Pulse radiolysis studies of mangiferin: A C-glycosyl xanthone isolated from Mangifera indica

B. Mishra, K.I. Priyadarsini, M. Sudheerkumar, M.K. Unnikrishhnan, H. Mohan

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Pulse radiolysis technique has been employed to study the reaction of different oxidizing and reducing radicals with mangiferin. The reaction of *OH radical showed the formation of transient species absorbing in 380-390 and 470-480 nm region. The reaction with specific one-electron oxidants (N 3*, CCl3O2*) also showed the formation of similar transient absorption bands and is assigned to phenoxyl radicals. The pKa values of the transient species have been determined to be 6.3 and 11.9. One-electron oxidation potential of mangiferin at pH 9 has been found to be 0.62 V vs. NHE. The reaction of eaq - showed the formation of transient species with λ max at 340 nm, which is assigned to the ketyl anion radical formed on addition of eaq- at carbonyl site. Reactions of one-electron oxidised mangiferin radicals with ascorbic acid have also been studied. © 2005 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)70-77
Number of pages8
JournalRadiation Physics and Chemistry
Volume75
Issue number1
DOIs
Publication statusPublished - 2006
Externally publishedYes

Fingerprint

radiolysis
pulses
electrons
ascorbic acid
anions
absorption spectra
oxidation

Cite this

Mishra, B. ; Priyadarsini, K.I. ; Sudheerkumar, M. ; Unnikrishhnan, M.K. ; Mohan, H. / Pulse radiolysis studies of mangiferin: A C-glycosyl xanthone isolated from Mangifera indica. In: Radiation Physics and Chemistry. 2006 ; Vol. 75, No. 1. pp. 70-77.
@article{9ded4bd7d06f4e3f97f2975aabaf6ad3,
title = "Pulse radiolysis studies of mangiferin: A C-glycosyl xanthone isolated from Mangifera indica",
abstract = "Pulse radiolysis technique has been employed to study the reaction of different oxidizing and reducing radicals with mangiferin. The reaction of *OH radical showed the formation of transient species absorbing in 380-390 and 470-480 nm region. The reaction with specific one-electron oxidants (N 3*, CCl3O2*) also showed the formation of similar transient absorption bands and is assigned to phenoxyl radicals. The pKa values of the transient species have been determined to be 6.3 and 11.9. One-electron oxidation potential of mangiferin at pH 9 has been found to be 0.62 V vs. NHE. The reaction of eaq - showed the formation of transient species with λ max at 340 nm, which is assigned to the ketyl anion radical formed on addition of eaq- at carbonyl site. Reactions of one-electron oxidised mangiferin radicals with ascorbic acid have also been studied. {\circledC} 2005 Elsevier Ltd. All rights reserved.",
author = "B. Mishra and K.I. Priyadarsini and M. Sudheerkumar and M.K. Unnikrishhnan and H. Mohan",
note = "Cited By :15 Export Date: 10 November 2017 CODEN: RPCHD Correspondence Address: Priyadarsini, K.I.; Radiation Chemistry and Chemical Dynamics Division, Bhabha Atomic Research Centre, Trombay, Mumbai 400085, India; email: kindira@apsara.barc.ernet.in Chemicals/CAS: mangiferin, 4773-96-0 References: Barik, A., Priyadarsini, K.I., Mohan, H., Redox reactions of 2-hydroxy-3-methoxybenzaldehyde (o-vanillin) in aqueous solution (2004) Radiat. Phys. Chem., 70, pp. 687-696; Bhattacharya, S.K., Sanyal, A.K., Ghosal, S., Monoamine oxidase inhibiting activity of mangiferin isolated from Canscora decussata (1972) Naturwissenschaften, 59, pp. 651-655; Cai, Z., Li, X., Katsumura, Y., Interaction of hydrated electron with dietary flavonoids and phenolic acids: Rate constants and transient spectra studied by pulse radiolysis (1999) Free. Radic. Bio. Med., 27, pp. 822-829; Cren-Olive, C., Hapiot, P., Pinson, J., Rolando, C., Free radical chemistry of flavan-3-ols: Determination of thermodynamic parameters and of kinetic reactivity from short (ns) to long (ms) time scale (2002) J. Am. Chem. Soc., 124, pp. 14027-14038; Fielden, E.M., Chemical dosimetry of pulsed electron and X-ray source in the MeV region (1982) The Study of Fast Processes and Transient Species by Electron Pulse Radiolysis, p. 59. , J.H. Baxandale F. Busi Reidel Publishing Co London; Guha, S.N., Moorthy, P.N., Naik, D.B., Rao, K.N., One electron reduction of thionine studied by pulse radiolysis (1987) Proc Indian Acad. Sci. (Chem. Sci.), 99, pp. 261-271; Guha, S., Ghosal, S., Chattopadhyay, U., Antitumor, immunomodulatory and anti HIV effect of mangiferin, a naturally occurring glucosylxanthone (1996) Chemotherapy, 42, pp. 