Identification of an N-Acetyl Keto Derivative of Fumonisin B1 in Corn Cultures of Fusarium proliferatum
A method is presented for the separation and identification of a new N-acetyl keto derivative of fumonisin B1 (FB1) produced in solid corn culture. Cultures of Fusarium proliferatum (M-1597) were purified using preparative hplc, and the new fumonisin was detected by negative-ion esms. Structures wer...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 1995-09, Vol.58 (9), p.1392-1397 |
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| container_end_page | 1397 |
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| container_issue | 9 |
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| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 58 |
| creator | Musser, Steven M Eppley, Robert M Mazzola, Eugene P Hadden, Chad E Shockcor, John P Crouch, Ronald C Martin, Gary E |
| description | A method is presented for the separation and identification of a new N-acetyl keto derivative of fumonisin B1 (FB1) produced in solid corn culture. Cultures of Fusarium proliferatum (M-1597) were purified using preparative hplc, and the new fumonisin was detected by negative-ion esms. Structures were confirmed by 1H- and 13C-nmr spectroscopy. The new fumonisin differs from FB1 in that the tricarballylic acid functionality at the C-15 position of the eicosane backbone is replaced by a ketone and the amino group is acetylated. Direct analysis of the culture material by negative-ion electrospray lc/ms confirmed that the new fumonisin is produced naturally by the fungus. |
| doi_str_mv | 10.1021/np50123a009 |
| format | Article |
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Cultures of Fusarium proliferatum (M-1597) were purified using preparative hplc, and the new fumonisin was detected by negative-ion esms. Structures were confirmed by 1H- and 13C-nmr spectroscopy. The new fumonisin differs from FB1 in that the tricarballylic acid functionality at the C-15 position of the eicosane backbone is replaced by a ketone and the amino group is acetylated. Direct analysis of the culture material by negative-ion electrospray lc/ms confirmed that the new fumonisin is produced naturally by the fungus.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np50123a009</identifier><identifier>PMID: 7494146</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Acetylation ; CETONAS ; CETONE ; CHEMICAL COMPOSITION ; COMPOSICION QUIMICA ; COMPOSITION CHIMIQUE ; ESPECTROMETRIA ; FILTRACION ; FILTRATION ; Fumonisins ; Fusarium - chemistry ; Fusarium - metabolism ; FUSARIUM PROLIFERATUM ; KETONES ; Ketones - chemistry ; Magnetic Resonance Spectroscopy ; METABOLITE ; METABOLITES ; METABOLITOS ; MICOTOXINAS ; MICROORGANISME ; MICROORGANISMOS ; MICROORGANISMS ; MOLECULAR CONFORMATION ; Molecular Structure ; MYCOTOXINE ; MYCOTOXINS ; Mycotoxins - chemistry ; Mycotoxins - isolation & purification ; Mycotoxins - metabolism ; SECONDARY METABOLITES ; SPECTRAL ANALYSIS ; SPECTROMETRIE ; SPECTROMETRY ; Zea mays - microbiology</subject><ispartof>Journal of natural products (Washington, D.C.), 1995-09, Vol.58 (9), p.1392-1397</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np50123a009$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np50123a009$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/7494146$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Musser, Steven M</creatorcontrib><creatorcontrib>Eppley, Robert M</creatorcontrib><creatorcontrib>Mazzola, Eugene P</creatorcontrib><creatorcontrib>Hadden, Chad E</creatorcontrib><creatorcontrib>Shockcor, John P</creatorcontrib><creatorcontrib>Crouch, Ronald