Palmyramide A, a Cyclic Depsipeptide from a Palmyra Atoll Collection of the Marine Cyanobacterium Lyngbya majuscula
Bioassay-guided fractionation of the extract of a consortium of a marine cyanobacterium and a red alga (Rhodophyta) led to the discovery of a novel compound, palmyramide A, along with the known compounds curacin D and malyngamide C. The planar structure of palmyramide A was determined by one- and tw...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2010-03, Vol.73 (3), p.393-398 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Taniguchi, Masatoshi Nunnery, Joshawna K Engene, Niclas Esquenazi, Eduardo Byrum, Tara Dorrestein, Pieter C Gerwick, William H |
| description | Bioassay-guided fractionation of the extract of a consortium of a marine cyanobacterium and a red alga (Rhodophyta) led to the discovery of a novel compound, palmyramide A, along with the known compounds curacin D and malyngamide C. The planar structure of palmyramide A was determined by one- and two-dimensional NMR studies and mass spectrometry. Palmyramide A is a cyclic depsipeptide that features an unusual arrangement of three amino acids and three hydroxy acids; one of the hydroxy acids is the rare 2,2-dimethyl-3-hydroxyhexanoic acid unit (Dmhha). The absolute configurations of the six residues were determined by Marfey’s analysis, chiral HPLC analysis, and GC/MS analysis of the hydrolysate. Morphological and phylogenetic studies revealed the sample to be composed of a Lyngbya majuscula−Centroceras sp. association. MALDI-imaging analysis of the cultured L. majuscula indicated that it was the true producer of this new depsipeptide. Pure palmyramide A showed sodium channel blocking activity in neuro-2a cells and cytotoxic activity in H-460 human lung carcinoma cells. |
| doi_str_mv | 10.1021/np900428h |
| format | Article |
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The planar structure of palmyramide A was determined by one- and two-dimensional NMR studies and mass spectrometry. Palmyramide A is a cyclic depsipeptide that features an unusual arrangement of three amino acids and three hydroxy acids; one of the hydroxy acids is the rare 2,2-dimethyl-3-hydroxyhexanoic acid unit (Dmhha). The absolute configurations of the six residues were determined by Marfey’s analysis, chiral HPLC analysis, and GC/MS analysis of the hydrolysate. Morphological and phylogenetic studies revealed the sample to be composed of a Lyngbya majuscula−Centroceras sp. association. MALDI-imaging analysis of the cultured L. majuscula indicated that it was the true producer of this new depsipeptide. Pure palmyramide A showed sodium channel blocking activity in neuro-2a cells and cytotoxic activity in H-460 human lung carcinoma cells.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np900428h</identifier><identifier>PMID: 19839606</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Northbrook, IL: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents ; Applied microbiology ; Biological and medical sciences ; Chromatography, High Pressure Liquid ; Cyanobacteria ; Cyanobacteria - chemistry ; Depsipeptides - chemistry ; Depsipeptides - isolation & purification ; Drug Screening Assays, Antitumor ; Fundamental and applied biological sciences. 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Nat. Prod</addtitle><description>Bioassay-guided fractionation of the extract of a consortium of a marine cyanobacterium and a red alga (Rhodophyta) led to the discovery of a novel compound, palmyramide A, along with the known compounds curacin D and malyngamide C. The planar structure of palmyramide A was determined by one- and two-dimensional NMR studies and mass spectrometry. Palmyramide A is a cyclic depsipeptide that features an unusual arrangement of three amino acids and three hydroxy acids; one of the hydroxy acids is the rare 2,2-dimethyl-3-hydroxyhexanoic acid unit (Dmhha). The absolute configurations of the six residues were determined by Marfey’s analysis, chiral HPLC analysis, and GC/MS analysis of the hydrolysate. Morphological and phylogenetic studies revealed the sample to be composed of a Lyngbya majuscula−Centroceras sp. association. MALDI-imaging analysis of the cultured L. majuscula indicated that it was the true producer of this new depsipeptide. 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Psychology</subject><subject>Gas Chromatography-Mass Spectrometry</subject><subject>General aspects</subject><subject>Humans</subject><subject>Lyngbya</subject><subject>Lyngbya majuscula</subject><subject>Marine Biology</subject><subject>Microbiology</subject><subject>Rhodophyta</subject><subject>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</subject><subject>Stereoisomerism</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0V2L1DAUBuAiiju7euEf0NyICI7mu-2NMMz6BSMKutfhNB8zGdqmm7RC_71ZpswqCBJoLs7Dy0nfonhG8FuCKXnXDzXGnFaHB8WKCIrXElPxsFhhItmaVZJfFJcpHTHGDNficXFB6orVEstVkb5D280ROm8s2rxBgLazbr1G13ZIfrDDeDdwMXR5tFi0GUPbom3-WD360KPg0Hiw6CtE39ucAH1oQI82-qlDu7nfNzOgDo5T0lMLT4pHDtpkny73VXHz8cPP7ef17tunL9vNbg1ciHFdSlFxzJ1pnGZWYFoKU5vKMNMAt7pyknDGrCkl465qGsbKkkFZA26wMbxhV8X7U-4wNZ012vZjhFYN0XcQZxXAq78nvT-offilaCUpEzgHvFoCYridbBpV55O2bQu9DVNSpeD50Fr-XzJWEZYXzfL1SeoYUorWnfchWN21qc5tZvv8zwfcy6W-DF4uAJKG1kXotU9nR6ngdSnL7F6cnIOgYB-zuflBMWGYVPm31fw-CXRSxzDFPjfzj5V-Ax5Nvic</recordid><startdate>20100326</startdate><enddate>20100326</enddate><creator>Taniguchi, Masatoshi</creator><creator>Nunnery, Joshawna