Characterization of Tamulamides A and B, Polyethers Isolated from the Marine Dinoflagellate Karenia brevis
Florida red tides occur as the result of blooms of the marine dinoflagellate Karenia brevis. K. brevis is known to produce several families of fused polyether ladder compounds. The most notable compounds are the brevetoxins, potent neurotoxins that activate mammalian sodium channels. Additional fuse...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2010-04, Vol.73 (4), p.536-540 |
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| description | Florida red tides occur as the result of blooms of the marine dinoflagellate Karenia brevis. K. brevis is known to produce several families of fused polyether ladder compounds. The most notable compounds are the brevetoxins, potent neurotoxins that activate mammalian sodium channels. Additional fused polyether ladder compounds produced by K. brevis include brevenal, brevisin, and hemibrevetoxin B, all with varying affinities for the same binding site on voltage-sensitive sodium channels. The structure elucidation and biological activity of two additional fused polyether ladder compounds containing seven fused ether rings will be described in this paper. Tamulamide A (MW = 638.30) and tamulamide B (MW = 624.29) were isolated from K. brevis cultures, and their structures elucidated using a combination of NMR spectroscopy and high-resolution mass spectrometry. Tamulamides A and B were both found to compete with tritiated brevetoxin-3 ([3H]-PbTx-3) for its binding site on rat brain synaptosomes. However, unlike the brevetoxins, tamulamides A and B showed no toxicity to fish at doses up to 200 nM and did not cause significant bronchoconstriction in sheep pulmonary assays. |
| doi_str_mv | 10.1021/np900541w |
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K. brevis is known to produce several families of fused polyether ladder compounds. The most notable compounds are the brevetoxins, potent neurotoxins that activate mammalian sodium channels. Additional fused polyether ladder compounds produced by K. brevis include brevenal, brevisin, and hemibrevetoxin B, all with varying affinities for the same binding site on voltage-sensitive sodium channels. The structure elucidation and biological activity of two additional fused polyether ladder compounds containing seven fused ether rings will be described in this paper. Tamulamide A (MW = 638.30) and tamulamide B (MW = 624.29) were isolated from K. brevis cultures, and their structures elucidated using a combination of NMR spectroscopy and high-resolution mass spectrometry. Tamulamides A and B were both found to compete with tritiated brevetoxin-3 ([3H]-PbTx-3) for its binding site on rat brain synaptosomes. However, unlike the brevetoxins, tamulamides A and B showed no toxicity to fish at doses up to 200 nM and did not cause significant bronchoconstriction in sheep pulmonary assays.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np900541w</identifier><identifier>PMID: 20218657</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Northbrook, IL: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Animals ; Biological and medical sciences ; Cyprinodontiformes ; Dinoflagellida - chemistry ; Ethers, Cyclic - chemistry ; Ethers, Cyclic - isolation & purification ; General pharmacology ; Karenia brevis ; Marine Biology ; Marine Toxins - chemistry ; Marine Toxins - isolation & purification ; Medical sciences ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Oxocins - chemistry ; Oxocins - isolation & purification ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Polycyclic Compounds - chemistry ; Polycyclic Compounds - isolation & purification ; Rats ; Sheep</subject><ispartof>Journal of natural products (Washington, D.C.), 2010-04, Vol.73 (4), p.536-540</ispartof><rights>Copyright © 2010 American Chemical Society and American Society of Pharmacognosy and American Society of Pharmacognosy</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a556t-d44c83df5fd3416e980df975546dc455d4c283c4355d6e3d2f2984691661d1393</citedby><cites>FETCH-LOGICAL-a556t-d44c83df5fd3416e980df975546dc455d4c283c4355d6e3d2f2984691661d1393</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/np900541w$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np900541w$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22702136$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20218657$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Truxal, Laura T</creatorcontrib><creatorcontrib>Bourdelais, Andrea J</creatorcontrib><creatorcontrib>Jacocks, Henry</creatorcontrib><creatorcontrib>Abraham, William M</creatorcontrib><creatorcontrib>Baden, Daniel G</creatorcontrib><title>Characterization of Tamulamides A and B, Polyethers Isolated from the Marine Dinoflagellate Karenia brevis</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Florida red tides occur as the result of blooms of the marine dinoflagellate Karenia brevis. K. brevis is known to produce several families of fused polyether ladder compounds. The most notable compounds are the brevetoxins, potent neurotoxins that activate mammalian sodium channels. Additional fused polyether ladder compounds produced by K. brevis include brevenal, brevisin, and hemibrevetoxin B, all with varying affinities for the same binding site on voltage-sensitive sodium channels. The structure elucidation and biological activity of two additional fused polyether ladder compounds containing seven fused ether rings will be described in this paper. Tamulamide A (MW = 638.30) and tamulamide B (MW = 624.29) were isolated from K. brevis cultures, and their structures elucidated using a combination of NMR spectroscopy and high-resolution mass spectrometry. Tamulamides A and B were both found to compete with tritiated brevetoxin-3 ([3H]-PbTx-3) for its binding site on rat brain synaptosomes. However, unlike the brevetoxins, tamulamides A and B showed no toxicity to fish at doses up to 200 nM and did not cause significant bronchoconstriction in sheep pulmonary assays.