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Volumn 40, Issue 2, 1997, Pages 137-145

Chlorogenic acid and synthetic chlorogenic acid derivatives: Novel inhibitors of hepatic glucose-6-phosphate translocase

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROGENIC ACID; CHLOROGENIC ACID DERIVATIVE; GLUCOSE 6 PHOSPHATE TRANSLOCASE; GLUCOSE 6 PHOSPHATE TRANSLOCASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 0031022886     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9607360     Document Type: Article
Times cited : (277)

References (46)
  • 1
    • 0000884121 scopus 로고
    • Glucose-6-Phosphatase of the liver in glycogen storage disease
    • Cori, G. T.; Cori, C. F. Glucose-6-Phosphatase of the liver in glycogen storage disease. J. Biol. Chem. 1952, 199, 661-667.
    • (1952) J. Biol. Chem. , vol.199 , pp. 661-667
    • Cori, G.T.1    Cori, C.F.2
  • 2
    • 0003086819 scopus 로고
    • The role of hepatic glucose-6-phosphatase in the regulation of carbohydrate metabolism
    • Ashmore, J.; Weber, G. The role of hepatic glucose-6-phosphatase in the regulation of carbohydrate metabolism. Vitamins Hormones 1959, 17, 91-132.
    • (1959) Vitamins Hormones , vol.17 , pp. 91-132
    • Ashmore, J.1    Weber, G.2
  • 4
    • 0025756453 scopus 로고
    • The molecular basis of the hepatic microsomal glucose-6-phosphatase system
    • Burchell, A.; Waddell, I. D. The molecular basis of the hepatic microsomal glucose-6-phosphatase system. Biochim. Biophys. Acta 1991, 1092, 129-137.
    • (1991) Biochim. Biophys. Acta , vol.1092 , pp. 129-137
    • Burchell, A.1    Waddell, I.D.2
  • 5
    • 0016362687 scopus 로고
    • Metabolic regulation by multifunctional glucose-6-phosphatase
    • Nordlie, R. C. Metabolic regulation by multifunctional glucose-6-phosphatase. Curr. Top. Cell. Regul. 1974, 8, 33-117.
    • (1974) Curr. Top. Cell. Regul. , vol.8 , pp. 33-117
    • Nordlie, R.C.1
  • 6
    • 0019012691 scopus 로고
    • Investigations on the possible involvement of phospholipids in the glucose-6-phosphate transport system of rat-liver microsomal glucose-6-phosphatase
    • Schulze, H. U.; Speth, M. Investigations on the possible involvement of phospholipids in the glucose-6-phosphate transport system of rat-liver microsomal glucose-6-phosphatase. Eur. J. Biochem. 1980, 106, 505-514.
    • (1980) Eur. J. Biochem. , vol.106 , pp. 505-514
    • Schulze, H.U.1    Speth, M.2
  • 7
    • 0029133653 scopus 로고
    • Evidence for a membrane exchangeable glucose pool in the functioning of rat liver glucose-6-phosphatase
    • Berteloot, A.; St Denis, J. F.; Van de Werve, G. Evidence for a membrane exchangeable glucose pool in the functioning of rat liver glucose-6-phosphatase. J. Biol. Chem. 1995, 270, 21098-21102
    • (1995) J. Biol. Chem. , vol.270 , pp. 21098-21102
    • Berteloot, A.1    St Denis, J.F.2    Van De Werve, G.3
  • 8
    • 0023848355 scopus 로고
    • The phosphohydrolase component of the hepatic microsomal glucose-6-phosphatase system is a 36.5-kilodalton polypeptide
    • Countaway, J. L.; Waddell, I. D.; Burchell, A.; Arion, W. J. The phosphohydrolase component of the hepatic microsomal glucose-6-phosphatase system is a 36.5-kilodalton polypeptide. J. Biol. Chem. 1988, 263, 2673-2678.
    • (1988) J. Biol. Chem. , vol.263 , pp. 2673-2678
    • Countaway, J.L.1    Waddell, I.D.2    Burchell, A.3    Arion, W.J.4
  • 9
    • 0016668016 scopus 로고
    • On the involvement of a glucose 6-phosphate transport system in the function of microsomal glucose 6-phosphatase
    • Arion, W. J.; Wallin, B. K.; Lange, A. J.; Ballas, L. M. On the involvement of a glucose 6-phosphate transport system in the function of microsomal glucose 6-phosphatase. Mol. Cell. Biochem. 1975, 6, 75-83.
