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Volumn 54, Issue 5, 2011, Pages 1529-1536

Increased bioavailability of tricin-amino acid derivatives via a prodrug approach

Author keywords

[No Author keywords available]

Indexed keywords

4',5,7 TRIHYDROXY 3',5' DIMETHOXYFLAVONE; FLAVONE DERIVATIVE; PRODRUG; QUERCETIN; QUERCETIN ALANINE GLUTAMIC ACID; TRICIN ALANINE; TRICIN ALANINE ASPARTIC ACID; TRICIN ALANINE GLUTAMIC ACID; TRICIN AMINO ACID DERIVATIVE; TRICIN ASPARTIC ACID; TRICIN GLUTAMIC ACID; TRICIN GLYCINE; TRICIN PHENYLALANINE; TRICIN VALINE; UNCLASSIFIED DRUG;

EID: 79952272904     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1015457     Document Type: Article
Times cited : (55)

References (46)
  • 1
    • 0034736046 scopus 로고    scopus 로고
    • Advances in flavonoid research since 1992
    • Harborne, J. B.; Williamson., C. A. Advances in flavonoid research since 1992 Phytochemistry 2000, 55, 481-504
    • (2000) Phytochemistry , vol.55 , pp. 481-504
    • Harborne, J.B.1    Williamson, C.A.2
  • 2
    • 0036849077 scopus 로고    scopus 로고
    • The biochemistry and medicinal significance of the flavonoids
    • Havsteen, B. H. The biochemistry and medicinal significance of the flavonoids Pharmacol. Ther. 2002, 96, 67-202
    • (2002) Pharmacol. Ther. , vol.96 , pp. 67-202
    • Havsteen, B.H.1
  • 3
    • 0024436842 scopus 로고
    • Inhibition of avian myeloblastosis virus reverse transcriptase by flavones and isoflavones
    • Inoue, Y.; Yamaguchi, K.; Take, Y.; Nakamura, S. Inhibition of avian myeloblastosis virus reverse transcriptase by flavones and isoflavones J. Antibiot. 1989, 42, 1523-1525 (Pubitemid 19263982)
    • (1989) Journal of Antibiotics , vol.42 , Issue.10 , pp. 1523-1525
    • Inouye, Y.1    Yamaguchi, K.2    Take, Y.3    Nakamura, S.4
  • 5
    • 0023897154 scopus 로고
    • Differential effects of flavonoids as inhibitors of tyrosine protein kinases and serine/threonine protein kinases
    • Hagiwara, M.; Inoue, S.; Tanaka, T.; Nunoki, K.; Ito, M.; Hidaka, H. Differential effects of flavonoids as inhibitors of tyrosine protein kinases and serine/threonine protein kinases Biochem. Pharmacol. 1988, 37, 2987-2992
    • (1988) Biochem. Pharmacol. , vol.37 , pp. 2987-2992
    • Hagiwara, M.1    Inoue, S.2    Tanaka, T.3    Nunoki, K.4    Ito, M.5    Hidaka, H.6
  • 6
    • 0024453108 scopus 로고
    • Inhibition of protein-tyrosine kinase activity by flavanoids and related compounds
    • Geahlen, R. L.; Koonchanok, N. M.; McLaughlin, J. L.; Pratt, D. E. Inhibition of protein-tyrosine kinase activity by flavonoids and related compounds J. Nat. Prod. 1989, 52, 982-986 (Pubitemid 19270608)
    • (1989) Journal of Natural Products (Lloydia) , vol.52 , Issue.5 , pp. 982-986
    • Geahlen, R.L.1    Koonchanok, N.M.2    McLaughlin, J.L.3
  • 7
    • 0024604665 scopus 로고
    • Antiproliferative effects of synthetic and naturally occurring flavonoids on tumor cells of the human breast carcinoma cell line, ZR-75-1
