Isoorientin, a Selective Inhibitor of Cyclooxygenase-2 (COX-2) from the Tubers of Pueraria tuberosa
Bioassay-guided fraction of the methanol extract of the roots of Pueraria tuberose DC yielded puerarin, an isoflavone C-glycoside (PT-1), isoorientin, a flavone C-glycoside (PT-2) and mangiferin, a xanthone C-glycoside (PT-3). The extracts and the isolated compounds were screened for potent antiinfl...
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| Veröffentlicht in: | Natural product communications 2015-10, Vol.10 (10), p.1703-1704 |
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| creator | Sumalatha, Manne Munikishore, Rachakunta Rammohan, Aluru Gunasekar, Duvvuru Kumar, Kotha Anil Reddy, Kakularam Kumar Azad, Rajaram Reddanna, Pallu Bodo, Bernard |
| description | Bioassay-guided fraction of the methanol extract of the roots of Pueraria tuberose DC yielded puerarin, an isoflavone C-glycoside (PT-1), isoorientin, a flavone C-glycoside (PT-2) and mangiferin, a xanthone C-glycoside (PT-3). The extracts and the isolated compounds were screened for potent antiinflammatory components inhibiting the cyclooxygenases (COX-1 and COX-2) and 5-lipoxygenase (5-LOX), the target enzymes of inflammation, by employing spectroscopic/polorographic methods. Among these, isoorientin was found to be a potent inhibitorof COX-2with an IC50 value of 39 μM. Docking studies were carried out to understand the interactions of isorientin (PT-2) with COX-2. The structures of the isolates were determined by mass spectrometry and 2D-NMR techniques including HSQC, HMBC, NOESY and 1H-1H COSY experiments. Although isoorientin and mangiferin have been reported from several plant sources, this is the first report of their isolation from a Pueraria species. |
| doi_str_mv | 10.1177/1934578X1501001017 |
| format | Article |
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The extracts and the isolated compounds were screened for potent antiinflammatory components inhibiting the cyclooxygenases (COX-1 and COX-2) and 5-lipoxygenase (5-LOX), the target enzymes of inflammation, by employing spectroscopic/polorographic methods. Among these, isoorientin was found to be a potent inhibitorof COX-2with an IC50 value of 39 μM. Docking studies were carried out to understand the interactions of isorientin (PT-2) with COX-2. The structures of the isolates were determined by mass spectrometry and 2D-NMR techniques including HSQC, HMBC, NOESY and 1H-1H COSY experiments. Although isoorientin and mangiferin have been reported from several plant sources, this is the first report of their isolation from a Pueraria species.</description><identifier>ISSN: 1934-578X</identifier><identifier>EISSN: 1555-9475</identifier><identifier>DOI: 10.1177/1934578X1501001017</identifier><identifier>PMID: 26669106</identifier><language>eng</language><publisher>Los Angeles, CA: SAGE Publications</publisher><subject>Cyclooxygenase 2 - metabolism ; Cyclooxygenase 2 Inhibitors - chemistry ; Cyclooxygenase 2 Inhibitors - pharmacology ; Humans ; Luteolin - chemistry ; Luteolin - pharmacology ; Models, Molecular ; Molecular Structure ; Plant Tubers - chemistry ; Pueraria - chemistry ; Recombinant Proteins</subject><ispartof>Natural product communications, 2015-10, Vol.10 (10), p.1703-1704</ispartof><rights>2015 SAGE Publications Inc.