메뉴 건너뛰기




Volumn 59, Issue 13, 2011, Pages 7083-7091

Synthesis, analytical features, and biological relevance of 5-(3′,4′-Dihydroxyphenyl)-γ-valerolactone, a microbial metabolite derived from the catabolism of dietary flavan-3-ols

Author keywords

valerolactone; 3 (3 ,4 dihydroxyphenyl) valerolactone; 5 (3 ,4 dihydroxyphenyl) valerolactone; Flavan 3 ols; gut microbiota

Indexed keywords

ANALYTICAL PARAMETERS; ANTIOXIDANT CAPACITY; COMMERCIAL STANDARDS; EPICATECHIN; FLAVAN-3-OLS; GRAPE SEEDS; HUMAN FECAL; IN-VITRO; MICROBIOTAS; PROPIONIC ACIDS; RELATED COMPOUNDS;

EID: 79960030756     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf2020182     Document Type: Article
Times cited : (48)

References (29)
  • 1
    • 0343247685 scopus 로고    scopus 로고
    • Antioxidant flavonols and coronary heart disease risk
    • Hertog, M. G. L.; Feskens, E. J. M.; Kromhout, D. Antioxidant flavonols and coronary heart disease risk Lancet 1997, 349, 699 (Pubitemid 27107753)
    • (1997) Lancet , vol.349 , Issue.9053 , pp. 699
    • Hertog, M.G.L.1    Feskens, E.J.M.2    Kromhout, D.3
  • 3
    • 38949131470 scopus 로고    scopus 로고
    • Flavan-3-ols: Nature, occurrence and biological activity
    • DOI 10.1002/mnfr.200700137
    • Aron, P. M.; Kennedy, J. A. Flavan-3-ols: Nature, occurrence and biological activity Mol. Nutr. Food Res. 2008, 52, 79-104 (Pubitemid 351211804)
    • (2008) Molecular Nutrition and Food Research , vol.52 , Issue.1 , pp. 79-104
    • Aron, P.M.1    Kennedy, J.A.2
  • 4
    • 68249114506 scopus 로고    scopus 로고
    • Interaction between phenolics and gut microbiota: Role in human health
    • Selma, M. V.; Espín, J. C.; Tomás-Barberán, F. A. Interaction between phenolics and gut microbiota: Role in human health J. Agric. Food Chem. 2009, 57, 6485-6501
    • (2009) J. Agric. Food Chem. , vol.57 , pp. 6485-6501
    • Selma, M.V.1    Espín, J.C.2    Tomás-Barberán, F.A.3
  • 5
    • 78049432112 scopus 로고    scopus 로고
    • Colonic metabolites of berry polyphenols: The missing link to biological activity ?
    • Williamson, G.; Clifford, M. N. Colonic metabolites of berry polyphenols: The missing link to biological activity ? Br. J. Nutr. 2010, 104, S48-S66
    • (2010) Br. J. Nutr. , vol.104
    • Williamson, G.1    Clifford, M.N.2
  • 6
    • 0031009218 scopus 로고    scopus 로고
    • Biotransformation of (-)-epicatechin 3-O-gallate by human intestinal bacteria
    • Meselhy, M. R.; Nakamura, N.; Hattori, M. Biotransformation of (-)-epicatechin 3-O-gallate by human intestinal bacteria Chem. Pharm. Bull. 1997, 45, 888-893 (Pubitemid 27255104)
    • (1997) Chemical and Pharmaceutical Bulletin , vol.45 , Issue.5 , pp. 888-893
    • Meselhy, M.R.1    Nakamura, N.2    Hattori, M.3
  • 7
    • 0042012824 scopus 로고    scopus 로고
    • Identification of metabolites of (-)-epicatechin gallate and their metabolic fate in the rat
    • Kohri, T.; Suzuki, M.; Nanjo, F. Identification of metabolites of (-)-epicatechin gallate and their metabolic fate in the rat J. Agric. Food Chem. 2003, 51, 5561-5566
    • (2003) J. Agric. Food Chem. , vol.51 , pp. 5561-5566
    • Kohri, T.1    Suzuki, M.2    Nanjo, F.3
  • 8
    • 74849132800 scopus 로고    scopus 로고
