메뉴 건너뛰기




Volumn 57, Issue 12, 2009, Pages 5623-5632

Dissimilar in vitro and in vivo effects of ellagic acid and its microbiota-derived metabolites, urolithins, on the cytochrome P450 1A1

Author keywords

Caco 2; Cancer; Colon mucosa; CYP1A1; Glucuronosyltransferases; Pomegranate; Sulfotransferases; Xenobiotic metabolism

Indexed keywords

3,8 DIHYDROXY 6H DIBENZO(B,D)PYRAN 6 ONE; 3,8-DIHYDROXY-6H-DIBENZO(B,D)PYRAN-6-ONE; COUMARIN DERIVATIVE; CYTOCHROME P450 1A1; ELLAGIC ACID;

EID: 67649214140     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf900725e     Document Type: Article
Times cited : (74)

References (42)
  • 1
    • 34547575782 scopus 로고    scopus 로고
    • Targeting carcinogen metabolism by dietary cancer preventive compounds
    • Yu, S.; Kong, A. N. Targeting carcinogen metabolism by dietary cancer preventive compounds. Curr. Cancer Drug Targets 2007, 7, 416-424.
    • (2007) Curr. Cancer Drug Targets , vol.7 , pp. 416-424
    • Yu, S.1    Kong, A.N.2
  • 2
    • 34047243800 scopus 로고    scopus 로고
    • Xenobiotic-metabolizing enzymes involved in activation and detoxification of carcinogenesis polycyclic aromatic hydrocarbons
    • Shimada, T. Xenobiotic-metabolizing enzymes involved in activation and detoxification of carcinogenesis polycyclic aromatic hydrocarbons. Drug Metab. Pharmacokinet. 2006, 21, 257-276.
    • (2006) Drug Metab. Pharmacokinet , vol.21 , pp. 257-276
    • Shimada, T.1
  • 3
    • 0027199218 scopus 로고
    • Xenobiotic metabolizing enzyme expression in colonic neoplasia
    • McKay, J. A.; Murray, G. I.; Weave, R. J.; Ewen, S. W.; Melvin, W. T.; Burke, M. D. Xenobiotic metabolizing enzyme expression in colonic neoplasia. Gut 1993, 34, 1234-1239.
    • (1993) Gut , vol.34 , pp. 1234-1239
    • McKay, J.A.1    Murray, G.I.2    Weave, R.J.3    Ewen, S.W.4    Melvin, W.T.5    Burke, M.D.6
  • 4
    • 0034128936 scopus 로고    scopus 로고
    • Human UDP-glucuronosyltransferases: Metabolism, expression and disease
    • Turkey, R. H.; Strassburg, C. P. Human UDP-glucuronosyltransferases: Metabolism, expression and disease. Annu. Rev. Pharmacol. Toxicol. 2000, 40, 581-616.
    • (2000) Annu. Rev. Pharmacol. Toxicol , vol.40 , pp. 581-616
    • Turkey, R.H.1    Strassburg, C.P.2
  • 7
    • 0242694978 scopus 로고    scopus 로고
    • Enzyme induction and dietary chemicals as approaches to cancer chemoprevention: The seventh DeWitt S. Goodman lecture
    • Conney, A. H. Enzyme induction and dietary chemicals as approaches to cancer chemoprevention: The seventh DeWitt S. Goodman lecture. Cancer Res. 2003, 63, 7005-7031.
    • (2003) Cancer Res , vol.63 , pp. 7005-7031
    • Conney, A.H.1
  • 8
    • 2142695286 scopus 로고    scopus 로고
    • Oral exposure to dibenzo[a,l]pyrene in the mouse: Detoxication by inducible cytochrome P450 is more important than metabolic activation
    • Uno, S.; Dalton, T. P.; Derkenne, S.; Curran, C. P.; Miller, M. L.; Shertzer, H. C.; Nebert, D. W. Oral exposure to dibenzo[a,l]pyrene in the mouse: Detoxication by inducible cytochrome P450 is more important than metabolic activation. Mol. Pharmacol. 2004, 65, 1225-1237.
