Sulfoureido Lipopeptides from the Marine Sponge Discodermia kiiensis
New N-sulfoureidylated lipopeptides, sulfolipodiscamides A–C (1–3), were isolated by gel filtration chromatography of the n-butanol fraction of the marine sponge Discodermia kiiensis. By extensive NMR analyses and high-resolution mass spectrometry, the structures of 1–3 were elucidated as having an...
Gespeichert in:
| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2016-09, Vol.79 (9), p.2418-2422 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 2422 |
|---|---|
| container_issue | 9 |
| container_start_page | 2418 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 79 |
| creator | Tan, Karen Co Wakimoto, Toshiyuki Abe, Ikuro |
| description | New N-sulfoureidylated lipopeptides, sulfolipodiscamides A–C (1–3), were isolated by gel filtration chromatography of the n-butanol fraction of the marine sponge Discodermia kiiensis. By extensive NMR analyses and high-resolution mass spectrometry, the structures of 1–3 were elucidated as having an unprecedented N-sulfoureidyl group on the d-citrulline residue, a distinct feature that was not found in the structurally related lipodiscamides A–C (4–6), derived from the ether fraction of the same sponge. Furthermore, the absolute configurations of 1–3 were confirmed by comparisons of the HPLC retention times of the hydrolytic products and the corresponding authentic lipodiscamides. Interestingly, sulfolipodiscamide A displayed a 2.3-fold increase in cytotoxicity against murine leukemia (P388) cells, compared to the unconjugated parent compound. |
| doi_str_mv | 10.1021/acs.jnatprod.6b00586 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1823037514</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1823037514</sourcerecordid><originalsourceid>FETCH-LOGICAL-a348t-343bcfd28a7e862a9f7399de7d27a92b8205dfea6a2c3094beb4cdb117273bfa3</originalsourceid><addsrcrecordid>eNp9kDtPwzAUhS0EoqXwDxDKyJLiRxwnIypPqYihMFt2fA0uTRzsZODfY2jLyHSXc84950PonOA5wZRcqSbO150a-uDNvNQY86o8QFPCKc5LTPkhmmJSspxVZTFBJzGuMcYM1_wYTajgnNS4mqKb1bixfgzgjM-Wrvc99IMzEDMbfJsN75A9qeA6yFa9794gu3Gx8QZC61T24Rx00cVTdGTVJsLZ7s7Q693ty-IhXz7fPy6ul7liRTXkrGC6sYZWSkBVUlVbweragDBUqJrqimJuLKhS0SYVLTToojGaEEEF01axGbrc5qbNnyPEQbapDWw2qgM_RkkqyjATnBRJWmylTfAxBrCyD65V4UsSLH_4ycRP7vnJHb9ku9h9GHUL5s-0B5YEeCv4tSdwXRr8f-Y35jiAvQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1823037514</pqid></control><display><type>article</type><title>Sulfoureido Lipopeptides from the Marine Sponge Discodermia kiiensis</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Tan, Karen Co ; Wakimoto, Toshiyuki ; Abe, Ikuro</creator><creatorcontrib>Tan, Karen Co ; Wakimoto, Toshiyuki ; Abe, Ikuro</creatorcontrib><description>New N-sulfoureidylated lipopeptides, sulfolipodiscamides A–C (1–3), were isolated by gel filtration chromatography of the n-butanol fraction of the marine sponge Discodermia kiiensis. By extensive NMR analyses and high-resolution mass spectrometry, the structures of 1–3 were elucidated as having an unprecedented N-sulfoureidyl group on the d-citrulline residue, a distinct feature that was not found in the structurally related lipodiscamides A–C (4–6), derived from the ether fraction of the same sponge. Furthermore, the absolute configurations of 1–3 were confirmed by comparisons of the HPLC retention times of the hydrolytic products and the corresponding authentic lipodiscamides. Interestingly, sulfolipodiscamide A displayed a 2.3-fold increase in cytotoxicity against murine leukemia (P388) cells, compared to the unconjugated parent compound.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/acs.jnatprod.6b00586</identifier><identifier>PMID: 27551908</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Animals ; Drug Screening Assays, Antitumor ; Humans ; Leukemia P388 ; Lipopeptides - chemistry ; Lipopeptides - isolation & purification ; Lipopeptides - pharmacology ; Marine Biology ; Mice ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Porifera - chemistry</subject><ispartof>Journal of natural products (Washington, D.C.), 2016-09, Vol.79 (9), p.2418-2422</ispartof><rights>Copyright © 2016 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a348t-343bcfd28a7e862a9f7399de7d27a92b8205dfea6a2c3094beb4cdb117273bfa3</citedby><cites>FETCH-LOGICAL-a348t-343bcfd28a7e862a9f7399de7d27a92b8205dfea6a2c3094beb4cdb117273bfa3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.jnatprod.6b00586$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jnatprod.6b00586$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27551908$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tan, Karen Co</creatorcontrib><creatorcontrib>Wakimoto, Toshiyuki</creatorcontrib><creatorcontrib>Abe, Ikuro</creatorcontrib><title>Sulfoureido Lipopeptides from the Marine Sponge Discodermia kiiensis</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>New N-sulfoureidylated lipopeptides, sulfolipodiscamides A–C (1–3), were isolated by gel filtration chromatography of the n-butanol fraction of the marine sponge Discodermia kiiensis. By extensive NMR analyses and high-resolution mass spectrometry, the structures of 1–3 were elucidated as having an unprecedented N-sulfoureidyl group on the d-citrulline residue, a distinct feature that was not found in the structurally related lipodiscamides A–C (4–6), derived from the ether fraction of the same sponge. Furthermore, the absolute configurations of 1–3 were confirmed by comparisons of the HPLC retention times of the hydrolytic products and the corresponding authentic lipodiscamides. Interestingly, sulfolipodiscamide A displayed a 2.3-fold increase in cytotoxicity against murine leukemia (P388) cells, compared to the unconjugated parent compound.