Effect of O-glycosilation on the antioxidant activity and free radical reactions of a plant flavonoid, chrysoeriol

B. Mishra, K.I. Priyadarsini, M.S. Kumar, M.K. Unnikrishnan, H. Mohan

Research output: Contribution to journalArticle

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Abstract

Chrysoeriol and its glycoside (chrysoeriol-6-O-acetyl-4′-β-D-glucoside) are two natural flavonoids extracted from the tropical plant Coronopus didymus. The aqueous solutions of both the flavonoids were tested for their ability to inhibit lipid peroxidation induced by γ-radiation, Fe (III) and Fe (II). In all these assays chrysoeriol showed better protecting effect than the glycoside. The compounds were also found to inhibit enzymatically produced superoxide anion by xanthine/xanthine oxidase system; here the glycoside is more effective than the aglycone. The rate constants for the reaction of the compounds with superoxide anion determined by using stopped-flow spectrometer were found to be nearly same. Chrysoeriol glycoside reacts with DPPH radicals at millimolar concentration, but the aglycone showed no reaction. Using nanosecond pulse radiolysis technique, reactions of these compounds with hydroxyl, azide, haloperoxyl radicals and hydrated electron were studied. The bimolecular rate constants for these reactions and the transient spectra of the one-electron oxidized species indicated that the site of oxidation for the two compounds is different. Reaction of hydrated electron with the two compounds was carried out at pH 7, where similar reactivity was observed with both the compounds. Based on all these studies it is concluded that chrysoeriol exhibits potent antioxidant activity. O-glycosylation of chrysoeriol decreases its ability to inhibit lipid peroxidation and reaction with peroxyl radicals. However the glycoside is a more efficient scavenger of DPPH radicals and a better inhibitor of xanthine/xanthine oxidase than the aglycone. © 2003 Elsevier Science Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)2677-2685
Number of pages9
JournalBioorganic and Medicinal Chemistry
Volume11
Issue number13
DOIs
Publication statusPublished - 2003

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Free radical reactions
Flavonoids
Free Radicals
Glycosides
Antioxidants
Xanthine
Xanthine Oxidase
Electrons
Superoxides
Lipid Peroxidation
Rate constants
Pulse Radiolysis
Glycosylation
Lipids
Radiolysis
Azides
Glucosides
Hydroxyl Radical
chrysoeriol
Spectrometers

