Free radical reactions and antioxidant activities of sesamol: Pulse radiolytic and biochemical studies. / Joshi, R.; Kumar, M.S.; Satyamoorthy, K.; Unnikrisnan, M.K.; Mukherjee, T.In: Journal of Agricultural and Food Chemistry, Vol. 53, No. 7, 2005, p. 2696-2703.
Research output: Contribution to journal › Article
TY - JOUR
T1 - Free radical reactions and antioxidant activities of sesamol: Pulse radiolytic and biochemical studies
AU - Joshi, R.
AU - Kumar, M.S.
AU - Satyamoorthy, K.
AU - Unnikrisnan, M.K.
AU - Mukherjee, T.
N1 - Cited By :91 Export Date: 10 November 2017 CODEN: JAFCA Correspondence Address: Joshi, R.; Radiat. Chem. and Chem. Dynam. Div., Chemistry Group, Bhabha Atomic Research Centre, Mumbai 400085, India; email: firstname.lastname@example.org Chemicals/CAS: deoxyribose, 533-67-5; hydroxyl radical, 3352-57-6; sesamol, 533-31-3; tryptophan, 6912-86-3, 73-22-3; Antioxidants; DNA, 9007-49-2; Deoxyribose, 533-67-5; Ferric Compounds; Free Radicals; Peroxides; Phenols; perhydroxyl radical, 3170-83-0; sesamol, 533-31-3 References: Ames, B.N., Dietary carcinogens and anticarcinogens (1983) Science, 227, pp. 1256-1264; Cadenas, E., Packer, L., (1996) Handbook of Antioxidants, , Marcel Dekker: New York; Aruoma, O.I., Nutrition and health aspects of free radical and antioxidants (1994) Free Radical Toxicol., 32, pp. 671-683; Proctor, P.H., Free radicals and human disease (1989) Handbook of Free Radicals and Antioxidants in Biomedicine, 1, pp. 209-221. , Miquel, J., Quintanilha, A. T., Weber, H., Eds.; CRC Press: Boca Raton, FL; Stocker, R., Frie, B., Endogenous antioxidant defense in human blood plasma (1991) Oxidative Stress: Oxidants and Antioxidants, pp. 213-243. , Sies, H., Ed.; Academic Press: London; Halliwell, B., Gutteridge, J.M.C., (1989) Free Radicals in Biology and Medicine, , Oxford University Press: Oxford; Cerutti, P.A., Prooxidant states and tumor promotion (1985) Science, 227, pp. 375-381; Budowski, P., Sesame oil III. Antioxidant properties of sesamol (1950) J. Am. Oil Chem. Soc., 27, pp. 264-270; Budowski, P., Menezes, F.G.T., Dollear, F.G., Sesame oil IV. The stability of sesame oil (1950) J. Am. Oil Chem. Soc., 27, pp. 377-380; Kikugawa, K., Arai, M., Kurechi, T., Participation of sesamol in stability of sesame oil (1983) J. Am. Oil Chem. Soc., 60, pp. 1528-1533; Kim, J.Y., Choi, D.S., Jung, M.Y., Antiphotooxidative activity of sesamol in methyleneblue- and chlorophyll-sensitized photooxidation of oil (2003) J. Agric. Food Chem., 51, pp. 3460-3465; Wright, J.S., Johnson, E.R., DiLabio, G.A., Predicting the activity of phenolic antioxidants: Theoretical method, analysis of substituent effects, and application to major families of antioxidants (2001) J. Am. Chem. Soc., 123, pp. 1173-1183; Joshi, R., Adhikari, S., Patro, B.S., Chattopadhyay, S., Mukherjee, T., Free radical scavenging behavior of folic acid: Evidence for possible antioxidant activity (2001) Free Radical Biol. Med., 30, pp. 1390-1399; Joshi, R., Kapoor, S., Mukherjee, T., Free radical reactions of pyridoxal (Vitamin B6): A pulse radiolysis study (2002) Res. Chem. Intermed., 28, pp. 505-515; McPhail, D.B., Hartley, R.C., Gardner, P.T., Duthie, G.G., Kinetic and stoichiometric assessment of the antioxidant activity of flavanoids by electron spin resonance spectroscopy (2003) J. Agric. Food Chem., 51, pp. 1684-1690; Mazziao, E.A., Harris, N., Soliman, K.F., Food constituents attenuate monoamine oxidase activity and peroxide levels in C6 astrocyte cells (1998) Planta Med., 64, pp. 603-606; Tseng, T.H., Tsheng, Y.M., Lee, Y.J., Cytotoxicity