메뉴 건너뛰기




Volumn 121, Issue , 2017, Pages 10-18

Formation of inclusion compounds of (+)catechin with β-cyclodextrin in different complexation media: Spectral, thermal and antioxidant properties

Author keywords

Antioxidant activity; Catechin; Characterization; Complexation; Cyclodextrin; Inclusion compounds

Indexed keywords

CARBON; CARBON DIOXIDE; CHARACTERIZATION; COMPLEXATION; CYCLODEXTRINS; FLAVONOIDS; ORGANIC COMPOUNDS; PHENOLS; SUPERCRITICAL FLUID EXTRACTION;

EID: 84997282706     PISSN: 08968446     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.supflu.2016.06.005     Document Type: Article
Times cited : (21)

References (42)
  • 1
    • 33845573098 scopus 로고    scopus 로고
    • Cyclodextrins and their pharmaceutical applications
    • [1] Loftsson, T., Duchene, D., Cyclodextrins and their pharmaceutical applications. Int. J. Pharm. 329 (2007), 1–11.
    • (2007) Int. J. Pharm. , vol.329 , pp. 1-11
    • Loftsson, T.1    Duchene, D.2
  • 2
    • 0025259927 scopus 로고
    • The effects of cyclodextrins on drug absorption II. In vivo observations
    • [2] Frijlink, H.W., Eissens, A.C., Schoonen, A.J.M., Lerk, C.F., The effects of cyclodextrins on drug absorption II. In vivo observations. Int. J. Pharm. 64 (1990), 195–205.
    • (1990) Int. J. Pharm. , vol.64 , pp. 195-205
    • Frijlink, H.W.1    Eissens, A.C.2    Schoonen, A.J.M.3    Lerk, C.F.4
  • 3
    • 0011575296 scopus 로고
    • Inclusion compounds. XIX. 1a. The formation of inclusion compounds of α-cyclodextrin in aqueous solutions. thermodynamics and kinetics
    • [3] Cramer, F., Saenger, W., Spatz, H.-C., Inclusion compounds. XIX. 1a. The formation of inclusion compounds of α-cyclodextrin in aqueous solutions. thermodynamics and kinetics. J. Am. Chem. Soc. 89 (1967), 14–20.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 14-20
    • Cramer, F.1    Saenger, W.2    Spatz, H.-C.3
  • 4
    • 4243366245 scopus 로고
    • Thermochemical study of cyclodextrin inclusion complexes
    • [4] Siimer, E., Kõbu, M., Kurvits, M., Thermochemical study of cyclodextrin inclusion complexes. Thermochim. Acta 170 (1990), 89–95.
    • (1990) Thermochim. Acta , vol.170 , pp. 89-95
    • Siimer, E.1    Kõbu, M.2    Kurvits, M.3
  • 6
    • 33947584244 scopus 로고    scopus 로고
    • Studies of inclusion complexes of natural and modified cyclodextrin with (+)catechin by NMR and molecular modeling
    • [6] Jullian, C., Miranda, S., Zapata-Torres, G., Mendizábal, F., Olea-Azar, C., Studies of inclusion complexes of natural and modified cyclodextrin with (+)catechin by NMR and molecular modeling. Bioorg. Med. Chem. 15 (2007), 3217–3224, 10.1016/j.bmc.2007.02.035.
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 3217-3224
    • Jullian, C.1    Miranda, S.2    Zapata-Torres, G.3    Mendizábal, F.4    Olea-Azar, C.5
  • 7
    • 34250180216 scopus 로고    scopus 로고
    • Binding constants of inclusion complexes of nitroimidazoles with β-cyclodextrins in the absence and presence of PVP
    • [7] Chadha, R., Jain, D.V.S., Aggarwal, A., Singh, S., Thakur, D., Binding constants of inclusion complexes of nitroimidazoles with β-cyclodextrins in the absence and presence of PVP. Thermochim. Acta 459 (2007), 111–115.
