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Volumn 33, Issue 12, 2002, Pages 1724-1735

Design, synthesis, and antioxidant activity of FeAOX-6, a novel agent deriving from a molecular combination of the chromanyl and polyisoprenyl moieties

Author keywords

Tocopherol; Antioxidant(s); Arachidonic acid solution; Chromanyl and polyisoprenyl moieties; FeAOX 6; Free radicals; Lipid peroxidation; Lycopene; ROS; Thymocytes

Indexed keywords

ALPHA TOCOPHEROL; ANTIOXIDANT; ARACHIDONIC ACID; CHROMAN DERIVATIVE; FREE RADICAL; HYDROGEN PEROXIDE; IRON DERIVATIVE; LYCOPENE; MALONALDEHYDE; REACTIVE OXYGEN METABOLITE; TOCOPHEROL DERIVATIVE;

EID: 0037114896     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(02)01168-1     Document Type: Article
Times cited : (34)

References (46)
  • 1
    • 0003536299 scopus 로고
    • B. Halliwell, & J.M.C. Gutteridge. Oxford, UK: Clarendon Press
    • Halliwell B., Gutteridge J.M.C. Free radicals in biology and medicine. 1985;Clarendon Press, Oxford, UK.
    • (1985) Free radicals in biology and medicine
  • 2
    • 0029945201 scopus 로고    scopus 로고
    • Beta-carotene, carotenoids, and disease prevention in humans
    • Mayne S.T. Beta-carotene, carotenoids, and disease prevention in humans. FASEB J. 10:1996;690-701.
    • (1996) FASEB J. , vol.10 , pp. 690-701
    • Mayne, S.T.1
  • 3
    • 0033577044 scopus 로고    scopus 로고
    • Tomatoes, tomato-based products, lycopene and cancer: Review of the epidemiological literature
    • Giovannucci E. Tomatoes, tomato-based products, lycopene and cancer review of the epidemiological literature . J. Natl. Cancer Inst. 91:1999;317-331.
    • (1999) J. Natl. Cancer Inst. , vol.91 , pp. 317-331
    • Giovannucci, E.1
  • 4
    • 0028856841 scopus 로고
    • Safety of antioxidant vitamins and β-carotene
    • Diplock, A. Safety of antioxidant vitamins and β-carotene. Am. J. Clin. Nutr. 62(6 Suppl.):1510S-1516S; 1995.
    • (1995) Am. J. Clin. Nutr. , vol.62 , Issue.6 SUPPL.
    • Diplock, A.1
  • 5
    • 0028345768 scopus 로고
    • Prevention of esophageal cancer: the nutrition intervention trials in Linxian, China
    • Linxian Nutrition Intervention Trials Study Group
    • Taylor, P. R.; Li, B.; Dawsey, S. M.; Li, J.-Y.; Yang, C. S.; Guo, W.; Blot, W. J. Prevention of esophageal cancer: the nutrition intervention trials in Linxian, China. Linxian Nutrition Intervention Trials Study Group. Cancer Res. 54(7 Suppl.):2029s-2031s; 1994.
    • (1994) Cancer Res. , vol.54 , Issue.7 SUPPL.
    • Taylor, P.R.1    Li, B.2    Dawsey, S.M.3    Li, J.-Y.4    Yang, C.S.5    Guo, W.6    Blot, W.J.7
  • 6
    • 0028864835 scopus 로고
    • Vitamins E and C, beta-carotene and other carotenoids as antioxidants
    • Sies, H.; Stahl, W. Vitamins E and C, beta-carotene and other carotenoids as antioxidants. Am. J. Clin. Nutr. 62(6 Suppl.):1315S-1321S; 1995.
    • (1995) Am. J. Clin. Nutr. , vol.62 , Issue.6 SUPPL.
    • Sies, H.1    Stahl, W.2
  • 7
    • 0029798873 scopus 로고    scopus 로고
    • Vitamin E in humans: Demand and delivery
    • Traber M.G., Sies W. Vitamin E in humans demand and delivery . Annu. Rev. Nutr. 16:1996;321-347.
