메뉴 건너뛰기




Volumn 57, Issue 16, 2009, Pages 7264-7267

Efficient synthesis of flavanone glucuronides

Author keywords

Artemisia dracunculus; Enzymatic deprotection; Flavanone glucuronides; Human metabolites; Synthesis; Tarragon

Indexed keywords

ARTEMISIA; ARTEMISIA DRACUNCULUS;

EID: 70349201149     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf9011467     Document Type: Article
Times cited : (17)

References (34)
  • 1
    • 0038217415 scopus 로고    scopus 로고
    • Flavanones, chalcones and dihydrochalcones - Nature, occurrence and dietary burden
    • DOI 10.1002/(SICI)1097-0010(20000515)80:7<1073::AID-JSFA568>3.0. CO;2-B
    • Tomas-Barberan, F. A.; Clifford, M. N. Flavanones, chalcones and dihydrochalcones-nature, occurrence and dietary burden. J. Sci. Food Agric. 2000, 80, 1073-1080. (Pubitemid 30319400)
    • (2000) Journal of the Science of Food and Agriculture , vol.80 , Issue.7 , pp. 1073-1080
    • Tomas-Barberan, F.A.1    Clifford, M.N.2
  • 3
    • 0010352638 scopus 로고
    • Chemical constituents of the aerial parts oí Artemisia dracunculus
    • Balza, F.; Jamieson, L.; Towers, G.H.N. Chemical constituents of the aerial parts oí Artemisia dracunculus. J. Nat. Prod. 1985, 48, 339-340.
    • (1985) J. Nat. Prod. , vol.48 , pp. 339-340
    • Balza, F.1    Jamieson, L.2    Towers, G.H.N.3
  • 4
    • 10044246299 scopus 로고    scopus 로고
    • Review of the flavonoids quercetin, hesperetin, and naringenin. Dietary sources, bioactivities, bioavailability, and epidemiology
    • DOI 10.1016/j.nutres.2004.07.005, PII S0271531704001344
    • Erlund, I. Review of the flavonoids quercetin, hesperetin, and naringenin. Dietary sources, bioactivities, bioavailability, and epidemiology. Nutr. Res. 2004, 24, 851-874. (Pubitemid 39600842)
    • (2004) Nutrition Research , vol.24 , Issue.10 , pp. 851-874
    • Erlund, I.1
  • 5
    • 50449111165 scopus 로고    scopus 로고
    • Update on uses and properties of Citrus flavonoids: New findings in anticancer, cardiovascular, and anti-inflammatory activity
    • Benavente-Garcia, O.; Castillo, J. Update on uses and properties of Citrus flavonoids: new findings in anticancer, cardiovascular, and anti-inflammatory activity. J. Agric. Food Chem. 2008, 56, 6185-6205.
    • (2008) J. Agric. Food Chem. , vol.56 , pp. 6185-6205
    • Benavente-Garcia, O.1    Castillo, J.2
  • 7
    • 0037327340 scopus 로고    scopus 로고
    • Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two dose of orange juice
    • DOI 10.1038/sj.ejcn.1601547
    • Manach, C.; Morand, C.; Gil-Izquierdo, A.; Bouteloup-Demange, C.; Remesy, C. Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice. Eur. J. Clin. Nutr. 2003, 57, 235-242. (Pubitemid 36240474)
    • (2003) European Journal of Clinical Nutrition , vol.57 , Issue.2 , pp. 235-242
    • Manach, C.1    Morand, C.2    Gil-Izquierdo, A.3    Bouteloup-Demange, C.4    Remesy, C.5
  • 9
    • 6344291786 scopus 로고    scopus 로고
    • Identification and quantification of the conjugated metabolites derived from orally administered hesperidin in rat plasma
    • Matsumoto, H.; Ikoma, Y.; Sugiura, M.; Yano, M.; Hasegawa, Y. Identification and quantification of the conjugated metabolites derived from orally administered hesperidin in rat plasma. J. Agric. Food Chem. 2004, 52, 6653-6659.
    • (2004) J. Agric. Food Chem. , vol.52 , pp. 6653-6659
    • Matsumoto, H.1    Ikoma, Y.2    Sugiura, M.3    Yano, M.4    Hasegawa, Y.5
  • 11
    • 67649422271 scopus 로고    scopus 로고