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c436t-dca59668954334a6768d46b64a7e6ab5c1ab7fd9d3bb8c75f439f51906c6a2083</citedby><cites>FETCH-LOGICAL-c436t-dca59668954334a6768d46b64a7e6ab5c1ab7fd9d3bb8c75f439f51906c6a2083</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://journals.sagepub.com/doi/pdf/10.1177/1934578X1501001017$$EPDF$$P50$$Gsage$$H</linktopdf><linktohtml>$$Uhttps://journals.sagepub.com/doi/10.1177/1934578X1501001017$$EHTML$$P50$$Gsage$$H</linktohtml><link.rule.ids>314,777,781,21947,27834,27905,27906,44926,45314</link.rule.ids><linktorsrc>$$Uhttps://journals.sagepub.com/doi/full/10.1177/1934578X1501001017?utm_source=summon&utm_medium=discovery-provider$$EView_record_in_SAGE_Publications$$FView_record_in_$$GSAGE_Publications</linktorsrc><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26669106$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sumalatha, Manne</creatorcontrib><creatorcontrib>Munikishore, Rachakunta</creatorcontrib><creatorcontrib>Rammohan, Aluru</creatorcontrib><creatorcontrib>Gunasekar, Duvvuru</creatorcontrib><creatorcontrib>Kumar, Kotha Anil</creatorcontrib><creatorcontrib>Reddy, Kakularam Kumar</creatorcontrib><creatorcontrib>Azad, Rajaram</creatorcontrib><creatorcontrib>Reddanna, Pallu</creatorcontrib><creatorcontrib>Bodo, Bernard</creatorcontrib><title>Isoorientin, a Selective Inhibitor of Cyclooxygenase-2 (COX-2) from the Tubers of Pueraria tuberosa</title><title>Natural product communications</title><addtitle>Nat Prod Commun</addtitle><description>Bioassay-guided fraction of the methanol extract of the roots of Pueraria tuberose DC yielded puerarin, an isoflavone C-glycoside (PT-1), isoorientin, a flavone C-glycoside (PT-2) and mangiferin, a xanthone C-glycoside (PT-3). The extracts and the isolated compounds were screened for potent antiinflammatory components inhibiting the cyclooxygenases (COX-1 and COX-2) and 5-lipoxygenase (5-LOX), the target enzymes of inflammation, by employing spectroscopic/polorographic methods. Among these, isoorientin was found to be a potent inhibitorof COX-2with an IC50 value of 39 μM. Docking studies were carried out to understand the interactions of isorientin (PT-2) with COX-2. The structures of the isolates were determined by mass spectrometry and 2D-NMR techniques including HSQC, HMBC, NOESY and 1H-1H COSY experiments. Although isoorientin and mangiferin have been reported from several plant sources, this is the first report of their isolation from a Pueraria species.</description><subject>Cyclooxygenase 2 - metabolism</subject><subject>Cyclooxygenase 2 Inhibitors - chemistry</subject><subject>Cyclooxygenase 2 Inhibitors - pharmacology</subject><subject>Humans</subject><subject>Luteolin - chemistry</subject><subject>Luteolin - pharmacology</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Plant Tubers - chemistry</subject><subject>Pueraria - chemistry</subject><subject>Recombinant Proteins</subject><issn>1934-578X</issn><issn>1555-9475</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1Lw0AQhhdRrNT-AQ-yRwVjd5P9yB6l-FEoKFiht7DZTNqUJKu7idh_74ZWL4LDwAzDMy8zL0IXlNxSKuWUqoRxma4oJ5SEpPIInVHOeaSY5MehD0A0ECM08X5LQqQpI0ydolEshFCUiDNk5t5aV0HbVe0N1vgVajBd9Ql43m6qvOqsw7bEs52prf3araHVHqIYX82eV1F8jUtnG9xtAC_7HJwf2JcenHaVxt0wsl6fo5NS1x4mhzpGbw_3y9lTtHh-nM_uFpFhieiiwmiuhEgVZ0nCtJAiLZjIBdMShM65oTqXZaGKJM9TI3nJElVyqogwQsckTcboaq_77uxHD77LmsobqGvdgu19RiUPTiVUDWi8R0040Dsos3dXNdrtMkqywd_sr79h6fKg3-cNFL8rP24GYLoHvF5DtrW9a8O__0l-A3I4gbU</recordid><startdate>201510</startdate><enddate>201510</enddate><creator>Sumalatha, Manne</creator><creator>Munikishore, Rachakunta</creator><creator>Rammohan, Aluru</creator><creator>Gunasekar, Duvvuru</creator><creator>Kumar, Kotha Anil</creator><creator>Reddy, Kakularam Kumar</creator><creator>Azad, Rajaram</creator><creator>Reddanna, Pallu</creator><creator>Bodo, Bernard</creator><general>SAGE Publications</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>7X8</scope></search><sort><creationdate>201510</creationdate><title>Isoorientin, a Selective Inhibitor of Cyclooxygenase-2 (COX-2) from the Tubers of Pueraria