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Mishra, B. ; Priyadarsini, K.I. ; Kumar, M.S. ; Unnikrishnan, M.K. ; Mohan, H. / Effect of O-glycosilation on the antioxidant activity and free radical reactions of a plant flavonoid, chrysoeriol. In: Bioorganic and Medicinal Chemistry. 2003 ; Vol. 11, No. 13. pp. 2677-2685.
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title = "Effect of O-glycosilation on the antioxidant activity and free radical reactions of a plant flavonoid, chrysoeriol",
abstract = "Chrysoeriol and its glycoside (chrysoeriol-6-O-acetyl-4′-β-D-glucoside) are two natural flavonoids extracted from the tropical plant Coronopus didymus. The aqueous solutions of both the flavonoids were tested for their ability to inhibit lipid peroxidation induced by γ-radiation, Fe (III) and Fe (II). In all these assays chrysoeriol showed better protecting effect than the glycoside. The compounds were also found to inhibit enzymatically produced superoxide anion by xanthine/xanthine oxidase system; here the glycoside is more effective than the aglycone. The rate constants for the reaction of the compounds with superoxide anion determined by using stopped-flow spectrometer were found to be nearly same. Chrysoeriol glycoside reacts with DPPH radicals at millimolar concentration, but the aglycone showed no reaction. Using nanosecond pulse radiolysis technique, reactions of these compounds with hydroxyl, azide, haloperoxyl radicals and hydrated electron were studied. The bimolecular rate constants for these reactions and the transient spectra of the one-electron oxidized species indicated that the site of oxidation for the two compounds is different. Reaction of hydrated electron with the two compounds was carried out at pH 7, where similar reactivity was observed with both the compounds. Based on all these studies it is concluded that chrysoeriol exhibits potent antioxidant activity. O-glycosylation of chrysoeriol decreases its ability to inhibit lipid peroxidation and reaction with peroxyl radicals. However the glycoside is a more efficient scavenger of DPPH radicals and a better inhibitor of xanthine/xanthine oxidase than the aglycone. {\circledC} 2003 Elsevier Science Ltd. All rights reserved.",
author = "B. Mishra and K.I. Priyadarsini and M.S. Kumar and M.K. Unnikrishnan and H. Mohan",
note = "Cited By :48 Export Date: 10 November 2017 CODEN: BMECE Correspondence Address: Priyadarsini, K.I.; Radiat. Chem./Chem. Dynam. Division, Bhabha Atomic Research Centre, Trombay, Mumbai-400085, India; email: kindira@apsara.barc.ernet.in Chemicals/CAS: azide, 12596-60-0, 14343-69-2; ferric ion, 20074-52-6; ferrous ion, 15438-31-0; superoxide, 11062-77-4; xanthine oxidase, 9002-17-9 References: Bors, W., Micheal, C., Stettmaier, K., (2001) Meth. Enzymol., 335, p. 166; Jovanovic, S.V., Steenken, S., Tosic, M., Marjanovic, B., Simic, M.G., (1994) J. Am. Chem. Soc., 116, p. 4846; Jovanovic, S.V., Steenken, S., Hara, Y., Simic, M.G., (1996) J. Chem. Soc., Perkin Trans. 2, p. 2497; Heim, K.E., Tagliaferro, A.R., Bobilya, D.J., (2002) J. Nutr. Biochem., 13, p. 572; Lian, L.Y., Ming, S.S., Hsiung, K.Y., Jern, T.W., Chih, C.C., (1999) Chinese-Pharma. J., 51, p. 397; Chen, Z.S., Lai, J.S., Kuo, Z.H., (1991) Chem. Pharmac. Bull., 39, p. 3034; Skaltsa, H., Bermejo, P., Lazari, D., Silvan, A.M., Skaltsounis, A.L., Sanz, A., Abad, M.J., (2000) Biol. Pharmac. Bull., 23, p. 47; Kim, Y., Kim, Y., Kim, J., (1997) J. Pharm. Sci., 22, p. 43; Chen, C.C., Huang, Y.L., Sun, C.M., Shen, C.C., Ko, F.N., Teng, C.M., (1996) J. Nat. Prod., 