    • Absorption, metabolism and excretion of flavanones from single portions of orange fruit and juice and effects of anthropometric variables and contraceptive pill use on flavanone excretion
    • Brett, G. M.; Hollands, W.; Needs, P. W.; Teucher, B.; Dainty, J. R.; Davis, B. D.; Brodbelt, J. S.; Kroon, P. A. Absorption, metabolism and excretion of flavanones from single portions of orange fruit and juice and effects of anthropometric variables and contraceptive pill use on flavanone excretion. Br. J. Nutr. 2009, 101, 664-675.
    • (2009) Br. J. Nutr. , vol.101 , pp. 664-675
    • Brett, G.M.1    Hollands, W.2    Needs, P.W.3    Teucher, B.4    Dainty, J.R.5    Davis, B.D.6    Brodbelt, J.S.7    Kroon, P.A.8
  • 12
    • 0033858161 scopus 로고    scopus 로고
    • Identification and antioxidant activity of flavonoid metabolites in plasma and urine of eriocitrin-treated rats
    • Miyake, Y.; Shimoi, K.; Kumazawa, S.; Yamamoto, K.; Kinae, N.; Osawa, T. Identification and antioxidant activity of flavonoid metabolites in plasma and urine of eriocitrin-treated rats. J. Agric. Food Chem. 2000, 48, 3217-3224.
    • (2000) J. Agric. Food Chem. , vol.48 , pp. 3217-3224
    • Miyake, Y.1    Shimoi, K.2    Kumazawa, S.3    Yamamoto, K.4    Kinae, N.5    Osawa, T.6
  • 13
    • 0035150315 scopus 로고    scopus 로고
    • Human nutrition and metabolism: Plasma kinetics and urinary excretion of the flavanones naringenin and hesperetin in humans after ingestion of orange juice and grapefruit juice
    • Erlund, I.; Meririnne, E.; Alfthan, G.; Aro, A. Plasma kinetics and urinary excretion of the flavanones naringenin and hesperetin in humans after ingestion of orange juice and grapefruit juice. J. Nutr. 2001, 131, 235-241. (Pubitemid 32115362)
    • (2001) Journal of Nutrition , vol.131 , Issue.2 , pp. 235-241
    • Erlund, I.1    Meririnne, E.2    Alfthan, G.3    Aro, A.4
  • 14
    • 34247212317 scopus 로고    scopus 로고
    • Pharmacokinetics of the citrus flavanone aglycones hesperetin and naringenin after single oral administration in human subjects
    • Kanaze, F. I.; Bounartzi, M. I.; Georgarakis, M.; Niopas, I. Pharmacokinetics of the citrus flavanone aglycones hesperetin and naringenin after single oral administration in human subjects. Eur. J. Clin. Nutr. 2001, 61, 472-477.
    • (2001) Eur. J. Clin. Nutr. , vol.61 , pp. 472-477
    • Kanaze, F.I.1    Bounartzi, M.I.2    Georgarakis, M.3    Niopas, I.4
  • 16
    • 19044377944 scopus 로고    scopus 로고
    • Chemical synthesis of flavonoid conjugates
    • SantosBuelga, C., Williamson, G., Eds.; Royal Society of Chemistry: Cambridge, U.K., Chapter 9
    • Barron, D.; Cren-Olive, C.; Needs, P. W. Chemical synthesis of flavonoid conjugates. In Methods in Polyphenol Analysis; SantosBuelga, C., Williamson, G., Eds.; Royal Society of Chemistry: Cambridge, U.K., 2003; Chapter 9, pp 187-213.
    • (2003) Methods in Polyphenol Analysis , pp. 187-213
    • Barron, D.1    Cren-Olive, C.2    Needs, P.W.3
  • 17
    • 19044388959 scopus 로고    scopus 로고
    • In vitro biological properties of flavonoid conjugates found in vivo
    • DOI 10.1080/10715760500053610
    • Williamson, G.; Barron, D.; Shimoi, K.; Terao, J. In vitro biological properties of flavonoid conjugates found in vivo. Free Radical Res. 2005, 39, 457-469. (Pubitemid 40711878)
    • (2005) Free Radical Research , vol.39 , Issue.5 , pp. 457-469
    • Williamson, G.1    Barron, D.2    Shimoi, K.3    Terao, J.4
  • 18
    • 70349203587 scopus 로고    scopus 로고
    • Recent advances in the chemical synthesis and biological activity of phenolic metabolites
