, 2016, 432: 55-61.

DOI：10.1016/j.carres.2016.06.011

• Amylomaltase
• Salicin-alpha-D-glucosides
• Anticoagulant agent
• Anti-inflammatory agent
• Tapioca starch

The focus of this study was the synthesis of alpha-glucosyl derivatives of salicin by a transglucosylation reaction. The reaction was catalyzed by recombinant amylomaltase using tapioca starch as a glucosyl donor. Several reaction parameters, such as the enzyme-substrate concentrations, pH, temperature and incubation time, were optimized. Using the optimum conditions, at least three products with retention times (R-t) of 6.2, 9.2 and 14.1 were observed. The maximum yield of glucosylated salicin derivatives was 63% (w/w) of the total products. The structures of the glucosylated salicin derivatives were confirmed to be salicin-alpha-D-glucopyranoside, salicin-alpha-D-maltopyranoside and salicin-alpha-D-maltotriopyranoside through a combination of enzyme treatments, mass spectrometry and NMR analyses. The glycosidic bond between glucose units consisted of an alpha-1,4-configuration. The water solubility of salicin-alpha-D-glucopyranoside, salicin-alpha-D-maltopyranoside and salicin-alpha-D-maltotriopyranoside was 3-, 5-and 8-fold higher, respectively, than that of salicin, whereas their relative sweetness values were lower than that of sucrose. Interestingly, the long-chain salicin-alpha-D-glucosides showed greater anticoagulant and anti-inflammatory activities than salicin. In addition, the synthesized salicin-alpha-D-glucosides were able to tolerate acidic and high temperature conditions, but not alpha-glucosidase or human digestive enzymes. Therefore, these salicin-alpha-D-glucosides should be applied by the injection route to achieve greater bioavailability than is possible by the oral route.

• 出版日期2016-9-2