    • (2007) Thermochim. Acta , vol.459 , pp. 111-115
    • Chadha, R.1    Jain, D.V.S.2    Aggarwal, A.3    Singh, S.4    Thakur, D.5
  • 8
    • 84927536875 scopus 로고    scopus 로고
    • β-cyclodextrin inclusion complexes containing Citrus sinensis (L.) Osbeck essential oil: an alternative to control Aedes aegypti larvae
    • [8] Galvão, J.G., Silva, V.F., Ferreira, S.G., França, F.R.M., Santos, D.A., Freitas, L.S., et al. β-cyclodextrin inclusion complexes containing Citrus sinensis (L.) Osbeck essential oil: an alternative to control Aedes aegypti larvae. Thermochim. Acta. 608 (2015), 14–19.
    • (2015) Thermochim. Acta. , vol.608 , pp. 14-19
    • Galvão, J.G.1    Silva, V.F.2    Ferreira, S.G.3    França, F.R.M.4    Santos, D.A.5    Freitas, L.S.6
  • 10
    • 42649106457 scopus 로고    scopus 로고
    • Effect of β-cyclodextrin on antioxidant activity of coumaric acids
    • [10] Stražišar, M., Andrenšek, S., Šmidovnik, A., Effect of β-cyclodextrin on antioxidant activity of coumaric acids. Food Chem. 110 (2008), 636–642.
    • (2008) Food Chem. , vol.110 , pp. 636-642
    • Stražišar, M.1    Andrenšek, S.2    Šmidovnik, A.3
  • 11
    • 52949148946 scopus 로고    scopus 로고
    • Complexation of resveratrol with cyclodextrins: solubility and antioxidant activity
    • [11] Lu, Z., Cheng, B., Hu, Y., Zhang, Y., Zou, G., Complexation of resveratrol with cyclodextrins: solubility and antioxidant activity. Food Chem. 113 (2009), 17–20.
    • (2009) Food Chem. , vol.113 , pp. 17-20
    • Lu, Z.1    Cheng, B.2    Hu, Y.3    Zhang, Y.4    Zou, G.5
  • 12
    • 73349099011 scopus 로고    scopus 로고
    • Chemical kinetics of 5-o-caffeoylquinic acid in superheated steam: effect of isomerization on mate (Ilex paraguariensis) manufacturing
    • [12] Zanoelo, E.F., Benincá, C., Chemical kinetics of 5-o-caffeoylquinic acid in superheated steam: effect of isomerization on mate (Ilex paraguariensis) manufacturing. J. Agric. Food Chem. 57 (2009), 11564–11569.
    • (2009) J. Agric. Food Chem. , vol.57 , pp. 11564-11569
    • Zanoelo, E.F.1    Benincá, C.2
  • 13
    • 42949109809 scopus 로고    scopus 로고
    • Synthesis and spectral investigation of Al(III) catechin/β-cyclodextrin and Al(III) quercetin/β-cyclodextrin inclusion compounds
    • [13] Dias, K., Nikolaou, S., De Giovani, W.F., Synthesis and spectral investigation of Al(III) catechin/β-cyclodextrin and Al(III) quercetin/β-cyclodextrin inclusion compounds. Spectrochim. Acta A Mol. Biomol. Spectrosc. 70 (2008), 154–161.
    • (2008) Spectrochim. Acta A Mol. Biomol. Spectrosc. , vol.70 , pp. 154-161
    • Dias, K.1    Nikolaou, S.2    De Giovani, W.F.3
  • 14
    • 84859163988 scopus 로고    scopus 로고
    • Synthesis and characterization of nano-encapsulated catechin by molecular inclusion with beta-cyclodextrin
    • [14] Krishnaswamy, K., Orsat, V., Thangavel, K., Synthesis and characterization of nano-encapsulated catechin by molecular inclusion with beta-cyclodextrin. J. Food Eng. 111 (2012), 255–264.
    • (2012) J. Food Eng. , vol.111 , pp. 255-264
    • Krishnaswamy, K.1    Orsat, V.2    Thangavel, K.3
  • 15
    • 0033859612 scopus 로고    scopus 로고
    • Flavonoids as antioxidants
    • [15] Pietta, P.-G., Flavonoids as antioxidants. J. Nat. Prod. 63 (2000), 1035–1042.