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Cyprinodontiformes</subject><subject>Dinoflagellida - chemistry</subject><subject>Ethers, Cyclic - chemistry</subject><subject>Ethers, Cyclic - isolation & purification</subject><subject>General pharmacology</subject><subject>Karenia brevis</subject><subject>Marine Biology</subject><subject>Marine Toxins - chemistry</subject><subject>Marine Toxins - isolation & purification</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Oxocins - chemistry</subject><subject>Oxocins - isolation & purification</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Polycyclic Compounds - chemistry</subject><subject>Polycyclic Compounds - isolation & purification</subject><subject>Rats</subject><subject>Sheep</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>eNpt0ctuEzEUBuARAtFQWPAC4A1CSAz4Pp4NUkm5VBSBRLu2Tn1JHM3YwZ60Kk-Po4QUJFa2fD7_vpymeUrwG4IpeRvXPcaCk5t7zYwIiluJqbjfzDCRrGVK8qPmUSkrjDHDvXjYHNG6S0nRzZrVfAkZzORy-AVTSBEljy5g3AwwBusKOkEQLXr_Gn1Pw62bli4XdFbSAJOzyOc0orqGvkIO0aHTEJMfYOGGbR19gexiAHSV3XUoj5sHHobinuzH4-by44eL-ef2_Nuns_nJeQtCyKm1nBvFrBfeMk6k6xW2vu-E4NIaLoTlhipmOKtT6ZilnvaKy55ISSxhPTtu3u1y15ur0Vnj4pRh0OscRsi3OkHQ_1ZiWOpFutZUKcIlrQEv9wE5_dy4MukxFLN9U3RpU3QnuOBMdbzKVztpciolO384hWC9bY0-tKbaZ39f6yD_9KKCF3sAxcDgM0QTyp2jXZVMVvd85zwkDYtczeUPignDRAmFO3mXBKboVdrkWP_7P1f6DSRcrEE</recordid><startdate>20100423</startdate><enddate>20100423</enddate><creator>Truxal, Laura T</creator><creator>Bourdelais, Andrea J</creator><creator>Jacocks, Henry</creator><creator>Abraham, William M</creator><creator>Baden, Daniel G</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>7TK</scope><scope>8FD</scope><scope>F1W</scope><scope>FR3</scope><scope>H98</scope><scope>H99</scope><scope>L.F</scope><scope>L.G</scope><scope>P64</scope><scope>5PM</scope></search><sort><creationdate>20100423</creationdate><title>Characterization of Tamulamides A and B, Polyethers Isolated from the Marine Dinoflagellate Karenia brevis</title><author>Truxal, Laura T ; Bourdelais, Andrea J ; Jacocks, Henry ; Abraham, William M ; Baden, Daniel G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a556t-d44c83df5fd3416e980df975546dc455d4c283c4355d6e3d2f2984691661d1393</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Cyprinodontiformes</topic><topic>Dinoflagellida - chemistry</topic><topic>Ethers, Cyclic - chemistry</topic><topic>Ethers, Cyclic - isolation & purification</topic><topic>General pharmacology</topic><topic>Karenia brevis</topic><topic>Marine Biology</topic><topic>Marine Toxins - chemistry</topic><topic>Marine Toxins - isolation & purification</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Oxocins - chemistry</topic><topic>Oxocins - isolation & purification</topic><topic>Pharmacognosy. 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Nat. Prod</addtitle><date>2010-04-23</date><risdate>2010</risdate><volume>73</volume><issue>4</issue><spage>536</spage><epage>540</epage><pages>536-540</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Florida red tides occur as the result of blooms of the marine dinoflagellate Karenia brevis. K. brevis is known to produce several families of fused polyether ladder compounds. The most notable compounds are the brevetoxins, potent neurotoxins that activate mammalian sodium channels. Additional fused polyether ladder compounds produced by K. brevis include brevenal, brevisin, and hemibrevetoxin B, all with varying affinities for the same binding site on voltage-sensitive sodium channels. The structure elucidation and biological activity of two additional fused polyether ladder compounds containing seven fused ether rings will be described in this paper. Tamulamide A (MW = 638.30) and tamulamide B (MW = 624.29) were isolated from K. brevis cultures, and their structures elucidated using a combination of NMR spectroscopy and high-resolution mass spectrometry. Tamulamides A and B were both found to compete with tritiated brevetoxin-3 ([3H]-PbTx-3) for its binding site on rat brain synaptosomes. However, unlike the brevetoxins, tamulamides A and B showed no toxicity to fish at doses up to 200 nM and did not cause significant bronchoconstriction in sheep pulmonary assays.</abstract><cop>Northbrook, IL</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>20218657</pmid><doi>10.1021/np900541w</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 2010-04, Vol.73 (4), p.536-540 |
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| source | MEDLINE; ACS Publications |
| subjects | Animals Biological and medical sciences Cyprinodontiformes Dinoflagellida - chemistry Ethers, Cyclic - chemistry Ethers, Cyclic - isolation & purification General pharmacology Karenia brevis Marine Biology Marine Toxins - chemistry Marine Toxins - isolation & purification Medical sciences Molecular Structure Nuclear Magnetic Resonance, Biomolecular Oxocins - chemistry Oxocins - isolation & purification Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Polycyclic Compounds - chemistry Polycyclic Compounds - isolation & purification Rats Sheep |
| title | Characterization of Tamulamides A and B, Polyethers Isolated from the Marine Dinoflagellate Karenia brevis |
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