    • Metabolism of (-)-epigallocatechin gallate by rat intestinal flora
    • Takagaki, A.; Nanjo, F. Metabolism of (-)-epigallocatechin gallate by rat intestinal flora J. Agric. Food Chem. 2010, 58, 1313-1321
    • (2010) J. Agric. Food Chem. , vol.58 , pp. 1313-1321
    • Takagaki, A.1    Nanjo, F.2
  • 9
    • 77956170874 scopus 로고    scopus 로고
    • Procyanidin B2 catabolism by human fecal microflora: Partial characterization of "dimeric" intermediates
    • Stoupi, S.; Williamson, G.; Drynan, J. W.; Barron, D.; Clifford, M. N. Procyanidin B2 catabolism by human fecal microflora: Partial characterization of "dimeric" intermediates Arch. Biochem. Biophys. 2010, 501, 73-78
    • (2010) Arch. Biochem. Biophys. , vol.501 , pp. 73-78
    • Stoupi, S.1    Williamson, G.2    Drynan, J.W.3    Barron, D.4    Clifford, M.N.5
  • 10
    • 61449211248 scopus 로고    scopus 로고
    • Procyanidin dimers are metabolized by human microbiota with 2-(3,4-dihydroxyphenyl)acetic acid and 5-(3,4-dihydroxyphenyl)-γ- valerolactone as the major metabolites
    • Appeldoorn, M. M.; Vincken, J. P.; Aura, A. M.; Hollman, P. C. H.; Gruppen, H. Procyanidin dimers are metabolized by human microbiota with 2-(3,4-dihydroxyphenyl)acetic acid and 5-(3,4-dihydroxyphenyl)-γ- valerolactone as the major metabolites J. Agric. Food Chem. 2009, 57, 1084-1092
    • (2009) J. Agric. Food Chem. , vol.57 , pp. 1084-1092
    • Appeldoorn, M.M.1    Vincken, J.P.2    Aura, A.M.3    Hollman, P.C.H.4    Gruppen, H.5
  • 11
    • 78149388236 scopus 로고    scopus 로고
    • Metabolomics study of human urinary metabolome modifications after intake of almond (Prunus dulcis (Mill.) D.A. Webb) skin polyphenols
    • Llorach, R.; Garrido, I.; Monagas, M.; Urpi-Sarda, M.; Tulipani, S.; Bartolome, B.; Andres-Lacueva, C. Metabolomics study of human urinary metabolome modifications after intake of almond (Prunus dulcis (Mill.) D.A. Webb) skin polyphenols J. Proteome Res. 2010, 9, 5859-5867
    • (2010) J. Proteome Res. , vol.9 , pp. 5859-5867
    • Llorach, R.1    Garrido, I.2    Monagas, M.3    Urpi-Sarda, M.4    Tulipani, S.5    Bartolome, B.6    Andres-Lacueva, C.7
  • 12
    • 70449426567 scopus 로고    scopus 로고
    • An LC-MS-based metabolomics approach for exploring urinary metabolome modifications after cocoa consumption
    • Llorach, R.; Urpi-Sarda, M.; Jauregui, O.; Monagas, M.; Andres-Lacueva, C. An LC-MS-based metabolomics approach for exploring urinary metabolome modifications after cocoa consumption J. Proteome Res. 2009, 8, 5060-5068
    • (2009) J. Proteome Res. , vol.8 , pp. 5060-5068
    • Llorach, R.1    Urpi-Sarda, M.2    Jauregui, O.3    Monagas, M.4    Andres-Lacueva, C.5
  • 13
    • 1342328148 scopus 로고    scopus 로고
    • Antioxidant activity and inhibition of matrix metalloproteinases by metabolites of maritime pine bark extract (Pycnogenol)
    • DOI 10.1016/j.freeradbiomed.2003.12.017
    • Grimm, T.; Schäfer, A.; Hoögger, P. Antioxidant activity and inhibition of matrix metalloproteinases by metabolites of maritime pine bark extract (Pycnogenol) Free Radical Biol. Med. 2004, 36, 811-822 (Pubitemid 38264423)
    • (2004) Free Radical Biology and Medicine , vol.36 , Issue.6 , pp. 811-822