59, p. 412; Lee, S.J., Chung, H.Y., Maier, C.G., Wood, A.R., Dixon, R.A., Mabry, T.J., (1998) J. Agric. Food Chem., 46, p. 3325; Nakasugi, T., Nakashima, M., Komai, K., (2000) J. Agric. Food Chem., 48, p. 3256; Cimanga, K.D., Bruyne, T., Hu, J.P., Cos, P., Apers, S., Pieters, L., Tona, L., Vlietinck, A.J., (1999) Pharm. Pharmacol. Commun., 5, p. 419; Hammerstone, J.F., Lazarus, S.A., Schmitz, H.H., (2000) J. Nutr., 130, p. 2086. , S; Ioku, K., Tsushida, T., Takei, Y., Nakatani, N., Terao, J., (1995) Biochim. Biophys. Acta, 1234, p. 99; Minotti, G., (1992) Arch. Biochem. Biophys., 297, p. 189; Ratty, K., Das, N.P., (1988) Biochem Med Metab Biol., 39, p. 69; Spencer, P.E., Chowrimootoo, G., Choudhury, R., Debnam, E.S., Srai, S.K., Evans, R.C., (1999) FEBS Lett., 458, p. 224; Day, A.J., DuPont, M.S., Ridley, S., Rhodes, M., Rhodes, M.J.C., Morgan, M.R.A., Williamson, G., (1998) FEBS Lett., 436, p. 71; Robak, J., Gryglewski, R.J., (1988) Biochem. Pharmacol., 37, p. 837; Hanasaki, Y., Ogawa, S., Fukui, S., (1994) Free Rad. Biol. Med., 16, p. 845; Valentine, J.S., Curtis, A.B., (1975) J. Am. Chem. Soc., 97, p. 224; Kyriakopoulou, I., Magiatis, P., Alexios, L.S., Aligiannis, N., Harvala, C.S., (2001) J. Nat. Prod., 64, p. 1095; Kosina, P., Kren, V., Gebhardt, R., Grambal, F., Ulrichova, J., Walterova, D., Phytother. Res. Marz., 116 (SUPPL. 1), pp. S33; Spinks, J.W., Woods, R.J., (1990) An Introduction to Radiation Chemistry, , New York: John Wiley. p 278; Alfassi, Z.B., Schuler, R.H., (1985) J. Phys. Chem., 89, p. 3359; Sonntag C.von, (1987) The Chemical Basis of Radiation Biology, , London: Taylor & Francis. p 65-84; Priyadarsini, K.I., (1997) Free Rad. Biol. Med., 23, p. 838; Scott, S.L., Chen, W.J., Bakae, A., Espenson, J.H., (1993) J. Phys. Chem., 97, p. 6710; Nagao, A., Seki, M., Kobayashi, H., (1999) . Biosci. Biotechnol. Biochem., 63, p. 1787; Prabhakar, K.R., Srinivasan, K.K., Padma, G.H.R., (2002) Pharm. Biol., 40, p. 490; Satav, J.G., Katyare, S., Fatterpekar, P., (1976) Sreenivasan. Biochem. J., 156, p. 215; Satav, J.G., Katyare, S.S., (1982) Mol. Cell. Endocrinal., 28, p. 178; Lowry, O.H., Rosenbrough, N.J., Parr, A.L., Fandall, R.J., (1951) J. Biol. Chem., 193, p. 265; Shivkumar, B.R., Anandatheerthavarda, H.K., Ravindranath, V., (1991) Int. J. Devel. Neurosci,, 9, p. 181; Khopde, S.M., Priyadarshini, K.I., Guha, S.N., Satav, J.G., Venkatesan, P., Rao, M.N.A., (2000) Biosci. Biotech. Biochem., 64, p. 503; Sreejayan, N., Rao, M.N.A., Priyadarshini, K.I., Devasagayam, T.P.A., (1997) Int. J. Pharmac., 151, p. 127; Braughler, J.M., Duncan, L.A., Chase, R.L., (1986) J. Biol. Chem., 261, p. 10282; Guha, S.N., Moorthy, P.N., Naik, D.B., Rao, K.N., (1987) Proc Indian Acad. Sci. (Chem. Sci.), 99, p. 261; Priyadarsini, K.I., Naik, D.B., Moorthy, P.N., Mittal, J.P., (1991) Proceedings of the 7th Tihany Symposium on Radiation Chemistry, p. 105; Fielden, E.M., (1984) The Study of Fast Processes and Transient Species by Electron Pulse Radiolysis, p. 59. , Baxndale, J. H. and Busi, F. (Eds), Reidel Publishing Co. London; Shen, X., Lind, J., Eriksen, T.E., Merenyi, G., (1989) J. Phys. Chem., 93, p. 553; Khopde, S.M., Priyadarsini, K.I., Guha, S.N., Mukherjee, T., (2001) Res. Chem. Interm., 27, p. 519",
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pages = "2677--2685",
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Effect of O-glycosilation on the antioxidant activity and free radical reactions of a plant flavonoid, chrysoeriol. / Mishra, B.; Priyadarsini, K.I.; Kumar, M.S.; Unnikrishnan, M.K.; Mohan, H.

