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Antioxidant Effects of Quinoline Alkaloids and 2,4-Di-tert-butylphenol Isolated from Scolopendra subspinipes
The oxidized low-density lipoprotein (ox-LDL) plays a critical role at the early stages of atherosclerosis. Thus, the prevention of LDL-oxidation by antioxidants may arrest the progression of atherosclerosis. Two quinoline alkaloids, 3,8-dihydroxyquinoline (1) and 2,8-dihydroxy-3,4-dimethoxyquinolin...
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| Published in: | Biological & Pharmaceutical Bulletin 2006, Vol.29(4), pp.735-739 |
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| container_title | Biological & Pharmaceutical Bulletin |
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| creator | Yoon, Mi-Ae Jeong, Tae-Sook Park, Doo-Sang Xu, Ming-Zhe Oh, Hyun-Woo Song, Kyoung-Bin Lee, Woo Song Park, Ho-Yong |
| description | The oxidized low-density lipoprotein (ox-LDL) plays a critical role at the early stages of atherosclerosis. Thus, the prevention of LDL-oxidation by antioxidants may arrest the progression of atherosclerosis. Two quinoline alkaloids, 3,8-dihydroxyquinoline (1) and 2,8-dihydroxy-3,4-dimethoxyquinoline (3), and 2,4-di-tert-butylphenol (2) were isolated from the dried body of Scolopendra subspinipes. Compounds 1—3 exhibited antioxidant activities on copper-mediated (1: IC50=2.6 μM, 2: IC50=8.2 μM, 3: IC50=63.0 μM), AAPH-mediated oxidation (1: IC50=3.9 μM, 2: IC50=9.9 μM, 3: IC50=71.8 μM), and SIN-1-mediated oxidation (1: 70%, 2: 52%, 3: 29% at 5.0 μM) in the TBARS assay. The antioxidant activities of compounds 1—3 were tested with respect to other parameters, such as the lag time of conjugated diene fromation, relative electrophoretic mobility (REM) of ox-LDL, and apoB-100 fragmentation on copper-mediated LDL-oxidation. In addition, compounds 1—3 showed 1,1-diphenyl-2-picrylhydrasyl (DPPH) radical scavenging activity and compound 1 also exhibited metal chelating activity. |
| doi_str_mv | 10.1248/bpb.29.735 |
| format | article |
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Thus, the prevention of LDL-oxidation by antioxidants may arrest the progression of atherosclerosis. Two quinoline alkaloids, 3,8-dihydroxyquinoline (1) and 2,8-dihydroxy-3,4-dimethoxyquinoline (3), and 2,4-di-tert-butylphenol (2) were isolated from the dried body of Scolopendra subspinipes. Compounds 1—3 exhibited antioxidant activities on copper-mediated (1: IC50=2.6 μM, 2: IC50=8.2 μM, 3: IC50=63.0 μM), AAPH-mediated oxidation (1: IC50=3.9 μM, 2: IC50=9.9 μM, 3: IC50=71.8 μM), and SIN-1-mediated oxidation (1: 70%, 2: 52%, 3: 29% at 5.0 μM) in the TBARS assay. The antioxidant activities of compounds 1—3 were tested with respect to other parameters, such as the lag time of conjugated diene fromation, relative electrophoretic mobility (REM) of ox-LDL, and apoB-100 fragmentation on copper-mediated LDL-oxidation. In addition, compounds 1—3 showed 1,1-diphenyl-2-picrylhydrasyl (DPPH) radical scavenging activity and compound 1 also exhibited metal chelating activity.</description><identifier>ISSN: 0918-6158</identifier><identifier>EISSN: 1347-5215</identifier><identifier>DOI: 10.1248/bpb.29.735</identifier><identifier>PMID: 16595909</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>2,4-di-tert-butylphenol ; 3,8-dihydroxyquinoline ; Alkaloids - pharmacology ; Amidines - chemistry ; Animals ; antioxidant ; Antioxidants - pharmacology ; Apolipoprotein B-100 ; Apolipoproteins B - metabolism ; Arthropods - chemistry ; Biphenyl Compounds ; Chelating Agents - pharmacology ; Copper - chemistry ; Electrophoretic Mobility Shift Assay ; Free Radical Scavengers - pharmacology ; Lipoproteins, LDL - blood ; low-density lipoprotein (LDL) ; Molsidomine - analogs & derivatives ; Molsidomine - pharmacology ; Oxidation-Reduction ; Oxyquinoline - analogs & derivatives ; Oxyquinoline - chemistry ; Oxyquinoline - pharmacology ; Picrates - chemistry ; Quinolines - pharmacology ; Scolopendra subspinipes ; Spectrophotometry, Infrared ; Spectroscopy, Fourier Transform Infrared ; Thiobarbituric Acid Reactive Substances</subject><ispartof>Biological and Pharmaceutical Bulletin, 2006, Vol.29(4), pp.735-739</ispartof><rights>2006 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2006</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c684t-979f59af1dbf5dc54065eec8a69b799a1f4d5efefc7c6c14b7129788191d18f83</citedby><cites>FETCH-LOGICAL-c684t-979f59af1dbf5dc54065eec8a69b799a1f4d5efefc7c6c14b7129788191d18f83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16595909$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yoon, Mi-Ae</creatorcontrib><creatorcontrib>Jeong, Tae-Sook</creatorcontrib><creatorcontrib>Park, Doo-Sang</creatorcontrib><creatorcontrib>Xu, Ming-Zhe</creatorcontrib><creatorcontrib>Oh, Hyun-Woo</creatorcontrib><creatorcontrib>Song, Kyoung-Bin</creatorcontrib><creatorcontrib>Lee, Woo Song</creatorcontrib><creatorcontrib>Park, Ho-Yong</creatorcontrib><creatorcontrib>aInsect Resources Laboratory</creatorcontrib><creatorcontrib>Korea Research Institute of Bioscience and Biotechnology</creatorcontrib><creatorcontrib>cDepartment of Food Science & Technology</creatorcontrib><creatorcontrib>Chungnam National University</creatorcontrib><creatorcontrib>bNational Research Laboratory of Lipid Metabolism & Atherosclerosis</creatorcontrib><title>Antioxidant Effects of Quinoline Alkaloids and 2,4-Di-tert-butylphenol Isolated from Scolopendra subspinipes</title><title>Biological & Pharmaceutical Bulletin</title><addtitle>Biol Pharm Bull</addtitle><description>The oxidized low-density lipoprotein (ox-LDL) plays a critical role at the early stages of atherosclerosis. Thus, the prevention of LDL-oxidation by antioxidants may arrest the progression of atherosclerosis. Two quinoline alkaloids, 3,8-dihydroxyquinoline (1) and 2,8-dihydroxy-3,4-dimethoxyquinoline (3), and 2,4-di-tert-butylphenol (2) were isolated from the dried body of Scolopendra subspinipes. Compounds 1—3 exhibited antioxidant activities on copper-mediated (1: IC50=2.6 μM, 2: IC50=8.2 μM, 3: IC50=63.0 μM), AAPH-mediated oxidation (1: IC50=3.9 μM, 2: IC50=9.9 μM, 3: IC50=71.8 μM), and SIN-1-mediated oxidation (1: 70%, 2: 52%, 3: 29% at 5.0 μM) in the TBARS assay. The antioxidant activities of compounds 1—3 were tested with respect to other parameters, such as the lag time of conjugated diene fromation, relative electrophoretic mobility (REM) of ox-LDL, and apoB-100 fragmentation on copper-mediated LDL-oxidation. In addition, compounds 1—3 showed 1,1-diphenyl-2-picrylhydrasyl (DPPH) radical scavenging activity and compound 1 also exhibited metal chelating activity.</description><subject>2,4-di-tert-butylphenol</subject><subject>3,8-dihydroxyquinoline</subject><subject>Alkaloids - pharmacology</subject><subject>Amidines - chemistry</subject><subject>Animals</subject><subject>antioxidant</subject><subject>Antioxidants - pharmacology</subject><subject>Apolipoprotein B-100</subject><subject>Apolipoproteins B - metabolism</subject><subject>Arthropods - chemistry</subject><subject>Biphenyl Compounds</subject><subject>Chelating Agents - pharmacology</subject><subject>Copper - chemistry</subject><subject>Electrophoretic Mobility Shift Assay</subject><subject>Free Radical Scavengers - pharmacology</subject><subject>Lipoproteins, LDL - blood</subject><subject>low-density lipoprotein (LDL)</subject><subject>Molsidomine - analogs & derivatives</subject><subject>Molsidomine - pharmacology</subject><subject>Oxidation-Reduction</subject><subject>Oxyquinoline - analogs & derivatives</subject><subject>Oxyquinoline - chemistry</subject><subject>Oxyquinoline - pharmacology</subject><subject>Picrates - chemistry</subject><subject>Quinolines - pharmacology</subject><subject>Scolopendra subspinipes</subject><subject>Spectrophotometry, Infrared</subject><subject>Spectroscopy, Fourier Transform Infrared</subject><subject>Thiobarbituric Acid Reactive Substances</subject><issn>0918-6158</issn><issn>1347-5215</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNpFkF1vFCEUhonR2G31xh9gSLwzzgoMMHBlNrWtTZoYo14Thg_LOgsjMIn997KZrb3gcHEe3nN4AHiD0RYTKj6O87glcjv07BnY4J4OHSOYPQcbJLHoOGbiDJyXskcIDYj0L8EZ5kwyieQGTLtYQ_obrI4VXnnvTC0wefhtCTFNITq4m37rKQVboI4Wkg-0-xy66nLtxqU-TPO9ayC8LWnS1VnoczrA7yZNaXbRZg3LMpY5xDC78gq88Hoq7vXpvgA_r69-XH7p7r7e3F7u7jrDBa2dHKRnUntsR8-sYRRx5pwRmstxkFJjTy1z3nkzGG4wHQdM5CAElthi4UV_Ad6tuXNOfxZXqtqnJcc2UmFKZc8Ep6xR71fK5FRKdl7NORx0flAYqaNY1cQqIlUT2-C3p8hlPDj7hJ5MNuB6BVo3mGYsHu09DTZlGEOzoghCXCFEJKIKkXZa_LG0XzMueAv6tAbtS9W_3P9JOtdgJve4FF3L8fFjx9zrrFzs_wGIYaH5</recordid><startdate>20060401</startdate><enddate>20060401</enddate><creator>Yoon, Mi-Ae</creator><creator>Jeong, Tae-Sook</creator><creator>Park, Doo-Sang</creator><creator>Xu, Ming-Zhe</creator><creator>Oh, Hyun-Woo</creator><creator>Song, Kyoung-Bin</creator><creator>Lee, Woo Song</creator><creator>Park, Ho-Yong</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QP</scope><scope>7QR</scope><scope>7TK</scope><scope>7U9</scope><scope>8FD</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope></search><sort><creationdate>20060401</creationdate><title>Antioxidant Effects of Quinoline Alkaloids and 2,4-Di-tert-butylphenol Isolated from Scolopendra subspinipes</title><author>Yoon, Mi-Ae ; Jeong, Tae-Sook ; Park, Doo-Sang ; Xu, Ming-Zhe ; Oh, Hyun-Woo ; Song, Kyoung-Bin ; Lee, Woo Song ; Park, Ho-Yong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c684t-979f59af1dbf5dc54065eec8a69b799a1f4d5efefc7c6c14b7129788191d18f83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>2,4-di-tert-butylphenol</topic><topic>3,8-dihydroxyquinoline</topic><topic>Alkaloids - pharmacology</topic><topic>Amidines - chemistry</topic><topic>Animals</topic><topic>antioxidant</topic><topic>Antioxidants - pharmacology</topic><topic>Apolipoprotein B-100</topic><topic>Apolipoproteins B - metabolism</topic><topic>Arthropods - chemistry</topic><topic>Biphenyl Compounds</topic><topic>Chelating Agents - pharmacology</topic><topic>Copper - chemistry</topic><topic>Electrophoretic Mobility Shift Assay</topic><topic>Free Radical Scavengers - pharmacology</topic><topic>Lipoproteins, LDL - blood</topic><topic>low-density lipoprotein (LDL)</topic><topic>Molsidomine - analogs & derivatives</topic><topic>Molsidomine - pharmacology</topic><topic>Oxidation-Reduction</topic><topic>Oxyquinoline - analogs & derivatives</topic><topic>Oxyquinoline - chemistry</topic><topic>Oxyquinoline - pharmacology</topic><topic>Picrates - chemistry</topic><topic>Quinolines - pharmacology</topic><topic>Scolopendra subspinipes</topic><topic>Spectrophotometry, Infrared</topic><topic>Spectroscopy, Fourier Transform Infrared</topic><topic>Thiobarbituric Acid Reactive Substances</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yoon, Mi-Ae</creatorcontrib><creatorcontrib>Jeong, Tae-Sook</creatorcontrib><creatorcontrib>Park, Doo-Sang</creatorcontrib><creatorcontrib>Xu, Ming-Zhe</creatorcontrib><creatorcontrib>Oh, Hyun-Woo</creatorcontrib><creatorcontrib>Song, Kyoung-Bin</creatorcontrib><creatorcontrib>Lee, Woo Song</creatorcontrib><creatorcontrib>Park, Ho-Yong</creatorcontrib><creatorcontrib>aInsect