    • (1975) Mol. Cell. Biochem. , vol.6 , pp. 75-83
    • Arion, W.J.1    Wallin, B.K.2    Lange, A.J.3    Ballas, L.M.4
  • 10
    • 0019122446 scopus 로고
    • Evidence for the participation of independent translocation for phosphate and glucose 6-phosphate in the microsomal glucose-6-phosphatase system. Interactions of the system with orthophosphate, inorganic pyrophosphate, and carbamyl phosphate
    • Arion, W. J.; Lange, A. J.; Walls, H. E.; Ballas, L. M. Evidence for the participation of independent translocation for phosphate and glucose 6-phosphate in the microsomal glucose-6-phosphatase system. Interactions of the system with orthophosphate, inorganic pyrophosphate, and carbamyl phosphate. J. Biol. Chem. 1980, 255, 10396-10406.
    • (1980) J. Biol. Chem. , vol.255 , pp. 10396-10406
    • Arion, W.J.1    Lange, A.J.2    Walls, H.E.3    Ballas, L.M.4
  • 11
    • 0017149031 scopus 로고
    • Microsomal membrane permeability and the hepatic glucose-6-phosphatase system. Interactions of the system with D-mannose 6-phosphate and D-mannose
    • Arion, W. J.; Ballas. L. M.; Lange, A, J.; Wallin, B. K. Microsomal membrane permeability and the hepatic glucose-6-phosphatase system. Interactions of the system with D-mannose 6-phosphate and D-mannose. J. Biol. Chem. 1976, 251, 4891-4897.
    • (1976) J. Biol. Chem. , vol.251 , pp. 4891-4897
    • Arion, W.J.1    Ballas, L.M.2    Lange, A.J.3    Wallin, B.K.4
  • 13
    • 0026699094 scopus 로고
    • The purification of a detergent-soluble glucose-6-phosphatase from rat liver
    • Speth, M.; Schulze, H. U. The purification of a detergent-soluble glucose-6-phosphatase from rat liver. Eur. J. Biochem. 1992, 208, 643-650.
    • (1992) Eur. J. Biochem. , vol.208 , pp. 643-650
    • Speth, M.1    Schulze, H.U.2
  • 14
    • 0027442493 scopus 로고
    • Isolation of the gene for murine glucose-6-phosphatase, the enzyme deficient in glycogen storage disease type 1A
    • Shelly, L. L.; Lei, K.-J.; Pan, C.-J.; Sakata, S. F.; Ruppert, S.; Schutz, G.; Chou, J. Y. Isolation of the gene for murine glucose-6-phosphatase, the enzyme deficient in glycogen storage disease type 1A. J. Biol. Chem. 1993, 268, 21482-21485.
    • (1993) J. Biol. Chem. , vol.268 , pp. 21482-21485
    • Shelly, L.L.1    Lei, K.-J.2    Pan, C.-J.3    Sakata, S.F.4    Ruppert, S.5    Schutz, G.6    Chou, J.Y.7
  • 15
    • 0023818962 scopus 로고
    • The identification of T2; the phosphate/pyrophosphate transport protein of the hepatic microsomal glucose-6-phosphatase system
    • Waddell, I. D.; Lindsay, J. G.; Burchell, A. The identification of T2; the phosphate/pyrophosphate transport protein of the hepatic microsomal glucose-6-phosphatase system. FEBS Lett. 1988, 229, 179-182.
    • (1988) FEBS Lett. , vol.229 , pp. 179-182
    • Waddell, I.D.1    Lindsay, J.G.2    Burchell, A.3
  • 16
    • 0028799765 scopus 로고
    • Mutations in the glucose-6-phosphatase gene are associated with glycogen storage disease types 1a and 1aSP but not 1b
    • Lei, K.; Shelly, L. L.; Lin, B.; Sidbury, J. B.; Chen, Y.; Nordlie, R. C.; Chou, J. Y. Mutations in the glucose-6-phosphatase gene are associated with glycogen storage disease types 1a and 1aSP but not 1b. J. Clin. Invest. 1995, 95, 234-240.
    • (1995) J. Clin. Invest. , vol.95 , pp. 234-240
    • Lei, K.1    Shelly, L.L.2    Lin, B.3    Sidbury, J.B.4    Chen, Y.5    Nordlie, R.C.6    Chou, J.Y.7
  • 18
    • 0015522944 scopus 로고
    • The specificity of glucose 6-phosphatase of intact liver microsomes
    • Arion, W. J.; Wallin, B. K.; Carlson, P. W.; Lange, A. J. The specificity of glucose 6-phosphatase of intact liver microsomes. J. Biol. Chem. 1972, 247, 2558-2565.