effects of di- and tri-hydroxybenzaldehydes as a chemopreventive potential agent on tumor cells (2001) Toxicology, 161, pp. 179-187; Tagashira, M., Ohtake, Y., A new antioxidant 1.3-benzodioxole from Melissa officinalis (1998) Planta Med., 64, pp. 555-558; Jurd, L., Narayana, V.L., Pauli, K.D., In vivo antitumor activity of 6-benzyl-1,3-benzodioxolederivatives against the P388, L1210, B16, and M5076 murine models (1987) J. Med. Chem., 30, pp. 1752-1756; Kumagai, Y., Lin, L.Y., Schmilz, D.A., Cho, A.K., Hydroxyl radical mediated demethylenation of (methlenedioxyl)phenyl compounds (1991) Chem. Res. Toxicol., 4, pp. 330-334; Chen, X., Ahn, D.U., Antioxidant activities of six natural phenolics against lipid peroxidation induced by Fe2+ or ultraviolet light (1998) J. Am. Oil Chem. Soc., 75, pp. 1717-1721; Kaur, I.P., Saini, A., Sesamol exhibits antimutagenic activity against oxygen species mediated mutagenicity (2000) Muta. Res., 470, pp. 71-76; Nakagawa, K., Photochemical reactions of antioxidant sesamol in aqueous solution (2000) J. Am. Oil Chem. Soc., 77, pp. 1205-1208; Nakagawa, K., Tero-Kuboto, S., Ikegami, Y., Tsuchihashi, N., EPR and TREPR studies of antioxidant sesamolyl and related phenoxyl radicals (1994) Photochem. Photobiol., 60, pp. 199-204; Tsutao, K., Kiyomi, K., Tetsuta, K., Studies on antioxidants. XIII. Hydrogen donating capability of antioxidants to 2,2-diphenyl-1-picrylhydrazyl (1980) Chem. Pharm. Bull., 28, pp. 2089-2093; Suja, K.P., Jayalekshmy, A., Arumughan, C., Free radical scavenging behavior of antioxidant compounds of sesame (Sesamum indicum L.) in DPPH system (2004) J. Agric. Food Chem., 52, pp. 912-915; Kato, T., Harashima, T., Moriya, N., Kikugawa, K., Hiramoto, K., Formation of the mutagenic/carcinogenic imidazoqunoxaline-type heterocyclic amines through the unstable free radical Maillard intermediates and its inhibition by phenolic antioxidants (1996) Carcinogenesis, 17, pp. 2469-2476; Hiramoto, K., Ojima, N., Sako, K., Kikugawa, K., Effect of plant phenolics on the formation of the spin-adduct of hydroxyl radical and the DNA strand breaking by hydroxyl radical (1996) Biol. Pharm. Bull., 19, pp. 558-563; Baxendale, J.H., Busi, F., (1982) The Study of Fast Processes and Transient Species by Electron Pulse Radiolysis, , D. Reidel Publishing Company: Dordrecht, The Netherlands; Mukherjee, T., Some recent studies of molecular dynamics at BARC (1997) Atomic, Molecular and Cluster Physics, pp. 299-316. , Ahmad, S. A., Ed.; Narosa: New Delhi; Buxton, G.V., Stuart, C.R., Reevaluation of the thiocyanate dosimeter for pulse radiolysis (1995) J. Chem. Soc., Faraday Trans., 97, pp. 279-281; Rajkumar, D.V., Rao, M.N.A., Antioxidant properties of phenyl styryl ketones (1995) Free Radical Res., 22, pp. 309-317; Braughler, J.M., Duncan, L.A., Chase, R.L., The involvement of iron in lipid peroxidation (1986) J. Biol. Chem., 261, pp. 10282-10289; Kunchandy, E., Rao, M.N.A., Effect of curcumin on hydroxyl radical generation through Fenton reaction (1989) Int. J. Pharm., 57, pp. 173-176; Buxton, G.V., Greenstock, C.L., Helman, W.P., Ross, A.B., Critical review of rate constants of hydrated electrons, hydrogen atoms and hydroxyl radicals (·OH/O.