tuberosa</title><author>Sumalatha, Manne ; Munikishore, Rachakunta ; Rammohan, Aluru ; Gunasekar, Duvvuru ; Kumar, Kotha Anil ; Reddy, Kakularam Kumar ; Azad, Rajaram ; Reddanna, Pallu ; Bodo, Bernard</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c436t-dca59668954334a6768d46b64a7e6ab5c1ab7fd9d3bb8c75f439f51906c6a2083</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Cyclooxygenase 2 - metabolism</topic><topic>Cyclooxygenase 2 Inhibitors - chemistry</topic><topic>Cyclooxygenase 2 Inhibitors - pharmacology</topic><topic>Humans</topic><topic>Luteolin - chemistry</topic><topic>Luteolin - pharmacology</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Plant Tubers - chemistry</topic><topic>Pueraria - chemistry</topic><topic>Recombinant Proteins</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sumalatha, Manne</creatorcontrib><creatorcontrib>Munikishore, Rachakunta</creatorcontrib><creatorcontrib>Rammohan, Aluru</creatorcontrib><creatorcontrib>Gunasekar, Duvvuru</creatorcontrib><creatorcontrib>Kumar, Kotha Anil</creatorcontrib><creatorcontrib>Reddy, Kakularam Kumar</creatorcontrib><creatorcontrib>Azad, Rajaram</creatorcontrib><creatorcontrib>Reddanna, Pallu</creatorcontrib><creatorcontrib>Bodo, Bernard</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Natural product communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>Sumalatha, Manne</au><au>Munikishore, Rachakunta</au><au>Rammohan, Aluru</au><au>Gunasekar, Duvvuru</au><au>Kumar, Kotha Anil</au><au>Reddy, Kakularam Kumar</au><au>Azad, Rajaram</au><au>Reddanna, Pallu</au><au>Bodo, Bernard</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isoorientin, a Selective Inhibitor of Cyclooxygenase-2 (COX-2) from the Tubers of Pueraria tuberosa</atitle><jtitle>Natural product communications</jtitle><addtitle>Nat Prod Commun</addtitle><date>2015-10</date><risdate>2015</risdate><volume>10</volume><issue>10</issue><spage>1703</spage><epage>1704</epage><pages>1703-1704</pages><issn>1934-578X</issn><eissn>1555-9475</eissn><abstract>Bioassay-guided fraction of the methanol extract of the roots of Pueraria tuberose DC yielded puerarin, an isoflavone C-glycoside (PT-1), isoorientin, a flavone C-glycoside (PT-2) and mangiferin, a xanthone C-glycoside (PT-3). The extracts and the isolated compounds were screened for potent antiinflammatory components inhibiting the cyclooxygenases (COX-1 and COX-2) and 5-lipoxygenase (5-LOX), the target enzymes of inflammation, by employing spectroscopic/polorographic methods. Among these, isoorientin was found to be a potent inhibitorof COX-2with an IC50 value of 39 μM. Docking studies were carried out to understand the interactions of isorientin (PT-2) with COX-2. The structures of the isolates were determined by mass spectrometry and 2D-NMR techniques including HSQC, HMBC, NOESY and 1H-1H COSY experiments. Although isoorientin and mangiferin have been reported from several plant sources, this is the first report of their isolation from a Pueraria species.</abstract><cop>Los Angeles, CA</cop><pub>SAGE Publications</pub><pmid>26669106</pmid><doi>10.1177/1934578X1501001017</doi><tpages>2</tpages><oa>free_for_read</oa></addata></record> |
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| source | Sage Journals GOLD Open Access 2024 |
| subjects | Cyclooxygenase 2 - metabolism Cyclooxygenase 2 Inhibitors - chemistry Cyclooxygenase 2 Inhibitors - pharmacology Humans Luteolin - chemistry Luteolin - pharmacology Models, Molecular Molecular Structure Plant Tubers - chemistry Pueraria - chemistry Recombinant Proteins |
| title | Isoorientin, a Selective Inhibitor of Cyclooxygenase-2 (COX-2) from the Tubers of Pueraria tuberosa |
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