    • (2000) J. Nat. Prod. , vol.63 , pp. 1035-1042
    • Pietta, P.-G.1
  • 16
    • 0028072649 scopus 로고
    • Role of chemopreventers in human diet
    • [16] Stavric, B., Role of chemopreventers in human diet. Clin. Biochem. 27 (1994), 319–332.
    • (1994) Clin. Biochem. , vol.27 , pp. 319-332
    • Stavric, B.1
  • 17
    • 3543098219 scopus 로고    scopus 로고
    • Antioxidant properties of complexes of flavonoids with metal ions
    • [17] De Souza, R.F.V., De Giovani, W.F., Antioxidant properties of complexes of flavonoids with metal ions. Redox Rep. 9 (2004), 97–104.
    • (2004) Redox Rep. , vol.9 , pp. 97-104
    • De Souza, R.F.V.1    De Giovani, W.F.2
  • 20
    • 84864450779 scopus 로고    scopus 로고
    • Preparation of the beta-cyclodextrin-vitamin C (beta-CD-Vc) inclusion complex under high hydrostatic pressure (HHP)
    • [20] Hu, X., Wei, B., Li, H., Wu, C., Bai, Y., Xu, X., et al. Preparation of the beta-cyclodextrin-vitamin C (beta-CD-Vc) inclusion complex under high hydrostatic pressure (HHP). Carbohydr. Polym. 90 (2012), 1193–1196.
    • (2012) Carbohydr. Polym. , vol.90 , pp. 1193-1196
    • Hu, X.1    Wei, B.2    Li, H.3    Wu, C.4    Bai, Y.5    Xu, X.6
  • 21
    • 84877276831 scopus 로고    scopus 로고
    • Characterization of ketoprofen/methyl-β-cyclodextrin complexes prepared using supercritical carbon dioxide
    • [21] Banchero, M., Ronchetti, S., Manna, L., Characterization of ketoprofen/methyl-β-cyclodextrin complexes prepared using supercritical carbon dioxide. J. Chem., 2013, 1–8.
    • (2013) J. Chem. , pp. 1-8
    • Banchero, M.1    Ronchetti, S.2    Manna, L.3
  • 22
    • 84862067753 scopus 로고    scopus 로고
    • The use of lysine to enhance the supercritical complexation of ketoprofen and cyclodextrins
    • [22] Banchero, M., Manna, L., The use of lysine to enhance the supercritical complexation of ketoprofen and cyclodextrins. J. Supercrit. Fluids 67 (2012), 76–83.
    • (2012) J. Supercrit. Fluids , vol.67 , pp. 76-83
    • Banchero, M.1    Manna, L.2
  • 26
    • 84997114140 scopus 로고    scopus 로고
    • Determinação de isoflavonas e capacidade antioxidante de alimentos industrializados à base de soja e/ou produtos derivados consumidos no Brasil, (2009) 113.
    • [26] M.R. Alezandro, Determinação de isoflavonas e capacidade antioxidante de alimentos industrializados à base de soja e/ou produtos derivados consumidos no Brasil, (2009) 113.
    • Alezandro, M.R.1
  • 27
    • 84919684006 scopus 로고    scopus 로고
    • Complexation of estragole as pure compound and as main component of basil and tarragon essential oils with cyclodextrins
    • [27] Kfoury, M., Auezova, L., Ruellan, S., Greige-Gerges, H., Fourmentin, S., Complexation of estragole as pure compound and as main component of basil and tarragon essential oils with cyclodextrins. Carbohydr. Polym. 118 (2015), 156–164.
    • (2015) Carbohydr. Polym. , vol.118 , pp. 156-164
    • Kfoury, M.1    Auezova, L.2    Ruellan, S.3    Greige-Gerges, H.4    Fourmentin, S.5
  • 28
    • 84997114143 scopus 로고    scopus 로고
    • Cyclodextrin Inclusion Complexes Probed by NMR Techniques, 1 (1998) (Researchgate.Net).
    • [28] F. Pessine, A. Calderini, G. Alexandrino, Cyclodextrin Inclusion Complexes Probed by NMR Techniques, 1 (1998) (Researchgate.Net).
