Efficient synthesis and activity of beneficial intestinal flora of two lactulose-derived oligosaccharides

•Two lactulose-derived oligosaccharides were synthesized for the first time.•Highly efficient and selective synthesis of two lactulose-derived oligosaccharides.•The derivatives have higher activities in regulating beneficial intestinal flora than lactulose.

Lactulose is considered as a prebiotic because it promotes the intestinal proliferation of Lactobacillus acidophilus which is added to various milk products. Moreover, lactulose is used in pharmaceuticals as a gentle laxative and to treat hyperammonemia. This study was aimed at the total synthesis of two Lactulose-derived oligosaccharides: one is 3-O-β-d-galactopyranosyl-d-fructose, d-fructose and β-d-galactose bounded together with β-1,3-glycosidic bound, the other is 1-O-β-d-galactopyranosyl-d-fructose, d-fructose and β-d-galactose bounded together with β-1,1-glycosidic bound, which were accomplished in seven steps from d-fructose and β-d-galactose and every step of yield above 75%. This synthetic route provided a practical and effective synthetic strategy for galactooligosaccharides, starting from commercially available monosaccharides. Then we evaluated on their prebiotic properties in the search for potential agents of regulating and improving the intestinal flora of human. The result showed that the prebiotic properties of Lactulose-derived oligosaccharides was much better than Lactulose. Among them, 3-O-β-d-galactopyranosyl-d-fructose displayed the most potent activity of proliferation of L. acidophilus.

Graphical abstractSynthesis of Lactulose-derived oligosaccharides (1-O-β-d-galactopyranosyl-d-fructose and 3-O-β-d-galactopyranosyl-d-fructose).Figure optionsDownload full-size imageDownload as PowerPoint slide