    • Grimm, T.1    Schafer, A.2    Hogger, P.3
  • 14
    • 16244391107 scopus 로고    scopus 로고
    • Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives
    • DOI 10.1016/j.bmcl.2004.12.070
    • Lambert, J. D.; Rice, J. E.; Hong, J.; Hou, Z.; Yang, C. S. Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives Bioorg. Med. Chem. 2005, 15, 873-876 (Pubitemid 40458616)
    • (2005) Bioorganic and Medicinal Chemistry Letters , vol.15 , Issue.4 , pp. 873-876
    • Lambert, J.D.1    Rice, J.E.2    Hong, J.3    Hou, Z.4    Yang, C.S.5
  • 15
    • 77955402178 scopus 로고    scopus 로고
    • Synthesis of optically pure lactone metabolites of tea catechins
    • Hamada, M.; Furuno, A.; Nakano, S.; Kishimoto, T.; Nakajima, N. Synthesis of optically pure lactone metabolites of tea catechins Synthesis 2010, 9, 1512-1520
    • (2010) Synthesis , vol.9 , pp. 1512-1520
    • Hamada, M.1    Furuno, A.2    Nakano, S.3    Kishimoto, T.4    Nakajima, N.5
  • 16
    • 61549136998 scopus 로고    scopus 로고
    • Synthesis of y-valerolactones as the tea catechin metabolites
    • Nakano, S.; Hamada, M.; Kishimoto, T.; Nakajima, N. Synthesis of y-valerolactones as the tea catechin metabolites Heterocycles 2008, 76, 1001-1005
    • (2008) Heterocycles , vol.76 , pp. 1001-1005
    • Nakano, S.1    Hamada, M.2    Kishimoto, T.3    Nakajima, N.4
  • 17
    • 0342264396 scopus 로고    scopus 로고
    • Urinary metabolites of French maritime pine bark extract in humans
    • Duweler, K. G.; Rohdewald, P. Urinary metabolites of French maritime pine bark extract in humans Pharmazie 2000, 55, 364-368 (Pubitemid 30322228)
    • (2000) Pharmazie , vol.55 , Issue.5 , pp. 364-368
    • Duweler, K.G.1    Rohdewald, P.2
  • 18
    • 84939655355 scopus 로고
    • The chemical structure of the intermediate metabolites of catechin. III. Synthesis of the intermediate metabolites (G and H)
    • Watanabe, H. The chemical structure of the intermediate metabolites of catechin. III. Synthesis of the intermediate metabolites (G and H) Bull. Agric. Chem. Soc. Jpn. 1959, 23, 263-276
    • (1959) Bull. Agric. Chem. Soc. Jpn. , vol.23 , pp. 263-276
    • Watanabe, H.1
  • 19
    • 0242267935 scopus 로고    scopus 로고
    • Urinary excretion of 5-(3′,4′-dihydroxyphenyl)-γ- valerolactone, a ring-fission metabolite of (-)-epicatechin, in rats and its in vitro antioxidant activity
    • Unno, T.; Tamemoto, K.; Yayabe, F.; Kakuda, T. Urinary excretion of 5-(3′,4′-dihydroxyphenyl)-γ-valerolactone, a ring-fission metabolite of (-)-epicatechin, in rats and its in vitro antioxidant activity J. Agric. Food Chem. 2003, 51, 6893-6898
    • (2003) J. Agric. Food Chem. , vol.51 , pp. 6893-6898
    • Unno, T.1    Tamemoto, K.2    Yayabe, F.3    Kakuda, T.4
  • 21
    • 17344380047 scopus 로고    scopus 로고
    • Extending applicability of the oxygen radical absorbance capacity (ORAC-Fluorescein) assay
    • Davalos, A.; Gomez-Cordoves, C.; Bartolome, B. Extending applicability of the oxygen radical absorbance capacity (ORAC-Fluorescein) assay J. Agric. Food Chem. 2004, 52, 48-54
    • (2004) J. Agric. Food Chem. , vol.52 , pp. 48-54
    • Davalos, A.1    Gomez-Cordoves, C.2    Bartolome, B.3
