Portobelamides A and B and Caciqueamide, Cytotoxic Peptidic Natural Products from a Caldora sp. Marine Cyanobacterium
Three new compounds, portobelamides A and B ( and ), 3-amino-2-methyl-7-octynoic acid (AMOYA) and hydroxyisovaleric acid (Hiva) containing cyclic depsipeptides, and one long chain lipopeptide caciqueamide ( ), were isolated from a field-collection of a sp. marine cyanobacterium obtained from Panama...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2021-08, Vol.84 (8), p.2081-2093 |
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| container_issue | 8 |
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| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 84 |
| creator | Demirkiran, Ozlem Almaliti, Jehad Leão, Tiago Navarro, Gabriel Byrum, Tara Valeriote, Frederick A Gerwick, Lena Gerwick, William H |
| description | Three new compounds, portobelamides A and B (
and
), 3-amino-2-methyl-7-octynoic acid (AMOYA) and hydroxyisovaleric acid (Hiva) containing cyclic depsipeptides, and one long chain lipopeptide caciqueamide (
), were isolated from a field-collection of a
sp. marine cyanobacterium obtained from Panama as part of the Panama International Cooperative Biodiversity Group Program. Their planar structures were elucidated through analysis of 2D NMR and MS data, especially high resolution (HR) MS
/MS
fragmentation methods. The absolute configurations of compounds
and
were deduced by traditional hydrolysis, derivative formation, and chromatographic analyses compared with standards. Portobelamide A (
) showed good cytotoxicity against H-460 human lung cancer cells (33% survival at 0.9 μM). |
| doi_str_mv | 10.1021/acs.jnatprod.0c01383 |
| format | Article |
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and
), 3-amino-2-methyl-7-octynoic acid (AMOYA) and hydroxyisovaleric acid (Hiva) containing cyclic depsipeptides, and one long chain lipopeptide caciqueamide (
), were isolated from a field-collection of a
sp. marine cyanobacterium obtained from Panama as part of the Panama International Cooperative Biodiversity Group Program. Their planar structures were elucidated through analysis of 2D NMR and MS data, especially high resolution (HR) MS
/MS
fragmentation methods. The absolute configurations of compounds
and
were deduced by traditional hydrolysis, derivative formation, and chromatographic analyses compared with standards. Portobelamide A (
) showed good cytotoxicity against H-460 human lung cancer cells (33% survival at 0.9 μM).</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/acs.jnatprod.0c01383</identifier><identifier>PMID: 34269583</identifier><language>eng</language><publisher>United States</publisher><subject>Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Aquatic Organisms - chemistry ; Biological Products - chemistry ; Biological Products - pharmacology ; Cell Line, Tumor ; Cyanobacteria - chemistry ; Depsipeptides - chemistry ; Depsipeptides - pharmacology ; Drug Screening Assays, Antitumor ; Humans ; Molecular Structure ; Panama</subject><ispartof>Journal of natural products (Washington, D.C.), 2021-08, Vol.84 (8), p.2081-2093</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c307t-b0a8e2aa6b2752f92562fbd136519cf092b1edc4865f628a819ad1336cc6d3873</citedby><cites>FETCH-LOGICAL-c307t-b0a8e2aa6b2752f92562fbd136519cf092b1edc4865f628a819ad1336cc6d3873</cites><orcidid>0000-0003-1034-9153 ; 0000-0001-6108-9000 ; 0000-0003-1403-4458</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,2751,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34269583$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Demirkiran, Ozlem</creatorcontrib><creatorcontrib>Almaliti, Jehad</creatorcontrib><creatorcontrib>Leão, Tiago</creatorcontrib><creatorcontrib>Navarro, Gabriel</creatorcontrib><creatorcontrib>Byrum, Tara</creatorcontrib><creatorcontrib>Valeriote, Frederick A</creatorcontrib><creatorcontrib>Gerwick, Lena</creatorcontrib><creatorcontrib>Gerwick, William H</creatorcontrib><title>Portobelamides A and B and Caciqueamide, Cytotoxic Peptidic Natural Products from a Caldora sp. Marine Cyanobacterium</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J Nat Prod</addtitle><description>Three new compounds, portobelamides A and B (
and
), 3-amino-2-methyl-7-octynoic acid (AMOYA) and hydroxyisovaleric acid (Hiva) containing cyclic depsipeptides, and one long chain lipopeptide caciqueamide (
), were isolated from a field-collection of a
sp. marine cyanobacterium obtained from Panama as part of the Panama International Cooperative Biodiversity Group Program. Their planar structures were elucidated through analysis of 2D NMR and MS data, especially high resolution (HR) MS
/MS
fragmentation methods. The absolute configurations of compounds
and
were deduced by traditional hydrolysis, derivative formation, and chromatographic analyses compared with standards. Portobelamide A (