    • Pessine, F.1    Calderini, A.2    Alexandrino, G.3
  • 29
    • 0000207035 scopus 로고    scopus 로고
    • NMR study of the solution structures of the inclusion complexes of β-cyclodextrin with (+)-catechin and (−)-epicatechin
    • [29] Ishizu, T., Kintsu, K., Yamamoto, H., NMR study of the solution structures of the inclusion complexes of β-cyclodextrin with (+)-catechin and (−)-epicatechin. J. Phys. Chem. B 103 (1999), 8992–8997.
    • (1999) J. Phys. Chem. B , vol.103 , pp. 8992-8997
    • Ishizu, T.1    Kintsu, K.2    Yamamoto, H.3
  • 30
    • 84989603742 scopus 로고
    • Cyclodextrins as chiral complexing agents in water, and their application to optical purity measurements
    • [30] Greatbanks, D., Pickford, R., Cyclodextrins as chiral complexing agents in water, and their application to optical purity measurements. Magn. Reson. Chem. 25 (1987), 208–215.
    • (1987) Magn. Reson. Chem. , vol.25 , pp. 208-215
    • Greatbanks, D.1    Pickford, R.2
  • 31
    • 0642274113 scopus 로고    scopus 로고
    • Investigation of the complexation of (+)-catechin by beta-cyclodextrin by a combination of NMR, microcalorimetry and molecular modeling techniques
    • [31] Kríz, Z., Koca, J., Imberty, A., Charlot, A., Auzély-Velty, R., Investigation of the complexation of (+)-catechin by beta-cyclodextrin by a combination of NMR, microcalorimetry and molecular modeling techniques. Org. Biomol. Chem. 1 (2003), 2590–2595.
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 2590-2595
    • Kríz, Z.1    Koca, J.2    Imberty, A.3    Charlot, A.4    Auzély-Velty, R.5
  • 32
    • 0000222105 scopus 로고
    • Crystalline beta-cyclodextrin hydrate at various humidities—fast continuous, and reversible dehydration studied by X-ray-diffraction
    • [32] Steiner, T., Koellner, G., Crystalline beta-cyclodextrin hydrate at various humidities—fast continuous, and reversible dehydration studied by X-ray-diffraction. J. Am. Chem. Soc. 116 (1994), 5122–5128.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 5122-5128
    • Steiner, T.1    Koellner, G.2
  • 33
    • 15044338646 scopus 로고    scopus 로고
    • Flow chart for infrared spectra interpretation of organic compounds
    • [33] a. Lopes, W., Fascio, M., Flow chart for infrared spectra interpretation of organic compounds. Quim. Nova 27 (2004), 670–673.
    • (2004) Quim. Nova , vol.27 , pp. 670-673
    • Lopes, W.A.1    Fascio, M.2
  • 34
    • 75149185326 scopus 로고    scopus 로고
    • Thermal analysis of β-cyclodextrin/berberine chloride inclusion compounds
    • [34] Li, N., Xu, L., Thermal analysis of β-cyclodextrin/berberine chloride inclusion compounds. Thermochim. Acta 499 (2010), 166–170.
    • (2010) Thermochim. Acta , vol.499 , pp. 166-170
    • Li, N.1    Xu, L.2
  • 35
    • 80054032357 scopus 로고    scopus 로고
    • DSC, X-ray and FTIR studies of a gemfibrozil/dimethyl-β-cyclodextrin inclusion complex produced by co-grinding
    • [35] Aigner, Z., Berkesi, O., Farkas, G., Szabó-Révész, P., DSC, X-ray and FTIR studies of a gemfibrozil/dimethyl-β-cyclodextrin inclusion complex produced by co-grinding. J. Pharm. Biomed. Anal. 57 (2012), 62–67.
    • (2012) J. Pharm. Biomed. Anal. , vol.57 , pp. 62-67
    • Aigner, Z.1    Berkesi, O.2    Farkas, G.3    Szabó-Révész, P.4
  • 36
    • 84930225928 scopus 로고    scopus 로고
    • Insulin complexation with hydroxypropyl-beta-cyclodextrin: spectroscopic evaluation of molecular inclusion and use of the complex in gel for healing of pressure ulcers
    • [36] Valentini, S.R., Fenelon, V.C., Nogueira, A.C., Sato, F., Medina, A.N., Baesso, M.L., et al. Insulin complexation with hydroxypropyl-beta-cyclodextrin: spectroscopic evaluation of molecular inclusion and use of the complex in gel for healing of pressure ulcers. Int. J. Pharm. 490 (2015), 229–239.