    • (2004) Mol. Pharmacol , vol.65 , pp. 1225-1237
    • Uno, S.1    Dalton, T.P.2    Derkenne, S.3    Curran, C.P.4    Miller, M.L.5    Shertzer, H.C.6    Nebert, D.W.7
  • 9
    • 30644456411 scopus 로고    scopus 로고
    • Dietary flavonoids: Effects on xenobiotic and carcinogen metabolism
    • Moon, Y. J.; Wang, X.; Morris, M. E. Dietary flavonoids: Effects on xenobiotic and carcinogen metabolism. Toxicol. In Vitro 2006, 20, 187-210.
    • (2006) Toxicol. In Vitro , vol.20 , pp. 187-210
    • Moon, Y.J.1    Wang, X.2    Morris, M.E.3
  • 10
    • 44149088311 scopus 로고    scopus 로고
    • Cancer phytotherapeutics: Role for flavonoids at the cellular level
    • Kale, A.; Gawande, S.; Kotwal, S. Cancer phytotherapeutics: Role for flavonoids at the cellular level. Phytother. Res. 2008, 22, 567-577.
    • (2008) Phytother. Res , vol.22 , pp. 567-577
    • Kale, A.1    Gawande, S.2    Kotwal, S.3
  • 11
    • 33846513021 scopus 로고    scopus 로고
    • Cytochrome P450 1A1 in Caco-2 cells: Modulation by apple juice extract and certain apple polyphenols
    • Pohl, C.; Will, F.; Dietrich, H.; Schrenk, D. Cytochrome P450 1A1 in Caco-2 cells: Modulation by apple juice extract and certain apple polyphenols. J. Agric. Food Chem. 2006, 54, 10262-10268.
    • (2006) J. Agric. Food Chem , vol.54 , pp. 10262-10268
    • Pohl, C.1    Will, F.2    Dietrich, H.3    Schrenk, D.4
  • 13
    • 33846430864 scopus 로고    scopus 로고
    • Effects of pomegranate juice on human cytochrome P4502C9 and tolbutamide pharne pharmacokinetics in rats
    • Nagata, M.; Hidaka, M.; Sekiya, H.; Kawano, Y.; Yamasaki, K. M.; Arimori, K. Effects of pomegranate juice on human cytochrome P4502C9 and tolbutamide pharne pharmacokinetics in rats. Drug Metab. Dispos. 2007, 35, 302-305.
    • (2007) Drug Metab. Dispos , vol.35 , pp. 302-305
    • Nagata, M.1    Hidaka, M.2    Sekiya, H.3    Kawano, Y.4    Yamasaki, K.M.5    Arimori, K.6
  • 14
    • 37549060998 scopus 로고    scopus 로고
    • Pomegranate juice effects on cytochrome P450S expression: In vivo studies
    • Faria, A.; Monteiro, R.; Azevedo, I.; Calhau, C. Pomegranate juice effects on cytochrome P450S expression: In vivo studies. J. Med. Food 2007, 70, 643-649.
    • (2007) J. Med. Food , vol.70 , pp. 643-649
    • Faria, A.1    Monteiro, R.2    Azevedo, I.3    Calhau, C.4
  • 15
    • 22544459923 scopus 로고    scopus 로고
    • Identification of urolithin A as a metabolite produced by human colon microflora from ellagic acid and related compounds
    • Cerdá, B.; Periago, P.; Espin, J. C.; Tomás- Barberán, F. A. Identification of urolithin A as a metabolite produced by human colon microflora from ellagic acid and related compounds. J. Agric. Food Chem. 2005, 53, 5571-5579.
    • (2005) J. Agric. Food Chem , vol.53 , pp. 5571-5579
    • Cerdá, B.1    Periago, P.2    Espin, J.C.3    Tomás- Barberán, F.A.4
  • 16
    • 38049054118 scopus 로고    scopus 로고
    • Iberian pig as a model to clarify obscure points in the bioavailability and metabolism of ellagitannins in humans
    • Espin, J. C.; González-Barrio, R.; Cerdá, B.; López-Bote, C.; Rey, A. I.; Tomás-Barberán, F. A. Iberian pig as a model to clarify obscure points in the bioavailability and metabolism of ellagitannins in humans. J. Agric. Food Chem. 2007, 55, 10476-10485.