C</creatorcontrib><creatorcontrib>Martin, Gary E</creatorcontrib><title>Identification of an N-Acetyl Keto Derivative of Fumonisin B1 in Corn Cultures of Fusarium proliferatum</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>A method is presented for the separation and identification of a new N-acetyl keto derivative of fumonisin B1 (FB1) produced in solid corn culture. Cultures of Fusarium proliferatum (M-1597) were purified using preparative hplc, and the new fumonisin was detected by negative-ion esms. Structures were confirmed by 1H- and 13C-nmr spectroscopy. The new fumonisin differs from FB1 in that the tricarballylic acid functionality at the C-15 position of the eicosane backbone is replaced by a ketone and the amino group is acetylated. Direct analysis of the culture material by negative-ion electrospray lc/ms confirmed that the new fumonisin is produced naturally by the fungus.</description><subject>Acetylation</subject><subject>CETONAS</subject><subject>CETONE</subject><subject>CHEMICAL COMPOSITION</subject><subject>COMPOSICION QUIMICA</subject><subject>COMPOSITION CHIMIQUE</subject><subject>ESPECTROMETRIA</subject><subject>FILTRACION</subject><subject>FILTRATION</subject><subject>Fumonisins</subject><subject>Fusarium - chemistry</subject><subject>Fusarium - metabolism</subject><subject>FUSARIUM PROLIFERATUM</subject><subject>KETONES</subject><subject>Ketones - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>METABOLITE</subject><subject>METABOLITES</subject><subject>METABOLITOS</subject><subject>MICOTOXINAS</subject><subject>MICROORGANISME</subject><subject>MICROORGANISMOS</subject><subject>MICROORGANISMS</subject><subject>MOLECULAR CONFORMATION</subject><subject>Molecular Structure</subject><subject>MYCOTOXINE</subject><subject>MYCOTOXINS</subject><subject>Mycotoxins - chemistry</subject><subject>Mycotoxins - isolation & purification</subject><subject>Mycotoxins - metabolism</subject><subject>SECONDARY METABOLITES</subject><subject>SPECTRAL ANALYSIS</subject><subject>SPECTROMETRIE</subject><subject>SPECTROMETRY</subject><subject>Zea mays - microbiology</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1995</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpNkUtLw0AUhQdRaq2u3AlCdq6idx6ZJEutVqullj7cDpNkUqbmUWaSYv-9U1LEzbmL7-PC4SB0jeEeA8EP1TYATKgEiE9QHwcEfA4kOEV9wJz6NOLsHF1YuwEACnHQQ72QxQwz3kfrcaaqRuc6lY2uK6_OPVl5U_8xVc2-8D5UU3vPyuidwzt1wKO2rCttdeU9Yc_lsDYu2qJpjbKdYKXRbeltTV3oXBnZtOUlOstlYdXV8Q7QavSyHL75k8_X8fBx4ksCEfdZTGSSuzo0ZRKnjGASx4pArCCIojCTFDIchIzxBAhIQkOOU4ITAhkFlWV0gG67v9s2KVUmtkaX0uzFsbDjfse1bdTPH5bmW_CQhoFYzhZi_jV7n-MIi6nzbzo_l7WQa6OtWC3igHNnO3jXQZlasalbU7lqAoM4zCL-zUJ_AQU8eZw</recordid><startdate>19950901</startdate><enddate>19950901</enddate><creator>Musser, Steven M</creator><creator>Eppley, Robert M</creator><creator>Mazzola, Eugene P</creator><creator>Hadden, Chad E</creator><creator>Shockcor, John P</creator><creator>Crouch, Ronald C</creator><creator>Martin, Gary E</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope></search><sort><creationdate>19950901</creationdate><title>Identification of an N-Acetyl Keto Derivative of Fumonisin B1 in Corn Cultures of Fusarium proliferatum</title><author>Musser, Steven M ; Eppley, Robert M ; Mazzola, Eugene P ; Hadden, Chad E ; Shockcor, John P ; Crouch, Ronald C ; Martin, Gary E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a2086-492abf5013c4a1c421299e209e05887da30d157446b020a23761c21b20d30edd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1995</creationdate><topic>Acetylation</topic><topic>CETONAS</topic><topic>CETONE</topic><topic>CHEMICAL COMPOSITION</topic><topic>COMPOSICION