    • (1972) J. Biol. Chem. , vol.247 , pp. 2558-2565
    • Arion, W.J.1    Wallin, B.K.2    Carlson, P.W.3    Lange, A.J.4
  • 19
    • 0010443512 scopus 로고
    • Identification of two new inhibitors of hepatic glucose-6-phosphate translocase
    • Schindler, P. W.; Below, P.; Hemmerle, H.; Burger, H.-J.; Arion, W. J.; Efendic, S. Identification of two new inhibitors of hepatic glucose-6-phosphate translocase. Diabetologia 1994, 37 [Suppl. 1], A134.
    • (1994) Diabetologia , vol.37 , Issue.1 SUPPL.
    • Schindler, P.W.1    Below, P.2    Hemmerle, H.3    Burger, H.-J.4    Arion, W.J.5    Efendic, S.6
  • 20
    • 15444360550 scopus 로고
    • Über Gerbstoffe; III Chlorogensäure, der gerbstoffartige Bestandteil der Kaffeebohnen
    • Freudenberger, K. Über Gerbstoffe; III Chlorogensäure, der gerbstoffartige Bestandteil der Kaffeebohnen. (About tannines: chlorogenic acid, a tannine like component of coffee beans.) Ber. 1920, 53. 237.
    • (1920) Ber. , vol.53 , pp. 237
    • Freudenberger, K.1
  • 21
    • 0014124761 scopus 로고
    • The biosynthesis of chlorogenic acid and lignin in potato cell cultures
    • Gamborg, O. L. The biosynthesis of chlorogenic acid and lignin in potato cell cultures. Can. J. Biochem. Cell. Biol. 1967, 45, 1451-1457.
    • (1967) Can. J. Biochem. Cell. Biol. , vol.45 , pp. 1451-1457
    • Gamborg, O.L.1
  • 22
    • 0001413182 scopus 로고
    • Enzymic oxidative reaction of catechin and chlorogenic acid in a model system
    • Oszmianski, J.; Lee, C. Y. Enzymic oxidative reaction of catechin and chlorogenic acid in a model system. J. Agric. Food. Chem. 1990, 38, 1202-1204.
    • (1990) J. Agric. Food. Chem. , vol.38 , pp. 1202-1204
    • Oszmianski, J.1    Lee, C.Y.2
  • 24
    • 0022828951 scopus 로고
    • Inhibition by chlorogenic acid of haematin-catalysed retinoic acid 5,6-epoxidation
    • Iwahashi, H.; Negoro, Y.; Ikeda, A.; Morishita, H.; Kido, R. Inhibition by chlorogenic acid of haematin-catalysed retinoic acid 5,6-epoxidation. Biochem. J. 1986, 239, 641-646.
    • (1986) Biochem. J. , vol.239 , pp. 641-646
    • Iwahashi, H.1    Negoro, Y.2    Ikeda, A.3    Morishita, H.4    Kido, R.5
  • 25
    • 0024026298 scopus 로고
    • Lilly lecture 1987. The triumvirate: Beta-cell, muscle, liver. A collusion responsible for NIDDM
    • DeFronzo, R. A. Lilly lecture 1987. The triumvirate: beta-cell, muscle, liver. A collusion responsible for NIDDM. Diabetes 1988, 37, 667-687.
    • (1988) Diabetes , vol.37 , pp. 667-687
    • DeFronzo, R.A.1
  • 26
    • 0020075847 scopus 로고
    • The effect of chronic sulfonylurea therapy on hepatic glucose production in non-insulin-dependent diabetes
    • Best, J. D.; Judzewitsch, R. G.; Pfeifer, M. A.; Beard, J. C.; Halter, J. B.; Porte, D. The effect of chronic sulfonylurea therapy on hepatic glucose production in non-insulin-dependent diabetes. Diabetes 1982, 31, 333-338.