    • Hirano, T.; Oka, K.; Akiba, M. Antiproliferative effects of synthetic and naturally occurring flavonoids on tumor cells of the human breast carcinoma cell line, ZR-75-1 Res. Commun. Chem. Pathol. Pharmacol. 1989, 64, 69-78 (Pubitemid 19123229)
    • (1989) Research Communications in Chemical Pathology and Pharmacology , vol.64 , Issue.1 , pp. 69-78
    • Hirano, T.1    Oka, K.2    Akiba, M.3
  • 8
    • 0036669812 scopus 로고    scopus 로고
    • Cancer preventive effects of flavonoids - A review
    • DOI 10.1016/S0753-3322(02)00186-5, PII S0753332202001865
    • Le Marchand, L. Cancer preventive effects of flavonoids - A review Biomed. Pharmacother. 2002, 56, 296-301 (Pubitemid 35245313)
    • (2002) Biomedicine and Pharmacotherapy , vol.56 , Issue.6 , pp. 296-301
    • Le Marchand, L.1
  • 9
    • 0025312054 scopus 로고
    • Natural products as a source of potential cancer chemotherapeutic and chemopreventive agents
    • DOI 10.1021/np50067a003
    • Cassady, J. M.; Baird, W. H.; Chang, C.-J. Natural products as a source of potential cancer chemotherapeutic and chemopreventive agents J. Nat. Prod. 1990, 53, 23-41 (Pubitemid 20152034)
    • (1990) Journal of Natural Products (Lloydia) , vol.53 , Issue.1 , pp. 23-41
    • Cassady, J.M.1    Baird, W.M.2    Chang, C.-J.3
  • 10
    • 0023777899 scopus 로고
    • Anti-human immunodeficiency virus phenolics from licorice
    • Hatano, T.; Yasuhara, T.; Miyamoto, K.; Okuda, T. Anti-human immunodeficiency virus phenolics from licorice Chem. Pharm. Bull. 1988, 36, 2286-2288
    • (1988) Chem. Pharm. Bull. , vol.36 , pp. 2286-2288
    • Hatano, T.1    Yasuhara, T.2    Miyamoto, K.3    Okuda, T.4
  • 11
    • 77956344127 scopus 로고    scopus 로고
    • Tricin - A potential multifunctional nutraceutical
    • Zhou, J.-M.; Ibrahim, R. K. Tricin - A potential multifunctional nutraceutical Phytochem. Rev. 2010, 9, 413-424
    • (2010) Phytochem. Rev. , vol.9 , pp. 413-424
    • Zhou, J.-M.1    Ibrahim, R.K.2
  • 13
    • 34547748514 scopus 로고    scopus 로고
    • Activity and allelopathy of soil of flavone O-glycosides from rice
    • DOI 10.1021/jf0703912
    • Kong, C. H.; Zhao, H.; Xu, X. H.; Wang, P.; Gu, Y. Activity and allelopathy of soil of flavone O -glycosides from rice J. Agric. Food Chem. 2007, 55, 6007-6012 (Pubitemid 47235651)
    • (2007) Journal of Agricultural and Food Chemistry , vol.55 , Issue.15 , pp. 6007-6012
    • Kong, C.H.1    Zhao, H.2    Xu, X.H.3    Wang, P.4    Gu, Y.5
  • 15
    • 0033231219 scopus 로고    scopus 로고
    • Antioxidative phenolic compounds from Japanese barnyard millet (Echinochloa utilis) grains
    • Watanabe, M. Antioxidative phenolic compounds from Japanese barnyard millet (Echinochloa utilis) grains J. Agric. Food Chem. 1999, 47, 4500-4505
    • (1999) J. Agric. Food Chem. , vol.47 , pp. 4500-4505
    • Watanabe, M.1
  • 16
    • 79952272426 scopus 로고    scopus 로고
    • Anti-influenza virus activity by tricin, isolated Sasa albo-marginata in Japan
