Structure Reassignment of Echinosulfone A and the Echinosulfonic Acids A–D Supported by Single-Crystal X‑ray Diffraction and Density Functional Theory Analysis
Two previously reported bis-indole alkaloids, echinosulfone A and echinosulfonic acid B, have been isolated for the first time from a Western Australian marine sponge, Crella sp. (order: Poecilosclerida, family: Crellidae). Single-crystal X-ray diffraction of a decomposition product of echinosulfone...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2020-01, Vol.83 (1), p.105-110 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Sala, Samuele Nealon, Gareth L Sobolev, Alexandre N Fromont, Jane Gomez, Oliver Flematti, Gavin R |
| description | Two previously reported bis-indole alkaloids, echinosulfone A and echinosulfonic acid B, have been isolated for the first time from a Western Australian marine sponge, Crella sp. (order: Poecilosclerida, family: Crellidae). Single-crystal X-ray diffraction of a decomposition product of echinosulfone A prompted our investigation and subsequent structure reassignment of the echinosulfonic acid natural product family, which we report here. The reassignments are supported by analysis of 1D and 2D NMR data, MS fragmentation, and DFT calculations of 13C NMR shifts. |
| doi_str_mv | 10.1021/acs.jnatprod.9b00902 |
| format | Article |
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(order: Poecilosclerida, family: Crellidae). Single-crystal X-ray diffraction of a decomposition product of echinosulfone A prompted our investigation and subsequent structure reassignment of the echinosulfonic acid natural product family, which we report here. 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The reassignments are supported by analysis of 1D and 2D NMR data, MS fragmentation, and DFT calculations of 13C NMR shifts.</description><subject>Animals</subject><subject>Australia</subject><subject>Crystallography, X-Ray</subject><subject>Density Functional Theory</subject><subject>Indole Alkaloids - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Structure</subject><subject>Porifera - chemistry</subject><subject>Sulfonic Acids - chemistry</subject><subject>X-Ray Diffraction</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kc1qGzEURkVpaNy0b1CKlt2Mo98Zz3Kwk7YQCMQpdDdopKtYYSy5kmYxu7xC6CP0zfIkndpOIJuuJC7n-4TuQegTJXNKGD1XOs3vvcq7GMy87gipCXuDZlQyUpSEybdoRmjJC74oxSl6n9I9IYSTWr5Dp5zWXFRlPUN_1jkOOg8R8A2olNyd34LPOFh8oTfOhzT0NnjADVbe4LyBV3OncaOdSbh5evi9wuthtwsxg8HdiNfO3_VQLOOYsurxz6eHx6hGvHLWRqWzC35fuQKfXB7x5eD3wwm93UCII26m-5hc-oBOrOoTfDyeZ-jH5cXt8ltxdf31-7K5KpSgIheWUUOMlRJYzaZfV0KKyirORamVBSpL2YGAitjK1rU0jHWsqwAMt11thOZn6Muhd1rprwFSbrcuaeh75SEMqWWcL4hccFZNqDigOoaUIth2F91WxbGlpP2np530tM962qOeKfb5-MLQbcG8hJ59TAA5APt4GOK0gvT_zr8Z26Tz</recordid><startdate>20200124</startdate><enddate>20200124</enddate><creator>Sala, Samuele</creator><creator>Nealon, Gareth L</creator><creator>Sobolev, Alexandre N</creator><creator>Fromont, Jane</creator><creator>Gomez, Oliver</creator><creator>Flematti, Gavin R</creator><general>American Chemical Society and American Society of Pharmacognosy</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>7X8</scope><orcidid>https://orcid.org/0000-0003-2545-6939</orcidid></search><sort><creationdate>20200124</creationdate><title>Structure Reassignment of Echinosulfone A and the Echinosulfonic Acids A–D Supported by Single-Crystal X‑ray Diffraction and Density Functional Theory Analysis</title><author>Sala, Samuele ; Nealon, Gareth L ; Sobolev, Alexandre N ; Fromont, Jane ; Gomez, Oliver ; Flematti, Gavin R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a414t-f21d0df55e29238674547fa3346cafe1565be4e70f7f995d22b2b7eed3fb9d4c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Animals</topic><topic>Australia</topic><topic>Crystallography, X-Ray</topic><topic>Density Functional Theory</topic><topic>Indole Alkaloids - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Structure</topic><topic>Porifera - chemistry</topic><topic>Sulfonic Acids - chemistry</topic><topic>X-Ray Diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sala, Samuele</creatorcontrib><creatorcontrib>Nealon, Gareth L</creatorcontrib><creatorcontrib>Sobolev, Alexandre N</creatorcontrib><creatorcontrib>Fromont, Jane</creatorcontrib><creatorcontrib>Gomez, Oliver</creatorcontrib><creatorcontrib>Flematti, Gavin R</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sala, Samuele</au><au>Nealon, Gareth L</au><au>Sobolev, Alexandre N</au><au>Fromont, Jane</au><au>Gomez, Oliver</au><au>Flematti, Gavin R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structure Reassignment of Echinosulfone A and the Echinosulfonic Acids A–D Supported by Single-Crystal X‑ray Diffraction and Density Functional Theory Analysis</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2020-01-24</date><risdate>2020</risdate><volume>83</volume><issue>1</issue><spage>105</spage><epage>110</epage><pages>105-110</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>Two previously reported bis-indole alkaloids, echinosulfone A and echinosulfonic acid B, have been isolated for the first time from a Western Australian marine sponge, Crella sp. (order: Poecilosclerida, family: Crellidae). Single-crystal X-ray diffraction of a decomposition product of echinosulfone A prompted our investigation and subsequent structure reassignment of the echinosulfonic acid natural product family, which we report here. 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| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2020-01, Vol.83 (1), p.105-110 |
| issn | 0163-3864 1520-6025 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Animals Australia Crystallography, X-Ray Density Functional Theory Indole Alkaloids - chemistry Magnetic Resonance Spectroscopy Molecular Structure Porifera - chemistry Sulfonic Acids - chemistry X-Ray Diffraction |
| title | Structure Reassignment of Echinosulfone A and the Echinosulfonic Acids A–D Supported by Single-Crystal X‑ray Diffraction and Density Functional Theory Analysis |
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