    • (1982) Diabetes , vol.31 , pp. 333-338
    • Best, J.D.1    Judzewitsch, R.G.2    Pfeifer, M.A.3    Beard, J.C.4    Halter, J.B.5    Porte, D.6
  • 27
    • 0025089269 scopus 로고
    • On the determination of basal glucose production rate in patients with type 2 (non-insulin-dependent) diabetes mellitus using primed-continuous 3-3H-glucose infusion
    • Hother Nielsen, O.; Beck Nielsen, H. On the determination of basal glucose production rate in patients with type 2 (non-insulin-dependent) diabetes mellitus using primed-continuous 3-3H-glucose infusion. Diabetologia 1990, 33, 603-610.
    • (1990) Diabetologia , vol.33 , pp. 603-610
    • Hother Nielsen, O.1    Beck Nielsen, H.2
  • 28
    • 0030034518 scopus 로고    scopus 로고
    • United Kingdom Prospective Diabetes Study 17: A 9-year update of a randomized, controlled trial on the effect of improved metabolic control on complications in non-insulin-dependent diabetes mellitus
    • Turner, R.; Cull, C.; Holman, R. United Kingdom Prospective Diabetes Study 17: a 9-year update of a randomized, controlled trial on the effect of improved metabolic control on complications in non-insulin-dependent diabetes mellitus. Ann. Intern. Med. 1996, 124, 136-145.
    • (1996) Ann. Intern. Med. , vol.124 , pp. 136-145
    • Turner, R.1    Cull, C.2    Holman, R.3
  • 29
    • 0028627739 scopus 로고
    • The liver as a target for therapy in non-insulin dependent diabetes mellitus
    • Yki-Jarvinen, H. The liver as a target for therapy in non-insulin dependent diabetes mellitus. Diab. Nutr. Metab. 1994, 7, 109-119.
    • (1994) Diab. Nutr. Metab. , vol.7 , pp. 109-119
    • Yki-Jarvinen, H.1
  • 30
    • 0025079179 scopus 로고
    • Failure of substrate-induced gluconeogenesis to increase overall glucose appearance in normal humans. Demonstration of hepatic auto-regulation without a change in plasma glucose concentration
    • Jenssen, T.; Nurjhan, N.; Consoli, A.; Gerich, J. E. Failure of substrate-induced gluconeogenesis to increase overall glucose appearance in normal humans. Demonstration of hepatic auto-regulation without a change in plasma glucose concentration. J. Clin. Invest. 1990, 86, 489-497.
    • (1990) J. Clin. Invest. , vol.86 , pp. 489-497
    • Jenssen, T.1    Nurjhan, N.2    Consoli, A.3    Gerich, J.E.4
  • 31
    • 0027192162 scopus 로고
    • The molecular basis of the genetic deficiencies of five of the components of the glucose-6-phosphatase system: Improved diagnosis
    • Burchell, A.; Waddell, I. D. The molecular basis of the genetic deficiencies of five of the components of the glucose-6-phosphatase system: Improved diagnosis. Eur. J. Pediatr. 1993, 152, Suppl. 1, S18-S21.
    • (1993) Eur. J. Pediatr. , vol.152 , Issue.1 SUPPL.
    • Burchell, A.1    Waddell, I.D.2
  • 32
    • 0015198060 scopus 로고
    • Ring-opening reactions of a diepoxide derived from (-)-quinic acid
    • Mercier, D.; Leboul, J.; Cleophax, J.; Gero, S. D. Ring-opening reactions of a diepoxide derived from (-)-quinic acid. Carbohydr. Res. 1971, 20, 299-304.
    • (1971) Carbohydr. Res. , vol.20 , pp. 299-304
    • Mercier, D.1    Leboul, J.2    Cleophax, J.3    Gero, S.D.4
  • 33
    • 0021265795 scopus 로고
    • Brief syntheses of (±)-methyl shikimate, (±)-methyl epishikimate and structural variants
    • Campbell, M. M.; Kaye, A. D.; Sainsbury, M.; Yavarzadeh, R. Brief syntheses of (±)-methyl shikimate, (±)-methyl epishikimate and structural variants. Tetrahedron 1984, 40, 2461-2470.
    • (1984) Tetrahedron , vol.40 , pp. 2461-2470
    • Campbell, M.M.1    Kaye, A.D.2    Sainsbury, M.3    Yavarzadeh, R.4
  • 34
    • 0001388669 scopus 로고
    • Partial purification and properties of p-hydroxycinnamoyl-CoA: Shikimate-p-hydroxycinnamoyl transferase from higher plants
    • Ulbrich, B.; Zenk, M. H. Partial purification and properties of p-hydroxycinnamoyl-CoA: shikimate-p-hydroxycinnamoyl transferase from higher plants. Phytochemistry 1980, 19, 1625-1629.
