Degradation of neohesperidin dihydrochalcone by human intestinal bacteria

被引:57
作者
Braune, A
Engst, W
Blaut, M
机构
[1] German Inst Human Nutr Potsdam Rehbrucke, Dept Gastrointestinal Microbiol, D-14558 Nuthetal, Germany
[2] German Inst Human Nutr Potsdam Rehbrucke, Dept Nutr Toxicol, D-14558 Nuthetal, Germany
关键词
neohesperidin dihydrochalcone; hesperetin dihydrochalcone 4 '-beta-D-glucoside; hesperetin dihydrochalcone; 3-(3-hydroxy-4-methoxyphenyl)propionic acid; 3-(3,4-dihydroxyphenyl)propionic acid; Eubacterium ramulus; Clostridium orbiscindens; phloretin hydrolase;
D O I
10.1021/jf0484982
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
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 neohesperdin 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.
引用
收藏
页码:1782 / 1790
页数:9
相关论文
共 55 条
[1]   Dietary flavonols: Chemistry, food content, and metabolism [J].
Aherne, SA ;
O'Brien, NM .
NUTRITION, 2002, 18 (01) :75-81
[2]  
[Anonymous], 1988, FLAVONOIDS ADV RES 1
[3]   Quercetin derivatives are deconjugated and converted to hydroxyphenylacetic acids but not methylated by human fecal flora in vitro [J].
Aura, AM ;
O'Leary, KA ;
Williamson, G ;
Ojala, M ;
Bailey, M ;
Puupponen-Pimiä, R ;
Nuutila, AM ;
Oksman-Caldentey, KM ;
Poutanen, K .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2002, 50 (06) :1725-1730
[4]   Dietary agents in cancer prevention: flavonoids and isoflavonoids [J].
Birt, DF ;
Hendrich, S ;
Wang, WQ .
PHARMACOLOGY & THERAPEUTICS, 2001, 90 (2-3) :157-177
[5]  
Bloor SJ, 2001, METHOD ENZYMOL, V335, P3
[6]  
Bohm B. A, 1994, FLAVONOIDS ADV RES 1, P387
[7]   HYDROLYSIS OF DIETARY FLAVONOID GLYCOSIDES BY STRAINS OF INTESTINAL BACTEROIDES FROM HUMANS [J].
BOKKENHEUSER, VD ;
SHACKLETON, CHL ;
WINTER, J .
BIOCHEMICAL JOURNAL, 1987, 248 (03) :953-956
[8]  
BOOTH AN, 1958, J BIOL CHEM, V230, P661
[9]  
BOOTH AN, 1958, J BIOL CHEM, V233, P280
[10]   NEOHESPERIDIN DIHYDROCHALCONE - STATE OF KNOWLEDGE REVIEW [J].
BORREGO, F ;
CANALES, I ;
LINDLEY, MG .
ZEITSCHRIFT FUR LEBENSMITTEL-UNTERSUCHUNG UND-FORSCHUNG, 1995, 200 (01) :32-37