Isolation of Yessotoxin 32- O-[β- l-arabinofuranosyl-(5′→1″)-β- l-arabinofuranoside] from Protoceratium reticulatum
Yessotoxin 32- O-[β- l-arabinofuranosyl-(5′→1″)-β- l-arabinofuranoside] ( 3) was isolated from extracts of Protoceratium reticulatum during a large scale isolation of yessotoxin ( 1). The structure was characterized by mass spectrometry and NMR spectroscopy. Di-glycoside- 3, along with the correspon...
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| Veröffentlicht in: | Toxicon (Oxford) 2006-04, Vol.47 (5), p.510-516 |
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| container_title | Toxicon (Oxford) |
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| creator | Miles, Christopher O. Wilkins, Alistair L. Selwood, Andrew I. Hawkes, Allan D. Jensen, Dwayne J. Cooney, Janine M. Beuzenberg, Veronica MacKenzie, A. Lincoln |
| description | Yessotoxin 32-
O-[β-
l-arabinofuranosyl-(5′→1″)-β-
l-arabinofuranoside] (
3) was isolated from extracts of
Protoceratium reticulatum during a large scale isolation of yessotoxin (
1). The structure was characterized by mass spectrometry and NMR spectroscopy. Di-glycoside-
3, along with the corresponding mono-glycoside (
2) were detected in cultures of
P. reticulatum originating from Europe and New Zealand, suggesting that production of arabinosides of
1 is a normal feature of this alga. Formation of multiply charged anions and fragmentation of
3 occurred much more readily than for
1 and
2 under the LC-MS conditions used in this study. |
| doi_str_mv | 10.1016/j.toxicon.2005.12.013 |
| format | Article |
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O-[β-
l-arabinofuranosyl-(5′→1″)-β-
l-arabinofuranoside] (
3) was isolated from extracts of
Protoceratium reticulatum during a large scale isolation of yessotoxin (
1). The structure was characterized by mass spectrometry and NMR spectroscopy. Di-glycoside-
3, along with the corresponding mono-glycoside (
2) were detected in cultures of
P. reticulatum originating from Europe and New Zealand, suggesting that production of arabinosides of
1 is a normal feature of this alga. Formation of multiply charged anions and fragmentation of
3 occurred much more readily than for
1 and
2 under the LC-MS conditions used in this study.</description><identifier>ISSN: 0041-0101</identifier><identifier>EISSN: 1879-3150</identifier><identifier>DOI: 10.1016/j.toxicon.2005.12.013</identifier><identifier>PMID: 16530240</identifier><identifier>CODEN: TOXIA6</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Animals ; Arabinoside ; Biological and medical sciences ; Medical sciences ; Models, Molecular ; Molecular Structure ; Mollusk Venoms - chemistry ; Mollusk Venoms - isolation & purification ; Oxocins - chemistry ; Oxocins - isolation & purification ; Plant poisons toxicology ; Protoceratium reticulatum ; Toxicology ; Yessotoxin</subject><ispartof>Toxicon (Oxford), 2006-04, Vol.47 (5), p.510-516</ispartof><rights>2006 Elsevier Ltd</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c490t-bf89f805519babebd89ef3b18791e45009a6089c357392d30d3d5350758b78713</citedby><cites>FETCH-LOGICAL-c490t-bf89f805519babebd89ef3b18791e45009a6089c357392d30d3d5350758b78713</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.toxicon.2005.12.013$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17696114$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16530240$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Miles, Christopher O.</creatorcontrib><creatorcontrib>Wilkins, Alistair L.</creatorcontrib><creatorcontrib>Selwood, Andrew I.</creatorcontrib><creatorcontrib>Hawkes, Allan D.</creatorcontrib><creatorcontrib>Jensen, Dwayne J.</creatorcontrib><creatorcontrib>Cooney, Janine M.</creatorcontrib><creatorcontrib>Beuzenberg, Veronica</creatorcontrib><creatorcontrib>MacKenzie, A. Lincoln</creatorcontrib><title>Isolation of Yessotoxin 32- O-[β- l-arabinofuranosyl-(5′→1″)-β- l-arabinofuranoside] from Protoceratium reticulatum</title><title>Toxicon (Oxford)</title><addtitle>Toxicon</addtitle><description>Yessotoxin 32-
O-[β-
l-arabinofuranosyl-(5′→1″)-β-
l-arabinofuranoside] (
3) was isolated from extracts of
Protoceratium reticulatum during a large scale isolation of yessotoxin (
1). The structure was characterized by mass spectrometry and NMR spectroscopy. Di-glycoside-
3, along with the corresponding mono-glycoside (
2) were detected in cultures of
P. reticulatum originating from Europe and New Zealand, suggesting that production of arabinosides of
1 is a normal feature of this alga. Formation of multiply charged anions and fragmentation of
3 occurred much more readily than for
1 and