    • (1996) Annu. Rev. Nutr. , vol.16 , pp. 321-347
    • Traber, M.G.1    Sies, W.2
  • 8
    • 0026676309 scopus 로고
    • Antioxidant effects of carotenoids in vitro and in vivo: An overview
    • Palozza P., Krinsky N.I. Antioxidant effects of carotenoids in vitro and in vivo an overview . Methods Enzymol. 213:1992;403-420.
    • (1992) Methods Enzymol. , vol.213 , pp. 403-420
    • Palozza, P.1    Krinsky, N.I.2
  • 9
    • 0030015296 scopus 로고    scopus 로고
    • The chemistry and antioxidant properties of tocopherols and tocotrienols
    • Kamal-Eldin A., Appelqvist L.-A. The chemistry and antioxidant properties of tocopherols and tocotrienols. Lipids. 31:1996;671-701.
    • (1996) Lipids , vol.31 , pp. 671-701
    • Kamal-Eldin, A.1    Appelqvist, L.-A.2
  • 10
    • 0029598850 scopus 로고
    • Structure and properties of carotenoids in relation to function
    • Britton G. Structure and properties of carotenoids in relation to function. FASEB J. 9:1995;1551-1558.
    • (1995) FASEB J. , vol.9 , pp. 1551-1558
    • Britton, G.1
  • 14
    • 0029995001 scopus 로고    scopus 로고
    • Scavenging of nitrogen dioxide, thiyl, and sulfonyl free radicals by the nutritional antioxidant β-carotene
    • Everett S.A., Dennis M.F., Patel K.B., Maddix S., Kundu S.C., Willson R.L. Scavenging of nitrogen dioxide, thiyl, and sulfonyl free radicals by the nutritional antioxidant β-carotene. J. Biol. Chem. 271:1996;3988-3994.
    • (1996) J. Biol. Chem. , vol.271 , pp. 3988-3994
    • Everett, S.A.1    Dennis, M.F.2    Patel, K.B.3    Maddix, S.4    Kundu, S.C.5    Willson, R.L.6
  • 15
    • 0019889416 scopus 로고
    • Free radicals and singlet oxygen scavengers: Reaction of a peroxyl-radical with beta-carotene, diphenyl furan and 1,4-diazobicyclo(2,2,2)-octane
    • Packer J.E., Mahood J.S., Mora-Arellano V.O., Slater T.F., Willson R.L., Wolfenden B.S. Free radicals and singlet oxygen scavengers reaction of a peroxyl-radical with beta-carotene, diphenyl furan and 1,4-diazobicyclo(2,2,2)-octane . Biochem. Biophys. Res. Commun. 98:1981;901-906.
    • (1981) Biochem. Biophys. Res. Commun. , vol.98 , pp. 901-906
    • Packer, J.E.1    Mahood, J.S.2    Mora-Arellano, V.O.3    Slater, T.F.4    Willson, R.L.5    Wolfenden, B.S.6
  • 16
    • 0035816459 scopus 로고    scopus 로고
    • One-electron reduction potentials of dietary carotenoid radical cations in aqueous micellar environments
    • Burke M., Edge R., Land E.J., McGarvey D.J., Truscott T.G. One-electron reduction potentials of dietary carotenoid radical cations in aqueous micellar environments. FEBS Lett. 500:2001;132-136.
    • (2001) FEBS Lett. , vol.500 , pp. 132-136
    • Burke, M.1    Edge, R.2    Land, E.J.3    McGarvey, D.J.4    Truscott, T.G.5
  • 18
    • 0021362463 scopus 로고
    • β-Carotene: An unusual type of lipid antioxidant
    • Burton G.W., Ingold K.U. β-Carotene an unusual type of lipid antioxidant . Science. 224:1984;569-573.