443-451; Halliwell, B., Gutteridge, J.M., (1993) Free Radicals in Biology and Medicine, , Oxford Clarendon Press Oxford, UK; Ichiki, H., Miura, T., Kubo, M., Ishihara, E., Komatsu, Y., Tanigawa, K., Okada, M., New antidiabetic compounds, mangiferin and its glucoside (1998) Biol. Pharm. Bull., 21, pp. 1389-1390; Leiro, J.M., {\'A}lvarez, E., Arranz, J.A., Siso, I.G., Orallo, F., In vitro effects of mangiferin on superoxide concentrations and expression of the inducible nitric oxide synthase, tumour necrosis factor-α and transforming growth factor-β genes (2003) Biochem. Pharm., 65, pp. 1361-1371; Li, H., Miyahara, T., Tezuka, Y., Namba, T., Nemoto, N., Tonami, S., Seto, H., Kadota, S., The effect of kampo formulae on bone resorption in vitro and in vivo. I. Active constituents of Tsu-kan-gan (1998) Biol. Pharm. Bull., 21, pp. 1322-1326; Lin, S.J., Tseng, H.H., Wen, K.C., Suen, T.T., Determination of gentiopicroside, mangiferin, palmatine, berberine, baicalin, wogonin and glycyrrhizin in the traditional Chinese medicinal preparation by high performance liquid chromatography (1996) J. Chromatogr. A., 730, pp. 17-23; Mishra, B., Priyadarsini, K.I., Mantena, S.K., Unnikrishnan, M.K., Mohan, H., Effect of O-glycosilation on the antioxidant activity and free radical reactions of a plant flavonoid chrysoeriol (2003) Bio-org. Med. Chem., 11, pp. 2677-2685; Moreira, R.R., Carlos, I.Z., Vilega, W., Release of intermediate reactive Hydrogen peroxide by macrophage cells activated by natural products (2001) Biol. Pharm. Bull., 24 (2), pp. 201-204; Nunez-Selles, A.J., Capote, H.R., Aguero-Aguero, J., Garrido-Garrido, G., Delgado-Hernandez, R., Martinez-Sanchez, G., Leon-Fernanez, O., Morales-Segura, M., New antioxidant product derived from Mangifera indica L (2000) 220th National Meeting of the American Chemical Society, , Abstracts of Papers, New Orleans, LA, 2000. American Chemical Society, Washington, DC, 2000, MEDI-155. ISSN:0065-7727. AN 2000:796153; Nunez-Selles, A.J., Velez Castro, H.T., Aguero- Aguero, J., Gonzalez-Gonzalez, J., Naddeo, F., De Simone, F., Rastrelli, L., Isolation and quantitative analysis of phenolic antioxidants, free sugars, and polyols from mango (Mangifera indica) stem bark aqueous decoction used in Cuba as a nutritional supplement (2002) J. Agric. Food Chem., 50, pp. 762-766; Pokorny, J., Yanishlieva, N., Gordon, M., (2001) Antioxidants in Food, , CRC Press New York; Priyadarsini, K.I., Naik, D.B., Moorthy, P.N., Mittal, J.P., Energy Transfer Studies of coumarin dyes using electron pulse radiolysis (1991) Proceedings of the Seventh Tihany Symposium on Radiation Chemistry, pp. 105-107. , Dobo, J., Nykis, L., Shiller, R. (Eds.) Hungarian Chemical Society, Budapest, Hungary; Priyadarsini, K.I., Khopde, S.M., Kumar, S.S., Mohan, H., Free radical studies of ellagic acid, a natural phenolic antioxidant (2002) J. Agri. Food. Chem., 50, pp. 2200-2206; Quisumbing, E., (1978) Medicinal Plants of the Philippines, , Katha Publishing Co & JMC Press Quezon; Sanchez, G.M., Re, L., Giuliani, A., Nu{\~n}ez-Selles, A.J., Davison, G.P., Leon-Fernandez, O.S., Protective effects of mangifera indica L. Extract, mangiferin and selected antioxidants against tpa induced biomolecules oxidation and peritoneal macrophage activation in mice (2000) Pharmacol. Res., 42, pp. 565-573; Stoner, G.D., Mukhtar, H., Polyphenols as cancer chemo preventive agents (1995) J. Cell. Biochem. Suppl., 22, pp. 169-180; Sonntag, C.von., (1987) The Chemical Basis of Radiation Biology, , Taylor & Francis London; Visioli, F., Bellomo, G., Galli, C., Free radical-scavenging properties of olive oil polyphenols (1998) Biochem. Biophy. Res Commun., 247, pp. 60-64; Wardman, P., Reduction potentials of one-electron couples involving free radicals in aqueous solutions (1989) J. Phys. Chem. Ref. Data, 18, pp. 1637-1754; Yoosook, C., Bunyapraphatsara, N., Boonyakiat, Y., Kantasuk, C., Anti-herpes simplex virus activities of crude water extracts of Thai medicinal plants (2000) Phytomedicine, 6, pp. 411-419; Yoshimia, N., Matsunagaa, K., Katayamaa, M., Yamadaa, Y., Kunoa, T., Qiaoa, Z., Haraa, A., Moria, H., The inhibitory effects of mangiferin, a naturally occurring glucosylxanthone, in bowel carcinogenesis of male F344 rats (2001) Cancer Lett., 163, pp. 163-170",
year = "2006",
doi = "10.1016/j.radphyschem.2005.05.015",
language = "English",
volume = "75",
pages = "70--77",
journal = "Radiation Physics and Chemistry",
issn = "0969-806X",
publisher = "Elsevier Science Inc., Tarrytown, NY, United States",
number = "1",