    • (2007) J. Agric. Food Chem , vol.55 , pp. 10476-10485
    • Espin, J.C.1    González-Barrio, R.2    Cerdá, B.3    López-Bote, C.4    Rey, A.I.5    Tomás-Barberán, F.A.6
  • 17
    • 20144381777 scopus 로고    scopus 로고
    • In vitro antiproliferative, apoptotic and antioxidant activities of punicalagin, ellagic acid and a total pomegranate tannin extract are enhanced in combination with other polyphenols as found in pomegranate juice
    • Seeram, N. P.; Adams, L. S.; Henning, S. M.; Niu, Y.; Zhang, Y.; Nair, M. G.; Heber, D. In vitro antiproliferative, apoptotic and antioxidant activities of punicalagin, ellagic acid and a total pomegranate tannin extract are enhanced in combination with other polyphenols as found in pomegranate juice. J. Nutr. Biochem. 2005, 16, 360-367.
    • (2005) J. Nutr. Biochem , vol.16 , pp. 360-367
    • Seeram, N.P.1    Adams, L.S.2    Henning, S.M.3    Niu, Y.4    Zhang, Y.5    Nair, M.G.6    Heber, D.7
  • 18
    • 33747026663 scopus 로고    scopus 로고
    • The dietary hydrolysable tannin punicalagin releases ellagic acid that induces apoptosis in human colon adenocarcinoma Caco-2 cells by using the mitochondrial pathway
    • Larrosa, M.; Tomás-Barberán, F. A.; Espin, J. C. The dietary hydrolysable tannin punicalagin releases ellagic acid that induces apoptosis in human colon adenocarcinoma Caco-2 cells by using the mitochondrial pathway. J. Nutr. Biochem. 2006, 17, 611-625.
    • (2006) J. Nutr. Biochem , vol.17 , pp. 611-625
    • Larrosa, M.1    Tomás-Barberán, F.A.2    Espin, J.C.3
  • 19
    • 33746519946 scopus 로고    scopus 로고
    • Ellagic acid and natural sources of ellagitannins as possible chemopreventive agents against intestinal tumorigenesis in the Min mouse
    • Päivärinta, E.; Pajari, A. M.; Törrönen, R.; Mutanen, M. Ellagic acid and natural sources of ellagitannins as possible chemopreventive agents against intestinal tumorigenesis in the Min mouse. Nutr. Cancer 2006, 1, 79-83.
    • (2006) Nutr. Cancer , vol.1 , pp. 79-83
    • Päivärinta, E.1    Pajari, A.M.2    Törrönen, R.3    Mutanen, M.4
  • 20
    • 67651022312 scopus 로고    scopus 로고
    • González-Sarrias, A.; Espin, J. C.; Tomás-Barberán, F. A.; Garcia-Conesa, M. T. Gene expression, cell cycle arrest and MAPK signalling regulation in Caco-2 cells exposed to acid ellagic and its metabolites, urolithins. Mol. Nutr. Food Res. 2009, [Epub ahead of print] PMID: 19437480.
    • González-Sarrias, A.; Espin, J. C.; Tomás-Barberán, F. A.; Garcia-Conesa, M. T. Gene expression, cell cycle arrest and MAPK signalling regulation in Caco-2 cells exposed to acid ellagic and its metabolites, urolithins. Mol. Nutr. Food Res. 2009, [Epub ahead of print] PMID: 19437480.
  • 21
    • 0037219635 scopus 로고    scopus 로고
    • Evaluation of the bioavailability and metabolism in the rat of punicalagin, an antioxidant polyphenol from pomegranate juice
    • Cerda, B.; Llorach, R.; Cerón, J. J.; Espin, J. C.; Tomás-Barberán, F. A. Evaluation of the bioavailability and metabolism in the rat of punicalagin, an antioxidant polyphenol from pomegranate juice. Eur. J. Nutr. 1003, 42, 18-28.