    • Barron, D. Recent advances in the chemical synthesis and biological activity of phenolic metabolites. Recent Adv. Polyphenol Res. 2008, 1, 317-358.
    • (2008) Recent Adv. Polyphenol Res. , vol.1 , pp. 317-358
    • Barron, D.1
  • 19
    • 33744906324 scopus 로고    scopus 로고
    • Convenient syntheses of metabolically important quercetin glucuronides and sulfates
    • Needs, P. W.; Kroon, P. A. Convenient syntheses of metabolically important quercetin glucuronides and sulfates. Tetrahedron 2006, 62, 6862-6868.
    • (2006) Tetrahedron , vol.62 , pp. 6862-6868
    • Needs, P.W.1    Kroon, P.A.2
  • 20
    • 23744440029 scopus 로고    scopus 로고
    • Towards the synthesis of aryl glucuronides as potential heparanase probes. An interesting outcome in the glycosidation of glucuronic acid with 4-hydroxycinnamic acid
    • Pearson, A. G.; Kiefel, M. J.; Ferro, V.; von Itzstein, M. Towards the synthesis of aryl glucuronides as potential heparanase probes. An interesting outcome in the glycosidation of glucuronic acid with 4-hydroxycinnamic acid. Carbohydr. Res. 2005, 340, 2077-2085.
    • (2005) Carbohydr. Res. , vol.340 , pp. 2077-2085
    • Pearson, A.G.1    Kiefel, M.J.2    Ferro, V.3    Von Itzstein, M.4
  • 21
    • 33750448323 scopus 로고    scopus 로고
    • A facile synthesis of isoflavone 7-O-glucuronides
    • Al Maharik, N.; Botting, N. P. A facile synthesis of isoflavone 7-O-glucuronides. Tetrahedron Lett. 2006, 47, 8703-8706.
    • (2006) Tetrahedron Lett. , vol.47 , pp. 8703-8706
    • Al Maharik, N.1    Botting, N.P.2
  • 22
    • 33746273193 scopus 로고    scopus 로고
    • Identification of isomeric flavonoid glucuronides in urine and plasma by metal complexation and LC-ESI-MS/MS
    • Davis, B. D.; Needs, P. W.; Kroon, P. A.; Brodbelt, J. S. Identification of isomeric flavonoid glucuronides in urine and plasma by metal complexation and LC-ESI-MS/MS. J. Mass Spectrom. 2006, 41, 911-920.
    • (2006) J. Mass Spectrom. , vol.41 , pp. 911-920
    • Davis, B.D.1    Needs, P.W.2    Kroon, P.A.3    Brodbelt, J.S.4
  • 24
    • 21344453042 scopus 로고    scopus 로고
    • Flavonoids from Vitex trifolio L. inhibit cell cycle progression at G2/M phase and induce apoptosis in mammalian cancer cells
    • Li, W. X.; Cui, C. B.; Cai, B.; Wang, H. Y.; Yao, X. S. Flavonoids from Vitex trifolio L. inhibit cell cycle progression at G2/M phase and induce apoptosis in mammalian cancer cells. J. Asian Nat. Prod. Res. 2005, 7, 615-626.
    • (2005) J. Asian Nat. Prod. Res. , vol.7 , pp. 615-626
    • Li, W.X.1    Cui, C.B.2    Cai, B.3    Wang, H.Y.4    Yao, X.S.5
  • 25
    • 0842334483 scopus 로고    scopus 로고
    • Inhibitory activity of flavonoids from Lychnophora sp. on generation of reactive oxygen species by neutrophils upon simulation by immune complexes
    • Kanashiro, A.; Kabeya, L. M.; Polizello, A. C. M.; Lopes, N. P.; Lopes, J. L. C.; Lucisano-Valim, Y. M. Inhibitory activity of flavonoids from Lychnophora sp. on generation of reactive oxygen species by neutrophils upon simulation by immune complexes. Phytother. Res. 2004, 18, 61-65.
    • (2004) Phytother. Res. , vol.18 , pp. 61-65
    • Kanashiro, A.1    Kabeya, L.M.2    Polizello, A.C.M.3    Lopes, N.P.4    Lopes, J.L.C.5    Lucisano-Valim, Y.M.6
  • 26
    • 34249981820 scopus 로고    scopus 로고
    • Platelet-activating factor (PAF) receptor binding antagonist activity of the methanol extracts and isolated flavonoids from Chromolaena odorata (L.) King and Robinson
