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Suberitamides A-C, Aryl Alkaloids from a Pseudosuberites sp. Marine Sponge that Inhibit Cbl-b Ubiquitin Ligase Activity
Three new aryl alkaloids named suberitamides A-C ( - ), were isolated from an extract of the marine sponge sp. collected along the coast of North Carolina. Their planar structures were established by extensive nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis. To assign the challe...
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| Published in: | Marine drugs 2020-10, Vol.18 (11), p.536 |
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| Main Authors: | , , , , , , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c444t-780088c1f79a7f9bd59c8f226122bbcbc54d8b4e8668dd143e1ed5983fcb1ff23 |
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| container_issue | 11 |
| container_start_page | 536 |
| container_title | Marine drugs |
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| creator | Kim, Chang-Kwon Wang, Dongdong Wilson, Brice A P Saurí, Josep Voeller, Donna Lipkowitz, Stanley O'Keefe, Barry R Gustafson, Kirk R |
| description | Three new aryl alkaloids named suberitamides A-C (
-
), were isolated from an extract of the marine sponge
sp. collected along the coast of North Carolina. Their planar structures were established by extensive nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis. To assign the challenging relative configuration of the saturated five-membered ring in suberitamide A (
), a simple and efficient NMR protocol was applied that is based on the analysis of 2- and 3-bond
H-
C spin-spin coupling constants using a PIP (pure in-phase) HSQMBC (heteronuclear single quantum multiple bond correlation) IPAP (in-phase and anti-phase) experiment. Suberitamides A (
) and B (
) inhibited Cbl-b, an E3 ubiquitin ligase that is an important modulator of immune cell function, with IC
values of approximately 11 μM. |
| doi_str_mv | 10.3390/md18110536 |
| format | article |
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-
), were isolated from an extract of the marine sponge
sp. collected along the coast of North Carolina. Their planar structures were established by extensive nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis. To assign the challenging relative configuration of the saturated five-membered ring in suberitamide A (
), a simple and efficient NMR protocol was applied that is based on the analysis of 2- and 3-bond
H-
C spin-spin coupling constants using a PIP (pure in-phase) HSQMBC (heteronuclear single quantum multiple bond correlation) IPAP (in-phase and anti-phase) experiment. Suberitamides A (
) and B (
) inhibited Cbl-b, an E3 ubiquitin ligase that is an important modulator of immune cell function, with IC
values of approximately 11 μM.</description><identifier>ISSN: 1660-3397</identifier><identifier>EISSN: 1660-3397</identifier><identifier>DOI: 10.3390/md18110536</identifier><identifier>PMID: 33126420</identifier><language>eng</language><publisher>Switzerland: MDPI</publisher><subject>Alkaloids - isolation & purification ; Alkaloids - pharmacology ; Animals ; Cbl-b ubiquitin ligase inhibition ; Enzyme Inhibitors - isolation & purification ; Enzyme Inhibitors - pharmacology ; marine sponge ; Molecular Structure ; PIP HSQMBC IPAP ; Porifera - metabolism ; Proto-Oncogene Proteins c-cbl - antagonists & inhibitors ; Proto-Oncogene Proteins c-cbl - metabolism ; Pseudosuberites sp ; Structure-Activity Relationship ; suberitamides</subject><ispartof>Marine drugs, 2020-10, Vol.18 (11), p.536</ispartof><rights>2020 by the authors. 