Resources Laboratory</creatorcontrib><creatorcontrib>Korea Research Institute of Bioscience and Biotechnology</creatorcontrib><creatorcontrib>cDepartment of Food Science & Technology</creatorcontrib><creatorcontrib>Chungnam National University</creatorcontrib><creatorcontrib>bNational Research Laboratory of Lipid Metabolism & Atherosclerosis</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Biological & Pharmaceutical Bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yoon, Mi-Ae</au><au>Jeong, Tae-Sook</au><au>Park, Doo-Sang</au><au>Xu, Ming-Zhe</au><au>Oh, Hyun-Woo</au><au>Song, Kyoung-Bin</au><au>Lee, Woo Song</au><au>Park, Ho-Yong</au><aucorp>aInsect Resources Laboratory</aucorp><aucorp>Korea Research Institute of Bioscience and Biotechnology</aucorp><aucorp>cDepartment of Food Science & Technology</aucorp><aucorp>Chungnam National University</aucorp><aucorp>bNational Research Laboratory of Lipid Metabolism & Atherosclerosis</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antioxidant Effects of Quinoline Alkaloids and 2,4-Di-tert-butylphenol Isolated from Scolopendra subspinipes</atitle><jtitle>Biological & Pharmaceutical Bulletin</jtitle><addtitle>Biol Pharm Bull</addtitle><date>2006-04-01</date><risdate>2006</risdate><volume>29</volume><issue>4</issue><spage>735</spage><epage>739</epage><pages>735-739</pages><issn>0918-6158</issn><eissn>1347-5215</eissn><abstract>The oxidized low-density lipoprotein (ox-LDL) plays a critical role at the early stages of atherosclerosis. Thus, the prevention of LDL-oxidation by antioxidants may arrest the progression of atherosclerosis. Two quinoline alkaloids, 3,8-dihydroxyquinoline (1) and 2,8-dihydroxy-3,4-dimethoxyquinoline (3), and 2,4-di-tert-butylphenol (2) were isolated from the dried body of Scolopendra subspinipes. Compounds 1—3 exhibited antioxidant activities on copper-mediated (1: IC50=2.6 μM, 2: IC50=8.2 μM, 3: IC50=63.0 μM), AAPH-mediated oxidation (1: IC50=3.9 μM, 2: IC50=9.9 μM, 3: IC50=71.8 μM), and SIN-1-mediated oxidation (1: 70%, 2: 52%, 3: 29% at 5.0 μM) in the TBARS assay. The antioxidant activities of compounds 1—3 were tested with respect to other parameters, such as the lag time of conjugated diene fromation, relative electrophoretic mobility (REM) of ox-LDL, and apoB-100 fragmentation on copper-mediated LDL-oxidation. In addition, compounds 1—3 showed 1,1-diphenyl-2-picrylhydrasyl (DPPH) radical scavenging activity and compound 1 also exhibited metal chelating activity.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>16595909</pmid><doi>10.1248/bpb.29.735</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Biological and Pharmaceutical Bulletin, 2006, Vol.29(4), pp.735-739 |
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| subjects | 2,4-di-tert-butylphenol 3,8-dihydroxyquinoline Alkaloids - pharmacology Amidines - chemistry Animals antioxidant Antioxidants - pharmacology Apolipoprotein B-100 Apolipoproteins B - metabolism Arthropods - chemistry Biphenyl Compounds Chelating Agents - pharmacology Copper - chemistry Electrophoretic Mobility Shift Assay Free Radical Scavengers - pharmacology Lipoproteins, LDL - blood low-density lipoprotein (LDL) Molsidomine - analogs & derivatives Molsidomine - pharmacology Oxidation-Reduction Oxyquinoline - analogs & derivatives Oxyquinoline - chemistry Oxyquinoline - pharmacology Picrates - chemistry Quinolines - pharmacology Scolopendra subspinipes Spectrophotometry, Infrared Spectroscopy, Fourier Transform Infrared Thiobarbituric Acid Reactive Substances |
| title | Antioxidant Effects of Quinoline Alkaloids and 2,4-Di-tert-butylphenol Isolated from Scolopendra subspinipes |
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