    • Yazawa, K.; Tsuchida, Y.; Yamada, R.; Sadanari, H.; Murayama, T. Anti-influenza virus activity by tricin, isolated Sasa albo-marginata in Japan Antiviral Res. 2010, 86, A49
    • (2010) Antiviral Res. , vol.86 , pp. 49
    • Yazawa, K.1    Tsuchida, Y.2    Yamada, R.3    Sadanari, H.4    Murayama, T.5
  • 17
    • 32644450768 scopus 로고    scopus 로고
    • Flavonoids from Artemisia copa with anti-inflammatory activity
    • DOI 10.1055/s-2005-873177
    • Moscatelli, V.; Hnatyszyn, O.; Acevedo, C.; Megias, J.; Alcaraz, M. J.; Ferrana, G. Flavonoids from Artemisia copa with anti-inflammatory activity Planta Med. 2006, 72, 72-74 (Pubitemid 43241597)
    • (2006) Planta Medica , vol.72 , Issue.1 , pp. 72-74
    • Moscatelli, V.1    Hnatyszyn, O.2    Acevedo, C.3    Megias, J.4    Alcaraz, M.J.5    Ferraro, G.6
  • 18
    • 0141454855 scopus 로고    scopus 로고
    • Tricin from a Malagasy connaraceous plant with potent antihistaminic activity
    • Kuwabara, H.; Mouri, K.; Otsuka, H.; Kasai, R.; Yamasaki, K. Tricin from a Malagasy connaraceous plant with potent antihistamic activity J. Nat. Prod. 2003, 66, 1273-1275 (Pubitemid 37204238)
    • (2003) Journal of Natural Products , vol.66 , Issue.9 , pp. 1273-1275
    • Kuwabara, H.1    Mouri, K.2    Otsuka, H.3    Kasai, R.4    Yamasaki, K.5
  • 19
    • 33846698320 scopus 로고    scopus 로고
    • P-glycoprotein inhibitory activity of two phenolic compounds, (-)-syringaresinol and tricin from Sasa borealis
    • DOI 10.1002/cbdv.200790001
    • Jeong, Y. H.; Chung, S. Y.; Han, A.-R.; Sung, M. K.; Jang, D. S.; Lee, J.; Kwon, Y.; Lee, H. J.; Seo, E.-K. P-Glycoprotein inhibitory activity of 2 phenolic compounds, (-)-syringaresinol and tricin from Sasa borealis Chem. Biodiversity 2007, 4, 12-16 (Pubitemid 46195859)
    • (2007) Chemistry and Biodiversity , vol.4 , Issue.1 , pp. 12-16
    • Jeong, Y.H.1    Chung, S.Y.2    Han, A.-R.3    Sung, M.K.4    Jang, D.S.5    Lee, J.6    Kwon, Y.7    Lee, H.J.8    Seo, E.-K.9
  • 21
    • 76549119214 scopus 로고    scopus 로고
    • Dietary tricin suppresses inflammation-related colon carcinogenesis in male Crj: CD-1 mice
    • Oyama, T.; Yasui, Y.; Sugie, S.; Koketsu, M.; Watanabe, K.; Tanaka, T. Dietary tricin suppresses inflammation-related colon carcinogenesis in male Crj: CD-1 mice Cancer Prev. Res. 2009, 2, 1031-1038
    • (2009) Cancer Prev. Res. , vol.2 , pp. 1031-1038
    • Oyama, T.1    Yasui, Y.2    Sugie, S.3    Koketsu, M.4    Watanabe, K.5    Tanaka, T.6
  • 23
    • 33748154221 scopus 로고    scopus 로고
    • Experimental study on the action of allitridin against human cytomegalovirus in vitro: Inhibitory effects on immediate-early genes
    • DOI 10.1016/j.antiviral.2006.03.017, PII S0166354206001148
    • Zhen, H.; Fang, F.; Ye, D. Y.; Shu, S. N.; Zhou, Y. F.; Dong, Y. S.; Nie, X. C.; Li, G. Experimental study on the action of allitridin against human cytomegalovirus in vitro: Inhibitory effects on immediate-early genes Antiviral Res. 2006, 72, 68-74 (Pubitemid 44308445)
    • (2006) Antiviral Research , vol.72 , Issue.1 , pp. 68-74