    • Ling, S. K.; Pisar, M. M.; Man, S. Platelet-activating factor (PAF) receptor binding antagonist activity of the methanol extracts and isolated flavonoids from Chromolaena odorata (L.) King and Robinson. Biol. Pharm. Bull. 2001, 30, 1150-1152.
    • (2001) Biol. Pharm. Bull. , Issue.30 , pp. 1150-1152
    • Ling, S.K.1    Pisar, M.M.2    Man, S.3
  • 27
    • 27444439652 scopus 로고    scopus 로고
    • Total synthesis of CRM646-A and -B, two fungal glucuronides with potent heparinase inhibition activities
    • DOI 10.1021/jo051384k
    • Wang, P.; Zhang, Z.; Yu, B. Total synthesis of CRM646-A and -B, two fungal glucuronides with potent heparinase inhibition activities. J. Org. Chem. 2005, 70, 8884-8889. (Pubitemid 41532821)
    • (2005) Journal of Organic Chemistry , vol.70 , Issue.22 , pp. 8884-8889
    • Wang, P.1    Zhang, Z.2    Yu, B.3
  • 28
    • 0000869835 scopus 로고
    • Synthesis of (±)-7,3′- And 7,4'-di-O-methyleriodictyol and of velutin and pilloin
    • Jain, A. C.; Sharma, B. N. Synthesis of (±)-7,3′- and 7,4'-di-O-methyleriodictyol and of velutin and pilloin. Phytochemistry 1973, 12, 1455-1458.
    • (1973) Phytochemistry , vol.12 , pp. 1455-1458
    • Jain, A.C.1    Sharma, B.N.2
  • 29
    • 70349226575 scopus 로고    scopus 로고
    • Synthesis of 5,7-dihydroxy-3′,4′-dimethoxy and 3′,5-dihydroxy-4′,7-dimethoxyflavanones
    • Sun, Z.; Wang, X. Synthesis of 5,7-dihydroxy-3′,4′-dimethoxy and 3′,5-dihydroxy-4′,7-dimethoxyflavanones. Zhongguo Yiyao Gongye Zazhi 1999, 30, 179-180.
    • (1999) Zhongguo Yiyao Gongye Zazhi , vol.30 , pp. 179-180
    • Sun, Z.1    Wang, X.2
  • 30
    • 47749137424 scopus 로고    scopus 로고
    • Semisynthesis of five bioactive flavonoids from hesperidin
    • Shan, Y.; Li, G. Y.; Wang, Q. A.; Li, Z. H. Semisynthesis of five bioactive flavonoids from hesperidin. Youji Huaxue 2008, 28, 1024-1028.
    • (2008) Youji Huaxue , vol.28 , pp. 1024-1028
    • Shan, Y.1    Li, G.Y.2    Wang, Q.A.3    Li, Z.H.4
  • 32
    • 28444458985 scopus 로고    scopus 로고
    • Sayed, H. M. Flavonoids and cyanogenic glycosides from the leaves and stem bark of Prunus persica (L.) Batsch (Meet Ghamr) peach local cultivar in Assiut region
    • Backheet, E. Y.; Farag, S. F.; Ahmed, A. S.; Sayed, H. M. Flavonoids and cyanogenic glycosides from the leaves and stem bark of Prunus persica (L.) Batsch (Meet Ghamr) peach local cultivar in Assiut region. Bull. Pharm. Sci., Assiut Univ. 2003, 26, 55-66.
    • (2003) Bull. Pharm. Sci., Assiut Univ. , vol.26 , pp. 55-66
    • Backheet, E.Y.1    Farag, S.F.2    Ahmed, A.S.3
  • 33
    • 0030733773 scopus 로고    scopus 로고
    • Studies in sugar chemistry VII. Glucuronides of podophyllum derivatives
    • DOI 10.1002/ardp.19973300904
    • Nudelman, A.; Ruse, M.; Gottlieb, H. E.; Fairchild, C. Studies in sugar chemistry. Part 8. Glucuronides of podophyllum derivatives. Arch. Pharm. (Weinheim, Germany) 1997, 330, 285-289. (Pubitemid 27483640)
    • (1997) Archiv der Pharmazie , vol.330 , Issue.9-10 , pp. 285-289
    • Nudelman, A.1    Ruse, M.2    Gottlieb, H.E.3    Fairchild, C.4
  • 34
    • 0037075079 scopus 로고    scopus 로고
    • And biological activity of the prodrug of class i major histocompatibility peptide GILGFVFTL activated by β-glucuronidase
    • Rawale, S.; Hrihorczuk, L. M.; Wei, W. Z.; Zemlicka, J. Synthesis and biological activity of the prodrug of class I major histocompatibility peptide GILGFVFTL activated by β-glucuronidase. J. Med. Chem. 2002, 45, 937-943.
    • (2002) J. Med. Chem. , vol.45 , pp. 937-943
    • Rawale, S.1    Hrihorczuk, L.M.2    Wei, W.Z.3    Synthesis, Z.J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.