    • Eur. J. Nutr , vol.1003 , Issue.42 , pp. 18-28
    • Cerda, B.1    Llorach, R.2    Cerón, J.J.3    Espin, J.C.4    Tomás-Barberán, F.A.5
  • 22
    • 33747026663 scopus 로고    scopus 로고
    • The dietary hydrolysable tannin punicalagin releases ellagic acid that induces apoptosis in human colon adenocarcinoma Caco-2 cells by using the mitochondrial pathway
    • Larrosa, M.; Tomás-Barberán, F. A.; Espin, J. C. The dietary hydrolysable tannin punicalagin releases ellagic acid that induces apoptosis in human colon adenocarcinoma Caco-2 cells by using the mitochondrial pathway. J. Nutr. Biochem. 2006, 17, 611-625.
    • (2006) J. Nutr. Biochem , vol.17 , pp. 611-625
    • Larrosa, M.1    Tomás-Barberán, F.A.2    Espin, J.C.3
  • 23
    • 38749111818 scopus 로고    scopus 로고
    • Sulindac and its metabolites induce carcinogen metabolizing enzymes in human colon cancer cells
    • Ciolino, H. P.; Bass, S. E.; MacDonald, C. J.; Cheng, R. Y. S.; Yeh, G. C. Sulindac and its metabolites induce carcinogen metabolizing enzymes in human colon cancer cells. Int. J. Cancer 2008, 122, 990-998.
    • (2008) Int. J. Cancer , vol.122 , pp. 990-998
    • Ciolino, H.P.1    Bass, S.E.2    MacDonald, C.J.3    Cheng, R.Y.S.4    Yeh, G.C.5
  • 24
    • 4544345237 scopus 로고    scopus 로고
    • The potent in vitro antioxidant ellagitannins from pomegranate juice are metabolised into bioavailable but poor antioxidant hydroxy-6ff-dibenzopyran-6-one derivatives by the colonic microflora of healthy humans
    • Cerdá, B.; Espin, J. C.; Parra, S.; Martínez, P.; Tomás-Barberán, F. A. The potent in vitro antioxidant ellagitannins from pomegranate juice are metabolised into bioavailable but poor antioxidant hydroxy-6ff-dibenzopyran-6-one derivatives by the colonic microflora of healthy humans. Eur. J. Nutr. 2004, 43, 205-220.
    • (2004) Eur. J. Nutr , vol.43 , pp. 205-220
    • Cerdá, B.1    Espin, J.C.2    Parra, S.3    Martínez, P.4    Tomás-Barberán, F.A.5
  • 26
    • 33646240144 scopus 로고    scopus 로고
    • Studies on apple and blueberry fruit constituents: Do the polyphenols reach the colon after ingestion?
    • Kahle, K.; Kraus, M.; Scheppach, W.; Ackermann, M.; Ridder, F.; Richling, E. Studies on apple and blueberry fruit constituents: Do the polyphenols reach the colon after ingestion?. Mol. Nutr. Food Res. 2006, 50, 418-423.
    • (2006) Mol. Nutr. Food Res , vol.50 , pp. 418-423
    • Kahle, K.1    Kraus, M.2    Scheppach, W.3    Ackermann, M.4    Ridder, F.5    Richling, E.6
  • 27
    • 0142231975 scopus 로고    scopus 로고
    • Discovery of cytochrome P450 1B1 inhibitors as new promising anti-cancer agents
    • Chun, Y.-J.; Kim, S. Discovery of cytochrome P450 1B1 inhibitors as new promising anti-cancer agents. Med. Res. Rev. 2003, 23, 657-668.
    • (2003) Med. Res. Rev , vol.23 , pp. 657-668
    • Chun, Y.-J.1    Kim, S.2
  • 28
    • 33846385587 scopus 로고    scopus 로고
    • Mammalian cytochromes P450-Importance of tissue specificity
    • Seliskar, M.; Rozman, D. Mammalian cytochromes P450-Importance of tissue specificity. Biochim. Biophys. Acta 2007, 1770, 458-466.