2 under the LC-MS conditions used in this study.</description><subject>Animals</subject><subject>Arabinoside</subject><subject>Biological and medical sciences</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Mollusk Venoms - chemistry</subject><subject>Mollusk Venoms - isolation & purification</subject><subject>Oxocins - chemistry</subject><subject>Oxocins - isolation & purification</subject><subject>Plant poisons toxicology</subject><subject>Protoceratium reticulatum</subject><subject>Toxicology</subject><subject>Yessotoxin</subject><issn>0041-0101</issn><issn>1879-3150</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM-K1TAUxoMoznX0EZRuFF2kntM0bbMaZPDPwMC40IWIhDQ9hVzaZkxacXAzKx_ARxnfw4e4T2IutzAbwVU2v-_7Tn6MPUbIEbB6uc1n_91ZP-UFgMyxyAHFHbbBplZcoIS7bANQIoeEH7EHMW4BQDSqus-OsJICihI27MdZ9IOZnZ8y32efKEa_750yUfDsgn_-c8OzgZtgWjf5fglm8vFq4M_l7vpm9_MX7q5_v-D_glxHX7I--DF7H1KlpZBWljELNDu7pMllfMju9WaI9Gh9j9nHN68_nL7j5xdvz05fnXNbKph52zeqb0BKVK1pqe0aRb1o9x9FKiWAMhU0ygpZC1V0AjrRSSGhlk1bNzWKY_bs0HsZ_NeF4qxHFy0Ng5nIL1GjKlSZogmUB9AGH2OgXl8GN5pwpRH03rre6tW63lvXWOhkPeWerANLO1J3m1o1J-DpCphozdAnQ9bFW66uVIVYJu7kwFHS8c1R0NE6mix1LpCddefdf075C9hAp0s</recordid><startdate>20060401</startdate><enddate>20060401</enddate><creator>Miles, Christopher O.</creator><creator>Wilkins, Alistair L.</creator><creator>Selwood, Andrew I.</creator><creator>Hawkes, Allan D.</creator><creator>Jensen, Dwayne J.</creator><creator>Cooney, Janine M.</creator><creator>Beuzenberg, Veronica</creator><creator>MacKenzie, A. Lincoln</creator><general>Elsevier Ltd</general><general>Elsevier Science</general><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>7U7</scope><scope>C1K</scope><scope>M7N</scope></search><sort><creationdate>20060401</creationdate><title>Isolation of Yessotoxin 32- O-[β- l-arabinofuranosyl-(5′→1″)-β- l-arabinofuranoside] from Protoceratium reticulatum</title><author>Miles, Christopher O. ; Wilkins, Alistair L. ; Selwood, Andrew I. ; Hawkes, Allan D. ; Jensen, Dwayne J. ; Cooney, Janine M. ; Beuzenberg, Veronica ; MacKenzie, A. Lincoln</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c490t-bf89f805519babebd89ef3b18791e45009a6089c357392d30d3d5350758b78713</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Animals</topic><topic>Arabinoside</topic><topic>Biological and medical sciences</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Mollusk Venoms - chemistry</topic><topic>Mollusk Venoms - isolation & purification</topic><topic>Oxocins - chemistry</topic><topic>Oxocins - isolation & purification</topic><topic>Plant poisons toxicology</topic><topic>Protoceratium reticulatum</topic><topic>Toxicology</topic><topic>Yessotoxin</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Miles, Christopher O.</creatorcontrib><creatorcontrib>Wilkins, Alistair L.</creatorcontrib><creatorcontrib>Selwood, Andrew I.</creatorcontrib><creatorcontrib>Hawkes, Allan D.</creatorcontrib><creatorcontrib>Jensen, Dwayne J.</creatorcontrib><creatorcontrib>Cooney, Janine M.</creatorcontrib><creatorcontrib>Beuzenberg, Veronica</creatorcontrib><creatorcontrib>MacKenzie, A. Lincoln</creatorcontrib><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>Toxicology Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><jtitle>Toxicon (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Miles, Christopher O.</au><au>Wilkins, Alistair L.</au><au>Selwood, Andrew I.</au><au>Hawkes, Allan D.</au><au>Jensen, Dwayne J.</au><au>Cooney, Janine M.</au><au>Beuzenberg, Veronica</au><au>MacKenzie, A. Lincoln</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isolation of Yessotoxin 32- O-[β- l-arabinofuranosyl-(5′→1″)-β- l-arabinofuranoside] from Protoceratium reticulatum</atitle><jtitle>Toxicon (Oxford)</jtitle><addtitle>Toxicon</addtitle><date>2006-04-01</date><risdate>2006</risdate><volume>47</volume><issue>5</issue><spage>510</spage><epage>516</epage><pages>510-516</pages><issn>0041-0101</issn><eissn>1879-3150</eissn><coden>TOXIA6</coden><abstract>Yessotoxin 32-
O-[β-
l-arabinofuranosyl-(5′→1″)-β-
l-arabinofuranoside] (
3) was isolated from extracts of
Protoceratium reticulatum during a large scale isolation of yessotoxin (
1). The structure was characterized by mass spectrometry and NMR spectroscopy. Di-glycoside-
3, along with the corresponding mono-glycoside (
2) were detected in cultures of
P. reticulatum originating from Europe and New Zealand, suggesting that production of arabinosides of
1 is a normal feature of this alga. Formation of multiply charged anions and fragmentation of
3 occurred much more readily than for
1 and
2 under the LC-MS conditions used in this study.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>16530240</pmid><doi>10.1016/j.toxicon.2005.12.013</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Toxicon (Oxford), 2006-04, Vol.47 (5), p.510-516 |
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| source | MEDLINE; ScienceDirect Freedom Collection (Elsevier) |
| subjects | Animals Arabinoside Biological and medical sciences Medical sciences Models, Molecular Molecular Structure Mollusk Venoms - chemistry Mollusk Venoms - isolation & purification Oxocins - chemistry Oxocins - isolation & purification Plant poisons toxicology Protoceratium reticulatum Toxicology Yessotoxin |
| title | Isolation of Yessotoxin 32- O-[β- l-arabinofuranosyl-(5′→1″)-β- l-arabinofuranoside] from Protoceratium reticulatum |
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