    • (1984) Science , vol.224 , pp. 569-573
    • Burton, G.W.1    Ingold, K.U.2
  • 19
    • 0025994821 scopus 로고
    • The inhibition of radical-initiated peroxidation of microsomal lipids by both α-tocopherol and β-carotene
    • Palozza P., Krinsky N.I. The inhibition of radical-initiated peroxidation of microsomal lipids by both α-tocopherol and β-carotene. Free Radic. Biol. Med. 11:1991;407-414.
    • (1991) Free Radic. Biol. Med. , vol.11 , pp. 407-414
    • Palozza, P.1    Krinsky, N.I.2
  • 20
    • 0031045424 scopus 로고    scopus 로고
    • Antioxidant and prooxidant role of β-carotene in murine normal and tumor thymocytes: Effects of oxygen partial pressure
    • Palozza P., Luberto C., Calviello G., Ricci P., Bartoli G.M. Antioxidant and prooxidant role of β-carotene in murine normal and tumor thymocytes effects of oxygen partial pressure . Free Radic. Biol. Med. 22:1997;1065-1073.
    • (1997) Free Radic. Biol. Med. , vol.22 , pp. 1065-1073
    • Palozza, P.1    Luberto, C.2    Calviello, G.3    Ricci, P.4    Bartoli, G.M.5
  • 21
    • 0026744118 scopus 로고
    • Peroxyl radical scavenging of β-carotene in lipid bilayers: Effect of oxygen partial pressure
    • Kennedy T.A., Liebler D.C. Peroxyl radical scavenging of β-carotene in lipid bilayers effect of oxygen partial pressure . J. Biol. Chem. 267:1992;4658-4663.
    • (1992) J. Biol. Chem. , vol.267 , pp. 4658-4663
    • Kennedy, T.A.1    Liebler, D.C.2
  • 22
    • 0021330425 scopus 로고
    • Inhibition of oxidation of methyl linoleate in solution by vitamin E and vitamin C
    • Niki E., Saito T., Kawakami A., Kamiya Y. Inhibition of oxidation of methyl linoleate in solution by vitamin E and vitamin C. J. Biol. Chem. 259:1984;4177-4182.
    • (1984) J. Biol. Chem. , vol.259 , pp. 4177-4182
    • Niki, E.1    Saito, T.2    Kawakami, A.3    Kamiya, Y.4
  • 23
    • 0024588311 scopus 로고
    • Synergistic interaction between vitamin E and the bile pigments bilirubin and biliverdin
    • Stocker R., Peterhans E. Synergistic interaction between vitamin E and the bile pigments bilirubin and biliverdin. Biochim. Biophys. Acta. 1002:1989;238-244.
    • (1989) Biochim. Biophys. Acta , vol.1002 , pp. 238-244
    • Stocker, R.1    Peterhans, E.2
  • 24
    • 0024557108 scopus 로고
    • Synergistic inhibition of oxidation in dispersed phosphatidylcholine liposomes by a combination of vitamin E and cysteine
    • Motoyama T., Miki M., Mino M., Takahashi M., Niki E. Synergistic inhibition of oxidation in dispersed phosphatidylcholine liposomes by a combination of vitamin E and cysteine. Arch. Biochem. Biophys. 270:1989;655-661.
    • (1989) Arch. Biochem. Biophys. , vol.270 , pp. 655-661
    • Motoyama, T.1    Miki, M.2    Mino, M.3    Takahashi, M.4    Niki, E.5
  • 25
    • 0026696022 scopus 로고
    • Effect of β-carotene and α-tocopherol on radical-initiated peroxidation of microsomes
    • Palozza P., Moualla S., Krinsky N.I. Effect of β-carotene and α-tocopherol on radical-initiated peroxidation of microsomes. Free Radic. Biol. Med. 13:1992;127-136.
    • (1992) Free Radic. Biol. Med. , vol.13 , pp. 127-136
    • Palozza, P.1    Moualla, S.2    Krinsky, N.I.3
  • 26
    • 0025915048 scopus 로고
    • Chatterjee, A.; Krinsky, N. I. Characterization of products formed during the autooxidation of β-carotene
    • Handelman G.J., van Kuijk F.J.G.M. Chatterjee, A.; Krinsky, N. I. Characterization of products formed during the autooxidation of β-carotene. Free Radic. Biol. Med. 10:1991;427-437.