    • (2007) Biochim. Biophys. Acta , vol.1770 , pp. 458-466
    • Seliskar, M.1    Rozman, D.2
  • 29
    • 0036845201 scopus 로고    scopus 로고
    • Phytoestrogens regulate vitamin D metabolism in the mouse colon: Relevance for colon tumor prevention and therapy
    • Kállay, E.; Adlercreutz, H.; Farhan, H.; Lechner, D.; Bajna, E.; Gerdenitsch, W.; Campbell, M.; Cross, H. S. Phytoestrogens regulate vitamin D metabolism in the mouse colon: Relevance for colon tumor prevention and therapy. J. Nutr. 2002, 132, 3490S-3493S.
    • (2002) J. Nutr , vol.132
    • Kállay, E.1    Adlercreutz, H.2    Farhan, H.3    Lechner, D.4    Bajna, E.5    Gerdenitsch, W.6    Campbell, M.7    Cross, H.S.8
  • 30
    • 0037048285 scopus 로고    scopus 로고
    • Expression of paclitaxel-inactiving CYP3A activity in human colorectal cancer: Implications for drug therapy
    • Martinez, C.; García-Marín, E.; Pizarro, R. M.; García-Gamito, F. J.; Agúndez, J. A. G. Expression of paclitaxel-inactiving CYP3A activity in human colorectal cancer: Implications for drug therapy. Br. J. Cancer 2002, 87, 681-686.
    • (2002) Br. J. Cancer , vol.87 , pp. 681-686
    • Martinez, C.1    García-Marín, E.2    Pizarro, R.M.3    García-Gamito, F.J.4    Agúndez, J.A.G.5
  • 31
    • 0033954736 scopus 로고    scopus 로고
    • Coordinate induction by antioxidants of UDP-glucuronosyltransferase UGT1A6 and the apical conjugate export pump MRP2 (multidrug resistance protein 2) in Caco-2 cells
    • Bock, K. W.; Eckle, T.; Ouzzine, M.; Fournel-Gigleux, S. Coordinate induction by antioxidants of UDP-glucuronosyltransferase UGT1A6 and the apical conjugate export pump MRP2 (multidrug resistance protein 2) in Caco-2 cells. Biochem. Pharmacol. 2000, 59, 467-470.
    • (2000) Biochem. Pharmacol , vol.59 , pp. 467-470
    • Bock, K.W.1    Eckle, T.2    Ouzzine, M.3    Fournel-Gigleux, S.4
  • 32
    • 0034950281 scopus 로고    scopus 로고
    • Induction of UDPglucuronosyltransferase UGT1A1 by the flavonoid Chrysin in Caco2 cells-Potential role in carcinogen bio-inactivation
    • Galijatovic, A.; Otake, Y.; Walle, K.; Walle, T. Induction of UDPglucuronosyltransferase UGT1A1 by the flavonoid Chrysin in Caco2 cells-Potential role in carcinogen bio-inactivation. Pharm. Res. 2001, 18, 374-379.
    • (2001) Pharm. Res , vol.18 , pp. 374-379
    • Galijatovic, A.1    Otake, Y.2    Walle, K.3    Walle, T.4
  • 33
    • 37049018023 scopus 로고    scopus 로고
    • Novel identification of UDP-glucuronosyltransferase 1A10 as an estrogen-regulated target gene
    • Starlard-Davenport, A.; Lyn-Cook, B.; Radominska-Pandya, A. Novel identification of UDP-glucuronosyltransferase 1A10 as an estrogen-regulated target gene. Steroids 2008, 73, 138-147.
    • (2008) Steroids , vol.73 , pp. 138-147
    • Starlard-Davenport, A.1    Lyn-Cook, B.2    Radominska-Pandya, A.3
  • 35
    • 3142652041 scopus 로고    scopus 로고
    • Gastrointestinal-distributed UDPglucuronosyltransferase IAlO, which metabolizes estrogens and nonsteroidal antiflammatory drugs, depends upon phosphorylation
    • Basu, N. K.; Kubota, S.; Meselhy, M. R.; Ciotti, M.; Chowdhury, B.; Hartori, M.; Owens, I. S. Gastrointestinal-distributed UDPglucuronosyltransferase IAlO, which metabolizes estrogens and nonsteroidal antiflammatory drugs, depends upon phosphorylation. J. Biol. Chem. 2004, 279, 28320-28329.
