Year 2016,
Volume: 2 Issue: 2, 45 - 63, 01.06.2016
Hüseyin Çiçek
Onur Çetinkaya
Melek Tezcan
Meryem Çiçek
Gökhan Koçak
References
- BARNES, J., Anderson, L.A., Phillipson, J.D., St. John wort (Hypericum perforatum L.): a review of its chemistry pharmacology and clinical properties. Journal of Pharmacy and Pharmacology, 53, 583– 600, (2001).
- BRONDZ, I., Greibrokk, J., Aasen, A.J., n-Alkanes of Hypericum perforatum: a revision. Phytochemistry, 2, 295–296, (1983).
- BUTTERWECK, V., Bockers, T., Korte, B., Wittkowski, W., Winterhoff, H.,. Long-term effects of St. John’s wort and hypericin on monoamine levels in rat hypothalamus and hippocampus. Brain Research, 930, 21– 29, (2002).
- BUTTERWECK, V., Jurgenliemk, G., Nahrstedt, A., Winterhoff, H., Flavonoids from Hypericum perforatum show antidepressant activity in the forced swimming test. Planta Medica, 66, 3–6, (2000). BUTTERWECK, V., Wall, A., Lieflander-Wulf, U., Winterhoff, H., Nahrsted, A.,. Effects of the total extract and fractions of Hypericum perforatum in animal assays for antidepressant activity. Pharmacopsychiatry, 30, 117–124, (1997).
- CAKIR, A., Duru M.E., Harmandar M., Ciriminna R., Passannanti S., Piozzi F., Comparison of the volatile oils of Hypericum scabrum L. and Hypericum perforatum L. from Turkey. Flavour and Fragrance Journal, 12, 285–287, (1997).
- CAKIR, A., Mavi A., Yıldırım A., Duru M.E., Harmandar M.ve Kazaz C., “Isolation and Characterization of Antioxidant Phenolic Compounds From the Aerial Parts of Hypericum hyssopifolium L. by Activity-Guided Fractionation” J. Ethnopharmacol, 87, 73-83, (2003).
- CHUNG, M.I., Lai, M.H., Yen, M.H., Wu, R.R., Lin, C.N., Phenolics from Hypericum geminiflorum. Phytochemistry, 44, 943–947, (1997).
- DECOSTERD, L.A., Stoeckli-Evans, H., Chapuis, J.C., Msonthi, J.D., Sordat, B., Hostettmann, K., New hyperforin derivatives from Hypericum revolutum Vahl with growth-inhibitory activity against a human colon carcinoma cell line, Helvetica Chimica Acta, 72, 464–471, (1989).
- DECOSTERD, L.A., Hoffmann, E., Kyburz, R., Bray, D., Hostettmann, K., A new pholoroglucinol derivative from Hypericum calycinum with antifungal and in vitro antimalarial activity, Planta Medica, 57, 548–551, (1991).
- DIAS, A.C.P., Tomas-Barberan, F.A., Fernandes-Ferreira, M., Ferreres, F., Unusual flavonoids produced by callus of Hypericum perforatum, Phytochemistry, 48, 1165–1168, (1998).
- FLAUSINO, O.A., Zangrossi, H., Salgado, J.V., Viana, M.B., Effects of acute and chronic treatment with Hypericum perforatum L. (LI 160) ondifferent anxiety-related responses in rats. Pharmacology Biochemistry and Behaviour, 71, 251–257, (2002).
- FU B.Q., Liu J., Li H., Li L., Lee F.S.C., Wang X.R., The application of macroporous resins in the separation of licorice flavonoids and glycyrrhizic acid, J. Chromatogr. A, 1089, 18, (2005).
- GENG X., RenP., Pi G., Shi R., Yuan Z., Wang C., High selective purification of flavonoids from natural plants based on polymeric adsorbent with hydrogen-bonding interaction, Journal of Chromatography A, 1216, 8331–8338, (2009).
- GUNATILAKA, A.A.L., Balasubramaniam, S., Kumar, V., 2,3-Dimetoxyxanthone from Hypericum mysorense. Phytochemistry, 18, 182– 183, 1979
- HE D.H., Otsuka H., Hirata E., Shinzato T., Bando M., Takeda Y., J. Nat. Prod. 65, 685, (2002).
- HUBNER, W.D., Kirste, T., Experience with St. John’s wort (Hypericum perforatum) in children under 12 years with symptoms of depression and psychovegetative disturbances, Phytotherapy Research, 15, 367–370, (2001).
