Inhibition of Aldose Reductase by Phenylethanoid Glycoside Isolated from the Seeds of Paulownia coreana
Aldose reductase (AR) inhibitors have considerable therapeutic potential against diabetic complications and do not increase the risk of hypoglycemia. Through bioassay-guided fractionation of the 70% acetone extract obtained from Paulownia coreana seeds, phenylpropanoid glycosides (compounds 1—4) and...
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| Veröffentlicht in: | Biological & Pharmaceutical Bulletin 2011/01/01, Vol.34(1), pp.160-163 |
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| creator | Kim, Jin Kyu Lee, Yeon Sil Kim, Seon Ha Bae, Young Soo Lim, Soon Sung |
| description | Aldose reductase (AR) inhibitors have considerable therapeutic potential against diabetic complications and do not increase the risk of hypoglycemia. Through bioassay-guided fractionation of the 70% acetone extract obtained from Paulownia coreana seeds, phenylpropanoid glycosides (compounds 1—4) and 5 phenolic coumpounds were isolated (compounds 5—9). Their structures were determined on the basis of spectroscopic analysis and comparison with reported data. All the isolates were subjected to in vitro bioassays to evaluate their inhibitory activities against recombinant human aldose reductase (rhAR) and sorbitol formation in human erythrocytes. Phenylethanoid glycosides showed more effective than the phenolic compounds in inhibiting rhAR. Among the compounds, isocampneoside II (3) was found to significantly inhibit rhAR with an IC50 value of 9.72 μM. In kinetic analyses performed using Lineweaver–Burk plots of 1/velocity and 1/concentration of substrate, isocampneoside II (3) showed uncompetitive inhibition against rhAR. Furthermore, it inhibited sorbitol formation in a rat lens incubated with a high concentration of glucose; this finding indicated that isocampneoside II (3) may effectively prevent osmotic stress in hyperglycemia. Thus, the P. coreana-derived phenylethanoid glycoside isocampneoside II (3) may have a potential therapeutics against diabetic complications. |
| doi_str_mv | 10.1248/bpb.34.160 |
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Through bioassay-guided fractionation of the 70% acetone extract obtained from Paulownia coreana seeds, phenylpropanoid glycosides (compounds 1—4) and 5 phenolic coumpounds were isolated (compounds 5—9). Their structures were determined on the basis of spectroscopic analysis and comparison with reported data. All the isolates were subjected to in vitro bioassays to evaluate their inhibitory activities against recombinant human aldose reductase (rhAR) and sorbitol formation in human erythrocytes. Phenylethanoid glycosides showed more effective than the phenolic compounds in inhibiting rhAR. Among the compounds, isocampneoside II (3) was found to significantly inhibit rhAR with an IC50 value of 9.72 μM. In kinetic analyses performed using Lineweaver–Burk plots of 1/velocity and 1/concentration of substrate, isocampneoside II (3) showed uncompetitive inhibition against rhAR. Furthermore, it inhibited sorbitol formation in a rat lens incubated with a high concentration of glucose; this finding indicated that isocampneoside II (3) may effectively prevent osmotic stress in hyperglycemia. Thus, the P. coreana-derived phenylethanoid glycoside isocampneoside II (3) may have a potential therapeutics against diabetic complications.</description><identifier>ISSN: 0918-6158</identifier><identifier>EISSN: 1347-5215</identifier><identifier>DOI: 10.1248/bpb.34.160</identifier><identifier>PMID: 21212537</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Aldehyde Reductase - antagonists & inhibitors ; aldose reductase ; Animals ; diabetic complication ; Erythrocytes - drug effects ; Erythrocytes - enzymology ; Glycosides - chemistry ; Glycosides - pharmacology ; Humans ; Kinetics ; Lens, Crystalline - drug effects ; Lens, Crystalline - metabolism ; Male ; Molecular Structure ; Paulownia coreana ; phenylpropanoid glycoside ; polyol pathway ; Rats ; Seeds - chemistry ; Sorbitol - metabolism</subject><ispartof>Biological and Pharmaceutical Bulletin, 2011/01/01, Vol.34(1), pp.160-163</ispartof><rights>2011 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2011</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c663t-a47a0b6bf356ace5586520e8106d2ecd40ab64d84eb5ae2d7849a974baddffdc3</citedby><cites>FETCH-LOGICAL-c663t-a47a0b6bf356ace5586520e8106d2ecd40ab64d84eb5ae2d7849a974baddffdc3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21212537$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kim, Jin