K</creator><creator>Engene, Niclas</creator><creator>Esquenazi, Eduardo</creator><creator>Byrum, Tara</creator><creator>Dorrestein, Pieter C</creator><creator>Gerwick, William H</creator><general>American Chemical Society and American Society of Pharmacognosy</general><general>American Society of Pharmacognosy</general><scope>FBQ</scope><scope>IQODW</scope><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>8FD</scope><scope>F1W</scope><scope>FR3</scope><scope>H95</scope><scope>H98</scope><scope>H99</scope><scope>L.F</scope><scope>L.G</scope><scope>M7N</scope><scope>P64</scope><scope>5PM</scope></search><sort><creationdate>20100326</creationdate><title>Palmyramide A, a Cyclic Depsipeptide from a Palmyra Atoll Collection of the Marine Cyanobacterium Lyngbya majuscula</title><author>Taniguchi, Masatoshi ; Nunnery, Joshawna K ; Engene, Niclas ; Esquenazi, Eduardo ; Byrum, Tara ; Dorrestein, Pieter C ; Gerwick, William H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a455t-7658404fdbfc3e50275d9d8d3dba4ec8f61433ed7634f8bb33773a79a0b0dd4b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents</topic><topic>Applied microbiology</topic><topic>Biological and medical sciences</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Cyanobacteria</topic><topic>Cyanobacteria - chemistry</topic><topic>Depsipeptides - chemistry</topic><topic>Depsipeptides - isolation & purification</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Gas Chromatography-Mass Spectrometry</topic><topic>General aspects</topic><topic>Humans</topic><topic>Lyngbya</topic><topic>Lyngbya majuscula</topic><topic>Marine Biology</topic><topic>Microbiology</topic><topic>Rhodophyta</topic><topic>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Taniguchi, Masatoshi</creatorcontrib><creatorcontrib>Nunnery, Joshawna K</creatorcontrib><creatorcontrib>Engene, Niclas</creatorcontrib><creatorcontrib>Esquenazi, Eduardo</creatorcontrib><creatorcontrib>Byrum, Tara</creatorcontrib><creatorcontrib>Dorrestein, Pieter C</creatorcontrib><creatorcontrib>Gerwick, William H</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><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>Technology Research Database</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Engineering Research Database</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 1: Biological Sciences & Living Resources</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Aquaculture Abstracts</collection><collection>ASFA: Marine Biotechnology Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Marine Biotechnology Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Taniguchi, Masatoshi</au><au>Nunnery, Joshawna K</au><au>Engene, Niclas</au><au>Esquenazi, Eduardo</au><au>Byrum, Tara</au><au>Dorrestein, Pieter C</au><au>Gerwick, William H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palmyramide A, a Cyclic Depsipeptide from a Palmyra Atoll Collection of the Marine Cyanobacterium Lyngbya majuscula</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2010-03-26</date><risdate>2010</risdate><volume>73</volume><issue>3</issue><spage>393</spage><epage>398</epage><pages>393-398</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Bioassay-guided fractionation of the extract of a consortium of a marine cyanobacterium and a red alga (Rhodophyta) led to the discovery of a novel compound, palmyramide A, along with the known compounds curacin D and malyngamide C. The planar structure of palmyramide A was determined by one- and two-dimensional NMR studies and mass spectrometry. Palmyramide A is a cyclic depsipeptide that features an unusual arrangement of three amino acids and three hydroxy acids; one of the hydroxy acids is the rare 2,2-dimethyl-3-hydroxyhexanoic acid unit (Dmhha). The absolute configurations of the six residues were determined by Marfey’s analysis, chiral HPLC analysis, and GC/MS analysis of the hydrolysate. Morphological and phylogenetic studies revealed the sample to be composed of a Lyngbya majuscula−Centroceras sp. association. MALDI-imaging analysis of the cultured L. majuscula indicated that it was the true producer of this new depsipeptide. Pure palmyramide A showed sodium channel blocking activity in neuro-2a cells and cytotoxic activity in H-460 human lung carcinoma cells.</abstract><cop>Northbrook, IL</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>19839606</pmid><doi>10.1021/np900428h</doi><tpages>6</tpages></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 2010-03, Vol.73 (3), p.393-398 |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents Applied microbiology Biological and medical sciences Chromatography, High Pressure Liquid Cyanobacteria Cyanobacteria - chemistry Depsipeptides - chemistry Depsipeptides - isolation & purification Drug Screening Assays, Antitumor Fundamental and applied biological sciences. Psychology Gas Chromatography-Mass Spectrometry General aspects Humans Lyngbya Lyngbya majuscula Marine Biology Microbiology Rhodophyta Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Stereoisomerism |
| title | Palmyramide A, a Cyclic Depsipeptide from a Palmyra Atoll Collection of the Marine Cyanobacterium Lyngbya majuscula |
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