title: Efficient synthesis and activity of beneficial intestinal flora of two lactulose-derived oligosaccharides.
abstract: 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.
authors.affiliation: Key Laboratory of Food Nutrition and Safety, Ministry of Education, College of Food Science and Biotechnology, Tianjin University of Science and Technology, Tianjin, 300457, PR China; Tianjin Food Safety & Low Carbon Manufacturing Collaborative Innovation Center, 300457, Tianjin, PR China. Electronic address: zhyuanzhu@tust.edu.cn.
authors.forename: Zhen-Yuan
authors.initials: ZY
authors.lastname: Zhu
authors.affiliation: Key Laboratory of Food Nutrition and Safety, Ministry of Education, College of Food Science and Biotechnology, Tianjin University of Science and Technology, Tianjin, 300457, PR China.
authors.forename: Di
authors.initials: D
authors.lastname: Cui
authors.affiliation: Key Laboratory of Food Nutrition and Safety, Ministry of Education, College of Food Science and Biotechnology, Tianjin University of Science and Technology, Tianjin, 300457, PR China.
authors.forename: Hui
authors.initials: H
authors.lastname: Gao
authors.affiliation: Key Laboratory of Food Nutrition and Safety, Ministry of Education, College of Food Science and Biotechnology, Tianjin University of Science and Technology, Tianjin, 300457, PR China.
authors.forename: Feng-Ying
authors.initials: FY
authors.lastname: Dong
authors.affiliation: Key Laboratory of Food Nutrition and Safety, Ministry of Education, College of Food Science and Biotechnology, Tianjin University of Science and Technology, Tianjin, 300457, PR China.
authors.forename: Xiao-cui
authors.initials: XC
authors.lastname: Liu
authors.affiliation: Key Laboratory of Food Nutrition and Safety, Ministry of Education, College of Food Science and Biotechnology, Tianjin University of Science and Technology, Tianjin, 300457, PR China.
authors.forename: Fei
authors.initials: F
authors.lastname: Liu
authors.affiliation: Key Laboratory of Food Nutrition and Safety, Ministry of Education, College of Food Science and Biotechnology, Tianjin University of Science and Technology, Tianjin, 300457, PR China.
authors.forename: Lu
authors.initials: L
authors.lastname: Chen
authors.affiliation: Sorbonne Universités, UPMC Univ Paris 06, Insititut Parisien de Chimie Moléculaire, CNRS UMR 8232, 4 Place Jussieu, 75005, Paris, France.
authors.forename: Yong-min
authors.initials: YM
authors.lastname: Zhang
mesh_terms: D002236:Carbohydrate Conformation; D049109:Cell Proliferation / Q000187:drug effects; D000069196:Gastrointestinal Microbiome / Q000187:drug effects*; D006801:Humans; D007779:Lactobacillus acidophilus / Q000166:cytology / Q000187:drug effects*; D007792:Lactulose / Q000737:chemistry / Q000494:pharmacology*; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D009844:Oligosaccharides; D007792:Lactulose
keywords: Lactobacillus acidophilus; Lactulose; Lactulose-derived oligosaccharides; Prebiotics