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Volumn 12, Issue 7, 2007, Pages 1274-1288

(-)-Catechin in cocoa and chocolate: Occurence and analysis of an atypical flavan-3-ol enantiomer

Author keywords

Capillary electrophoresis; Catechin; Chocolate; Cocoa; Enantioseparation; Epicatechin; Epimerization; Flavonoids; Isolation; LC MS; Purification

Indexed keywords

ALKALI; CATECHIN; FLAVAN 3 OL; FLAVAN-3-OL; FLAVONOID; UNCLASSIFIED DRUG;

EID: 34547633460     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/12071274     Document Type: Article
Times cited : (101)

References (35)
  • 1
    • 0034106431 scopus 로고    scopus 로고
    • Catechin contents of foods commonly consumed in The Netherlands. 1. Fruits, vegetables, staple foods, and processed foods
    • Arts, I.C.W.; van de Putte, B.; Hollman, P.C.H. Catechin contents of foods commonly consumed in The Netherlands. 1. Fruits, vegetables, staple foods, and processed foods. J. Agric. Food Chem. 2000, 48, 1746-1751.
    • (2000) J. Agric. Food Chem , vol.48 , pp. 1746-1751
    • Arts, I.C.W.1    van de Putte, B.2    Hollman, P.C.H.3
  • 3
    • 33748644400 scopus 로고    scopus 로고
    • A review of the health potential of bioactive compounds
    • Hooper, L.; Cassidy, A. A review of the health potential of bioactive compounds. J. Sci. Food Agric. 2006, 86, 1805-1813.
    • (2006) J. Sci. Food Agric , vol.86 , pp. 1805-1813
    • Hooper, L.1    Cassidy, A.2
  • 4
    • 33746496150 scopus 로고    scopus 로고
    • Significane of flavonoids in plant resistance: A review
    • Treutter, D. Significane of flavonoids in plant resistance: A review. Environ. Chem. Lett. 2006, 4, 147-157.
    • (2006) Environ. Chem. Lett , vol.4 , pp. 147-157
    • Treutter, D.1
  • 5
    • 33846419121 scopus 로고    scopus 로고
    • Overview of antibacterial, antitoxin, antiviral, and antifungal activities of tea flavonoids and teas
    • Friedman, M. Overview of antibacterial, antitoxin, antiviral, and antifungal activities of tea flavonoids and teas. Mol. Nutr. Food Res. 2006, 51, 116-134.
    • (2006) Mol. Nutr. Food Res , vol.51 , pp. 116-134
    • Friedman, M.1
  • 6
    • 33846510561 scopus 로고    scopus 로고
    • Protection of lipids from oxidation by epicatechin, trans-resveratrol, and gallic and caffeic acids in intestinal model systems
    • Kermez, Z.; Chetrit, D.; Shoseyov, O.; Regev-Shosani, G. Protection of lipids from oxidation by epicatechin, trans-resveratrol, and gallic and caffeic acids in intestinal model systems J. Agric. Food Chem. 2006, 54, 10288-10293.
    • (2006) J. Agric. Food Chem , vol.54 , pp. 10288-10293
    • Kermez, Z.1    Chetrit, D.2    Shoseyov, O.3    Regev-Shosani, G.4
  • 8
    • 0033024963 scopus 로고    scopus 로고
    • Inhibition of non-haem iron aborption in man by polyphenolic-containing beverages
    • Hurell, R.F.; Reddy, M.; Cook, J.D. Inhibition of non-haem iron aborption in man by polyphenolic-containing beverages. Brit. J. Nutr. 1999, 81, 289-295.
    • (1999) Brit. J. Nutr , vol.81 , pp. 289-295
    • Hurell, R.F.1    Reddy, M.2    Cook, J.D.3
  • 9
    • 33751234225 scopus 로고    scopus 로고
    • Chocolate is a powerfull ex vivo and in vivo antioxidant, an antiathereosclerotic agent in animal model, and a significant contributor to antioxidants in european and american diets
    • Vinson, J.A.; Proch, J.; Bose, P.; Muchler, S.; Taffera, P.; Shuta, D.; Samman, N.; Agbor, G.A. Chocolate is a powerfull ex vivo and in vivo antioxidant, an antiathereosclerotic agent in animal model, and a significant contributor to antioxidants in european and american diets. J. Agric. Food Chem. 2006, 54, 8071-8076.
    • (2006) J. Agric. Food Chem , vol.54 , pp. 8071-8076
    • Vinson, J.A.1    Proch, J.2    Bose, P.3    Muchler, S.4    Taffera, P.5    Shuta, D.6    Samman, N.7    Agbor, G.A.8
  • 10
