Antimicrobial bianthrones from the crinoid Heterometra sp
Antimicrobial resistance is a global public health problem and identification of new chemical scaffolds is important to overcoming this threat. In a recent high-throughput discovery campaign, fractions derived from the organic extract of crinoid, sp. (Echinodermata), showed antibacterial activity. C...
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| Veröffentlicht in: | RSC advances 2024-11, Vol.14 (51), p.38200-38207 |
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| creator | Freire, Vítor F Martínez-Fructuoso, Lucero Kumar, Rohitesh Akee, Rhone K Thornburg, Christopher C Ensel, Susan Okoroafor, Ekene Evans, Jason R Wang, Dongdong Peyser, Brian D Grkovic, Tanja O'Keefe, Barry R |
| description | Antimicrobial resistance is a global public health problem and identification of new chemical scaffolds is important to overcoming this threat. In a recent high-throughput discovery campaign, fractions derived from the organic extract of crinoid,
sp. (Echinodermata), showed antibacterial activity. Chemical investigation of this extract led to the isolation of three natural products, namely crinemodin bianthrone (1), the new structure 1''-dehydrocrinemodin bianthrone (2), and 1''-hydroxycrinemodin bianthrone (3). Their planar structures were determined through HRESIMS and 1D and 2D NMR analysis while a combination of chemical and chirooptical methods was employed to define their absolute configurations for the first time. Variations in proton chemical shifts as well as instability in DMSO and pyridine were observed for 3. Compounds 1 and 3 showed selective antimicrobial activity against Gram-positive bacterial strains. |
| doi_str_mv | 10.1039/d4ra05594b |
| format | Article |
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sp. (Echinodermata), showed antibacterial activity. Chemical investigation of this extract led to the isolation of three natural products, namely crinemodin bianthrone (1), the new structure 1''-dehydrocrinemodin bianthrone (2), and 1''-hydroxycrinemodin bianthrone (3). Their planar structures were determined through HRESIMS and 1D and 2D NMR analysis while a combination of chemical and chirooptical methods was employed to define their absolute configurations for the first time. Variations in proton chemical shifts as well as instability in DMSO and pyridine were observed for 3. Compounds 1 and 3 showed selective antimicrobial activity against Gram-positive bacterial strains.</description><subject>Antiinfectives and antibacterials</subject><subject>Chemical activity</subject><subject>Chemical compounds</subject><subject>Chemistry</subject><subject>Natural products</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Planar structures</subject><subject>Public health</subject><subject>Two dimensional analysis</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpdkV1LwzAUhoMobszd-AOk4I0I1Xw1Ta5kzo8JA0H0OqRp6jLaZiat4L83bnNMc5GE5OE957wvAKcIXiFIxHVJvYJZJmhxAIYYUpZiyMTh3n0AxiEsYVwsQ5ihYzAggmFKST4EYtJ2trHau8KqOolb2y28a01IKu-apFuYRHvbOlsmM9OZ-GY6r5KwOgFHlaqDGW_PEXh7uH-dztL58-PTdDJPNWawS1VGCeUEIUXzXHGKWMWJQEKXOeVZJXIitGAIZkVVYapKQUti4jiCG1xyzckI3Gx0V33RmFKbNtav5crbRvkv6ZSVf39au5Dv7lMiFGWjRVHhYqvg3UdvQicbG7Spa9Ua1wdJEIUCRw_ziJ7_Q5eu922cb03xnKLo2whcbqhoWwjeVLtuEJQ_qcg7-jJZp3Ib4bP9_nfobwbkG-fvhic</recordid><startdate>20241125</startdate><enddate>20241125</enddate><creator>Freire, Vítor F</creator><creator>Martínez-Fructuoso, Lucero</creator><creator>Kumar, Rohitesh</creator><creator>Akee, Rhone K</creator><creator>Thornburg, Christopher C</creator><creator>Ensel, Susan</creator><creator>Okoroafor, Ekene</creator><creator>Evans, Jason R</creator><creator>Wang, Dongdong</creator><creator>Peyser, Brian D</creator><creator>Grkovic, Tanja</creator><creator>O'Keefe, Barry R</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-3455-5181</orcidid><orcidid>https://orcid.org/0000-0001-6565-1830</orcidid><orcidid>https://orcid.org/0000-0002-7733-1065</orcidid><orcidid>https://orcid.org/0000-0002-6537-3997</orcidid><orcidid>https://orcid.org/0000-0002-7187-937X</orcidid><orcidid>https://orcid.org/0000-0002-7824-2507</orcidid><orcidid>https://orcid.org/0000-0002-4657-6895</orcidid><orcidid>https://orcid.org/0000-0003-0772-4856</orcidid></search><sort><creationdate>20241125</creationdate><title>Antimicrobial