Iriomoteolides-10a and 12a, Cytotoxic Macrolides from Marine Dinoflagellate Amphidinium Species
Two new macrolides, iriomoteolides-10a (1) and -12a (2), have been isolated from a marine dinoflagellate Amphidinium sp. (KCA09053 strain), and their structures were elucidated on the basis of a detailed two dimensional (2D)-NMR analysis. Compound 1 is a novel 21-membered Amphidinium macrolide, whic...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2016/07/01, Vol.64(7), pp.1019-1023 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | Akakabe, Mai Kumagai, Keiko Tsuda, Masayuki Konishi, Yuko Tominaga, Akira Kaneno, Daisuke Fukushi, Eri Kawabata, Jun Masuda, Atsunori Tsuda, Masashi |
| description | Two new macrolides, iriomoteolides-10a (1) and -12a (2), have been isolated from a marine dinoflagellate Amphidinium sp. (KCA09053 strain), and their structures were elucidated on the basis of a detailed two dimensional (2D)-NMR analysis. Compound 1 is a novel 21-membered Amphidinium macrolide, which contains one tetrahydrofuran ring, two ketone carbonyls, two hydroxyl groups, and six one-carbon branches. Compound 2 is a new 12-membered macrolide related to amphidinolide Q. Compound 1 exhibited cytotoxic activity against human cervix adenocarcinoma HeLa and murine hepatocellular carcinoma MH134 cells. |
| doi_str_mv | 10.1248/cpb.c16-00026 |
| format | Article |
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(KCA09053 strain), and their structures were elucidated on the basis of a detailed two dimensional (2D)-NMR analysis. Compound 1 is a novel 21-membered Amphidinium macrolide, which contains one tetrahydrofuran ring, two ketone carbonyls, two hydroxyl groups, and six one-carbon branches. Compound 2 is a new 12-membered macrolide related to amphidinolide Q. 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Pharm. Bull.</addtitle><description>Two new macrolides, iriomoteolides-10a (1) and -12a (2), have been isolated from a marine dinoflagellate Amphidinium sp. (KCA09053 strain), and their structures were elucidated on the basis of a detailed two dimensional (2D)-NMR analysis. Compound 1 is a novel 21-membered Amphidinium macrolide, which contains one tetrahydrofuran ring, two ketone carbonyls, two hydroxyl groups, and six one-carbon branches. Compound 2 is a new 12-membered macrolide related to amphidinolide Q. Compound 1 exhibited cytotoxic activity against human cervix adenocarcinoma HeLa and murine hepatocellular carcinoma MH134 cells.</description><subject>Amphidinium</subject><subject>Animals</subject><subject>Cell Line, Tumor</subject><subject>Cell Survival - drug effects</subject><subject>cytotoxic activity</subject><subject>dinoflagellate</subject><subject>Dinoflagellida - chemistry</subject><subject>Dose-Response Relationship, Drug</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>macrolide</subject><subject>Macrolides - chemistry</subject><subject>Macrolides - isolation & purification</subject><subject>Macrolides - pharmacology</subject><subject>Mice</subject><subject>Molecular Conformation</subject><subject>Structure-Activity Relationship</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkc1v1DAQxS0EokvhyBVF4sKhKR47_sixWmipVMQBOFuOM2G9SuJgJ1L73-PdlK3EictY9vz05nkeIW-BXgKr9Ec3NZcOZEkpZfIZ2QCvVCkY48_JJr_VJeOSn5FXKe0zIajiL8kZU1xxKcWGmNvowxBmDL1vMZVAbWHHtgBmL4rtwxzmcO9d8dW6uBJFF8OQ79GPWHzyY-h6-wv73s5YXA3Tzrd-9MtQfJ_QeUyvyYvO9gnfPJ7n5Of15x_bL-Xdt5vb7dVd6RQXc9k0gikUUglntVC6RsFQYuskRRTgqKtA1gwazJ2KUi2wtSih6nRTV0zzc_Jh1Z1i-L1gms3gkzv4GjEsyYCmWmoJov4fFLSktYCMvv8H3YcljvkjK8W0Bp6pcqXyjlKK2Jkp-sHGBwPUHEIyOSSTQzLHkDL_7lF1aQZsT_TfVDJwswK5653tw9jnbT_Ndkm5HQ7eMHoUlRVVhooqz4M6F8aZrAHYwdp2VdqnOcd0GmXj7F2PR2OyMupQTgafujsbDY78D6jhuZU</recordid><startdate>2016</startdate><enddate>2016</enddate><creator>Akakabe, Mai</creator><creator>Kumagai, Keiko</creator><creator>Tsuda, Masayuki</creator><creator>Konishi, Yuko</creator><creator>Tominaga, Akira</creator><creator>Kaneno, Daisuke</creator><creator>Fukushi, Eri</creator><creator>Kawabata, Jun</creator><creator>Masuda, Atsunori</creator><creator>Tsuda, Masashi</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><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>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope><scope>M7N</scope></search><sort><creationdate>2016</creationdate><title>Iriomoteolides-10a and 12a, Cytotoxic Macrolides from Marine Dinoflagellate Amphidinium Species</title><author>Akakabe, Mai ; Kumagai, Keiko ; Tsuda, Masayuki ; Konishi, Yuko ; Tominaga, Akira ; Kaneno, Daisuke ; Fukushi, Eri ; Kawabata, Jun ; Masuda, Atsunori ; Tsuda, Masashi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c735t-bb527e5675ca85789e52e6edc60ee51c0c416921be9e540085edae614f8b94283</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Amphidinium</topic><topic>Animals</topic><topic>Cell Line, Tumor</topic><topic>Cell Survival - drug effects</topic><topic>cytotoxic activity</topic><topic>dinoflagellate</topic><topic>Dinoflagellida - chemistry</topic><topic>Dose-Response Relationship, Drug</topic><topic>HeLa Cells</topic><topic>Humans</topic><topic>macrolide</topic><topic>Macrolides - chemistry</topic><topic>Macrolides - isolation & purification</topic><topic>Macrolides - pharmacology</topic><topic>Mice</topic><topic>Molecular Conformation</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Akakabe, Mai</creatorcontrib><creatorcontrib>Kumagai, Keiko</creatorcontrib><creatorcontrib>Tsuda, Masayuki</creatorcontrib><creatorcontrib>Konishi, Yuko</creatorcontrib><creatorcontrib>Tominaga, Akira</creatorcontrib><creatorcontrib>Kaneno, Daisuke</creatorcontrib><creatorcontrib>Fukushi, Eri</creatorcontrib><creatorcontrib>Kawabata, Jun</creatorcontrib><creatorcontrib>Masuda, Atsunori</creatorcontrib><creatorcontrib>Tsuda, Masashi</creatorcontrib><creatorcontrib>fCenter for Advanced Marine Core Research</creatorcontrib><creatorcontrib>RIKEN</creatorcontrib><creatorcontrib>Present address:College of Agriculture</creatorcontrib><creatorcontrib>bGraduate School of Kuroshio Science and Kochi Medical School</creatorcontrib><creatorcontrib>Tamagawa University</creatorcontrib><creatorcontrib>Hokkaido University</creatorcontrib><creatorcontrib>Present address:Synthetic Organic Chemistry Laboratory</creatorcontrib><creatorcontrib>Kochi University</creatorcontrib><creatorcontrib>dFaculty of Science</creatorcontrib><creatorcontrib>aScience Research Center</creatorcontrib><creatorcontrib>cResearch Faculty of Agriculture</creatorcontrib><creatorcontrib>eYanmar Environmental Sustainability Support Association</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Akakabe, Mai</au><au>Kumagai, Keiko</au><au>Tsuda, Masayuki</au><au>Konishi, Yuko</au><au>Tominaga, Akira</au><au>Kaneno, Daisuke</au><au>Fukushi, Eri</au><au>Kawabata, Jun</au><au>Masuda, Atsunori</au><au>Tsuda, Masashi</au><aucorp>fCenter for Advanced Marine Core Research</aucorp><aucorp>RIKEN</aucorp><aucorp>Present address:College of Agriculture</aucorp><aucorp>bGraduate School of Kuroshio Science and Kochi Medical School</aucorp><aucorp>Tamagawa University</aucorp><aucorp>Hokkaido University</aucorp><aucorp>Present address:Synthetic Organic Chemistry Laboratory</aucorp><aucorp>Kochi University</aucorp><aucorp>dFaculty of Science</aucorp><aucorp>aScience Research Center</aucorp><aucorp>cResearch Faculty of Agriculture</aucorp><aucorp>eYanmar Environmental Sustainability Support Association</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Iriomoteolides-10a and 12a, Cytotoxic Macrolides from Marine Dinoflagellate Amphidinium Species</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2016</date><risdate>2016</risdate><volume>64</volume><issue>7</issue><spage>1019</spage><epage>1023</epage><pages>1019-1023</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>Two new macrolides, iriomoteolides-10a (1) and -12a (2), have been isolated from a marine dinoflagellate Amphidinium sp. (KCA09053 strain), and their structures were elucidated on the basis of a detailed two dimensional (2D)-NMR analysis. Compound 1 is a novel 21-membered Amphidinium macrolide, which contains one tetrahydrofuran ring, two ketone carbonyls, two hydroxyl groups, and six one-carbon branches. Compound 2 is a new 12-membered macrolide related to amphidinolide Q. Compound 1 exhibited cytotoxic activity against human cervix adenocarcinoma HeLa and murine hepatocellular carcinoma MH134 cells.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>27373665</pmid><doi>10.1248/cpb.c16-00026</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 2016/07/01, Vol.64(7), pp.1019-1023 |
| issn | 0009-2363 1347-5223 |
| language | eng |
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| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Amphidinium Animals Cell Line, Tumor Cell Survival - drug effects cytotoxic activity dinoflagellate Dinoflagellida - chemistry Dose-Response Relationship, Drug HeLa Cells Humans macrolide Macrolides - chemistry Macrolides - isolation & purification Macrolides - pharmacology Mice Molecular Conformation Structure-Activity Relationship |
| title | Iriomoteolides-10a and 12a, Cytotoxic Macrolides from Marine Dinoflagellate Amphidinium Species |
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