-) in aqueous solution (1988) J. Phys. Chem. Ref. Data, 77, pp. 513-886; Alfassi, Z.B., Schuler, R.H., Reaction of azide radicals with aromatic compounds. Azide as a selective oxidant (1985) J. Phys. Chem., 89, pp. 3359-3363; Neta, P., Huie, R.E., Ross, A.B., Rate constants for reactions of inorganic radicals in aqueous solution (1988) J. Phys. Chem. Ref. Data, 17, pp. 1027-1284; Das, T.N., Dhanasekaran, T., Alfassi, Z.B., Neta, P., Reduction potential of the tert-butyl peroxyl radical in aqueous solutions (1998) J. Phys. Chem. A, 702, pp. 280-284; Chevion, S., Roberts, M.A., Chevion, M., The use of cyclic voltammetry for the evaluation of antioxidant capacity (2000) Free Radical Biol. Med., 28, pp. 860-870; Steenken, S., Neta, P., One-electron redox potentials of phenols. Hydroxy and aminophenols and related compounds of biological interest (1982) J. Phys. Chem., 86, pp. 3661-3667; Sousa, W.R., DaRocha, C., Cardoso, C.L., Silva, D.H.S., Zanoni, M.V.B., Determination of the relative contribution of phenolic antioxidants in orange juice by voltammetric methods (2004) J. Food Compos. Anal., 17, pp. 619-633; Priyadarsini, K.I., Maity, D.K., Naik, G.H., Kumar, M.S., Unnikrishnan, M.K., Satav, J.G., Mohan, H., Role of phenolic O-H and methylene hydrogen on the free radical reactions and antioxidant activity of curcumin (2003) Free Radical Biol. Med., 55, pp. 475-484; Joshi, R., Mukherjee, T., Charge transfer between tryptophan and tyrosine in casein: A pulse radiolysis study (2002) Biophys. Chem., 96, pp. 15-19; Joshi, R., Mukherjee, T., Effect of solvent viscosity, polarity and pH on the charge transfer between tryptophan radical and tyrosine in bovine serum albumin: A pulse radiolysis study (2003) Biophys. Chem., 705, pp. 89-98; Schuler, R.H., Oxidation of ascorbate anion by electron transfer to phenoxyl radicals (1977) Radiat. Res., 69, pp. 417-433; Halliwell, B., How to characterize a biological antioxidant (1990) Free Radical Res. Commun., 9, pp. 1-32; Bindoli, A., Cavallini, L., Jocelyn, P., Mitochondrial lipid peroxidation by cumene hydroperoxide and its prevention by succinate (1982) Biochim. Biophys. Acta, 681, pp. 496-503; Sreejayan, Rao, M.N.A., Curcumin inhibits iron-dependent lipid peroxidation (1993) Int. J. Pharm., 100, pp. 93-97
PY - 2005
Y1 - 2005
N2 - Sesamol (from Sesamum indicum) is a dietary compound, which is soluble in aqueous as well as lipid phases. Free radical scavenging reactions of sesamol, 5-hydroxy-1,3-benzodioxole, have been studied using a nanosecond pulse radiolysis technique. Sesamol efficiently scavenges hydroxyl, one-electron oxidizing, organo-haloperoxyl, lipid peroxyl, and tryptophanyl radicals. Its antioxidant activity has also been evaluated with cyclic voltammetry. In biochemical studies, it has been found to inhibit lipid peroxidation, hydroxyl radical-induced deoxyribose degradation, and DNA cleavage. These antioxidant and free radical scavenging activities of sesamol have been reported in the paper. © 2005 American Chemical Society.
AB - Sesamol (from Sesamum indicum) is a dietary compound, which is soluble in aqueous as well as lipid phases. Free radical scavenging reactions of sesamol, 5-hydroxy-1,3-benzodioxole, have been studied using a nanosecond pulse radiolysis technique. Sesamol efficiently scavenges hydroxyl, one-electron oxidizing, organo-haloperoxyl, lipid peroxyl, and tryptophanyl radicals. Its antioxidant activity has also been evaluated with cyclic voltammetry. In biochemical studies, it has been found to inhibit lipid peroxidation, hydroxyl radical-induced deoxyribose degradation, and DNA cleavage. These antioxidant and free radical scavenging activities of sesamol have been reported in the paper. © 2005 American Chemical Society.
U2 - 10.1021/jf0489769
DO - 10.1021/jf0489769
M3 - Article
VL - 53
SP - 2696
EP - 2703
JO - Journal of Agricultural and Food Chemistry
JF - Journal of Agricultural and Food Chemistry
SN - 0021-8561
IS - 7