RESUMEN
ß-Glucosylglycerol (ß-GG) and their derivatives have potential applications in food, cosmetics and the healthcare industry, including antitumor medications. In this study, ß-GG and its unnatural glycosides were synthesized through the transglycosylation of two enzymes, Sulfolobus shibatae ß-glycosidase (SSG) and Deinococcus geothermalis amylosucrase (DGAS). SSG catalyzed a transglycosylation reaction with glycerol as an acceptor and cellobiose as a donor to produce 56% of ß-GGs [ß-D-glucopyranosyl-(1â1/3)-D-glycerol and ß-D-glucopyranosyl- (1â2)-D-glycerol]. In the second transglycosylation reaction, ß-D-glucopyranosyl-(1 â 1/3)-Dglycerol was used as acceptor molecules of the DGAS reaction. As a result, 61% of α-Dglucopyranosyl-( 1â4)-ß-D-glucopyranosyl-(1â1/3)-D-glycerol and 28% of α-D-maltopyranosyl- (1â4)-ß-D-glucopyranosyl-(1â1/3)-D-glycerol were synthesized as unnatural glucosylglycerols. In conclusion, the combined enzymatic synthesis of the unnatural glycosides of ß-GG was established. The synthesis of these unnatural glycosides may provide an opportunity to discover new applications in the biotechnological industry.
Asunto(s)
Glucósidos/biosíntesis , Glucosiltransferasas/metabolismo , Glicósido Hidrolasas/metabolismo , Glicósidos/biosíntesis , Biotecnología , Celobiosa/metabolismo , Deinococcus/enzimología , Deinococcus/genética , Escherichia coli/genética , Glucosidasas/metabolismo , Glucósidos/análisis , Glucósidos/química , Glucosiltransferasas/genética , Glicerol/metabolismo , Glicósido Hidrolasas/genética , Glicósidos/análisis , Glicósidos/químicaRESUMEN
Three new sesquiterpene glycosides (1-3), three new glycerol glycosides (4-6), two new alkaloids (7-8), together with seven known compounds (9-15) all of which were isolated from the genus Pilea for the first time, were isolated from the whole plants of Pilea cavaleriei Levl subsp. cavaleriei. Their structures were determined by extensive spectroscopic techniques and chemical methods. The cytotoxic activity of the isolated compounds was evaluated against four cancer cell lines, and none of the tested compounds caused a significant reduction of the cell number.