    • (2015) Int. J. Pharm. , vol.490 , pp. 229-239
    • Valentini, S.R.1    Fenelon, V.C.2    Nogueira, A.C.3    Sato, F.4    Medina, A.N.5    Baesso, M.L.6
  • 37
    • 80054731103 scopus 로고    scopus 로고
    • Mechanical grinding effect on thermodynamics and inclusion efficiency of loratadine–cyclodextrin inclusion complex formation
    • [37] Lin, H.-L., Lin, S.-Y., Lin, C.-C., Hsu, C.-H., Wu, T.-K., Huang, Y.-T., Mechanical grinding effect on thermodynamics and inclusion efficiency of loratadine–cyclodextrin inclusion complex formation. Carbohydr. Polym. 87 (2012), 512–517.
    • (2012) Carbohydr. Polym. , vol.87 , pp. 512-517
    • Lin, H.-L.1    Lin, S.-Y.2    Lin, C.-C.3    Hsu, C.-H.4    Wu, T.-K.5    Huang, Y.-T.6
  • 38
    • 84892608100 scopus 로고    scopus 로고
    • Curcumin–β-cyclodextrin inclusion complex: stability, solubility, characterisation by FT-IR, FT-Raman, X-ray diffraction and photoacoustic spectroscopy, and food application
    • [38] Mangolim, C.S., Moriwaki, C., Nogueira, A.C., Sato, F., Baesso, M.L., Neto, A.M., et al. Curcumin–β-cyclodextrin inclusion complex: stability, solubility, characterisation by FT-IR, FT-Raman, X-ray diffraction and photoacoustic spectroscopy, and food application. Food Chem. 153 (2014), 361–370.
    • (2014) Food Chem. , vol.153 , pp. 361-370
    • Mangolim, C.S.1    Moriwaki, C.2    Nogueira, A.C.3    Sato, F.4    Baesso, M.L.5    Neto, A.M.6
  • 39
    • 40649124459 scopus 로고    scopus 로고
    • Study on thermal decomposition behavior of survived β-cyclodextrin in its inclusion complex of clove oil by nonisothermal thermogravimetry and gas chromatography coupled to time-of-flight mass spectrometry analyses
    • [39] Xu, P., Song, L.X., Wang, H.M., Study on thermal decomposition behavior of survived β-cyclodextrin in its inclusion complex of clove oil by nonisothermal thermogravimetry and gas chromatography coupled to time-of-flight mass spectrometry analyses. Thermochim. Acta 469 (2008), 36–42.
    • (2008) Thermochim. Acta , vol.469 , pp. 36-42
    • Xu, P.1    Song, L.X.2    Wang, H.M.3
  • 41
    • 84937064890 scopus 로고    scopus 로고
    • Physicochemical analysis and molecular modeling of the fosinopril β-cyclodextrin inclusion complex
    • [41] Udrescu, L., Sbârcea, L., Fulias, A., Ledeti, I., Vlase, G., Barvinschi, P., et al. Physicochemical analysis and molecular modeling of the fosinopril β-cyclodextrin inclusion complex. J. Spectrosc., 2014, 2014.
    • (2014) J. Spectrosc. , vol.2014
    • Udrescu, L.1    Sbârcea, L.2    Fulias, A.3    Ledeti, I.4    Vlase, G.5    Barvinschi, P.6
  • 42
    • 77957105955 scopus 로고    scopus 로고
    • Antioxidant activity of inclusion complexes of tea catechins with β-cyclodextrins by ORAC assays
    • [42] Folch-Cano, C., Jullian, C., Speisky, H., Olea-Azar, C., Antioxidant activity of inclusion complexes of tea catechins with β-cyclodextrins by ORAC assays. Food Res. Int., 43, 2010.
    • (2010) Food Res. Int. , vol.43
    • Folch-Cano, C.1    Jullian, C.2    Speisky, H.3    Olea-Azar, C.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.