    • (1991) Free Radic. Biol. Med. , vol.10 , pp. 427-437
    • Handelman, G.J.1    Van Kuijk, F.J.G.M.2
  • 27
    • 84986469609 scopus 로고
    • Inhibitory effects of tocopherols and β-carotene on singlet oxygen-initiated photooxidation of methyl linoleate and soybean oil
    • Terao J., Yamauchi R., Murakami K., Matsushita S. Inhibitory effects of tocopherols and β-carotene on singlet oxygen-initiated photooxidation of methyl linoleate and soybean oil. J. Food Proc. Preserv. 4:1980;79-93.
    • (1980) J. Food Proc. Preserv. , vol.4 , pp. 79-93
    • Terao, J.1    Yamauchi, R.2    Murakami, K.3    Matsushita, S.4
  • 28
    • 0000203065 scopus 로고    scopus 로고
    • Effects of lutein, lycopene, annatto, and γ-tocopherol on autooxidation of triglicerides
    • Haila K.M., Lievonen S.M., Heinonen M.I. Effects of lutein, lycopene, annatto, and γ-tocopherol on autooxidation of triglicerides. J. Agric. Food Chem. 44:1996;2096-2100.
    • (1996) J. Agric. Food Chem. , vol.44 , pp. 2096-2100
    • Haila, K.M.1    Lievonen, S.M.2    Heinonen, M.I.3
  • 29
    • 0026688491 scopus 로고
    • β-Carotene and α-tocopherol are synergistic antioxidants
    • Palozza P., Krinsky N.I. β-Carotene and α-tocopherol are synergistic antioxidants. Arch. Biochem. Biophys. 297:1992;184-187.
    • (1992) Arch. Biochem. Biophys. , vol.297 , pp. 184-187
    • Palozza, P.1    Krinsky, N.I.2
  • 30
    • 0033757325 scopus 로고    scopus 로고
    • Novel antioxidant agents deriving from molecular combinations of vitamins C and E analogues: 3,4-dihydroxy-5(R)-[2(R,S)-(6-hydroxy-2,5,7,8-tetramethyl-chroman-2(R,S)-yl- methyl)-[1,3]dioxolan-4(S)-yl]-5H-furan-2-one and 3-O-octadecyl derivatives
    • Manfredini S., Vertuani S., Manfredi B., Rossoni G., Calviello G., Palozza P. Novel antioxidant agents deriving from molecular combinations of vitamins C and E analogues 3,4-dihydroxy-5(R)-[2(R,S)-(6-hydroxy-2,5,7,8-tetramethyl-chroman-2(R,S)-yl- methyl)-[1,3]dioxolan-4(S)-yl]-5H-furan-2-one and 3-O-octadecyl derivatives . Bioorg. Med. Chem. 8:2000;2791-2801.
    • (2000) Bioorg. Med. Chem. , vol.8 , pp. 2791-2801
    • Manfredini, S.1    Vertuani, S.2    Manfredi, B.3    Rossoni, G.4    Calviello, G.5    Palozza, P.6
  • 31
    • 0034892957 scopus 로고    scopus 로고
    • Synthesis of a triantioxidant compound: Combination of beta-apo-8′-carotenoic acid, selenacapryloic acid and trolox in a triglyceride
    • Naalsund T., Malterud K.E., Partali V., Sliwka H.R. Synthesis of a triantioxidant compound combination of beta-apo-8′-carotenoic acid, selenacapryloic acid and trolox in a triglyceride . Chem. Phys. Lipids. 112:2001;59-65.