bianthrones from the crinoid Heterometra sp</title><author>Freire, Vítor F ; Martínez-Fructuoso, Lucero ; Kumar, Rohitesh ; Akee, Rhone K ; Thornburg, Christopher C ; Ensel, Susan ; Okoroafor, Ekene ; Evans, Jason R ; Wang, Dongdong ; Peyser, Brian D ; Grkovic, Tanja ; O'Keefe, Barry R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c260t-a54348311a477a8416f83919cd7485f9739c96105bff24ad94d3e59498e2d8c83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Antiinfectives and antibacterials</topic><topic>Chemical activity</topic><topic>Chemical compounds</topic><topic>Chemistry</topic><topic>Natural products</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Planar structures</topic><topic>Public health</topic><topic>Two dimensional analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Freire, Vítor F</creatorcontrib><creatorcontrib>Martínez-Fructuoso, Lucero</creatorcontrib><creatorcontrib>Kumar, Rohitesh</creatorcontrib><creatorcontrib>Akee, Rhone K</creatorcontrib><creatorcontrib>Thornburg, Christopher C</creatorcontrib><creatorcontrib>Ensel, Susan</creatorcontrib><creatorcontrib>Okoroafor, Ekene</creatorcontrib><creatorcontrib>Evans, Jason R</creatorcontrib><creatorcontrib>Wang, Dongdong</creatorcontrib><creatorcontrib>Peyser, Brian D</creatorcontrib><creatorcontrib>Grkovic, Tanja</creatorcontrib><creatorcontrib>O'Keefe, Barry R</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Freire, Vítor F</au><au>Martínez-Fructuoso, Lucero</au><au>Kumar, Rohitesh</au><au>Akee, Rhone K</au><au>Thornburg, Christopher C</au><au>Ensel, Susan</au><au>Okoroafor, Ekene</au><au>Evans, Jason R</au><au>Wang, Dongdong</au><au>Peyser, Brian D</au><au>Grkovic, Tanja</au><au>O'Keefe, Barry R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antimicrobial bianthrones from the crinoid Heterometra sp</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2024-11-25</date><risdate>2024</risdate><volume>14</volume><issue>51</issue><spage>38200</spage><epage>38207</epage><pages>38200-38207</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>Antimicrobial resistance is a global public health problem and identification of new chemical scaffolds is important to overcoming this threat. In a recent high-throughput discovery campaign, fractions derived from the organic extract of crinoid,
sp. (Echinodermata), showed antibacterial activity. Chemical investigation of this extract led to the isolation of three natural products, namely crinemodin bianthrone (1), the new structure 1''-dehydrocrinemodin bianthrone (2), and 1''-hydroxycrinemodin bianthrone (3). Their planar structures were determined through HRESIMS and 1D and 2D NMR analysis while a combination of chemical and chirooptical methods was employed to define their absolute configurations for the first time. Variations in proton chemical shifts as well as instability in DMSO and pyridine were observed for 3. Compounds 1 and 3 showed selective antimicrobial activity against Gram-positive bacterial strains.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>39624437</pmid><doi>10.1039/d4ra05594b</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-3455-5181</orcidid><orcidid>https://orcid.org/0000-0001-6565-1830</orcidid><orcidid>https://orcid.org/0000-0002-7733-1065</orcidid><orcidid>https://orcid.org/0000-0002-6537-3997</orcidid><orcidid>https://orcid.org/0000-0002-7187-937X</orcidid><orcidid>https://orcid.org/0000-0002-7824-2507</orcidid><orcidid>https://orcid.org/0000-0002-4657-6895</orcidid><orcidid>https://orcid.org/0000-0003-0772-4856</orcidid><oa>free_for_read</oa></addata></record> |
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| source | DOAJ Directory of Open Access Journals; PubMed Central; EZB Electronic Journals Library; PubMed Central Open Access |
| subjects | Antiinfectives and antibacterials Chemical activity Chemical compounds Chemistry Natural products NMR Nuclear magnetic resonance Planar structures Public health Two dimensional analysis |
| title | Antimicrobial bianthrones from the crinoid Heterometra sp |
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