</description><subject>Animals</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Humans</subject><subject>Leukemia P388</subject><subject>Lipopeptides - chemistry</subject><subject>Lipopeptides - isolation & purification</subject><subject>Lipopeptides - pharmacology</subject><subject>Marine Biology</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Porifera - chemistry</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kDtPwzAUhS0EoqXwDxDKyJLiRxwnIypPqYihMFt2fA0uTRzsZODfY2jLyHSXc84950PonOA5wZRcqSbO150a-uDNvNQY86o8QFPCKc5LTPkhmmJSspxVZTFBJzGuMcYM1_wYTajgnNS4mqKb1bixfgzgjM-Wrvc99IMzEDMbfJsN75A9qeA6yFa9794gu3Gx8QZC61T24Rx00cVTdGTVJsLZ7s7Q693ty-IhXz7fPy6ul7liRTXkrGC6sYZWSkBVUlVbweragDBUqJrqimJuLKhS0SYVLTToojGaEEEF01axGbrc5qbNnyPEQbapDWw2qgM_RkkqyjATnBRJWmylTfAxBrCyD65V4UsSLH_4ycRP7vnJHb9ku9h9GHUL5s-0B5YEeCv4tSdwXRr8f-Y35jiAvQ</recordid><startdate>20160923</startdate><enddate>20160923</enddate><creator>Tan, Karen Co</creator><creator>Wakimoto, Toshiyuki</creator><creator>Abe, Ikuro</creator><general>American Chemical Society and American Society of Pharmacognosy</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>20160923</creationdate><title>Sulfoureido Lipopeptides from the Marine Sponge Discodermia kiiensis</title><author>Tan, Karen Co ; Wakimoto, Toshiyuki ; Abe, Ikuro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a348t-343bcfd28a7e862a9f7399de7d27a92b8205dfea6a2c3094beb4cdb117273bfa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Animals</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Humans</topic><topic>Leukemia P388</topic><topic>Lipopeptides - chemistry</topic><topic>Lipopeptides - isolation & purification</topic><topic>Lipopeptides - pharmacology</topic><topic>Marine Biology</topic><topic>Mice</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Porifera - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tan, Karen Co</creatorcontrib><creatorcontrib>Wakimoto, Toshiyuki</creatorcontrib><creatorcontrib>Abe, Ikuro</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>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tan, Karen Co</au><au>Wakimoto, Toshiyuki</au><au>Abe, Ikuro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sulfoureido Lipopeptides from the Marine Sponge Discodermia kiiensis</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2016-09-23</date><risdate>2016</risdate><volume>79</volume><issue>9</issue><spage>2418</spage><epage>2422</epage><pages>2418-2422</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>New N-sulfoureidylated lipopeptides, sulfolipodiscamides A–C (1–3), were isolated by gel filtration chromatography of the n-butanol fraction of the marine sponge Discodermia kiiensis. By extensive NMR analyses and high-resolution mass spectrometry, the structures of 1–3 were elucidated as having an unprecedented N-sulfoureidyl group on the d-citrulline residue, a distinct feature that was not found in the structurally related lipodiscamides A–C (4–6), derived from the ether fraction of the same sponge. Furthermore, the absolute configurations of 1–3 were confirmed by comparisons of the HPLC retention times of the hydrolytic products and the corresponding authentic lipodiscamides. Interestingly, sulfolipodiscamide A displayed a 2.3-fold increase in cytotoxicity against murine leukemia (P388) cells, compared to the unconjugated parent compound.</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>27551908</pmid><doi>10.1021/acs.jnatprod.6b00586</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2016-09, Vol.79 (9), p.2418-2422 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1823037514 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Animals Drug Screening Assays, Antitumor Humans Leukemia P388 Lipopeptides - chemistry Lipopeptides - isolation & purification Lipopeptides - pharmacology Marine Biology Mice Molecular Structure Nuclear Magnetic Resonance, Biomolecular Porifera - chemistry |
| title | Sulfoureido Lipopeptides from the Marine Sponge Discodermia kiiensis |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-25T21%3A22%3A51IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Sulfoureido%20Lipopeptides%20from%20the%20Marine%20Sponge%20Discodermia%20kiiensis&rft.jtitle=Journal%20of%20natural%20products%20(Washington,%20D.C.)&rft.au=Tan,%20Karen%20Co&rft.date=2016-09-23&rft.volume=79&rft.issue=9&rft.spage=2418&rft.epage=2422&rft.pages=2418-2422&rft.issn=0163-3864&rft.eissn=1520-6025&rft_id=info:doi/10.1021/acs.jnatprod.6b00586&rft_dat=%3Cproquest_cross%3E1823037514%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1823037514&rft_id=info:pmid/27551908&rfr_iscdi=true |