  • 22
    • 0034653974 scopus 로고    scopus 로고
    • An improved method for the determination of green and black tea polyphenols in biomatrices by high-performance liquid chromatography with coulometric array detection
    • DOI 10.1006/abio.2000.4487
    • Lee, M. J.; Prabhu, S.; Meng, X.; Li, C.; Yang, C. S. An improved method for the determination of green and black tea polyphenols in biomatrices by high-performance liquid chromatography with coulometric array detection Anal. Biochem. 2000, 279, 164-169 (Pubitemid 30165004)
    • (2000) Analytical Biochemistry , vol.279 , Issue.2 , pp. 164-169
    • Lee, M.-J.1    Prabhu, S.2    Meng, X.3    Li, C.4    Yang, C.S.5
  • 24
    • 74849092330 scopus 로고    scopus 로고
    • Green tea flavan-3-ols: Colonic degradation and urinary excretion of catabolites by humans
    • Roowi, S.; Stalmach, A.; Mullen, W.; Lean, M. E.; Edwards, C. A.; Crozier, A. Green tea flavan-3-ols: Colonic degradation and urinary excretion of catabolites by humans J. Agric. Food Chem. 2010, 58, 1296-304
    • (2010) J. Agric. Food Chem. , vol.58 , pp. 1296-304
    • Roowi, S.1    Stalmach, A.2    Mullen, W.3    Lean, M.E.4    Edwards, C.A.5    Crozier, A.6
  • 26
    • 0036667454 scopus 로고    scopus 로고
    • Identification and characterization of methylated and ring-fission metabolites of tea catechins formed in humans, mice, and rats
    • DOI 10.1021/tx010184a
    • Meng, X.; Sang, S.; Zhu, N.; Lu, H.; Sheng, S.; Lee, M. J.; Ho, C. T.; Yang, C. S. Identification and characterization of methylated and ring-fission metabolites of tea catechins formed in humans, mice, and rats Chem. Res. Toxicol. 2002, 15, 1042-1050 (Pubitemid 34977270)
    • (2002) Chemical Research in Toxicology , vol.15 , Issue.8 , pp. 1042-1050
    • Meng, X.1    Sang, S.2    Zhu, N.3    Lu, H.4    Sheng, S.5    Lee, M.-J.6    Ho, C.-T.7    Yang, C.S.8
  • 28
    • 0036712084 scopus 로고    scopus 로고
    • Urinary tea polyphenols in relation to gastric and esophageal cancers: A prospective study of men in Shanghai, China
    • Sun, C. L.; Yuan, J. M.; Lee, M. J.; Yang, C. S.; Gao, Y. T.; Ross, R. K.; Yu, M. C. Urinary tea polyphenols in relation to gastric and esophageal cancers: A prospective study of men in Shanghai, China Carcinogenesis 2002, 23, 1497-1503 (Pubitemid 35012430)
    • (2002) Carcinogenesis , vol.23 , Issue.9 , pp. 1497-1503
    • Sun, C.-L.1    Yuan, J.-M.2    Lee, M.-J.3    Yang, C.S.4    Gao, Y.-T.5    Ross, R.K.6    Yu, M.C.7
  • 29
    • 77954631104 scopus 로고    scopus 로고
    • Genetic association between the COMT genotype and urinary levels of tea polyphenols and their metabolites among daily green tea drinkers
    • Inoue-Choi, M.; Yuan, J. M.; Yang, C. S.; van den Berg, D. J.; Lee, M. J.; Gao, Y. T.; Yu, M. C. Genetic association between the COMT genotype and urinary levels of tea polyphenols and their metabolites among daily green tea drinkers Int. J. Mol. Epidemiol. Genet. 2010, 1 (2) 114-123
    • (2010) Int. J. Mol. Epidemiol. Genet. , vol.1 , Issue.2 , pp. 114-123
    • Inoue-Choi, M.1    Yuan, J.M.2    Yang, C.S.3    Van Den Berg, D.J.4    Lee, M.J.5    Gao, Y.T.6    Yu, M.C.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.