In: Bioorganic and Medicinal Chemistry, Vol. 11, No. 13, 2003, p. 2677-2685.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Effect of O-glycosilation on the antioxidant activity and free radical reactions of a plant flavonoid, chrysoeriol

AU - Mishra, B.

AU - Priyadarsini, K.I.

AU - Kumar, M.S.

AU - Unnikrishnan, M.K.

AU - Mohan, H.

N1 - Cited By :48 Export Date: 10 November 2017 CODEN: BMECE Correspondence Address: Priyadarsini, K.I.; Radiat. Chem./Chem. Dynam. Division, Bhabha Atomic Research Centre, Trombay, Mumbai-400085, India; email: kindira@apsara.barc.ernet.in Chemicals/CAS: azide, 12596-60-0, 14343-69-2; ferric ion, 20074-52-6; ferrous ion, 15438-31-0; superoxide, 11062-77-4; xanthine oxidase, 9002-17-9 References: Bors, W., Micheal, C., Stettmaier, K., (2001) Meth. Enzymol., 335, p. 166; Jovanovic, S.V., Steenken, S., Tosic, M., Marjanovic, B., Simic, M.G., (1994) J. Am. Chem. Soc., 116, p. 4846; Jovanovic, S.V., Steenken, S., Hara, Y., Simic, M.G., (1996) J. Chem. Soc., Perkin Trans. 2, p. 2497; Heim, K.E., Tagliaferro, A.R., Bobilya, D.J., (2002) J. Nutr. Biochem., 13, p. 572; Lian, L.Y., Ming, S.S., Hsiung, K.Y., Jern, T.W., Chih, C.C., (1999) Chinese-Pharma. J., 51, p. 397; Chen, Z.S., Lai, J.S., Kuo, Z.H., (1991) Chem. Pharmac. Bull., 39, p. 3034; Skaltsa, H., Bermejo, P., Lazari, D., Silvan, A.M., Skaltsounis, A.L., Sanz, A., Abad, M.J., (2000) Biol. Pharmac. Bull., 23, p. 47; Kim, Y., Kim, Y., Kim, J., (1997) J. Pharm. Sci., 22, p. 43; Chen, C.C., Huang, Y.L., Sun, C.M., Shen, C.C., Ko, F.N., Teng, C.M., (1996) J. Nat. Prod., 59, p. 412; Lee, S.J., Chung, H.Y., Maier, C.G., Wood, A.R., Dixon, R.A., Mabry, T.J., (1998) J. Agric. Food Chem., 46, p. 3325; Nakasugi, T., Nakashima, M., Komai, K., (2000) J. Agric. Food Chem., 48, p. 3256; Cimanga, K.D., Bruyne, T., Hu, J.P., Cos, P., Apers, S., Pieters, L., Tona, L., Vlietinck, A.J., (1999) Pharm. Pharmacol. Commun., 5, p. 419; Hammerstone, J.F., Lazarus, S.A., Schmitz, H.H., (2000) J. Nutr., 130, p. 2086. , S; Ioku, K., Tsushida, T., Takei, Y., Nakatani, N., Terao, J., (1995) Biochim. Biophys. Acta, 1234, p. 99; Minotti, G., (1992) Arch. Biochem. Biophys., 297, p. 189; Ratty, K., Das, N.P., (1988) Biochem Med Metab Biol., 39, p. 69; Spencer, P.E., Chowrimootoo, G., Choudhury, R., Debnam, E.S., Srai, S.K., Evans, R.C., (1999) FEBS Lett., 458, p. 224; Day, A.J., DuPont, M.S., Ridley, S., Rhodes, M., Rhodes, M.J.C., Morgan, M.R.A., Williamson, G., (1998) FEBS Lett., 436, p. 71; Robak, J., Gryglewski, R.J., (1988) Biochem. Pharmacol., 37, p. 837; Hanasaki, Y., Ogawa, S., Fukui, S., (1994) Free Rad. Biol. Med., 16, p. 845; Valentine, J.S., Curtis, A.B., (1975) J. Am. Chem. Soc., 97, p. 224; Kyriakopoulou, I., Magiatis, P., Alexios, L.S., Aligiannis, N., Harvala, C.S., (2001) J. Nat. Prod., 64, p. 1095; Kosina, P., Kren, V., Gebhardt, R., Grambal, F., Ulrichova, J., Walterova, D., Phytother. Res. Marz., 116 (SUPPL. 1), pp. S33; Spinks, J.W., Woods, R.J., (1990) An Introduction to Radiation Chemistry, , New York: John Wiley. p 278; Alfassi, Z.B., Schuler, R.H., (1985) J. Phys. Chem., 89, p. 3359; Sonntag C.von, (1987) The Chemical Basis of Radiation Biology, , London: Taylor & Francis. p 65-84; Priyadarsini, K.I., (1997) Free Rad. Biol. Med., 23, p. 838; Scott, S.L., Chen, W.J., Bakae, A., Espenson, J.H., (1993) J. Phys. Chem., 97, p. 6710; Nagao, A., Seki, M., Kobayashi, H., (1999) . Biosci. Biotechnol. Biochem., 63, p. 1787; Prabhakar, K.R., Srinivasan, K.K., Padma, G.H.R., (2002) Pharm. Biol., 40, p. 490; Satav, J.G., Katyare, S., Fatterpekar, P., (1976) Sreenivasan. Biochem. J., 156, p. 215; Satav, J.G., Katyare, S.S., (1982) Mol. Cell. Endocrinal., 28, p. 178; Lowry, O.H., Rosenbrough, N.J., Parr, A.L., Fandall, R.J., (1951) J. Biol. Chem., 193, p. 265; Shivkumar, B.R., Anandatheerthavarda, H.K., Ravindranath, V., (1991) Int. J. Devel. Neurosci,, 9, p. 181; Khopde, S.M., Priyadarshini, K.I., Guha, S.N., Satav, J.G., Venkatesan, P., Rao, M.N.A., (2000) Biosci. Biotech. Biochem., 64, p. 503; Sreejayan, N., Rao, M.N.A., Priyadarshini, K.I., Devasagayam, T.P.A., (1997) Int. J. Pharmac., 151, p. 127; Braughler, J.M., Duncan, L.A., Chase, R.L., (1986) J. Biol. Chem., 261, p. 10282; Guha, S.N., Moorthy, P.N., Naik, D.B., Rao, K.N., (1987) Proc Indian Acad. Sci. (Chem. Sci.), 99, p. 261; Priyadarsini, K.I., Naik, D.B., Moorthy, P.N., Mittal, J.P., (1991) Proceedings of the 7th Tihany Symposium on Radiation Chemistry, p. 105; Fielden, E.M., (1984) The Study of Fast Processes and Transient Species by Electron Pulse Radiolysis, p. 59. , Baxndale, J. H. and Busi, F. (Eds), Reidel Publishing Co. London; Shen, X., Lind, J., Eriksen, T.E., Merenyi, G., (1989) J. Phys. Chem., 93, p. 553; Khopde, S.M., Priyadarsini, K.I., Guha, S.N., Mukherjee, T., (2001) Res. Chem. Interm., 27, p. 519