    • (2001) Chem. Phys. Lipids , vol.112 , pp. 59-65
    • Naalsund, T.1    Malterud, K.E.2    Partali, V.3    Sliwka, H.R.4
  • 32
    • 84987505467 scopus 로고
    • Synthesis, isolation, and NMR-spectroscopic characterization of fourteen (Z)-isomers of lycopene and some acetylenic didehydro- and tetrahydrolycopenes
    • Hengartner U., Bernhard K., Meyer K. Synthesis, isolation, and NMR-spectroscopic characterization of fourteen (Z)-isomers of lycopene and some acetylenic didehydro- and tetrahydrolycopenes. Helv. Chim. Acta. 75:1992;1848-1865.
    • (1992) Helv. Chim. Acta , vol.75 , pp. 1848-1865
    • Hengartner, U.1    Bernhard, K.2    Meyer, K.3
  • 33
    • 0027175112 scopus 로고
    • Separation of beta-carotene and lycopene geometrical isomers in biological samples
    • Stahl W., Sundquist A.R., Hanusch M., Schwarz W., Sies H. Separation of beta-carotene and lycopene geometrical isomers in biological samples. Clin. Chem. 39:1993;810-814.
    • (1993) Clin. Chem. , vol.39 , pp. 810-814
    • Stahl, W.1    Sundquist, A.R.2    Hanusch, M.3    Schwarz, W.4    Sies, H.5
  • 34
    • 0025259264 scopus 로고
    • Measurement of malondialdehyde by high performance liquid chromatography with fluorescence detection
    • Tatum V.L., Changohit C., Chow C.K. Measurement of malondialdehyde by high performance liquid chromatography with fluorescence detection. Lipids. 25:1990;226-229.
    • (1990) Lipids , vol.25 , pp. 226-229
    • Tatum, V.L.1    Changohit, C.2    Chow, C.K.3
  • 36
    • 0029671249 scopus 로고    scopus 로고
    • Effect of β-carotene and canthaxanthin on tert-butyl hydroperoxide-induced lipid peroxidation in murine normal and tumor thymocytes
    • Palozza P., Luberto C., Ricci P., Sgarlata E., Calviello G., Bartoli G.M. Effect of β-carotene and canthaxanthin on tert-butyl hydroperoxide-induced lipid peroxidation in murine normal and tumor thymocytes. Arch. Biochem. Biophys. 325:1996;145-151.
    • (1996) Arch. Biochem. Biophys. , vol.325 , pp. 145-151
    • Palozza, P.1    Luberto, C.2    Ricci, P.3    Sgarlata, E.4    Calviello, G.5    Bartoli, G.M.6
  • 37
    • 0025082043 scopus 로고
    • Free radical initiators as source water- or lipid-soluble peroxyl radicals
    • Niki E. Free radical initiators as source water- or lipid-soluble peroxyl radicals. Methods Enzymol. 186:1990;100-108.
    • (1990) Methods Enzymol. , vol.186 , pp. 100-108
    • Niki, E.1
  • 38
    • 0028294151 scopus 로고
    • Protection by vitamin E selenium, trolox C, ascorbic acid palmitate, acetylcysteine, coenzyme Q, beta-carotene, canthaxanthin, and (+)-catechin against oxidative damage to liver slices measured by oxidized heme proteins
    • Chen H., Tappel A.L. Protection by vitamin E selenium, trolox C, ascorbic acid palmitate, acetylcysteine, coenzyme Q, beta-carotene, canthaxanthin, and (+)-catechin against oxidative damage to liver slices measured by oxidized heme proteins. Free Radic. Biol. Med. 16:1994;437-444.
    • (1994) Free Radic. Biol. Med. , vol.16 , pp. 437-444
    • Chen, H.1    Tappel, A.L.2
  • 39
    • 0242644199 scopus 로고    scopus 로고
    • β-Carotene with vitamins E and C offers synergistic cell protection against NOx
    • Bohm F., Edge R., Mcgarvey D.J., Truscott T.G. β-Carotene with vitamins E and C offers synergistic cell protection against NOx. FEBS Lett. 436:1998;387-389.