    • (2004) J. Biol. Chem , vol.279 , pp. 28320-28329
    • Basu, N.K.1    Kubota, S.2    Meselhy, M.R.3    Ciotti, M.4    Chowdhury, B.5    Hartori, M.6    Owens, I.S.7
  • 36
    • 0034812454 scopus 로고    scopus 로고
    • Sulfation of flavonoids and other phenolic dietary compounds by the human cytosolic sulfotransferases
    • Pai, T. G.; Suiko, M.; Sakakibara, Y.; Liu, M.-C. Sulfation of flavonoids and other phenolic dietary compounds by the human cytosolic sulfotransferases. Biochem. Biophys. Res. Commun. 2001, 255, 1175-1179.
    • (2001) Biochem. Biophys. Res. Commun , vol.255 , pp. 1175-1179
    • Pai, T.G.1    Suiko, M.2    Sakakibara, Y.3    Liu, M.-C.4
  • 37
    • 0030022005 scopus 로고    scopus 로고
    • Flavonoids, potent inhibitors of the human P-form phenolsulfotransferase. Potencial role in drug metabolism and chemoprevention
    • Eaton, E. A.; Walle, U. K.; Lewis, A. J.; Hudson, T.; Wilson, A. A.; Walle, T. Flavonoids, potent inhibitors of the human P-form phenolsulfotransferase. Potencial role in drug metabolism and chemoprevention. Drug Metab. Dispos. 1996, 24, 232-237.
    • (1996) Drug Metab. Dispos , vol.24 , pp. 232-237
    • Eaton, E.A.1    Walle, U.K.2    Lewis, A.J.3    Hudson, T.4    Wilson, A.A.5    Walle, T.6
  • 38
  • 39
    • 33645457770 scopus 로고    scopus 로고
    • Urolithins, ellagic acid-derived metabolites produced by human colonic microflora, exhibit estrogenic and antiestrogenic activities
    • Larrosa, M.; González-Sarrias, A.; García-Conesa, M. T.; Tomás-Barberán, F. A.; Espin, J. C. Urolithins, ellagic acid-derived metabolites produced by human colonic microflora, exhibit estrogenic and antiestrogenic activities. J. Agric. Food Chem. 2006, 54, 1611-1620.
    • (2006) J. Agric. Food Chem , vol.54 , pp. 1611-1620
    • Larrosa, M.1    González-Sarrias, A.2    García-Conesa, M.T.3    Tomás-Barberán, F.A.4    Espin, J.C.5
  • 40
    • 33645554647 scopus 로고    scopus 로고
    • Primary structure and organ-specific expression of the rat aryl hydrocarbon receptor repressor gene
    • Nishihashi, H.; Kanno, Y.; Tomuro, K.; Nakahama, T.; Inouye, Y. Primary structure and organ-specific expression of the rat aryl hydrocarbon receptor repressor gene. Biol. Pharm. Bull. 2006, 29, 640-647.
    • (2006) Biol. Pharm. Bull , vol.29 , pp. 640-647
    • Nishihashi, H.1    Kanno, Y.2    Tomuro, K.3    Nakahama, T.4    Inouye, Y.5
  • 42
    • 33847113977 scopus 로고    scopus 로고
    • Pomegranate juice does not impair clearance of oral or intravenous midazolam, a probe for cytochrome P450-3A activity: Comparison with grapefruit juice
    • Farkas, D.; Oleson, L. E.; Zhao, Y. L.; Harmatz, J. S.; Zinny, M. A.; Court, M. H.; Greenblatt, D. J. Pomegranate juice does not impair clearance of oral or intravenous midazolam, a probe for cytochrome P450-3A activity: Comparison with grapefruit juice. J. Clin. Pharm. 2007, 47, 286-294.
    • (2007) J. Clin. Pharm , vol.47 , pp. 286-294
    • Farkas, D.1    Oleson, L.E.2    Zhao, Y.L.3    Harmatz, J.S.4    Zinny, M.A.5    Court, M.H.6    Greenblatt, D.J.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.