}

Pulse radiolysis studies of mangiferin: A C-glycosyl xanthone isolated from Mangifera indica. / Mishra, B.; Priyadarsini, K.I.; Sudheerkumar, M.; Unnikrishhnan, M.K.; Mohan, H.

In: Radiation Physics and Chemistry, Vol. 75, No. 1, 2006, p. 70-77.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Pulse radiolysis studies of mangiferin: A C-glycosyl xanthone isolated from Mangifera indica

AU - Mishra, B.

AU - Priyadarsini, K.I.

AU - Sudheerkumar, M.

AU - Unnikrishhnan, M.K.

AU - Mohan, H.

N1 - Cited By :15 Export Date: 10 November 2017 CODEN: RPCHD Correspondence Address: Priyadarsini, K.I.; Radiation Chemistry and Chemical Dynamics Division, Bhabha Atomic Research Centre, Trombay, Mumbai 400085, India; email: kindira@apsara.barc.ernet.in Chemicals/CAS: mangiferin, 4773-96-0 References: Barik, A., Priyadarsini, K.I., Mohan, H., Redox reactions of 2-hydroxy-3-methoxybenzaldehyde (o-vanillin) in aqueous solution (2004) Radiat. Phys. Chem., 70, pp. 687-696; Bhattacharya, S.K., Sanyal, A.K., Ghosal, S., Monoamine oxidase inhibiting activity of mangiferin isolated from Canscora decussata (1972) Naturwissenschaften, 59, pp. 651-655; Cai, Z., Li, X., Katsumura, Y., Interaction of hydrated electron with dietary flavonoids and phenolic acids: Rate constants and transient spectra studied by pulse radiolysis (1999) Free. Radic. Bio. Med., 27, pp. 822-829; Cren-Olive, C., Hapiot, P., Pinson, J., Rolando, C., Free radical chemistry of flavan-3-ols: Determination of thermodynamic parameters and of kinetic reactivity from short (ns) to long (ms) time scale (2002) J. Am. Chem. Soc., 124, pp. 14027-14038; Fielden, E.M., Chemical dosimetry of pulsed electron and X-ray source in the MeV region (1982) The Study of Fast Processes and Transient Species by Electron Pulse Radiolysis, p. 59. , J.H. Baxandale F. Busi Reidel Publishing Co London; Guha, S.N., Moorthy, P.N., Naik, D.B., Rao, K.N., One electron reduction of thionine studied by pulse radiolysis (1987) Proc Indian Acad. Sci. (Chem. Sci.), 99, pp. 261-271; Guha, S., Ghosal, S., Chattopadhyay, U., Antitumor, immunomodulatory and anti HIV effect of mangiferin, a naturally occurring glucosylxanthone (1996) Chemotherapy, 42, pp. 443-451; Halliwell, B., Gutteridge, J.M., (1993) Free Radicals in Biology and Medicine, , Oxford Clarendon Press Oxford, UK; Ichiki, H., Miura, T., Kubo, M., Ishihara, E., Komatsu, Y., Tanigawa, K., Okada, M., New antidiabetic compounds, mangiferin and its glucoside (1998) Biol. Pharm. Bull., 21, pp. 1389-1390; Leiro, J.M., Álvarez, E., Arranz, J.A., Siso, I.G., Orallo, F., In vitro effects of mangiferin on superoxide concentrations and expression of the inducible nitric oxide synthase, tumour necrosis factor-α and transforming growth factor-β genes (2003) Biochem. Pharm., 65, pp. 1361-1371; Li, H., Miyahara, T., Tezuka, Y., Namba, T., Nemoto, N., Tonami, S., Seto, H., Kadota, S., The effect of kampo formulae on bone resorption in vitro and in vivo. I. Active constituents of Tsu-kan-gan (1998) Biol. Pharm. Bull., 21, pp. 1322-1326; Lin, S.J., Tseng, H.H., Wen, K.C., Suen, T.T., Determination of gentiopicroside, mangiferin, palmatine, berberine, baicalin, wogonin and glycyrrhizin in the traditional Chinese medicinal preparation