    • Zhen, H.1    Fang, F.2    Ye, D.-y.3    Shu, S.-n.4    Zhou, Y.-f.5    Dong, Y.-s.6    Nie, X.-c.7    Li, G.8
  • 24
    • 0029610477 scopus 로고
    • Review of the biology of quercetin and related bioflavonoids
    • DOI 10.1016/0278-6915(95)00077-1
    • Formica, J. V.; Regelson, W. Review of the biology of quercetin and related flavonoids Food Chem. Toxicol. 1995, 33, 1061-1080 (Pubitemid 26009773)
    • (1995) Food and Chemical Toxicology , vol.33 , Issue.12 , pp. 1061-1080
    • Formica, J.V.1
  • 25
    • 0034054933 scopus 로고    scopus 로고
    • Bioavailabilities of quercetin-3-glucoside and quercetin-4'- glucoside do not differ in humans
    • Olthof, M. R.; Hollman, P. C. H.; Vree, T. B.; Katan, M. B. Bioavailabilities of quercetin-3-glucoside and quercetin-4′-glucoside do not differ in humans J. Nutr. 2000, 130, 1200-1203 (Pubitemid 30233268)
    • (2000) Journal of Nutrition , vol.130 , Issue.5 , pp. 1200-1203
    • Olthof, M.R.1    Hollman, P.C.H.2    Vree, T.B.3    Katan, M.B.4
  • 28
    • 79952254710 scopus 로고    scopus 로고
    • Pharmacokinetics in mice and metabolism in murine and human liver fractions of the putative cancer chemopreventive agents 3′,4′, 5′,5,7-pentamethoxyflavone and tricin (4′,5,7-trihydroxy-3′, 5′-dimethoxyflavone)
    • Cai, H.; Sale, S.; Britton, R. G.; Brown, K.; Steward, W. P.; Gescher, A. J. Pharmacokinetics in mice and metabolism in murine and human liver fractions of the putative cancer chemopreventive agents 3′,4′,5′,5,7- pentamethoxyflavone and tricin (4′,5,7-trihydroxy-3′,5′- dimethoxyflavone) Cancer Chemother. Pharmacol. 2011, 67, 255-263
    • (2011) Cancer Chemother. Pharmacol. , vol.67 , pp. 255-263
    • Cai, H.1    Sale, S.2    Britton, R.G.3    Brown, K.4    Steward, W.P.5    Gescher, A.J.6
  • 29
    • 58949103807 scopus 로고    scopus 로고
    • In vitro solubility, stability and permeability of novel quercetin-amino acid conjugates
    • Kim, M. K.; Park, K.-S.; Yeo, W.-S.; Choo, H.; Chong, Y. In vitro solubility, stability and permeability of novel quercetin-amino acid conjugates Bioorg. Med. Chem. 2009, 17, 1164-1171
    • (2009) Bioorg. Med. Chem. , vol.17 , pp. 1164-1171
    • Kim, M.K.1    Park, K.-S.2    Yeo, W.-S.3    Choo, H.4    Chong, Y.5
  • 31
    • 0000474234 scopus 로고
    • A short and facile synthetic route to hydroxylated flavones. New synthesis of apigenin, tricin, and luteolin
    • Nagarathnam, D.; Cushman, M. A short and facile synthetic route to hydroxylated flavones. New synthesis of apigenin, tricin, and luteolin J. Org. Chem. 1991, 56, 4884-4887
    • (1991) J. Org. Chem. , vol.56 , pp. 4884-4887
    • Nagarathnam, D.1    Cushman, M.2
  • 32
    • 0242693874 scopus 로고    scopus 로고
    • Determination of the flavone tricin in human plasma by high-performance liquid chromatography
    • DOI 10.1002/bmc.260
    • Cai, H.; Verschoyle, R. D.; Steward, W. P.; Gescher, A. J. Determination of the flavone tricin in human plasma by high-performance liquid chromatography Biomed. Chromatogr. 2003, 17, 435-439 (Pubitemid 37406998)