- ISHIGURO K., Nagareya N., Fukumoto H., A phloroglucinol derivative from cell suspension cultures of Hypericum patulum, Phytochemistry, 47, 1041–1043, (1998).
- ISHIGURO K., Nagata S., Fukumoto H., Yamaki M., Isoi K., Oyama Y., An isopentenylated flavonol from Hypericum japonicum, Phytochemistry, 32, 1583–1585, (1993).
- ISHIGURO K., Nagata S., Fukumoto H., Yamaki M., Isoi K., Pholoroglucinol derivatives from Hypericum japonicum, Phytochemistry, 35, 469–471, (1994).
- ISHIGURO K., Nagata S., Fukumoto H., Yamaki M., Takagi S., Isoi K., A flavanonol rha mnoside from Hypericum japonicum, Phytochemistry, 30, 3152–3153, (1991).
- ISHIGURO K., Yamaki M., Kashihara M., Takagi S., Isoi K., Srothralin G: a new antimicrobial compound from Hypericum japonicum, Planta Medica, 56, 274–276, (1990).
- ISHIGURO K., Yamaki M., Kashihara M., Takagi S., Isoi K., A chromene from Hypericum japonicum, Phytochemistry, 29, 1010–1011, (1993).
- KITANOV G.M., Hypericin and pseudohypericine in some Hypericum species. Biochemical Systematics and Ecology, 29, 171–178, (2001).
- LI, Xiaobao., Justin Pennington, John F. Stobaugh, and Christian Schöneich, Synthesis of Sulfonamide- and Sulfonyl- Phenylboronic Acid Modified Silica Phases for Boronate Affinity Chromatography at Physiological pH, Anal Biochem. 2008 January 15; 372(2): 227–236.
- ONUR Cetinkaya, Mehmet Emin Duru, Hüseyin Çiçek¸ Journal of Chromatography B, 909 (2012) 51– 60
- PI G.P., Ren P., Yu J.M., Shi R.F., Yuan Z., Wang C.H., J. Chromatogr. A, 1192, 17, (2008).
- RATH G., Potterat O., Mavi S., Hostettmann K., Xanthones from Hypericum roeperanum. Phytochemistry, 43, 513–520, (1996).
- SAKAR M.K., Tamer A.U., Antimicrobial activity of different extracts from Hypericum species. Fitoterapia, 61, 464–466, (1990).
- SCORDINO M., Mauro A.D., Passerini A., Maccarone E., Adsorption of flavonoids on resins: Hesperidin, J. Agric. Food Chem., 51, 6998, (2003).
- SENEL S., Camli S.T., Tuncel M., Tuncel A., Nucleotide adsorption–desorption behaviour of boronic acid functionalized uniform-porous particles, Journal of Chromatography B, 769, 283–295, (2002).
- SEPEHRİANAZAR A. Synthesis of allyl amine homo and copolymers and investigation of their polyelectrolyte behaviours doctoral thesis, (2008).
- TAKEDA Y., Fatope M.O., New phenolic glucosides from Lawsonia inermis, J. Nat. Prod. 51, 725, (1988).
- WALLE T., Absorption and metabolism of flavonoids, Free Radic. Biol. Med., 7, 829, (2004).
- WU Q.L., Wang S.P., Du L.J., Yang J.S., Xiao P.G., Xanthones from Hypericum japonicum and H. henryi, Phytochemistry 49, 1395–1402, (1998).
- WU Q.L., Wang S.P., Du L.J., Zhang S.M., Yang J.S., Xiao P.G., Chromone glycosides and flavonoids from Hypericum japonicum, Phytochemistry, 49, 1417–1420, (1998).
- XU M.C., Shi Z.Q., Shi R.F., Liu J.X., Lu Y.L., He B.L., React. Funct. Polym., 43, 297, (2000).
- ZHANG Y., Li S.F., Wu X.W., Zhao X., Chin. J. Chem. Eng., 6, 872, (2007).