) showed good cytotoxicity against H-460 human lung cancer cells (33% survival at 0.9 μM).</description><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Aquatic Organisms - chemistry</subject><subject>Biological Products - chemistry</subject><subject>Biological Products - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Cyanobacteria - chemistry</subject><subject>Depsipeptides - chemistry</subject><subject>Depsipeptides - pharmacology</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Humans</subject><subject>Molecular Structure</subject><subject>Panama</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kMlOwzAQhi0EoqXwBgj5yIEUL7HrHEvFJhXoAc7RxHakVElcbEeib4_pwmVmpH_-WT6ErimZUsLoPegwXfcQN96ZKdGEcsVP0JgKRjJJmDhFY0Ilz7iS-QhdhLAmhHBSiHM04jmThVB8jIaV89FVtoWuMTbgOYbe4IddXIBuvge7U-7wYhtddD-Nxiu7iY1JxTvEwUOLV-mEQceAa-86DMnYGucBh80Uv4Fvepvc0LsKdLS-GbpLdFZDG-zVIU_Q19Pj5-IlW348vy7my0xzMotZRUBZBiArNhOsLpiQrK4M5VLQQtekYBW1RudKiloyBYoWkFQutZaGqxmfoNv93AQpfRJi2TVB27aF3rohlEwIVhRc5TS15vtW7V0I3tblxjcd-G1JSfkHvEzAyyPw8gA82W4OG4aqs-bfdCTMfwEqCIBY</recordid><startdate>20210827</startdate><enddate>20210827</enddate><creator>Demirkiran, Ozlem</creator><creator>Almaliti, Jehad</creator><creator>Leão, Tiago</creator><creator>Navarro, Gabriel</creator><creator>Byrum, Tara</creator><creator>Valeriote, Frederick A</creator><creator>Gerwick, Lena</creator><creator>Gerwick, William H</creator><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><orcidid>https://orcid.org/0000-0003-1034-9153</orcidid><orcidid>https://orcid.org/0000-0001-6108-9000</orcidid><orcidid>https://orcid.org/0000-0003-1403-4458</orcidid></search><sort><creationdate>20210827</creationdate><title>Portobelamides A and B and Caciqueamide, Cytotoxic Peptidic Natural Products from a Caldora sp. Marine Cyanobacterium</title><author>Demirkiran, Ozlem ; Almaliti, Jehad ; Leão, Tiago ; Navarro, Gabriel ; Byrum, Tara ; Valeriote, Frederick A ; Gerwick, Lena ; Gerwick, William H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c307t-b0a8e2aa6b2752f92562fbd136519cf092b1edc4865f628a819ad1336cc6d3873</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Aquatic Organisms - chemistry</topic><topic>Biological Products - chemistry</topic><topic>Biological Products - pharmacology</topic><topic>Cell Line, Tumor</topic><topic>Cyanobacteria - chemistry</topic><topic>Depsipeptides - chemistry</topic><topic>Depsipeptides - pharmacology</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Humans</topic><topic>Molecular Structure</topic><topic>Panama</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Demirkiran, Ozlem</creatorcontrib><creatorcontrib>Almaliti, Jehad</creatorcontrib><creatorcontrib>Leão, Tiago</creatorcontrib><creatorcontrib>Navarro, Gabriel</creatorcontrib><creatorcontrib>Byrum, Tara</creatorcontrib><creatorcontrib>Valeriote, Frederick A</creatorcontrib><creatorcontrib>Gerwick, Lena</creatorcontrib><creatorcontrib>Gerwick, William H</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>Demirkiran, Ozlem</au><au>Almaliti, Jehad</au><au>Leão, Tiago</au><au>Navarro, Gabriel</au><au>Byrum, Tara</au><au>Valeriote, Frederick A</au><au>Gerwick, Lena</au><au>Gerwick, William H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Portobelamides A and B and Caciqueamide, Cytotoxic Peptidic Natural Products from a Caldora sp. Marine Cyanobacterium</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J Nat Prod</addtitle><date>2021-08-27</date><risdate>2021</risdate><volume>84</volume><issue>8</issue><spage>2081</spage><epage>2093</epage><pages>2081-2093</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>Three new compounds, portobelamides A and B (
and
), 3-amino-2-methyl-7-octynoic acid (AMOYA) and hydroxyisovaleric acid (Hiva) containing cyclic depsipeptides, and one long chain lipopeptide caciqueamide (
), were isolated from a field-collection of a
sp. marine cyanobacterium obtained from Panama as part of the Panama International Cooperative Biodiversity Group Program. Their planar structures were elucidated through analysis of 2D NMR and MS data, especially high resolution (HR) MS
/MS
fragmentation methods. The absolute configurations of compounds
and
were deduced by traditional hydrolysis, derivative formation, and chromatographic analyses compared with standards. Portobelamide A (
) showed good cytotoxicity against H-460 human lung cancer cells (33% survival at 0.9 μM).</abstract><cop>United States</cop><pmid>34269583</pmid><doi>10.1021/acs.jnatprod.0c01383</doi><tpages>13</tpages><orcidid>https://orcid.org/0000-0003-1034-9153</orcidid><orcidid>https://orcid.org/0000-0001-6108-9000</orcidid><orcidid>https://orcid.org/0000-0003-1403-4458</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2021-08, Vol.84 (8), p.2081-2093 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2552993841 |
| source | MEDLINE; ACS Publications |
| subjects | Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Aquatic Organisms - chemistry Biological Products - chemistry Biological Products - pharmacology Cell Line, Tumor Cyanobacteria - chemistry Depsipeptides - chemistry Depsipeptides - pharmacology Drug Screening Assays, Antitumor Humans Molecular Structure Panama |
| title | Portobelamides A and B and Caciqueamide, Cytotoxic Peptidic Natural Products from a Caldora sp. Marine Cyanobacterium |
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