    • (2003) Biomedical Chromatography , vol.17 , Issue.7 , pp. 435-439
    • Cai, H.1    Verschoyle, R.D.2    Steward, W.P.3    Gescher, A.J.4
  • 33
    • 24944471223 scopus 로고    scopus 로고
    • Determination of the putative cancer chemopreventive flavone tricin in plasma and tissues of mice by HPLC with UV-visible detection
    • DOI 10.1002/bmc.473
    • Cai, H.; Steward, W. P.; Gescher, A. J. Determination of the putative cancer chemopreventive flavone tricin in plasma and tissues of mice by HPLC with UV-visible detection Biomed. Chromatogr. 2005, 19, 518-522 (Pubitemid 41320495)
    • (2005) Biomedical Chromatography , vol.19 , Issue.7 , pp. 518-522
    • Cai, H.1    Steward, W.P.2    Gescher, A.J.3
  • 35
    • 0033051339 scopus 로고    scopus 로고
    • Transport of the flavonoid chrysin and its conjugated metabolites by the human intestinal cell line Caco-2
    • DOI 10.1016/S0006-2952(99)00133-1, PII S0006295299001331
    • Walle, U. K.; Galijatovic, A.; Walle, T. Transport of the flavonoid chrysin and its conjugated metabolites by the human intestinal cell line Caco-2 Biochem. Pharmacol. 1999, 58, 431-438 (Pubitemid 29281542)
    • (1999) Biochemical Pharmacology , vol.58 , Issue.3 , pp. 431-438
    • Kristina Walle, U.1    Galijatovic, A.2    Walle, T.3
  • 36
    • 21644436299 scopus 로고    scopus 로고
    • Enteric excretion of baicalein, a flavone of Scutellariae Radix, via glucuronidation in rat: Involvement of multidrug resistance-associated protein 2
    • DOI 10.1023/B:PHAM.0000048205.02478.b5
    • Akao, T.; Sakashita, Y.; Hamada, M.; Goto, H.; Shimada, Y.; Terasawa, K. Enteric excretion of baicalein, a flavone of Scutellaria radix, via glucuronidation in rat: Involvement of multidrug resistance-associated protein 2 Pharm. Res. 2004, 21, 2120-2126 (Pubitemid 40941234)
    • (2004) Pharmaceutical Research , vol.21 , Issue.11 , pp. 2120-2126
    • Akao, T.1    Sakashita, Y.2    Hanada, M.3    Goto, H.4    Shimada, Y.5    Terasawa, K.6
  • 37
    • 34248350462 scopus 로고    scopus 로고
    • Tissue distribution in mice and metabolism in murine and human liver of apigenin and tricin, flavones with putative cancer chemopreventive properties
    • DOI 10.1007/s00280-006-0368-5
    • Cai, H.; Boocock, D. J.; Steward, W. P.; Gescher, A. J. Tissue distribution in mice and metabolism in murine and human liver of apigenin and tricin, flavones with putative cancer chemopreventive properties Cancer Chemother. Pharmacol. 2007, 60, 257-266 (Pubitemid 46742541)
    • (2007) Cancer Chemotherapy and Pharmacology , vol.60 , Issue.2 , pp. 257-266
    • Cai, H.1    Boocock, D.J.2    Steward, W.P.3    Gescher, A.J.4
  • 38
    • 0029960775 scopus 로고    scopus 로고
    • Similarities and differences in the glucuronidation of estradiol and estrone by UDP-glucuronosyltransferase in liver microsomes from male and female rats
    • DOI 10.1016/0006-2952(96)00062-7
    • Zhu, B. T.; Suchar, L. A.; Huang, M.-T.; Conney, A. H. Similarities and differences in the glucuronidation of estradiol and estrone by UDP-glucuronosyltransferase in liver microsomes from male and female rats Biochem. Pharmacol. 1996, 51, 1195-1202 (Pubitemid 26127889)
