Biotransformation of aesculin by human gut bacteria and identification of its metabolites in rat urine

World Journal of Gastroenterology

Volumn 15, Issue 12, 2009, Pages 1518-1523

  Ding, Wei Jun ^a   Deng, Yun ^a   Feng, Hao ^b   Liu, Wei Wei ^a   Hu, Rong ^a   Li, Xiang ^a   Gu, Zhe Ming ^b   Dong, Xiao Ping ^a  

^a CHENGDU UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

^b XENOBIOTIC LABORATORIES INC   (United States)

Author keywords

Aesculin; Aseculetin; Biotransformation; Human gut bacteria; LC ESI MS; Rat urine; Sulfated derivatives

Indexed keywords

6 GLC 7 GLUCOCOUMARIN; 6 HYDROXY 7 GLUCOCOUMARIN; 6 HYDROXY 7 SULFCOUMARIN; 6 O METHYL 7 GLUCOCOUMARIN; 6 O METHYL 7 SULFCOUMARIN; 6,7 DIGLUCOUMARIN; DRUG METABOLITE; ESCULETIN; ESCULIN; UNCLASSIFIED DRUG; UMBELLIFERONE DERIVATIVE;

ADULT; ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; DRUG ISOLATION; DRUG MECHANISM; DRUG TRANSFORMATION; DRUG URINE LEVEL; FEMALE; HUMAN; HUMAN EXPERIMENT; IN VITRO STUDY; IN VIVO STUDY; INCUBATION TIME; INTESTINE FLORA; MALE; NONHUMAN; NORMAL HUMAN; PLEIOTROPY; RAT; URINALYSIS; ANAEROBIC BACTERIUM; ANIMAL; BIOTRANSFORMATION; CULTURE MEDIUM; GROWTH, DEVELOPMENT AND AGING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTESTINE; ISOLATION AND PURIFICATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; MICROBIOLOGY; MIDDLE AGED; URINE;

ANIMALS; BACTERIA, ANAEROBIC; BIOTRANSFORMATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, LIQUID; CULTURE MEDIA; ESCULIN; FEMALE; HUMANS; INTESTINES; MALE; MASS SPECTROMETRY; MIDDLE AGED; RATS; UMBELLIFERONES;

EID: 65549153605     PISSN: 10079327     EISSN: None     Source Type: Journal    
DOI: 10.3748/wjg.15.1518     Document Type: Article

References (19)

1. Kaneko T, Tahara S, Takabayashi F. Inhibitory effect of natural coumarin compounds, esculetin and esculin, on oxidative DNA damage and formation of aberrant crypt foci and tumors induced by 1,2-dimethylhydrazine in rat colons. Biol Pharm Bull 2007; 30: 2052-2057
2. Kaneko T, Tahara S, Takabayashi F, Harada N. Suppression of 8-oxo-2′-deoxyguanosine formation and carcinogenesis induced by N-nitrosobis (2-oxopropyl)amine in hamsters by esculetin and esculin. Free Radic Res 2004; 38: 839-846
3. Masamoto Y, Murata Y, Baba K, Shimoishi Y, Tada M, Takahata K. Inhibitory effects of esculetin on melanin biosynthesis. Biol Pharm Bull 2004; 27: 422-425
4. Wang CJ, Hsieh YJ, Chu CY, Lin YL, Tseng TH. Inhibition of cell cycle progression in human leukemia HL-60 cells by esculetin. Cancer Lett 2002; 183: 163-168
5. Lee BC, Lee SY, Lee HJ, Sim GS, Kim JH, Kim JH, Cho YH, Lee DH, Pyo HB, Choe TB, Moon DC, Yun YP, Hong JT. Antioxidative and photo-protective effects of coumarins isolated from Fraxinus chinensis. Arch Pharm Res 2007; 30: 1293-1301
6. Yang JY, Della-Fera MA, Hartzell DL, Nelson-Dooley C, Hausman DB, Baile CA. Esculetin induces apoptosis and inhibits adipogenesis in 3T3-L1 cells. Obesity (Silver Spring) 2006; 14: 1691-1699
7. Lacy A, O'Kennedy R. Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer. Curr Pharm Des 2004; 10: 3797-3811
8. Leung KN, Leung PY, Kong LP, Leung PK. Immunomodulatory effects of esculetin (6,7-dihydroxycoumarin) on murine lymphocytes and peritoneal macrophages. Cell Mol Immunol 2005; 2: 181-188
9. Kim BG, Lee Y, Hur HG, Lim Y, Ahn JH. Production of three O-methhylated esculetins with Escherichia coli expressing O-methyltransferase from poplar. Biosci Biotechnol Biochem 2006; 70: 1269-1272
10. Duncan SH, Flint HJ, Stewart CS. Inhibitory activity of gut bacteria against Escherichia coli O157 mediated by dietary plant metabolites. FEMS Microbiol Lett 1998; 164: 283-288
11. Kanho H, Yaoya S, Itani T, Nakane T, Kawahara N, Takase Y, Masuda K, Kuroyanagi M. Glucosylation of phenolic compounds by Pharbitis nil hairy roots: I. Glucosylation of coumarin and flavone derivatives. Biosci Biotechnol Biochem 2004; 68: 2032-2039
12. Gumbinger HG, Vahlensieck U, Winterhoff H. Metabolism of caffeic acid in the isolated perfused rat liver. Planta Med 1993; 59: 491-493
13. Stern N, Nozawa K, Kisch E, Tuck ML, Golub M, Eggena P, Knoll E. Tonic inhibition of renin secretion by the 12 lipoxygenase pathway: augmentation by high salt intake. Endocrinology 1996; 137: 1878-1884
14. Munoz-Munoz JL, Garcia-Molina F, Varon R, Rodriguez-Lopez JN, Garcia-Canovas F, Tudela J. Kinetic characterization of the oxidation of esculetin by polyphenol oxidase and peroxidase. Biosci Biotechnol Biochem 2007; 71: 390-396
15. Park C, Jin CY, Kim GY, Choi IW, Kwon TK, Choi BT, Lee SJ, Lee WH, Choi YH. Induction of apoptosis by esculetin in human leukemia U937 cells through activation of JNK and ERK. Toxicol Appl Pharmacol 2008; 227: 219-228
16. Yang JY, Della-Fera MA, Baile CA. Esculetin induces mitochondria-mediated apoptosis in 3T3-L1 adipocytes. Apoptosis 2006; 11: 1371-1378
17. Turnbaugh PJ, Ley RE, Mahowald MA, Magrini V, Mardis ER, Gordon JI. An obesity-associated gut microbiome with increased capacity for energy harvest. Nature 2006; 444: 1027-1031
18. Ley RE, Turnbaugh PJ, Klein S, Gordon JI. Microbial ecology: human gut microbes associated with obesity. Nature 2006; 444: 1022-1023
19. Gill SR, Pop M, Deboy RT, Eckburg PB, Turnbaugh PJ, Samuel BS, Gordon JI, Relman DA, Fraser-Liggett CM, Nelson KE. Metagenomic analysis of the human distal gut microbiome. Science 2006; 312: 1355-1359