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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
2
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pubmed:dateCreated |
1997-7-10
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pubmed:abstractText |
To develop a novel potent radical-scavenging antioxidant, the ideal structure of a phenolic compound was designed considering the factors that determine antioxidant potency. 2,3-Dihydro-5-hydroxy-2,2-dipentyl-4, 6-di-tert-butylbenzofuran (BO-653) was thus synthesized and its antioxidant activity was evaluated against lipid peroxidations in vitro. The electron spin resonance study showed that the phenoxyl radical derived from BO-653 was more stable than alpha-tocopheroxyl radical. BO-653 reduced alpha-tocopheroxyl radical rapidly, but alpha-tocopherol did not reduce the phenoxyl radical derived from BO-653. However, the chemical reactivity of BO-653 toward peroxyl radical was smaller than that of alpha-tocopherol. This was interpreted as the steric effect of bulky tert-butyl groups at both ortho positions which hindered the access of peroxyl radical to the phenolic hydrogen. However, the tertbutyl substituents increased the stability of BO-653 radical and also lipophilicity, and its antioxidant potency against lipid peroxidation in phosphatidylcholine liposomal membranes was superior to that of alpha-tocopherol. Ascorbic acid reduced the phenoxyl radical derived from BO-653 and spared BO-653 during the oxidation of lipid in the homogeneous solution. On the other hand, ascorbic acid did not spare BO-653 in the oxidation of liposomal membranes. It was concluded that BO-653 is a potent novel radical-scavenging antioxidant.
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/2,2'-azobis(2,4-dimethylvaleronitril...,
http://linkedlifedata.com/resource/pubmed/chemical/Antioxidants,
http://linkedlifedata.com/resource/pubmed/chemical/Ascorbic Acid,
http://linkedlifedata.com/resource/pubmed/chemical/Azo Compounds,
http://linkedlifedata.com/resource/pubmed/chemical/Benzhydryl Compounds,
http://linkedlifedata.com/resource/pubmed/chemical/Benzofurans,
http://linkedlifedata.com/resource/pubmed/chemical/Free Radical Scavengers,
http://linkedlifedata.com/resource/pubmed/chemical/Linoleic Acids,
http://linkedlifedata.com/resource/pubmed/chemical/Liposomes,
http://linkedlifedata.com/resource/pubmed/chemical/Nitriles,
http://linkedlifedata.com/resource/pubmed/chemical/Peroxides,
http://linkedlifedata.com/resource/pubmed/chemical/Phenols,
http://linkedlifedata.com/resource/pubmed/chemical/Phosphatidylcholines,
http://linkedlifedata.com/resource/pubmed/chemical/Spin Labels,
http://linkedlifedata.com/resource/pubmed/chemical/Vitamin E,
http://linkedlifedata.com/resource/pubmed/chemical/galvinoxyl,
http://linkedlifedata.com/resource/pubmed/chemical/methyl linoleate,
http://linkedlifedata.com/resource/pubmed/chemical/perhydroxyl radical
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pubmed:status |
MEDLINE
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pubmed:month |
Jun
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pubmed:issn |
0003-9861
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pubmed:author |
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pubmed:issnType |
Print
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pubmed:day |
15
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pubmed:volume |
342
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
236-43
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pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading |
pubmed-meshheading:9186484-Antioxidants,
pubmed-meshheading:9186484-Ascorbic Acid,
pubmed-meshheading:9186484-Azo Compounds,
pubmed-meshheading:9186484-Benzhydryl Compounds,
pubmed-meshheading:9186484-Benzofurans,
pubmed-meshheading:9186484-Chromatography, High Pressure Liquid,
pubmed-meshheading:9186484-Drug Design,
pubmed-meshheading:9186484-Electron Spin Resonance Spectroscopy,
pubmed-meshheading:9186484-Free Radical Scavengers,
pubmed-meshheading:9186484-Kinetics,
pubmed-meshheading:9186484-Linoleic Acids,
pubmed-meshheading:9186484-Lipid Peroxidation,
pubmed-meshheading:9186484-Liposomes,
pubmed-meshheading:9186484-Molecular Structure,
pubmed-meshheading:9186484-Nitriles,
pubmed-meshheading:9186484-Oxidation-Reduction,
pubmed-meshheading:9186484-Peroxides,
pubmed-meshheading:9186484-Phenols,
pubmed-meshheading:9186484-Phosphatidylcholines,
pubmed-meshheading:9186484-Spin Labels,
pubmed-meshheading:9186484-Vitamin E
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pubmed:year |
1997
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pubmed:articleTitle |
2,3-Dihydro-5-hydroxy-2,2-dipentyl-4,6-di-tert-butylbenzofuran: design and evaluation as a novel radical-scavenging antioxidant against lipid peroxidation.
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pubmed:affiliation |
Research Center for Advanced Science and Technology, University of Tokyo, Japan.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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