QUIMICA</topic><topic>COMPOSITION CHIMIQUE</topic><topic>ESPECTROMETRIA</topic><topic>FILTRACION</topic><topic>FILTRATION</topic><topic>Fumonisins</topic><topic>Fusarium - chemistry</topic><topic>Fusarium - metabolism</topic><topic>FUSARIUM PROLIFERATUM</topic><topic>KETONES</topic><topic>Ketones - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>METABOLITE</topic><topic>METABOLITES</topic><topic>METABOLITOS</topic><topic>MICOTOXINAS</topic><topic>MICROORGANISME</topic><topic>MICROORGANISMOS</topic><topic>MICROORGANISMS</topic><topic>MOLECULAR CONFORMATION</topic><topic>Molecular Structure</topic><topic>MYCOTOXINE</topic><topic>MYCOTOXINS</topic><topic>Mycotoxins - chemistry</topic><topic>Mycotoxins - isolation & purification</topic><topic>Mycotoxins - metabolism</topic><topic>SECONDARY METABOLITES</topic><topic>SPECTRAL ANALYSIS</topic><topic>SPECTROMETRIE</topic><topic>SPECTROMETRY</topic><topic>Zea mays - microbiology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Musser, Steven M</creatorcontrib><creatorcontrib>Eppley, Robert M</creatorcontrib><creatorcontrib>Mazzola, Eugene P</creatorcontrib><creatorcontrib>Hadden, Chad E</creatorcontrib><creatorcontrib>Shockcor, John P</creatorcontrib><creatorcontrib>Crouch, Ronald C</creatorcontrib><creatorcontrib>Martin, Gary E</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Musser, Steven M</au><au>Eppley, Robert M</au><au>Mazzola, Eugene P</au><au>Hadden, Chad E</au><au>Shockcor, John P</au><au>Crouch, Ronald C</au><au>Martin, Gary E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identification of an N-Acetyl Keto Derivative of Fumonisin B1 in Corn Cultures of Fusarium proliferatum</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>1995-09-01</date><risdate>1995</risdate><volume>58</volume><issue>9</issue><spage>1392</spage><epage>1397</epage><pages>1392-1397</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>A method is presented for the separation and identification of a new N-acetyl keto derivative of fumonisin B1 (FB1) produced in solid corn culture. Cultures of Fusarium proliferatum (M-1597) were purified using preparative hplc, and the new fumonisin was detected by negative-ion esms. Structures were confirmed by 1H- and 13C-nmr spectroscopy. The new fumonisin differs from FB1 in that the tricarballylic acid functionality at the C-15 position of the eicosane backbone is replaced by a ketone and the amino group is acetylated. Direct analysis of the culture material by negative-ion electrospray lc/ms confirmed that the new fumonisin is produced naturally by the fungus.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>7494146</pmid><doi>10.1021/np50123a009</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 1995-09, Vol.58 (9), p.1392-1397 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_pubmed_primary_7494146 |
| source | ACS Publications; MEDLINE |
| subjects | Acetylation CETONAS CETONE CHEMICAL COMPOSITION COMPOSICION QUIMICA COMPOSITION CHIMIQUE ESPECTROMETRIA FILTRACION FILTRATION Fumonisins Fusarium - chemistry Fusarium - metabolism FUSARIUM PROLIFERATUM KETONES Ketones - chemistry Magnetic Resonance Spectroscopy METABOLITE METABOLITES METABOLITOS MICOTOXINAS MICROORGANISME MICROORGANISMOS MICROORGANISMS MOLECULAR CONFORMATION Molecular Structure MYCOTOXINE MYCOTOXINS Mycotoxins - chemistry Mycotoxins - isolation & purification Mycotoxins - metabolism SECONDARY METABOLITES SPECTRAL ANALYSIS SPECTROMETRIE SPECTROMETRY Zea mays - microbiology |
| title | Identification of an N-Acetyl Keto Derivative of Fumonisin B1 in Corn Cultures of Fusarium proliferatum |
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