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Content Provider | World Health Organization (WHO)-Global Index Medicus |
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Author | Kim, Jin Young Cho, Jeong-Yong Ma, Young Kyu Lee, Yu Geon Moon, Jae-Hak |
Description | Author Affiliation: Kim JY ( Department of Food Science & Technology and Functional Food Research Center, Chonnam National University, Gwangju 500-757, Republic of Korea.); Cho JY ( Department of Food Science & Technology and Functional Food Research Center, Chonnam National University, Gwangju 500-757, Republic of Korea.); Ma YK ( Department of Food Science & Technology and Functional Food Research Center, Chonnam National University, Gwangju 500-757, Republic of Korea.); Lee YG ( Department of Food Science & Technology and Functional Food Research Center, Chonnam National University, Gwangju 500-757, Republic of Korea.); Moon JH ( Department of Food Science & Technology and Functional Food Research Center, Chonnam National University, Gwangju 500-757, Republic of Korea. Electronic address: nutrmoon@jnu.ac.kr.) |
Abstract | Urushiols consist of an o-dihydroxybenzene (catechol) structure and an alkyl chain of 15 or 17 carbons in the 3-position of a benzene ring and are allergens found in the family Anacardiaceae. We synthesized various veratrole (1,2-dimethoxybenzene)-type and catechol-type urushiol derivatives that contained alkyl chains of various carbon atom lengths, including -H, -C1H3, -C5H11, -C10H21, -C15H31, and -C20H41, and investigated their contact hypersensitivities and antioxidative activities. 3-Decylcatechol and 3-pentadecylcatechol displayed contact hypersensitivity, but the other compounds did not induce an allergic reaction, when the ears of rats were sensitized by treatment with the compounds every day for 20 days. Catechol-type urushiol derivatives (CTUDs) exerted very high radical-scavenging activity on the 1,1-diphenyl-2-picrylhydrazyl radical and inhibited lipid peroxidation in a methyl linoleate solution induced by 2,2'-azobis(2,4-dimethylvaleronitrile) (AMVN). However, veratrole-type urushiol derivatives did not scavenge or inhibit lipid peroxidation. CTUDs also acted as effective inhibitors of lipid peroxidation of the egg yolk phosphatidylcholine large unilamellar vesicle (PC LUV) liposome system induced by various radical generators such as AMVN, 2,2'-azobis(2-amidino-propane) dihydrochloride, and copper ions, although their efficiencies differed slightly. In addition, CTUDs suppressed formation of cholesteryl ester hydroperoxides in rat blood plasma induced with copper ions. CTUDs containing more than five carbon atoms in the alkyl chain showed excellent lipophilicity in a n-octanol/water partition experiment. These compounds also exhibited high affinities to the liposome membrane using the ultrafiltration method of the PC LUV liposome system. Therefore, CTUDs seem to act as efficient antioxidative compounds against membranous lipid peroxidation owing to their localization in the phospholipid bilayer. These results suggest that nonallergenic CTUDs act as antioxidants to protect against oxidative damage of cellular and subcellular membranes. |
File Format | HTM / HTML |
ISSN | 08915849 |
Volume Number | 71 |
e-ISSN | 18734596 |
Journal | Free Radical Biology and Medicine |
Language | English |
Publisher | Elsevier |
Publisher Date | 2014-06-01 |
Publisher Place | United States |
Access Restriction | Subscribed |
Subject Keyword | Discipline Free radicals biology Anisoles Chemistry Catechols Free Radical Scavengers Unilamellar Liposomes Animals Pharmacology Azo Compounds Antagonists & Inhibitors Biphenyl Compounds Cholesterol Esters Copper Dermatitis, Contact Blood Immunology Ear, External Drug Effects Linoleic Acids Male Nitriles Oxidation-reduction Phosphatidylcholines Picrates Rats Rats, Sprague-dawley Structure-activity Relationship Journal Article Research Support, Non-u.s. Gov't |
Content Type | Text |
Resource Type | Article |
Subject Domain (in MeSH) | Sense Organs Eukaryota Skin and Connective Tissue Diseases Inorganic Chemicals Organic Chemicals Polycyclic Compounds Lipids Biomedical and Dental Materials Chemical Actions and Uses Chemical Phenomena |
Subject | Biochemistry Physiology (medical) |
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