by high performance liquid chromatography (1996) J. Chromatogr. A., 730, pp. 17-23; Mishra, B., Priyadarsini, K.I., Mantena, S.K., Unnikrishnan, M.K., Mohan, H., Effect of O-glycosilation on the antioxidant activity and free radical reactions of a plant flavonoid chrysoeriol (2003) Bio-org. Med. Chem., 11, pp. 2677-2685; Moreira, R.R., Carlos, I.Z., Vilega, W., Release of intermediate reactive Hydrogen peroxide by macrophage cells activated by natural products (2001) Biol. Pharm. Bull., 24 (2), pp. 201-204; Nunez-Selles, A.J., Capote, H.R., Aguero-Aguero, J., Garrido-Garrido, G., Delgado-Hernandez, R., Martinez-Sanchez, G., Leon-Fernanez, O., Morales-Segura, M., New antioxidant product derived from Mangifera indica L (2000) 220th National Meeting of the American Chemical Society, , Abstracts of Papers, New Orleans, LA, 2000. American Chemical Society, Washington, DC, 2000, MEDI-155. ISSN:0065-7727. AN 2000:796153; Nunez-Selles, A.J., Velez Castro, H.T., Aguero- Aguero, J., Gonzalez-Gonzalez, J., Naddeo, F., De Simone, F., Rastrelli, L., Isolation and quantitative analysis of phenolic antioxidants, free sugars, and polyols from mango (Mangifera indica) stem bark aqueous decoction used in Cuba as a nutritional supplement (2002) J. Agric. Food Chem., 50, pp. 762-766; Pokorny, J., Yanishlieva, N., Gordon, M., (2001) Antioxidants in Food, , CRC Press New York; Priyadarsini, K.I., Naik, D.B., Moorthy, P.N., Mittal, J.P., Energy Transfer Studies of coumarin dyes using electron pulse radiolysis (1991) Proceedings of the Seventh Tihany Symposium on Radiation Chemistry, pp. 105-107. , Dobo, J., Nykis, L., Shiller, R. (Eds.) Hungarian Chemical Society, Budapest, Hungary; Priyadarsini, K.I., Khopde, S.M., Kumar, S.S., Mohan, H., Free radical studies of ellagic acid, a natural phenolic antioxidant (2002) J. Agri. Food. Chem., 50, pp. 2200-2206; Quisumbing, E., (1978) Medicinal Plants of the Philippines, , Katha Publishing Co & JMC Press Quezon; Sanchez, G.M., Re, L., Giuliani, A., Nuñez-Selles, A.J., Davison, G.P., Leon-Fernandez, O.S., Protective effects of mangifera indica L. Extract, mangiferin and selected antioxidants against tpa induced biomolecules oxidation and peritoneal macrophage activation in mice (2000) Pharmacol. Res., 42, pp. 565-573; Stoner, G.D., Mukhtar, H., Polyphenols as cancer chemo preventive agents (1995) J. Cell. Biochem. Suppl., 22, pp. 169-180; Sonntag, C.von., (1987) The Chemical Basis of Radiation Biology, , Taylor & Francis London; Visioli, F., Bellomo, G., Galli, C., Free radical-scavenging properties of olive oil polyphenols (1998) Biochem. Biophy. Res Commun., 247, pp. 60-64; Wardman, P., Reduction potentials of one-electron couples involving free radicals in aqueous solutions (1989) J. Phys. Chem. Ref. Data, 18, pp. 1637-1754; Yoosook, C., Bunyapraphatsara, N., Boonyakiat, Y., Kantasuk, C., Anti-herpes simplex virus activities of crude water extracts of Thai medicinal plants (2000) Phytomedicine, 6, pp. 411-419; Yoshimia, N., Matsunagaa, K., Katayamaa, M., Yamadaa, Y., Kunoa, T., Qiaoa, Z., Haraa, A., Moria, H., The inhibitory effects of mangiferin, a naturally occurring glucosylxanthone, in bowel carcinogenesis of male F344 rats (2001) Cancer Lett., 163, pp. 163-170

