Chemistry and inhibitory activity of long chain fatty acid oxidation of emeriamine and its analogues
Emericedins A, B, and C, new betaines having inhibitory activity of long chain fatty acid oxidation, were isolated from the culture broth of Emericella quadrilineata IFO 5859. Their structures were determined by spectroscopic analyses as (R)-3-(acylamino)-4-(trimethylammonio)butyrate (acyl: A, acety...
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| Veröffentlicht in: | Journal of medicinal chemistry 1987-08, Vol.30 (8), p.1458-1463 |
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| container_end_page | 1463 |
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| container_issue | 8 |
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| container_title | Journal of medicinal chemistry |
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| creator | SHINAGAWA, S KANAMARU, T HARADA, S ASAI, M OKAZAKI, H |
| description | Emericedins A, B, and C, new betaines having inhibitory activity of long chain fatty acid oxidation, were isolated from the culture broth of Emericella quadrilineata IFO 5859. Their structures were determined by spectroscopic analyses as (R)-3-(acylamino)-4-(trimethylammonio)butyrate (acyl: A, acetyl; B, propionyl; C, n-butyryl). Structural confirmation and assignment of absolute configuration were made by chemical synthesis from L-asparagine. Deacylation of emericedin gave a potent derivative, (R)-3-amino-4-(trimethylammonio)butyrate, designated as emeriamine. In order to study the structure-activity relations, various analogues of emeriamine, including a stereoisomer, were prepared. Among them, N-palmitoyl and N-myristoyl derivatives showed much stronger inhibition of fatty acid oxidation than emeriamine. |
| doi_str_mv | 10.1021/jm00391a030 |
| format | Article |
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Among them, N-palmitoyl and N-myristoyl derivatives showed much stronger inhibition of fatty acid oxidation than emeriamine.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00391a030</identifier><identifier>PMID: 3612690</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Aliphatic compounds ; Animals ; Betaine - analogs & derivatives ; Betaine - pharmacology ; Carnitine ; Carnitine O-Palmitoyltransferase - antagonists & inhibitors ; Chemical Phenomena ; Chemistry ; Exact sciences and technology ; Fatty Acids - metabolism ; Male ; Mitochondria, Liver - drug effects ; Mitochondria, Liver - metabolism ; Molecular Conformation ; Organic chemistry ; Oxidation-Reduction ; Preparations and properties ; Rats ; Rats, Inbred Strains ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 1987-08, Vol.30 (8), p.1458-1463</ispartof><rights>1988 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=7484835$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/3612690$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>SHINAGAWA, S</creatorcontrib><creatorcontrib>KANAMARU, T</creatorcontrib><creatorcontrib>HARADA, S</creatorcontrib><creatorcontrib>ASAI, M</creatorcontrib><creatorcontrib>OKAZAKI, H</creatorcontrib><title>Chemistry and inhibitory activity of long chain fatty acid oxidation of emeriamine and its analogues</title><title>Journal of medicinal chemistry</title><addtitle>J Med Chem</addtitle><description>Emericedins A, B, and C, new betaines having inhibitory activity of long chain fatty acid oxidation, were isolated from the culture broth of Emericella quadrilineata IFO 5859. Their structures were determined by spectroscopic analyses as (R)-3-(acylamino)-4-(trimethylammonio)butyrate (acyl: A, acetyl; B, propionyl; C, n-butyryl). Structural confirmation and assignment of absolute configuration were made by chemical synthesis from L-asparagine. Deacylation of emericedin gave a potent derivative, (R)-3-amino-4-(trimethylammonio)butyrate, designated as emeriamine. In order to study the structure-activity relations, various analogues of emeriamine, including a stereoisomer, were prepared. Among them, N-palmitoyl and N-myristoyl derivatives showed much stronger inhibition of fatty acid oxidation than emeriamine.