Kyu</creatorcontrib><creatorcontrib>Lee, Yeon Sil</creatorcontrib><creatorcontrib>Kim, Seon Ha</creatorcontrib><creatorcontrib>Bae, Young Soo</creatorcontrib><creatorcontrib>Lim, Soon Sung</creatorcontrib><creatorcontrib>Hallym University</creatorcontrib><creatorcontrib>aInstitute of Natural Medicine</creatorcontrib><creatorcontrib>Kangwon National University</creatorcontrib><creatorcontrib>bCenter for Efficacy Assessment and Development of Functional Foods and Drugs</creatorcontrib><creatorcontrib>cDepartement of Forest Biomaterials Engineering</creatorcontrib><creatorcontrib>dDepartment of Food Science and Nutrition</creatorcontrib><title>Inhibition of Aldose Reductase by Phenylethanoid Glycoside Isolated from the Seeds of Paulownia coreana</title><title>Biological & Pharmaceutical Bulletin</title><addtitle>Biol Pharm Bull</addtitle><description>Aldose reductase (AR) inhibitors have considerable therapeutic potential against diabetic complications and do not increase the risk of hypoglycemia. Through bioassay-guided fractionation of the 70% acetone extract obtained from Paulownia coreana seeds, phenylpropanoid glycosides (compounds 1—4) and 5 phenolic coumpounds were isolated (compounds 5—9). Their structures were determined on the basis of spectroscopic analysis and comparison with reported data. All the isolates were subjected to in vitro bioassays to evaluate their inhibitory activities against recombinant human aldose reductase (rhAR) and sorbitol formation in human erythrocytes. Phenylethanoid glycosides showed more effective than the phenolic compounds in inhibiting rhAR. Among the compounds, isocampneoside II (3) was found to significantly inhibit rhAR with an IC50 value of 9.72 μM. In kinetic analyses performed using Lineweaver–Burk plots of 1/velocity and 1/concentration of substrate, isocampneoside II (3) showed uncompetitive inhibition against rhAR. Furthermore, it inhibited sorbitol formation in a rat lens incubated with a high concentration of glucose; this finding indicated that isocampneoside II (3) may effectively prevent osmotic stress in hyperglycemia. Thus, the P. coreana-derived phenylethanoid glycoside isocampneoside II (3) may have a potential therapeutics against diabetic complications.</description><subject>Aldehyde Reductase - antagonists & inhibitors</subject><subject>aldose reductase</subject><subject>Animals</subject><subject>diabetic complication</subject><subject>Erythrocytes - drug effects</subject><subject>Erythrocytes - enzymology</subject><subject>Glycosides - chemistry</subject><subject>Glycosides - pharmacology</subject><subject>Humans</subject><subject>Kinetics</subject><subject>Lens, Crystalline - drug effects</subject><subject>Lens, Crystalline - metabolism</subject><subject>Male</subject><subject>Molecular Structure</subject><subject>Paulownia coreana</subject><subject>phenylpropanoid glycoside</subject><subject>polyol pathway</subject><subject>Rats</subject><subject>Seeds - chemistry</subject><subject>Sorbitol - metabolism</subject><issn>0918-6158</issn><issn>1347-5215</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkFtr3DAQRk1paTZpX_oDiqEPhYK3ulm2n0oI7WYh0NDLsxhJ41iLVtpaNmH_fbU42UIRjARzdGb4iuIdJWvKRPtZH_SaizWV5EWxolw0Vc1o_bJYkY62laR1e1FcprQjhDSE8dfFBaP51LxZFQ_bMDjtJhdDGfvy2tuYsPyBdjYT5Jc-lvcDhqPHaYAQnS03_mhichbLbYoeJrRlP8Z9OQ1Y_kS06eS5h9nHx-CgNHFECPCmeNWDT_j26b4qfn_7-uvmtrr7vtneXN9VRko-VSAaIFrqntcSDNZ1K2tGsKVEWobGCgJaCtsK1DUgs00rOugaocHavreGXxUfF-9hjH9mTJPau2TQewgY56RaxjrCuZCZ_PAfuYvzGPJyigrR8aZlvM7Up4UyY0xpxF4dRreH8agoUaf0VU5fcaFy-hl-_6Sc9R7tGX2OOwObBchdZ8DH4F3Af4NNarSLPipGKFWEcEHyxTpFsv5UOOUd5y3Npi-LaZcmeMDzKBgnZzyet1rK6fdzxwwwKgz8LziJrbs</recordid><startdate>20110101</startdate><enddate>20110101</enddate><creator>Kim, Jin Kyu</creator><creator>Lee, Yeon Sil</creator><creator>Kim, Seon Ha</creator><creator>Bae, Young Soo</creator><creator>Lim, Soon Sung</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><scope>7X8</scope></search><sort><creationdate>20110101</creationdate><title>Inhibition of Aldose Reductase by Phenylethanoid Glycoside Isolated from the Seeds of Paulownia coreana</title><author>Kim, Jin Kyu ; Lee, Yeon Sil ; Kim, Seon Ha ; Bae, Young Soo ; Lim, Soon Sung</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c663t-a47a0b6bf356ace5586520e8106d2ecd40ab64d84eb5ae2d7849a974baddffdc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Aldehyde Reductase - antagonists & inhibitors</topic><topic>aldose reductase</topic><topic>Animals</topic><topic>diabetic complication</topic><topic>Erythrocytes - drug effects</topic><topic>Erythrocytes - enzymology</topic><topic>Glycosides - chemistry</topic><topic>Glycosides - pharmacology</topic><topic>Humans</topic><topic>Kinetics</topic><topic>Lens, Crystalline - drug effects</topic><topic>Lens, Crystalline - metabolism</topic><topic>Male</topic><topic>Molecular Structure</topic><topic>Paulownia coreana</topic><topic>phenylpropanoid glycoside</topic><topic>polyol pathway</topic><topic>Rats</topic><topic>Seeds - chemistry</topic><topic>Sorbitol - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kim, Jin Kyu</creatorcontrib><creatorcontrib>Lee, Yeon Sil</creatorcontrib><creatorcontrib>Kim, Seon Ha</creatorcontrib><creatorcontrib>Bae, Young Soo</creatorcontrib><creatorcontrib>Lim, Soon Sung</creatorcontrib><creatorcontrib>Hallym University</creatorcontrib><creatorcontrib>aInstitute of Natural Medicine</creatorcontrib><creatorcontrib>Kangwon National University</creatorcontrib><creatorcontrib>bCenter for Efficacy Assessment and Development of Functional Foods and Drugs</creatorcontrib><creatorcontrib>cDepartement of Forest Biomaterials Engineering</creatorcontrib><creatorcontrib>dDepartment of Food Science and Nutrition</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><collection>MEDLINE - Academic</collection><jtitle>Biological & Pharmaceutical Bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kim, Jin Kyu</au><au>Lee, Yeon Sil</au><au>Kim, Seon Ha</au><au>Bae, Young Soo</au><au>Lim, Soon Sung</au><aucorp>Hallym University</aucorp><aucorp>aInstitute of Natural Medicine</aucorp><aucorp>Kangwon National University</aucorp><aucorp>bCenter for Efficacy Assessment and Development of Functional Foods and Drugs</aucorp><aucorp>cDepartement of Forest Biomaterials Engineering</aucorp><aucorp>dDepartment of Food Science and Nutrition</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Inhibition of Aldose Reductase by Phenylethanoid Glycoside Isolated from the Seeds of Paulownia coreana</atitle><jtitle>Biological & Pharmaceutical Bulletin</jtitle><addtitle>Biol Pharm Bull</addtitle><date>2011-01-01</date><risdate>2011</risdate><volume>34</volume><issue>1</issue><spage>160</spage><epage>163</epage><pages>160-163</pages><issn>0918-6158</issn><eissn>1347-5215</eissn><abstract>Aldose reductase (AR) inhibitors have considerable therapeutic potential against diabetic complications and do not increase the risk of hypoglycemia. Through bioassay-guided fractionation of the 70% acetone extract obtained from Paulownia coreana seeds, phenylpropanoid glycosides (compounds 1—4) and 5 phenolic coumpounds were isolated (compounds 5—9). Their structures were determined on the basis of spectroscopic analysis and comparison with reported data. All the isolates were subjected to in vitro bioassays to evaluate their inhibitory activities against recombinant human aldose reductase (rhAR) and sorbitol formation in human erythrocytes. Phenylethanoid glycosides showed more effective than the phenolic compounds in inhibiting rhAR. Among the compounds, isocampneoside II (3) was found to significantly inhibit rhAR with an IC50 value of 9.72 μM. In kinetic analyses performed using Lineweaver–Burk plots of 1/velocity and 1/concentration of substrate, isocampneoside II (3) showed uncompetitive inhibition against rhAR. Furthermore, it inhibited sorbitol formation in a rat lens incubated with a high concentration of glucose; this finding indicated that isocampneoside II (3) may effectively prevent osmotic stress in hyperglycemia. Thus, the P. coreana-derived phenylethanoid glycoside isocampneoside II (3) may have a potential therapeutics against diabetic complications.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>21212537</pmid><doi>10.1248/bpb.34.160</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Aldehyde Reductase - antagonists & inhibitors aldose reductase Animals diabetic complication Erythrocytes - drug effects Erythrocytes - enzymology Glycosides - chemistry Glycosides - pharmacology Humans Kinetics Lens, Crystalline - drug effects Lens, Crystalline - metabolism Male Molecular Structure Paulownia coreana phenylpropanoid glycoside polyol pathway Rats Seeds - chemistry Sorbitol - metabolism |
| title | Inhibition of Aldose Reductase by Phenylethanoid Glycoside Isolated from the Seeds of Paulownia coreana |
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