ISOLATION OF HIGHLY ACTIVE ANTIRADICAL AND ANTIOXIDANT POLYPHENOLICS FROM PLANT EXTRACTS USING NOVEL POLYMERIC ADSORBENT PARTICLES
Year 2016,
Volume: 2 Issue: 2, 45 - 63, 01.06.2016
Hüseyin Çiçek
Onur Çetinkaya
Melek Tezcan
Meryem Çiçek
Gökhan Koçak
Abstract
Boronic acids monomers shows optimum adsorption of diols at pH 8.5. In this study, we were able to reduce this pH to 7 by using 4- N-allylsulfamoil phenylboronic acid ASPBA monomer copolymer. Methacrylate MA and our synthesized ASPBA were used to prepare millimeter sized poly[methacrylate-co-4- N-allylsulfamoil phenylboronic acid] poly[MA-co-ASPBA] particles. These particles were characterized by 1HNMR, FTIR and TGA. The prepared particles were mixed with the extract of Hypericum perforatum L. centaury and showed highly selective interaction with the flavonoids. Antioxidant and antiradical compounds were adsorbed over the surface of the particles and later desorbed. These macroporous particles can be used in selective isolation of natural products from plant extracts, especially cis-diols. Our prepared particles can be used as packing materials in the columns to selectively capture the target polyphenolics. Alternatively, the particles can be mixed with the extracts to adsorb the target polyphenolics, and then desorb to obtain selective isolation
References
- BARNES, J., Anderson, L.A., Phillipson, J.D., St. John wort (Hypericum perforatum L.): a review of its chemistry pharmacology and clinical properties. Journal of Pharmacy and Pharmacology, 53, 583– 600, (2001).
- BRONDZ, I., Greibrokk, J., Aasen, A.J., n-Alkanes of Hypericum perforatum: a revision. Phytochemistry, 2, 295–296, (1983).
- BUTTERWECK, V., Bockers, T., Korte, B., Wittkowski, W., Winterhoff, H.,. Long-term effects of St. John’s wort and hypericin on monoamine levels in rat hypothalamus and hippocampus. Brain Research, 930, 21– 29, (2002).
- BUTTERWECK, V., Jurgenliemk, G., Nahrstedt, A., Winterhoff, H., Flavonoids from Hypericum perforatum show antidepressant activity in the forced swimming test. Planta Medica, 66, 3–6, (2000). BUTTERWECK, V., Wall, A., Lieflander-Wulf, U., Winterhoff, H., Nahrsted, A.,. Effects of the total extract and fractions of Hypericum perforatum in animal assays for antidepressant activity. Pharmacopsychiatry, 30, 117–124, (1997).
- CAKIR, A., Duru M.E., Harmandar M., Ciriminna R., Passannanti S., Piozzi F., Comparison of the volatile oils of Hypericum scabrum L. and Hypericum perforatum L. from Turkey. Flavour and Fragrance Journal, 12, 285–287, (1997).
- CAKIR, A., Mavi A., Yıldırım A., Duru M.E., Harmandar M.ve Kazaz C., “Isolation and Characterization of Antioxidant Phenolic Compounds From the Aerial Parts of Hypericum hyssopifolium L. by Activity-Guided Fractionation” J. Ethnopharmacol, 87, 73-83, (2003).
- CHUNG, M.I., Lai, M.H., Yen, M.H., Wu, R.R., Lin, C.N., Phenolics from Hypericum geminiflorum. Phytochemistry, 44, 943–947, (1997).
- DECOSTERD, L.A., Stoeckli-Evans, H., Chapuis, J.C., Msonthi, J.D., Sordat, B., Hostettmann, K., New hyperforin derivatives from Hypericum revolutum Vahl with growth-inhibitory activity against a human colon carcinoma cell line, Helvetica Chimica Acta, 72, 464–471, (1989).
- DECOSTERD, L.A., Hoffmann, E., Kyburz, R., Bray, D., Hostettmann, K., A new pholoroglucinol derivative from Hypericum calycinum with antifungal and in vitro antimalarial activity, Planta Medica, 57, 548–551, (1991).
- DIAS, A.C.P., Tomas-Barberan, F.A., Fernandes-Ferreira, M., Ferreres, F., Unusual flavonoids produced by callus of Hypericum perforatum, Phytochemistry, 48, 1165–1168, (1998).
- FLAUSINO, O.A., Zangrossi, H., Salgado, J.V., Viana, M.B., Effects of acute and chronic treatment with Hypericum perforatum L. (LI 160) ondifferent anxiety-related responses in rats. Pharmacology Biochemistry and Behaviour, 71, 251–257, (2002).
- FU B.Q., Liu J., Li H., Li L., Lee F.S.C., Wang X.R., The application of macroporous resins in the separation of licorice flavonoids and glycyrrhizic acid, J. Chromatogr. A, 1089, 18, (2005).
- GENG X., RenP., Pi G., Shi R., Yuan Z., Wang C., High selective purification of flavonoids from natural plants based on polymeric adsorbent with hydrogen-bonding interaction, Journal of Chromatography A, 1216, 8331–8338, (2009).
