Anthraquinones from the Seeds of Cassia tora with Inhibitory Activity on Protein Glycation and Aldose Reductase
Nine anthraquinones, aurantio-obtusin (1), chryso-obtusin (2), obtusin (3), chryso-obtusin-2-O-β-D-glucoside (4), physcion (5), emodin (6), chrysophanol (7), obtusifolin (8), and obtusifolin-2-O-β-D-glucoside (9), isolated from an EtOAc-soluble extract of the seeds of Cassia tora, were subjected to...
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| Veröffentlicht in: | Biological & pharmaceutical bulletin 2007/11/01, Vol.30(11), pp.2207-2210 |
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| creator | Jang, Dae Sik Lee, Ga Young Kim, Young Sook Lee, Yun Mi Kim, Chan-Sik Yoo, Jeong Lim Kim, Jin Sook |
| description | Nine anthraquinones, aurantio-obtusin (1), chryso-obtusin (2), obtusin (3), chryso-obtusin-2-O-β-D-glucoside (4), physcion (5), emodin (6), chrysophanol (7), obtusifolin (8), and obtusifolin-2-O-β-D-glucoside (9), isolated from an EtOAc-soluble extract of the seeds of Cassia tora, were subjected to in vitro bioassays to evaluate their inhibitory activity against advanced glycation end products (AGEs) formation and rat lens aldose reductase (RLAR). Among the isolates, compounds 6 and 8 exhibited a significant inhibitory activity on AGEs formation with observed IC50 values of 118 and 28.9 μM, respectively, in an AGEs-bovine serum albumin (BSA) assay by specific fluorescence. Furthermore, compounds 6 and 8 inhibited AGEs-BSA formation more effectively than aminoguanidine, an AGEs inhibitor, by indirect AGEs-ELISA. Nε-Carboxymethyllysine (CML)-BSA formation was also inhibited by compounds 6 and 8. Whereas compounds 1, 4, and 6 showed a significant inhibitory activity on RLAR with IC50 values of 13.6, 8.8, and 15.9 μM, respectively. |
| doi_str_mv | 10.1248/bpb.30.2207 |
| format | Article |
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Among the isolates, compounds 6 and 8 exhibited a significant inhibitory activity on AGEs formation with observed IC50 values of 118 and 28.9 μM, respectively, in an AGEs-bovine serum albumin (BSA) assay by specific fluorescence. Furthermore, compounds 6 and 8 inhibited AGEs-BSA formation more effectively than aminoguanidine, an AGEs inhibitor, by indirect AGEs-ELISA. Nε-Carboxymethyllysine (CML)-BSA formation was also inhibited by compounds 6 and 8. Whereas compounds 1, 4, and 6 showed a significant inhibitory activity on RLAR with IC50 values of 13.6, 8.8, and 15.9 μM, respectively.</description><identifier>ISSN: 0918-6158</identifier><identifier>EISSN: 1347-5215</identifier><identifier>DOI: 10.1248/bpb.30.2207</identifier><identifier>PMID: 17978503</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject><![CDATA[advanced glycation end product ; Aldehyde Reductase - analysis ; Aldehyde Reductase - antagonists & inhibitors ; aldose reductase ; Animals ; anthraquinone ; Anthraquinones - chemistry ; Anthraquinones - isolation & purification ; Anthraquinones - pharmacology ; Biological Assay ; Cassia - chemistry ; Cassia tora ; Cattle ; Dose-Response Relationship, Drug ; Enzyme-Linked Immunosorbent Assay ; Ethanol - chemistry ; Glycation End Products, Advanced - analysis ; Glycation End Products, Advanced - antagonists & inhibitors ; Glycation End Products, Advanced - biosynthesis ; Inhibitory Concentration 50 ; Leguminosae ; Lens, Crystalline - enzymology ; Lysine - analogs & derivatives ; Lysine - analysis ; Lysine - antagonists & inhibitors ; Lysine - biosynthesis ; Molecular Structure ; Plant Extracts - chemistry ; Rats ; Rats, Sprague-Dawley ; Seeds - chemistry ; Serum Albumin, Bovine - antagonists & inhibitors ; Solubility ; Solvents - chemistry ; Spectrometry, Fluorescence]]></subject><ispartof>Biological and Pharmaceutical Bulletin, 2007/11/01, Vol.30(11), pp.2207-2210</ispartof><rights>2007 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2007</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c501t-91fb4104ca5bb2702cc8a997623e816620d5cff29527e7fc25a94e683acf68cc3</citedby><cites>FETCH-LOGICAL-c501t-91fb4104ca5bb2702cc8a997623e816620d5cff29527e7fc25a94e683acf68cc3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17978503$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jang, Dae Sik</creatorcontrib><creatorcontrib>Lee, Ga Young</creatorcontrib><creatorcontrib>Kim, Young Sook</creatorcontrib><creatorcontrib>Lee, Yun Mi</creatorcontrib><creatorcontrib>Kim, Chan-Sik</creatorcontrib><creatorcontrib>Yoo, Jeong