PY - 2006

Y1 - 2006

N2 - Pulse radiolysis technique has been employed to study the reaction of different oxidizing and reducing radicals with mangiferin. The reaction of *OH radical showed the formation of transient species absorbing in 380-390 and 470-480 nm region. The reaction with specific one-electron oxidants (N 3*, CCl3O2*) also showed the formation of similar transient absorption bands and is assigned to phenoxyl radicals. The pKa values of the transient species have been determined to be 6.3 and 11.9. One-electron oxidation potential of mangiferin at pH 9 has been found to be 0.62 V vs. NHE. The reaction of eaq - showed the formation of transient species with λ max at 340 nm, which is assigned to the ketyl anion radical formed on addition of eaq- at carbonyl site. Reactions of one-electron oxidised mangiferin radicals with ascorbic acid have also been studied. © 2005 Elsevier Ltd. All rights reserved.

AB - Pulse radiolysis technique has been employed to study the reaction of different oxidizing and reducing radicals with mangiferin. The reaction of *OH radical showed the formation of transient species absorbing in 380-390 and 470-480 nm region. The reaction with specific one-electron oxidants (N 3*, CCl3O2*) also showed the formation of similar transient absorption bands and is assigned to phenoxyl radicals. The pKa values of the transient species have been determined to be 6.3 and 11.9. One-electron oxidation potential of mangiferin at pH 9 has been found to be 0.62 V vs. NHE. The reaction of eaq - showed the formation of transient species with λ max at 340 nm, which is assigned to the ketyl anion radical formed on addition of eaq- at carbonyl site. Reactions of one-electron oxidised mangiferin radicals with ascorbic acid have also been studied. © 2005 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.radphyschem.2005.05.015

DO - 10.1016/j.radphyschem.2005.05.015

M3 - Article

VL - 75

SP - 70

EP - 77

JO - Radiation Physics and Chemistry

JF - Radiation Physics and Chemistry

SN - 0969-806X

IS - 1

ER -