    • 33749241530 scopus 로고    scopus 로고
    • (+)-Catechin is more bioavailable than (-)-catechin: Relevance to the bioavailability of catechin from cocoa
    • Donovan, J.L.; Crespy, V.; Oliveira, M.; Cooper K.A.; Gibson, B.B.; Williamson, G. (+)-Catechin is more bioavailable than (-)-catechin: Relevance to the bioavailability of catechin from cocoa. Free Radical Res. 2006, 40, 1029-1034.
    • (2006) Free Radical Res , vol.40 , pp. 1029-1034
    • Donovan, J.L.1    Crespy, V.2    Oliveira, M.3    Cooper, K.A.4    Gibson, B.B.5    Williamson, G.6
  • 11
    • 0020529060 scopus 로고
    • Stereospecific effects of (+)- and (-)-catechin on glycogen metabolism in isolated rat hepatocytes
    • Nyfeler, F.; Moser, U.K.; Walter, P. Stereospecific effects of (+)- and (-)-catechin on glycogen metabolism in isolated rat hepatocytes. Biochim. Biophys. Acta 1983, 763, 50-57.
    • (1983) Biochim. Biophys. Acta , vol.763 , pp. 50-57
    • Nyfeler, F.1    Moser, U.K.2    Walter, P.3
  • 12
    • 34547622492 scopus 로고    scopus 로고
    • Protection of (-)-catechin gallate and (+)-epicatechin on xanthine-xanthine oxidase system injury in cultered cardiomyocytes
    • Cao, Y., Liang, R.; Yang, B.; Wang, L.; Yang, Q.; Wang, Y. Protection of (-)-catechin gallate and (+)-epicatechin on xanthine-xanthine oxidase system injury in cultered cardiomyocytes. Zhongguo Shiyan Fangjixue Zazhi 2006, 12, 36-38.
    • (2006) Zhongguo Shiyan Fangjixue Zazhi , vol.12 , pp. 36-38
    • Cao, Y.1    Liang, R.2    Yang, B.3    Wang, L.4    Yang, Q.5    Wang, Y.6
  • 13
    • 34047241705 scopus 로고    scopus 로고
    • Cho, S.Y.; Park, P.J.; Shin, H.J.; Kim, Y.K.; Shin, D.W.; Shin, E.S.; Lee, H.H.; Lee, B.G.; Baik, J.H.; Lee, T.R. (-)-Catechin suppresses expression of Kruppel-like factor 7 and increases expression and secretion of adiponectin protein in 3T3-L1 cells. Am. J. Physiol. Endocrinol. Metab. 2007, 292, E1166-E1172.
    • Cho, S.Y.; Park, P.J.; Shin, H.J.; Kim, Y.K.; Shin, D.W.; Shin, E.S.; Lee, H.H.; Lee, B.G.; Baik, J.H.; Lee, T.R. (-)-Catechin suppresses expression of Kruppel-like factor 7 and increases expression and secretion of adiponectin protein in 3T3-L1 cells. Am. J. Physiol. Endocrinol. Metab. 2007, 292, E1166-E1172.
  • 14
    • 33748060964 scopus 로고    scopus 로고
    • Biosynthesis of flavan-3-ols by leucoanthocyanidin 4-reductase and anthocyanidin reductase in leaves of grape (Vitis vinifera L.), apple (Malus x domestica Borkh.) and other crops
    • Pfeiffer, J.; Kühnel, C.; Brandt, J.; Duy, D.; Punyasiri, P.A.N.; Forkmann, G.; Fischer, T.C. Biosynthesis of flavan-3-ols by leucoanthocyanidin 4-reductase and anthocyanidin reductase in leaves of grape (Vitis vinifera L.), apple (Malus x domestica Borkh.) and other crops. Plant Physiol. Bioch. 2006, 44, 323-334.
    • (2006) Plant Physiol. Bioch , vol.44 , pp. 323-334
    • Pfeiffer, J.1    Kühnel, C.2    Brandt, J.3    Duy, D.4    Punyasiri, P.A.N.5    Forkmann, G.6    Fischer, T.C.7
  • 15
    • 0001220835 scopus 로고
    • A characteristic of the proanthocyanidin chemistry of the Monocotyledonae
    • Ellis, C.J.; Yeap Foo L.; Porter, L.J. Enantiomerism: A characteristic of the proanthocyanidin chemistry of the Monocotyledonae. Phytochem. 1983, 22, 483-487.
    • (1983) Phytochem , vol.22 , pp. 483-487
    • Ellis, C.J.1    Yeap Foo, L.2    Porter3    Enantiomerism, L.J.4
  • 16
    • 34347235215 scopus 로고    scopus 로고
    • A lack of evidence for an ecological role of the putative allelochemical (+/-)-catechin in spotted knapweed invasion success
    • Blair, A.C.; Nissen, S.J.; Brunk, G.R.; Hufbauer, R.A. A lack of evidence for an ecological role of the putative allelochemical (+/-)-catechin in spotted knapweed invasion success. J. Chem. Ecol. 2006, 32, 2327- 2331.
    • (2006) J. Chem. Ecol , vol.32 , pp. 2327-2331