PY - 2003

Y1 - 2003

N2 - Chrysoeriol and its glycoside (chrysoeriol-6-O-acetyl-4′-β-D-glucoside) are two natural flavonoids extracted from the tropical plant Coronopus didymus. The aqueous solutions of both the flavonoids were tested for their ability to inhibit lipid peroxidation induced by γ-radiation, Fe (III) and Fe (II). In all these assays chrysoeriol showed better protecting effect than the glycoside. The compounds were also found to inhibit enzymatically produced superoxide anion by xanthine/xanthine oxidase system; here the glycoside is more effective than the aglycone. The rate constants for the reaction of the compounds with superoxide anion determined by using stopped-flow spectrometer were found to be nearly same. Chrysoeriol glycoside reacts with DPPH radicals at millimolar concentration, but the aglycone showed no reaction. Using nanosecond pulse radiolysis technique, reactions of these compounds with hydroxyl, azide, haloperoxyl radicals and hydrated electron were studied. The bimolecular rate constants for these reactions and the transient spectra of the one-electron oxidized species indicated that the site of oxidation for the two compounds is different. Reaction of hydrated electron with the two compounds was carried out at pH 7, where similar reactivity was observed with both the compounds. Based on all these studies it is concluded that chrysoeriol exhibits potent antioxidant activity. O-glycosylation of chrysoeriol decreases its ability to inhibit lipid peroxidation and reaction with peroxyl radicals. However the glycoside is a more efficient scavenger of DPPH radicals and a better inhibitor of xanthine/xanthine oxidase than the aglycone. © 2003 Elsevier Science Ltd. All rights reserved.

AB - Chrysoeriol and its glycoside (chrysoeriol-6-O-acetyl-4′-β-D-glucoside) are two natural flavonoids extracted from the tropical plant Coronopus didymus. The aqueous solutions of both the flavonoids were tested for their ability to inhibit lipid peroxidation induced by γ-radiation, Fe (III) and Fe (II). In all these assays chrysoeriol showed better protecting effect than the glycoside. The compounds were also found to inhibit enzymatically produced superoxide anion by xanthine/xanthine oxidase system; here the glycoside is more effective than the aglycone. The rate constants for the reaction of the compounds with superoxide anion determined by using stopped-flow spectrometer were found to be nearly same. Chrysoeriol glycoside reacts with DPPH radicals at millimolar concentration, but the aglycone showed no reaction. Using nanosecond pulse radiolysis technique, reactions of these compounds with hydroxyl, azide, haloperoxyl radicals and hydrated electron were studied. The bimolecular rate constants for these reactions and the transient spectra of the one-electron oxidized species indicated that the site of oxidation for the two compounds is different. Reaction of hydrated electron with the two compounds was carried out at pH 7, where similar reactivity was observed with both the compounds. Based on all these studies it is concluded that chrysoeriol exhibits potent antioxidant activity. O-glycosylation of chrysoeriol decreases its ability to inhibit lipid peroxidation and reaction with peroxyl radicals. However the glycoside is a more efficient scavenger of DPPH radicals and a better inhibitor of xanthine/xanthine oxidase than the aglycone. © 2003 Elsevier Science Ltd. All rights reserved.

U2 - 10.1016/S0968-0896(03)00232-3

DO - 10.1016/S0968-0896(03)00232-3

M3 - Article

VL - 11

SP - 2677

EP - 2685

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

SN - 0968-0896

IS - 13

ER -