Degradation of neohesperidin dihydrochalcone by human intestinal bacteria.
The degradation of neohesperidin dihydrochalcone by human intestinal microbiota was studied in vitro. Human fecal slurries converted neohesperidin dihydrochalcone anoxically to 3-(3-hydroxy-4-methoxyphenyl)propionic acid or 3-(3,4-dihydroxyphenyl)propionic acid. Two transient intermediates were identified as hesperetin dihydrochalcone 4'-beta-d-glucoside and hesperetin dihydrochalcone. These metabolites suggest that neohesperidin dihydrochalcone is first deglycosylated to hesperetin dihydrochalcone 4'-beta-d-glucoside and subsequently to the aglycon hesperetin dihydrochalcone. The latter is hydrolyzed to the corresponding 3-(3-hydroxy-4-methoxyphenyl)propionic acid and probably phloroglucinol. Eubacterium ramulus and Clostridium orbiscindens were not capable of converting neohesperidin dihydrochalcone. However, hesperetin dihydrochalcone 4'-beta-d-glucoside was converted by E. ramulus to hesperetin dihydrochalcone and further to 3-(3-hydroxy-4-methoxyphenyl)propionic acid, but not by C. orbiscindens. In contrast, hesperetin dihydrochalcone was cleaved to 3-(3-hydroxy-4-methoxyphenyl)propionic acid by both species. The latter reaction was shown to be catalyzed by the phloretin hydrolase from E. ramulus.
Braune
Annett
A
Department of Gastrointestinal Microbiology and of Nutritional Toxicology, German Institute of Human Nutrition Potsdam-Rehbruecke, Arthur-Scheunert-Allee 114-116, D-14558 Nuthetal, Germany. braune@mail.dife.de
Engst
Wolfram
W
Blaut
Michael
M
D001419:Bacteria / Q000378:metabolism*; D002599:Chalcone / Q000031:analogs & derivatives* / Q000378:metabolism*; D047188:Chalcones; D003013:Clostridium / Q000378:metabolism; D005051:Eubacterium / Q000201:enzymology / Q000378:metabolism; D005243:Feces / Q000382:microbiology; D005285:Fermentation; D006569:Hesperidin / Q000031:analogs & derivatives* / Q000378:metabolism*; D006801:Humans; D007422:Intestines / Q000382:microbiology*; D010694:Lactase-Phlorizin Hydrolase / Q000378:metabolism
D047188:Chalcones; C013613:neohesperidin dihydrochalcone; D002599:Chalcone; D006569:Hesperidin; D010694:Lactase-Phlorizin Hydrolase