</description><subject>Aliphatic compounds</subject><subject>Animals</subject><subject>Betaine - analogs & derivatives</subject><subject>Betaine - pharmacology</subject><subject>Carnitine</subject><subject>Carnitine O-Palmitoyltransferase - antagonists & inhibitors</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Fatty Acids - metabolism</subject><subject>Male</subject><subject>Mitochondria, Liver - drug effects</subject><subject>Mitochondria, Liver - metabolism</subject><subject>Molecular Conformation</subject><subject>Organic chemistry</subject><subject>Oxidation-Reduction</subject><subject>Preparations and properties</subject><subject>Rats</subject><subject>Rats, Inbred Strains</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1987</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kM1Lw0AUxBdRaq2ePAs5iLfo291sNjlK8QsKXvQc3n61W5JszW7F_vemGDwNj_kxjxlCrincU2D0YdsB8JoicDghcyoY5EUFxSmZAzCWs5Lxc3IR4xZGjjI-IzNeUlbWMCdmubGdj2k4ZNibzPcbr3wKx1Mn_-3TIQsua0O_zvQGfZ85TOloepOFH28w-dAfEdvZwWPne_sXlOKo2Ib13sZLcuawjfZq0gX5fH76WL7mq_eXt-XjKt8xLlKuQConrUVZUJRgnDMFouZjGVczVWohWGVtCYg150ZpXYJVTBiprJQF4wty95e7G8LX-Dc1YzVt2xZ7G_axkbLkIIQYwZsJ3KvOmmY3-A6HQzPNMvq3k49RY-sG7LWP_5gsqqLigv8CusJyhA</recordid><startdate>19870801</startdate><enddate>19870801</enddate><creator>SHINAGAWA, S</creator><creator>KANAMARU, T</creator><creator>HARADA, S</creator><creator>ASAI, M</creator><creator>OKAZAKI, H</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>19870801</creationdate><title>Chemistry and inhibitory activity of long chain fatty acid oxidation of emeriamine and its analogues</title><author>SHINAGAWA, S ; KANAMARU, T ; HARADA, S ; ASAI, M ; OKAZAKI, H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p235t-b07bf7eea741a70dffd4aac3480f92b6c5528ee60aa933dbcc60eb25d7be77423</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1987</creationdate><topic>Aliphatic compounds</topic><topic>Animals</topic><topic>Betaine - analogs & derivatives</topic><topic>Betaine - pharmacology</topic><topic>Carnitine</topic><topic>Carnitine O-Palmitoyltransferase - antagonists & inhibitors</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Fatty Acids - metabolism</topic><topic>Male</topic><topic>Mitochondria, Liver - drug effects</topic><topic>Mitochondria, Liver - metabolism</topic><topic>Molecular Conformation</topic><topic>Organic chemistry</topic><topic>Oxidation-Reduction</topic><topic>Preparations and properties</topic><topic>Rats</topic><topic>Rats, Inbred Strains</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>SHINAGAWA, S</creatorcontrib><creatorcontrib>KANAMARU, T</creatorcontrib><creatorcontrib>HARADA, S</creatorcontrib><creatorcontrib>ASAI, M</creatorcontrib><creatorcontrib>OKAZAKI, H</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>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>SHINAGAWA, S</au><au>KANAMARU, T</au><au>HARADA, S</au><au>ASAI, M</au><au>OKAZAKI, H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemistry and inhibitory activity of long chain fatty acid oxidation of emeriamine and its analogues</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J Med Chem</addtitle><date>1987-08-01</date><risdate>1987</risdate><volume>30</volume><issue>8</issue><spage>1458</spage><epage>1463</epage><pages>1458-1463</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>Emericedins A, B, and C, new betaines having inhibitory activity of long chain fatty acid oxidation, were isolated from the culture broth of Emericella quadrilineata IFO 5859. Their structures were determined by spectroscopic analyses as (R)-3-(acylamino)-4-(trimethylammonio)butyrate (acyl: A, acetyl; B, propionyl; C, n-butyryl). Structural confirmation and assignment of absolute configuration were made by chemical synthesis from L-asparagine. Deacylation of emericedin gave a potent derivative, (R)-3-amino-4-(trimethylammonio)butyrate, designated as emeriamine. In order to study the structure-activity relations, various analogues of emeriamine, including a stereoisomer, were prepared. Among them, N-palmitoyl and N-myristoyl derivatives showed much stronger inhibition of fatty acid oxidation than emeriamine.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>3612690</pmid><doi>10.1021/jm00391a030</doi><tpages>6</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 1987-08, Vol.30 (8), p.1458-1463 |
| issn | 0022-2623 1520-4804 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Aliphatic compounds Animals Betaine - analogs & derivatives Betaine - pharmacology Carnitine Carnitine O-Palmitoyltransferase - antagonists & inhibitors Chemical Phenomena Chemistry Exact sciences and technology Fatty Acids - metabolism Male Mitochondria, Liver - drug effects Mitochondria, Liver - metabolism Molecular Conformation Organic chemistry Oxidation-Reduction Preparations and properties Rats Rats, Inbred Strains Structure-Activity Relationship |
| title | Chemistry and inhibitory activity of long chain fatty acid oxidation of emeriamine and its analogues |
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