2020</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c444t-780088c1f79a7f9bd59c8f226122bbcbc54d8b4e8668dd143e1ed5983fcb1ff23</citedby><cites>FETCH-LOGICAL-c444t-780088c1f79a7f9bd59c8f226122bbcbc54d8b4e8668dd143e1ed5983fcb1ff23</cites><orcidid>0000-0001-8988-1964 ; 0000-0002-4637-3764 ; 0000-0002-7824-2507 ; 0000-0001-6821-4943 ; 0000-0003-0772-4856</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC7693676/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC7693676/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,27922,27923,37011,53789,53791</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33126420$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kim, Chang-Kwon</creatorcontrib><creatorcontrib>Wang, Dongdong</creatorcontrib><creatorcontrib>Wilson, Brice A P</creatorcontrib><creatorcontrib>Saurí, Josep</creatorcontrib><creatorcontrib>Voeller, Donna</creatorcontrib><creatorcontrib>Lipkowitz, Stanley</creatorcontrib><creatorcontrib>O'Keefe, Barry R</creatorcontrib><creatorcontrib>Gustafson, Kirk R</creatorcontrib><title>Suberitamides A-C, Aryl Alkaloids from a Pseudosuberites sp. Marine Sponge that Inhibit Cbl-b Ubiquitin Ligase Activity</title><title>Marine drugs</title><addtitle>Mar Drugs</addtitle><description>Three new aryl alkaloids named suberitamides A-C (
-
), were isolated from an extract of the marine sponge
sp. collected along the coast of North Carolina. Their planar structures were established by extensive nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis. To assign the challenging relative configuration of the saturated five-membered ring in suberitamide A (
), a simple and efficient NMR protocol was applied that is based on the analysis of 2- and 3-bond
H-
C spin-spin coupling constants using a PIP (pure in-phase) HSQMBC (heteronuclear single quantum multiple bond correlation) IPAP (in-phase and anti-phase) experiment. Suberitamides A (
) and B (
) inhibited Cbl-b, an E3 ubiquitin ligase that is an important modulator of immune cell function, with IC
values of approximately 11 μM.</description><subject>Alkaloids - isolation & purification</subject><subject>Alkaloids - pharmacology</subject><subject>Animals</subject><subject>Cbl-b ubiquitin ligase inhibition</subject><subject>Enzyme Inhibitors - isolation & purification</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>marine sponge</subject><subject>Molecular Structure</subject><subject>PIP HSQMBC IPAP</subject><subject>Porifera - metabolism</subject><subject>Proto-Oncogene Proteins c-cbl - antagonists & inhibitors</subject><subject>Proto-Oncogene Proteins c-cbl - metabolism</subject><subject>Pseudosuberites sp</subject><subject>Structure-Activity Relationship</subject><subject>suberitamides</subject><issn>1660-3397</issn><issn>1660-3397</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>DOA</sourceid><recordid>eNpVkV1rFDEUhoMotlZv_AGSSylOzddkkhthWPxYWFGovQ753E2dmWyTTGX_vaNba3t1Duc8POfAC8BrjC4olej96LDAGLWUPwGnmHPULOPu6YP-BLwo5Roh2grJnoMTSjHhjKBT8OtyNj7HqsfofIF9s3oH-3wYYD_81EOKrsCQ0wg1_F787FI54gta9hfwq85x8vByn6ath3WnK1xPu2hihSszNAZemXgzxxonuIlbXTzsbY23sR5egmdBD8W_uqtn4OrTxx-rL83m2-f1qt80ljFWm04gJITFoZO6C9K4VloRCOGYEGOssS1zwjAvOBfOYUY99gsjaLAGh0DoGVgfvS7pa7XPcdT5oJKO6u8g5a3SuUY7eEWDlhYj2XaUMmqlQC3xdNFTY7VB3eL6cHTtZzN6Z_1Usx4eSR9vprhT23SrOi4p7_gieHsnyOlm9qWqMRbrh0FPPs1FEdZyhinp8IKeH1GbUynZh_szGKk_qav_qS_wm4eP3aP_Yqa_AUdtqKI</recordid><startdate>20201028</startdate><enddate>20201028</enddate><creator>Kim, Chang-Kwon</creator><creator>Wang, Dongdong</creator><creator>Wilson, Brice A P</creator><creator>Saurí, Josep</creator><creator>Voeller, Donna</creator><creator>Lipkowitz, Stanley</creator><creator>O'Keefe, Barry R</creator><creator>Gustafson, Kirk R</creator><general>MDPI</general><general>MDPI AG</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><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0001-8988-1964</orcidid><orcidid>https://orcid.org/0000-0002-4637-3764</orcidid><orcidid>https://orcid.org/0000-0002-7824-2507</orcidid><orcidid>https://orcid.org/0000-0001-6821-4943</orcidid><orcidid>https://orcid.org/0000-0003-0772-4856</orcidid></search><sort><creationdate>20201028</creationdate><title>Suberitamides A-C, Aryl Alkaloids from a Pseudosuberites sp. Marine Sponge that Inhibit Cbl-b Ubiquitin Ligase Activity</title><author>Kim, Chang-Kwon ; Wang, Dongdong ; Wilson, Brice A P ; Saurí, Josep ; Voeller, Donna ; Lipkowitz, Stanley ; O'Keefe, Barry R ; Gustafson, Kirk