    • (1998) FEBS Lett. , vol.436 , pp. 387-389
    • Bohm, F.1    Edge, R.2    Mcgarvey, D.J.3    Truscott, T.G.4
  • 40
    • 0034003859 scopus 로고    scopus 로고
    • Carotenoids and carotenoids plus vitamin E protect against ultraviolet light-induced erythema in humans
    • Stahl W., Heinrich U., Jungmann H., Sies H., Tronnier H. Carotenoids and carotenoids plus vitamin E protect against ultraviolet light-induced erythema in humans. Am. J. Clin. Nutr. 71:2000;795-798.
    • (2000) Am. J. Clin. Nutr. , vol.71 , pp. 795-798
    • Stahl, W.1    Heinrich, U.2    Jungmann, H.3    Sies, H.4    Tronnier, H.5
  • 41
    • 0030838318 scopus 로고    scopus 로고
    • Relative stability of carotenoid radical cations and homologue tocopheroxyl radicals. A real time kinetic study of antioxidant hierarchy
    • Mortensen A., Skibsted L.H. Relative stability of carotenoid radical cations and homologue tocopheroxyl radicals. A real time kinetic study of antioxidant hierarchy. FEBS Lett. 417:1997;261-266.
    • (1997) FEBS Lett. , vol.417 , pp. 261-266
    • Mortensen, A.1    Skibsted, L.H.2
  • 42
    • 0030670198 scopus 로고    scopus 로고
    • Carotenoids and protection of phospholipids in solution or in liposomes against oxidation by peroxyl radicals: Relationship between carotenoid structure and protective ability
    • Woodall A.A., Britton G., Jackson M.J. Carotenoids and protection of phospholipids in solution or in liposomes against oxidation by peroxyl radicals relationship between carotenoid structure and protective ability . Biochim. Biophys. Acta. 1336:1997;575-586.
    • (1997) Biochim. Biophys. Acta , vol.1336 , pp. 575-586
    • Woodall, A.A.1    Britton, G.2    Jackson, M.J.3
  • 43
    • 0030813933 scopus 로고    scopus 로고
    • Oxidation of carotenoids by free radicals: Relationship between structure and reactivity
    • Woodall A.A., Lee S.W., Weesie R.J., Jackson M.J., Britton G. Oxidation of carotenoids by free radicals relationship between structure and reactivity . Biochim. Biophys. Acta. 1336:1997;33-42.
    • (1997) Biochim. Biophys. Acta , vol.1336 , pp. 33-42
    • Woodall, A.A.1    Lee, S.W.2    Weesie, R.J.3    Jackson, M.J.4    Britton, G.5
  • 44
    • 0021444491 scopus 로고
    • Study of the orientational ordering of carotenoids in lipid bilayers by resonance-Raman spectroscopy
    • Van de Ven M., Kattenberg M., van Ginkel G., Levine Y.K. Study of the orientational ordering of carotenoids in lipid bilayers by resonance-Raman spectroscopy. Biophys. J. 45:1984;1203-1210.
    • (1984) Biophys. J. , vol.45 , pp. 1203-1210
    • Van de Ven, M.1    Kattenberg, M.2    Van Ginkel, G.3    Levine, Y.K.4
  • 45
    • 0029787986 scopus 로고    scopus 로고
    • β-Carotene and lutein protect HepG2 human liver cells against oxidant-induced damage
    • Martin K.R., Failla M.L., Smith J.C. Jr. β-Carotene and lutein protect HepG2 human liver cells against oxidant-induced damage. J. Nutr. 126:1996;2098-2106.
    • (1996) J. Nutr. , vol.126 , pp. 2098-2106
    • Martin, K.R.1    Failla, M.L.2    Smith J.C., Jr.3
  • 46
    • 0024563906 scopus 로고
    • Antioxidant action of carotenoids
    • Burton G.W. Antioxidant action of carotenoids. J. Nutr. 119:1989;109-111.
    • (1989) J. Nutr. , vol.119 , pp. 109-111
    • Burton, G.W.1


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