    • (1996) Biochemical Pharmacology , vol.51 , Issue.9 , pp. 1195-1202
    • Zhu, B.T.1    Suchar, L.A.2    Huang, M.-T.3    Conney, A.H.4
  • 40
    • 0034853840 scopus 로고    scopus 로고
    • Application of enzymatically stable dipeptides for enhancement of intestinal permeability. Synthesis and in vitro evaluation of dipeptide-coupled compounds
    • DOI 10.1016/S0968-0896(01)00066-9, PII S0968089601000669
    • Friedrichsen, G. M.; Jakobsen, P.; Taub, M.; Begtrup, M. Application of enzymatically stable dipeptides for enhancement of intestinal permeability. Synthesis and in vitro evaluation of dipeptide-coupled compounds Bioorg. Med. Chem. Lett. 2001, 9, 2625-2632 (Pubitemid 32824165)
    • (2001) Bioorganic and Medicinal Chemistry , vol.9 , Issue.10 , pp. 2625-2632
    • Friedrichsen, G.M.1    Jakobsen, P.2    Taub, M.3    Begtrup, M.4
  • 42
    • 0017891781 scopus 로고
    • Polarized monolayers formed by epithelial cells on a permeable and translucent support
    • Cereijido, M.; Robbins, E. S.; Dolan, W. J.; Rotunno, C. A.; Sabatini, D. D. Polarized monolayers formed by epithelial cells on a permeable and translucent support J. Cell Biol. 1978, 77, 853-880 (Pubitemid 8347746)
    • (1978) Journal of Cell Biology , vol.77 , Issue.3 , pp. 853-880
    • Cereijido, M.1    Robbins, E.S.2    Dolan, W.J.3
  • 43
    • 64649096522 scopus 로고    scopus 로고
    • Targeted disruption of peptide transporter Pept1 gene in mice significantly reduces dipeptide absorption in intestine
    • Hu, Y.; Smith, D. E.; Ma, K.; Jappar, D.; Thomas, W.; Hillgren, K. M. Targeted disruption of peptide transporter Pept1 gene in mice significantly reduces dipeptide absorption in intestine Mol. Pharmaceutics 2008, 5, 1122-1130
    • (2008) Mol. Pharmaceutics , vol.5 , pp. 1122-1130
    • Hu, Y.1    Smith, D.E.2    Ma, K.3    Jappar, D.4    Thomas, W.5    Hillgren, K.M.6
  • 45
    • 0035907176 scopus 로고    scopus 로고
    • Model prodrugs for the intestinal oligopeptide transporter: Model drug release in aqueous solution and in various biological media
    • DOI 10.1016/S0168-3659(01)00233-4, PII S0168365901002334
    • Nielsen, C. U.; Andersen, R.; Brodin, B.; Frokjaer, S.; Steffansen, B. Model prodrugs for the internal oligopeptide transporter: model drug release in aqueous solution and in various biological media J. Controlled Release 2001, 73, 21-30 (Pubitemid 32406098)
    • (2001) Journal of Controlled Release , vol.73 , Issue.1 , pp. 21-30
    • Nielsen, C.U.1    Andersen, R.2    Brodin, B.3    Frokjaer, S.4    Steffansen, B.5
  • 46
    • 0003448569 scopus 로고
    • Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY
    • Harlow, E.; Lane, D. Antibodies: A Laboratory Manual; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, 1988; p 449.
    • (1988) Antibodies: A Laboratory Manual , pp. 449
    • Harlow, E.1    Lane, D.2


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