R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c444t-780088c1f79a7f9bd59c8f226122bbcbc54d8b4e8668dd143e1ed5983fcb1ff23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkaloids - isolation & purification</topic><topic>Alkaloids - pharmacology</topic><topic>Animals</topic><topic>Cbl-b ubiquitin ligase inhibition</topic><topic>Enzyme Inhibitors - isolation & purification</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>marine sponge</topic><topic>Molecular Structure</topic><topic>PIP HSQMBC IPAP</topic><topic>Porifera - metabolism</topic><topic>Proto-Oncogene Proteins c-cbl - antagonists & inhibitors</topic><topic>Proto-Oncogene Proteins c-cbl - metabolism</topic><topic>Pseudosuberites sp</topic><topic>Structure-Activity Relationship</topic><topic>suberitamides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kim, Chang-Kwon</creatorcontrib><creatorcontrib>Wang, Dongdong</creatorcontrib><creatorcontrib>Wilson, Brice A P</creatorcontrib><creatorcontrib>Saurí, Josep</creatorcontrib><creatorcontrib>Voeller, Donna</creatorcontrib><creatorcontrib>Lipkowitz, Stanley</creatorcontrib><creatorcontrib>O'Keefe, Barry R</creatorcontrib><creatorcontrib>Gustafson, Kirk R</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><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Marine drugs</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kim, Chang-Kwon</au><au>Wang, Dongdong</au><au>Wilson, Brice A P</au><au>Saurí, Josep</au><au>Voeller, Donna</au><au>Lipkowitz, Stanley</au><au>O'Keefe, Barry R</au><au>Gustafson, Kirk R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Suberitamides A-C, Aryl Alkaloids from a Pseudosuberites sp. Marine Sponge that Inhibit Cbl-b Ubiquitin Ligase Activity</atitle><jtitle>Marine drugs</jtitle><addtitle>Mar Drugs</addtitle><date>2020-10-28</date><risdate>2020</risdate><volume>18</volume><issue>11</issue><spage>536</spage><pages>536-</pages><issn>1660-3397</issn><eissn>1660-3397</eissn><abstract>Three new aryl alkaloids named suberitamides A-C (
-
), were isolated from an extract of the marine sponge
sp. collected along the coast of North Carolina. Their planar structures were established by extensive nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis. To assign the challenging relative configuration of the saturated five-membered ring in suberitamide A (
), a simple and efficient NMR protocol was applied that is based on the analysis of 2- and 3-bond
H-
C spin-spin coupling constants using a PIP (pure in-phase) HSQMBC (heteronuclear single quantum multiple bond correlation) IPAP (in-phase and anti-phase) experiment. Suberitamides A (
) and B (
) inhibited Cbl-b, an E3 ubiquitin ligase that is an important modulator of immune cell function, with IC
values of approximately 11 μM.</abstract><cop>Switzerland</cop><pub>MDPI</pub><pmid>33126420</pmid><doi>10.3390/md18110536</doi><orcidid>https://orcid.org/0000-0001-8988-1964</orcidid><orcidid>https://orcid.org/0000-0002-4637-3764</orcidid><orcidid>https://orcid.org/0000-0002-7824-2507</orcidid><orcidid>https://orcid.org/0000-0001-6821-4943</orcidid><orcidid>https://orcid.org/0000-0003-0772-4856</orcidid><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 1660-3397 |
| ispartof | Marine drugs, 2020-10, Vol.18 (11), p.536 |
| issn | 1660-3397 1660-3397 |
| language | eng |
| recordid | cdi_doaj_primary_oai_doaj_org_article_3fa9c109573343c98052e3d8b3bcab07 |
| source | Publicly Available Content Database; PubMed Central |
| subjects | Alkaloids - isolation & purification Alkaloids - pharmacology Animals Cbl-b ubiquitin ligase inhibition Enzyme Inhibitors - isolation & purification Enzyme Inhibitors - pharmacology marine sponge Molecular Structure PIP HSQMBC IPAP Porifera - metabolism Proto-Oncogene Proteins c-cbl - antagonists & inhibitors Proto-Oncogene Proteins c-cbl - metabolism Pseudosuberites sp Structure-Activity Relationship suberitamides |
| title | Suberitamides A-C, Aryl Alkaloids from a Pseudosuberites sp. Marine Sponge that Inhibit Cbl-b Ubiquitin Ligase Activity |
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