    • Blair, A.C.1    Nissen, S.J.2    Brunk, G.R.3    Hufbauer, R.A.4
  • 17
    • 33846900942 scopus 로고    scopus 로고
    • Chemical facilitation and induced pathogen resistance mediated by root-secreted phytotoxin
    • Prithiviraj, B.; Perry, L.G.; Badri, D.V.; Vivanco, J. M. Chemical facilitation and induced pathogen resistance mediated by root-secreted phytotoxin. New Phytol. 2007, 173, 852-860.
    • (2007) New Phytol , vol.173 , pp. 852-860
    • Prithiviraj, B.1    Perry, L.G.2    Badri, D.V.3    Vivanco, J.M.4
  • 18
    • 34250612588 scopus 로고    scopus 로고
    • Enantioseparation of catechin and epicatechin in plant food by chiral capillary electrophoresis
    • Kofink, M.; Papagiannopoulos, M.; Galensa, R. Enantioseparation of catechin and epicatechin in plant food by chiral capillary electrophoresis. Eur. Food Res. Technol. 2007, 225, 569-577.
    • (2007) Eur. Food Res. Technol , vol.225 , pp. 569-577
    • Kofink, M.1    Papagiannopoulos, M.2    Galensa, R.3
  • 19
    • 0642350800 scopus 로고
    • Harborne, J.B, Ed, Chapman and Hall: London, Chapter 10, p
    • Haslam, E. In The flavonoids; Harborne, J.B., Ed.; Chapman and Hall: London, 1975; Chapter 10, p 550-553
    • (1975) The flavonoids , pp. 550-553
    • Haslam, E.1
  • 20
  • 21
    • 4544291039 scopus 로고    scopus 로고
    • Direct enatioseparation of catechin and epicatechin in tea drinks by 6-O-α-D-glucosyl-β- cyclodextrin-modified micellar electrokinetic chromatography
    • Kodama, S.; Yamamoto, A.; Akinobu, M.; Yanai, H. Direct enatioseparation of catechin and epicatechin in tea drinks by 6-O-α-D-glucosyl-β- cyclodextrin-modified micellar electrokinetic chromatography. Electrophoresis 2004, 25, 2892-2898.
    • (2004) Electrophoresis , vol.25 , pp. 2892-2898
    • Kodama, S.1    Yamamoto, A.2    Akinobu, M.3    Yanai, H.4
  • 22
    • 33645834300 scopus 로고    scopus 로고
    • Analysis of catechins in Theobroma cacoa beans by cyclodextrin-modified micellar electrokinetic chromatography
    • Gotti, R.; Furlanetto, S.; Pinzauti, S.; Cavrini, V. Analysis of catechins in Theobroma cacoa beans by cyclodextrin-modified micellar electrokinetic chromatography. J. Chromatogr. A 2006, 1112, 345-352.
    • (2006) J. Chromatogr. A , vol.1112 , pp. 345-352
    • Gotti, R.1    Furlanetto, S.2    Pinzauti, S.3    Cavrini, V.4
  • 24
    • 34547616319 scopus 로고    scopus 로고
    • Hammerstone JR, J.F, Acquarone, V. Process for controlling the isomerization of, )-epicatechin and, -catechin in edible products. U.S. Pat. Appl. 2007/0003640, 2007
    • Hammerstone JR., J.F.; Acquarone, V. Process for controlling the isomerization of (-)-epicatechin and (+)-catechin in edible products. U.S. Pat. Appl. 2007/0003640, 2007.
  • 26
    • 34547623967 scopus 로고    scopus 로고
    • Heat-processed products having altered monomer profiles and processes for controlling the epimerization of (-)-epicatechin and (+)-catechin in the products
    • Hammerstone JR., J.F.; Acquarone, V. Heat-processed products having altered monomer profiles and processes for controlling the epimerization of (-)-epicatechin and (+)-catechin in the products. WO 2007/002852, 2007.
    • (2007) WO 2007/002852
    • Hammerstone, J.J.F.1    Acquarone, V.2
  • 27
    • 0012493887 scopus 로고    scopus 로고
    • Royal Society of Chemistry: Cambridge
    • Beckett, S.T. The science of chocolate; Royal Society of Chemistry: Cambridge, 2000; pp. 31-47.
    • (2000) The science of chocolate , pp. 31-47
    • Beckett, S.T.1
  • 28
    • 84866028070 scopus 로고
    • Effects of pH and temperature on reaction kinetics of catechins in green tea infusion
    • Komatsu, Y.; Suematsu, S.; Hisanobu, Y.; Saigo, H.; Matsuda, R.; Hara, K. Effects of pH and temperature on reaction kinetics of catechins in green tea infusion. Biosci. Biotech. Biochem. 1993, 57(6), 907-910.