    • (1980) Phytochemistry , vol.19 , pp. 1625-1629
    • Ulbrich, B.1    Zenk, M.H.2
  • 35
    • 0023850134 scopus 로고
    • Diastereospecific, non-racemic synthesis of the C-20 to C-34 segment of the novel immunosuppressant FK-506
    • Mills, S.; Desmond, R.; Reamer, R. A.; Volante, R. P.; Shinkai, I. Diastereospecific, non-racemic synthesis of the C-20 to C-34 segment of the novel immunosuppressant FK-506. Tetrahedron Lett. 1988, 29, 281-284.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 281-284
    • Mills, S.1    Desmond, R.2    Reamer, R.A.3    Volante, R.P.4    Shinkai, I.5
  • 36
    • 0000653744 scopus 로고
    • (-)-Methyl cis-3-hydroxy-4,5-oxycyclohex-1-enecarboxylate: Stereospecific formation from and conversion to (-)-methyl shikimate; complex formation with bis(carbomethoxy)hydrazine
    • McGowan, D. A.; Berchtold, G. A. (-)-Methyl cis-3-hydroxy-4,5-oxycyclohex-1-enecarboxylate: stereospecific formation from and conversion to (-)-methyl shikimate; complex formation with bis(carbomethoxy)hydrazine. J. Org. Chem. 1981, 46, 2381-2383.
    • (1981) J. Org. Chem. , vol.46 , pp. 2381-2383
    • McGowan, D.A.1    Berchtold, G.A.2
  • 37
    • 0021688352 scopus 로고
    • Studies on the activities of tannins and related compounds; V. Inhibitory effects on lipid peroxidation in mitochondria and microsomes of liver
    • Kimura, Y.; Okuda, H.; Okuda, T.; Hatano, T.; Agata, I.; Arichi, S. Studies on the activities of tannins and related compounds; V. Inhibitory effects on lipid peroxidation in mitochondria and microsomes of liver. Planta Med. 1984, 50, 473-477.
    • (1984) Planta Med. , vol.50 , pp. 473-477
    • Kimura, Y.1    Okuda, H.2    Okuda, T.3    Hatano, T.4    Agata, I.5    Arichi, S.6
  • 39
    • 0015916436 scopus 로고
    • Synthesis of 2-hydroxyquinic and 2-hydroxyepiquinic acids from shikimic acid
    • Adlersberg, M.; Bondinell, W. E.; Sprinson, D. B. Synthesis of 2-hydroxyquinic and 2-hydroxyepiquinic acids from shikimic acid. J. Am. Chem. Soc. 1973, 95, 887-896.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 887-896
    • Adlersberg, M.1    Bondinell, W.E.2    Sprinson, D.B.3
  • 40
    • 0008794451 scopus 로고
    • Synthesis of enantiomerically pure substituted cyclopentenes from (-)-quinic acid
    • Barriere, J. C.; Cleophax, J.; Gero, S. D.; Vuilhorgne, M. Synthesis of enantiomerically pure substituted cyclopentenes from (-)-quinic acid. Helv. Chim. Acta 1983, 66, 296-307.
    • (1983) Helv. Chim. Acta , vol.66 , pp. 296-307
    • Barriere, J.C.1    Cleophax, J.2    Gero, S.D.3    Vuilhorgne, M.4
  • 43
    • 0024827284 scopus 로고
    • Measurement of intactness of rat liver endoplasmic reticulum
    • Arion, W. J. Measurement of intactness of rat liver endoplasmic reticulum. Methods Enzymol. 1989, 174, 58-67.
    • (1989) Methods Enzymol. , vol.174 , pp. 58-67
    • Arion, W.J.1
  • 44
    • 0023656695 scopus 로고
    • The isolated perfused rat liver: Preparation and application
    • Wolkoff, A. W.; Johansen, K. L.; Goeser T. The isolated perfused rat liver: preparation and application. Anal. Biochem. 1987, 167, 1-14.
    • (1987) Anal. Biochem. , vol.167 , pp. 1-14
    • Wolkoff, A.W.1    Johansen, K.L.2    Goeser, T.3
  • 46
    • 15444349243 scopus 로고    scopus 로고
    • note
    • For the Xray analysis we deprotected 24 with p-toluolsulfonic acid in methanol to the tetrol which was subsequently transformed to the well crystallizing tetraacetate 24a. (Matrix Presented)


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