Lim</creatorcontrib><creatorcontrib>Kim, Jin Sook</creatorcontrib><title>Anthraquinones from the Seeds of Cassia tora with Inhibitory Activity on Protein Glycation and Aldose Reductase</title><title>Biological & pharmaceutical bulletin</title><addtitle>Biol Pharm Bull</addtitle><description>Nine anthraquinones, aurantio-obtusin (1), chryso-obtusin (2), obtusin (3), chryso-obtusin-2-O-β-D-glucoside (4), physcion (5), emodin (6), chrysophanol (7), obtusifolin (8), and obtusifolin-2-O-β-D-glucoside (9), isolated from an EtOAc-soluble extract of the seeds of Cassia tora, were subjected to in vitro bioassays to evaluate their inhibitory activity against advanced glycation end products (AGEs) formation and rat lens aldose reductase (RLAR). Among the isolates, compounds 6 and 8 exhibited a significant inhibitory activity on AGEs formation with observed IC50 values of 118 and 28.9 μM, respectively, in an AGEs-bovine serum albumin (BSA) assay by specific fluorescence. Furthermore, compounds 6 and 8 inhibited AGEs-BSA formation more effectively than aminoguanidine, an AGEs inhibitor, by indirect AGEs-ELISA. Nε-Carboxymethyllysine (CML)-BSA formation was also inhibited by compounds 6 and 8. Whereas compounds 1, 4, and 6 showed a significant inhibitory activity on RLAR with IC50 values of 13.6, 8.8, and 15.9 μM, respectively.</description><subject>advanced glycation end product</subject><subject>Aldehyde Reductase - analysis</subject><subject>Aldehyde Reductase - antagonists & inhibitors</subject><subject>aldose reductase</subject><subject>Animals</subject><subject>anthraquinone</subject><subject>Anthraquinones - chemistry</subject><subject>Anthraquinones - isolation & purification</subject><subject>Anthraquinones - pharmacology</subject><subject>Biological Assay</subject><subject>Cassia - chemistry</subject><subject>Cassia tora</subject><subject>Cattle</subject><subject>Dose-Response Relationship, Drug</subject><subject>Enzyme-Linked Immunosorbent Assay</subject><subject>Ethanol - chemistry</subject><subject>Glycation End Products, Advanced - analysis</subject><subject>Glycation End Products, Advanced - antagonists & inhibitors</subject><subject>Glycation End Products, Advanced - biosynthesis</subject><subject>Inhibitory Concentration 50</subject><subject>Leguminosae</subject><subject>Lens, Crystalline - enzymology</subject><subject>Lysine - analogs & derivatives</subject><subject>Lysine - analysis</subject><subject>Lysine - antagonists & inhibitors</subject><subject>Lysine - biosynthesis</subject><subject>Molecular Structure</subject><subject>Plant Extracts - chemistry</subject><subject>Rats</subject><subject>Rats, Sprague-Dawley</subject><subject>Seeds - chemistry</subject><subject>Serum Albumin, Bovine - antagonists & inhibitors</subject><subject>Solubility</subject><subject>Solvents - chemistry</subject><subject>Spectrometry, Fluorescence</subject><issn>0918-6158</issn><issn>1347-5215</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkE1rGzEQhkVpaJy0p96LoMewrj5Wu6ujaxLHYGjox1lotaOujC05kjZh_33W2EkuM4z08MzwIvSVkjllZfOjPbRzTuaMkfoDmlFe1oVgVHxEMyJpU1RUNJfoKqUtIaQmjH9Cl7SWdSMIn6Gw8LmP-nFwPnhI2Mawx7kH_AegSzhYvNQpOY1ziBo_u9zjte9d66Z5xAuT3ZPLIw4eP8SQwXm82o1GZze9aN_hxa4LCfBv6AaTdYLP6MLqXYIv536N_t3d_l3eF5tfq_VysSmMIDQXktq2pKQ0WrQtm642ptFS1hXj0NCqYqQTxlomBauhtoYJLUuoGq6NrRpj-DX6fvIeYngcIGW1DUP000pFy1LyildUTtTNiTIxpBTBqkN0ex1HRYk6hqumcBUn6hjuRH87O4d2D907e05zAn6egG3K-j-8ATpmZ3bwKqP0XI_Wt0_T66jA8xe4o40h</recordid><startdate>20071101</startdate><enddate>20071101</enddate><creator>Jang, Dae Sik</creator><creator>Lee, Ga Young</creator><creator>Kim, Young Sook</creator><creator>Lee, Yun Mi</creator><creator>Kim, Chan-Sik</creator><creator>Yoo, Jeong Lim</creator><creator>Kim, Jin Sook</creator><general>The 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>20071101</creationdate><title>Anthraquinones from the Seeds of Cassia tora with Inhibitory Activity on Protein Glycation and Aldose Reductase</title><author>Jang, Dae Sik ; Lee, Ga Young ; Kim, Young Sook ; Lee, Yun Mi ; Kim, Chan-Sik ; Yoo, Jeong Lim ; Kim, Jin Sook</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c501t-91fb4104ca5bb2702cc8a997623e816620d5cff29527e7fc25a94e683acf68cc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>advanced glycation end product</topic><topic>Aldehyde Reductase - analysis</topic><topic>Aldehyde Reductase - antagonists & inhibitors</topic><topic>aldose reductase</topic><topic>Animals</topic><topic>anthraquinone</topic><topic>Anthraquinones - chemistry</topic><topic>Anthraquinones - isolation & purification</topic><topic>Anthraquinones - pharmacology</topic><topic>Biological Assay</topic><topic>Cassia - chemistry</topic><topic>Cassia tora</topic><topic>Cattle</topic><topic>Dose-Response Relationship, Drug</topic><topic>Enzyme-Linked Immunosorbent Assay</topic><topic>Ethanol - chemistry</topic><topic>Glycation End Products, Advanced - analysis</topic><topic>Glycation End Products, Advanced - antagonists & inhibitors</topic><topic>Glycation End Products, Advanced - biosynthesis</topic><topic>Inhibitory Concentration 50</topic><topic>Leguminosae</topic><topic>Lens, Crystalline - enzymology</topic><topic>Lysine - analogs & derivatives</topic><topic>Lysine - analysis</topic><topic>Lysine - antagonists & inhibitors</topic><topic>Lysine - biosynthesis</topic><topic>Molecular Structure</topic><topic>Plant Extracts - chemistry</topic><topic>Rats</topic><topic>Rats, Sprague-Dawley</topic><topic>Seeds - chemistry</topic><topic>Serum Albumin, Bovine - antagonists & inhibitors</topic><topic>Solubility</topic><topic>Solvents - chemistry</topic><topic>Spectrometry, Fluorescence</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jang, Dae Sik</creatorcontrib><creatorcontrib>Lee, Ga Young</creatorcontrib><creatorcontrib>Kim, Young Sook</creatorcontrib><creatorcontrib>Lee, Yun Mi</creatorcontrib><creatorcontrib>Kim, Chan-Sik</creatorcontrib><creatorcontrib>Yoo, Jeong Lim</creatorcontrib><creatorcontrib>Kim, Jin Sook</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>Jang, Dae Sik</au><au>Lee, Ga Young</au><au>Kim, Young Sook</au><au>Lee, Yun Mi</au><au>Kim, Chan-Sik</au><au>Yoo, Jeong Lim</au><au>Kim, Jin Sook</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anthraquinones from the Seeds of Cassia tora with Inhibitory Activity on Protein Glycation and Aldose Reductase</atitle><jtitle>Biological & pharmaceutical bulletin</jtitle><addtitle>Biol Pharm Bull</addtitle><date>2007-11-01</date><risdate>2007</risdate><volume>30</volume><issue>11</issue><spage>2207</spage><epage>2210</epage><pages>2207-2210</pages><issn>0918-6158</issn><eissn>1347-5215</eissn><abstract>Nine anthraquinones, aurantio-obtusin (1), chryso-obtusin (2), obtusin (3), chryso-obtusin-2-O-β-D-glucoside (4), physcion (5), emodin (6), chrysophanol (7), obtusifolin (8), and obtusifolin-2-O-β-D-glucoside (9), isolated from an EtOAc-soluble extract of the seeds of Cassia tora, were subjected to in vitro bioassays to evaluate their inhibitory activity against advanced glycation end products (AGEs) formation and rat lens aldose reductase (RLAR). Among the isolates, compounds 6 and 8 exhibited a significant inhibitory activity on AGEs formation with observed IC50 values of 118 and 28.9 μM, respectively, in an AGEs-bovine serum albumin (BSA) assay by specific fluorescence. Furthermore, compounds 6 and 8 inhibited AGEs-BSA formation more effectively than aminoguanidine, an AGEs inhibitor, by indirect AGEs-ELISA. Nε-Carboxymethyllysine (CML)-BSA formation was also inhibited by compounds 6 and 8. Whereas compounds 1, 4, and 6 showed a significant inhibitory activity on RLAR with IC50 values of 13.6, 8.8, and 15.9 μM, respectively.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>17978503</pmid><doi>10.1248/bpb.30.2207</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | advanced glycation end product Aldehyde Reductase - analysis Aldehyde Reductase - antagonists & inhibitors aldose reductase Animals anthraquinone Anthraquinones - chemistry Anthraquinones - isolation & purification Anthraquinones - pharmacology Biological Assay Cassia - chemistry Cassia tora Cattle Dose-Response Relationship, Drug Enzyme-Linked Immunosorbent Assay Ethanol - chemistry Glycation End Products, Advanced - analysis Glycation End Products, Advanced - antagonists & inhibitors Glycation End Products, Advanced - biosynthesis Inhibitory Concentration 50 Leguminosae Lens, Crystalline - enzymology Lysine - analogs & derivatives Lysine - analysis Lysine - antagonists & inhibitors Lysine - biosynthesis Molecular Structure Plant Extracts - chemistry Rats Rats, Sprague-Dawley Seeds - chemistry Serum Albumin, Bovine - antagonists & inhibitors Solubility Solvents - chemistry Spectrometry, Fluorescence |
| title | Anthraquinones from the Seeds of Cassia tora with Inhibitory Activity on Protein Glycation and Aldose Reductase |
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