Abstract
Sphingoid base derivatives have attracted increasing attention as promising chemotherapeutic candidates against lifestyle diseases such as diabetes and cancer. Natural sphingoid bases can be a potential resource instead of those derived by time-consuming total organic synthesis. In particular, glucosylceramides (GlcCers) in food plants are enriched sources of sphingoid bases, differing from those of animals. Several chemical methodologies to transform GlcCers to sphingoid bases have already investigated; however, these conventional methods using acid or alkaline hydrolysis are not efficient due to poor reaction yield, producing complex by-products and resulting in separation problems. In this study, an extremely efficient and practical chemoenzymatic transformation method has been developed using microwave-enhanced butanolysis of GlcCers and a large amount of readily available almond β-glucosidase for its deglycosylation reaction of lysoGlcCers. The method is superior to conventional acid/base hydrolysis methods in its rapidity and its reaction cleanness (no isomerization, no rearrangement) with excellent overall yield.
Highlights
Sphingoid base derivatives have attracted increasing attention as promising chemotherapeutic candidates against lifestyle diseases such as diabetes and cancer
GlcCers are composed of a sphingoid base whose amino group at the C-2 positon is N-acylated with a fatty acid and a hydroxyl group at the C-1 position glycosylated with a glucose
Ba(OH)2 was used for hydrolysis of GlcCer 1 resulting in lysoGlcCer 2 (1--glucosyl4E,8E-9-methyl-sphingadienine) with 50% yield; in this method, sphingoid base 3 was produced as a minor component with a qualitative yield [12]
Summary
Sphingoid base derivatives have attracted increasing attention as promising chemotherapeutic candidates against lifestyle diseases such as diabetes and cancer. The conventional transformation of GlcCers to sphingoid bases is accomplished by an acid or alkali hydrolysis reaction with heating These methods have practical disadvantages, such as purification problems and low efficiency. In the case of the acid-catalyzed hydrolysis reaction, isomerization and degradation are frequently observed This is caused by an allylic alcohol group of GlcCers, which readily reacts with solvents such as methanol leading to the introduction of a methoxy group at the C3 position, which reacts as an ester via N-acyl migration and more allylic rearrangements [3, 8]. These complex reactions cause a separation problem as well as a low yield.
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