- GUNATILAKA, A.A.L., Balasubramaniam, S., Kumar, V., 2,3-Dimetoxyxanthone from Hypericum mysorense. Phytochemistry, 18, 182– 183, 1979
- HE D.H., Otsuka H., Hirata E., Shinzato T., Bando M., Takeda Y., J. Nat. Prod. 65, 685, (2002).
- HUBNER, W.D., Kirste, T., Experience with St. John’s wort (Hypericum perforatum) in children under 12 years with symptoms of depression and psychovegetative disturbances, Phytotherapy Research, 15, 367–370, (2001).
- ISHIGURO K., Nagareya N., Fukumoto H., A phloroglucinol derivative from cell suspension cultures of Hypericum patulum, Phytochemistry, 47, 1041–1043, (1998).
- ISHIGURO K., Nagata S., Fukumoto H., Yamaki M., Isoi K., Oyama Y., An isopentenylated flavonol from Hypericum japonicum, Phytochemistry, 32, 1583–1585, (1993).
- ISHIGURO K., Nagata S., Fukumoto H., Yamaki M., Isoi K., Pholoroglucinol derivatives from Hypericum japonicum, Phytochemistry, 35, 469–471, (1994).
- ISHIGURO K., Nagata S., Fukumoto H., Yamaki M., Takagi S., Isoi K., A flavanonol rha mnoside from Hypericum japonicum, Phytochemistry, 30, 3152–3153, (1991).
- ISHIGURO K., Yamaki M., Kashihara M., Takagi S., Isoi K., Srothralin G: a new antimicrobial compound from Hypericum japonicum, Planta Medica, 56, 274–276, (1990).
- ISHIGURO K., Yamaki M., Kashihara M., Takagi S., Isoi K., A chromene from Hypericum japonicum, Phytochemistry, 29, 1010–1011, (1993).
- KITANOV G.M., Hypericin and pseudohypericine in some Hypericum species. Biochemical Systematics and Ecology, 29, 171–178, (2001).
- LI, Xiaobao., Justin Pennington, John F. Stobaugh, and Christian Schöneich, Synthesis of Sulfonamide- and Sulfonyl- Phenylboronic Acid Modified Silica Phases for Boronate Affinity Chromatography at Physiological pH, Anal Biochem. 2008 January 15; 372(2): 227–236.
- ONUR Cetinkaya, Mehmet Emin Duru, Hüseyin Çiçek¸ Journal of Chromatography B, 909 (2012) 51– 60
- PI G.P., Ren P., Yu J.M., Shi R.F., Yuan Z., Wang C.H., J. Chromatogr. A, 1192, 17, (2008).
- RATH G., Potterat O., Mavi S., Hostettmann K., Xanthones from Hypericum roeperanum. Phytochemistry, 43, 513–520, (1996).
- SAKAR M.K., Tamer A.U., Antimicrobial activity of different extracts from Hypericum species. Fitoterapia, 61, 464–466, (1990).
- SCORDINO M., Mauro A.D., Passerini A., Maccarone E., Adsorption of flavonoids on resins: Hesperidin, J. Agric. Food Chem., 51, 6998, (2003).
- SENEL S., Camli S.T., Tuncel M., Tuncel A., Nucleotide adsorption–desorption behaviour of boronic acid functionalized uniform-porous particles, Journal of Chromatography B, 769, 283–295, (2002).
- SEPEHRİANAZAR A. Synthesis of allyl amine homo and copolymers and investigation of their polyelectrolyte behaviours doctoral thesis, (2008).
- TAKEDA Y., Fatope M.O., New phenolic glucosides from Lawsonia inermis, J. Nat. Prod. 51, 725, (1988).
- WALLE T., Absorption and metabolism of flavonoids, Free Radic. Biol. Med., 7, 829, (2004).
- WU Q.L., Wang S.P., Du L.J., Yang J.S., Xiao P.G., Xanthones from Hypericum japonicum and H. henryi, Phytochemistry 49, 1395–1402, (1998).
- WU Q.L., Wang S.P., Du L.J., Zhang S.M., Yang J.S., Xiao P.G., Chromone glycosides and flavonoids from Hypericum japonicum, Phytochemistry, 49, 1417–1420, (1998).
- XU M.C., Shi Z.Q., Shi R.F., Liu J.X., Lu Y.L., He B.L., React. Funct. Polym., 43, 297, (2000).
- ZHANG Y., Li S.F., Wu X.W., Zhao X., Chin. J. Chem. Eng., 6, 872, (2007).