Melibiose
IUPAC 名称
2,3,4,5-tetrahydroxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexanal; 2-[2-hydroxy-2-(3,4,5-trihydroxyoxolan-2-yl)ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol; 6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol
描述
Isolated from coffee beans, apple (Pyrus malus) and other plants
Melibiose is disaccharide consisting of one galactose and one glucose moiety in an alpha (1-6) glycosidic linkage. This sugar is produced and metabolized only by enteric and lactic acid bacteria and other microbes. It is not an endogenous metabolite but may be obtained from the consumption of partially fermented molasses, brown sugar or honey. Antibodies to melibiose will appear in individuals affected by Chagas' disease (Trypanosoma cruzi infection). Melibiose is not metabolized by humans, but can be broken down by gut microflora, such as E. coli. In fact, E. coli is able to utilize melibiose as a sole source of carbon. Melibiose is first imported by the melibiose permease, MelB and then converted to β-D-glucose and β-D-galactose by the α-galactosidase encoded by melA. Because of its poor digestability Melibiose (along with rhamnose) can be used together for noninvasive intestinal mucosa barrier testing. This test can be used to assess malabsorption or impairment of intestinal permeability. Recent studies with dietary melibiose have shown that can strongly affected the Th cell responses to an ingested antigen. It has been suggested that melibiose could be used to enhance the induction of oral tolerance. (PMID 17986780). Melibiose is found in many foods, some of which are sesbania flower, mugwort, olive, and jerusalem artichoke.
异构
OCC1OC(OCC(O)C(O)C(O)C(O)C=O)C(O)C(O)C1O.OCC1OC(OCC(O)C2OC(O)C(O)C2O)C(O)C(O)C1O.OCC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1O
InChI标识符
InChI=1S/3C12H22O11/c13-1-4-5(15)6(16)9(19)12(22-4)21-2-3(14)10-7(17)8(18)11(20)23-10;13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4;13-1-4(15)7(17)8(18)5(16)3-22-12-11(21)10(20)9(19)6(2-14)23-12/h2*3-20H,1-2H2;1,4-12,14-21H,2-3H2
键
YFSMDFMEDLKMOS-UHFFFAOYSA-N