    • (1993) Biosci. Biotech. Biochem , vol.57 , Issue.6 , pp. 907-910
    • Komatsu, Y.1    Suematsu, S.2    Hisanobu, Y.3    Saigo, H.4    Matsuda, R.5    Hara, K.6
  • 29
    • 33845291142 scopus 로고    scopus 로고
    • One for all-all for one: Proof of authenticity and tracing of foods with flavonoids. Analysis of proanthocyanidins in barley and malt
    • Zimmermann, B.F.; Galensa, R. One for all-all for one: Proof of authenticity and tracing of foods with flavonoids. Analysis of proanthocyanidins in barley and malt. Eur. Food Res. Technol. 2006, 24, 385-393.
    • (2006) Eur. Food Res. Technol , vol.24 , pp. 385-393
    • Zimmermann, B.F.1    Galensa, R.2
  • 30
    • 0033946356 scopus 로고    scopus 로고
    • Review on polyphenols in Theobroma cacao: Changes in composition during the manufacture of chocolate and methodology for identification and quantification
    • Wollgast, J.; Anklam, E. Review on polyphenols in Theobroma cacao: Changes in composition during the manufacture of chocolate and methodology for identification and quantification. Food Res. Int. 2000, 33, 423-447
    • (2000) Food Res. Int , vol.33 , pp. 423-447
    • Wollgast, J.1    Anklam, E.2
  • 31
    • 0001689670 scopus 로고
    • Kinetics of epimerization of (+)-catechin and its rearrangement to catechinic acid
    • Kiatgrajai, P.; Wellons, J.D.; Gollob, L.; White, J.D. Kinetics of epimerization of (+)-catechin and its rearrangement to catechinic acid. J. Org. Chem. 1982, 47, 2910-2912.
    • (1982) J. Org. Chem , vol.47 , pp. 2910-2912
    • Kiatgrajai, P.1    Wellons, J.D.2    Gollob, L.3    White, J.D.4
  • 32
    • 0031773804 scopus 로고    scopus 로고
    • Strategies for capillary electrophoresis: Method development and validation for pharmaceutical and biological applications
    • Wätzig, H.; Degenhardt, M.; Kunkel, A. Strategies for capillary electrophoresis: Method development and validation for pharmaceutical and biological applications. Electrophoresis 1998, 19, 2695-2752.
    • (1998) Electrophoresis , vol.19 , pp. 2695-2752
    • Wätzig, H.1    Degenhardt, M.2    Kunkel, A.3
  • 33
    • 2942528726 scopus 로고    scopus 로고
    • Identification and quantification of polyphenols in Carob Fruits (Ceratonia siliqua L.) and derived products by HPLC-UV-ESI/MSn
    • Papagiannopoulos, M.; Wollseifen, H.R.; Mellenthin, A.; Haber, B.; Galensa, R. Identification and quantification of polyphenols in Carob Fruits (Ceratonia siliqua L.) and derived products by HPLC-UV-ESI/MSn. J. Agric. Food Chem. 2004, 52, 3784-3791.
    • (2004) J. Agric. Food Chem , vol.52 , pp. 3784-3791
    • Papagiannopoulos, M.1    Wollseifen, H.R.2    Mellenthin, A.3    Haber, B.4    Galensa, R.5
  • 34
    • 0001805268 scopus 로고    scopus 로고
    • Investigations of proanthocyanidins by HPLC with electrospray ionization mass spectrometry
    • Friedrich, W.; Eberhardt, A.; Galensa, R. Investigations of proanthocyanidins by HPLC with electrospray ionization mass spectrometry. Eur. Food Res. Technol. 2000, 211, 56-64.
    • (2000) Eur. Food Res. Technol , vol.211 , pp. 56-64
    • Friedrich, W.1    Eberhardt, A.2    Galensa, R.3
  • 35
    • 0037035816 scopus 로고    scopus 로고
    • Online coupling of pressurized liquid extraction, solid-phase-extraction and high-performance liquid chromatography for automated analysis of proanthocyanidins in malt
    • Papagiannopoulos, M.; Zimmermann, B.; Mellenthin, A.; Krappe, M.; Maio, G.; Galensa, R. Online coupling of pressurized liquid extraction, solid-phase-extraction and high-performance liquid chromatography for automated analysis of proanthocyanidins in malt. J. Chromatogr. A 2002, 958, 9-16.
    • (2002) J. Chromatogr. A , vol.958 , pp. 9-16
    • Papagiannopoulos, M.1    Zimmermann, B.2    Mellenthin, A.3    Krappe, M.4    Maio, G.5    Galensa, R.6


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