Oxirapentyns F–K from the Marine-Sediment-Derived Fungus Isaria felina KMM 4639
Six new highly oxygenated chromene derivatives, oxirapentyns F–K (2–7), one new polyketide (8), one new benzofurane (9), and two known cyclodepsipeptides, isoisariin B and isaridin E, were isolated from the lipophilic extract of the marine-derived fungus Isaria felina KMM 4639. The structures of com...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2014-06, Vol.77 (6), p.1321-1328 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Yurchenko, Anton N Smetanina, Olga F Kalinovsky, Anatoly I Pushilin, Michael A Glazunov, Valeriy P Khudyakova, Yuliya V Kirichuk, Natalya N Ermakova, Svetlana P Dyshlovoy, Sergey A Yurchenko, Ekaterina A Afiyatullov, Shamil Sh |
| description | Six new highly oxygenated chromene derivatives, oxirapentyns F–K (2–7), one new polyketide (8), one new benzofurane (9), and two known cyclodepsipeptides, isoisariin B and isaridin E, were isolated from the lipophilic extract of the marine-derived fungus Isaria felina KMM 4639. The structures of compounds 2–9 were determined using spectroscopic methods. The relative configurations of compounds 2–7 were established through a combination of NOE data and spin coupling constants, and these results were confirmed by X-ray crystallographic analysis of 4. The absolute structures of all oxirapentyns were assumed based on their biogenetic relationship and confirmed using the modified Mosher’s method on 2 and 7. Isariketide (8) showed moderate cytotoxicity toward HL-60 cells. |
| doi_str_mv | 10.1021/np500014m |
| format | Article |
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The structures of compounds 2–9 were determined using spectroscopic methods. The relative configurations of compounds 2–7 were established through a combination of NOE data and spin coupling constants, and these results were confirmed by X-ray crystallographic analysis of 4. The absolute structures of all oxirapentyns were assumed based on their biogenetic relationship and confirmed using the modified Mosher’s method on 2 and 7. Isariketide (8) showed moderate cytotoxicity toward HL-60 cells.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np500014m</identifier><identifier>PMID: 24911656</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Alkynes - chemistry ; Alkynes - isolation & purification ; Alkynes - pharmacology ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - isolation & purification ; Antineoplastic Agents - pharmacology ; Benzopyrans - chemistry ; Benzopyrans - isolation & purification ; Benzopyrans - pharmacology ; Cell Survival - drug effects ; Crystallography, X-Ray ; Depsipeptides - chemistry ; Depsipeptides - isolation & purification ; Drug Screening Assays, Antitumor ; Geologic Sediments - chemistry ; HL-60 Cells ; Humans ; Hypocreales - chemistry ; Marine Biology ; Microbial Sensitivity Tests ; Molecular Conformation ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Oceans and Seas</subject><ispartof>Journal of natural products (Washington, D.C.), 2014-06, Vol.77 (6), p.1321-1328</ispartof><rights>Copyright © 2014 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a348t-d28c673e5c907c6d1d68b0e92ef15de801a0d037810a2950e5080704390d41ca3</citedby><cites>FETCH-LOGICAL-a348t-d28c673e5c907c6d1d68b0e92ef15de801a0d037810a2950e5080704390d41ca3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np500014m$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np500014m$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27081,27929,27930,56743,56793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24911656$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yurchenko, Anton N</creatorcontrib><creatorcontrib>Smetanina, Olga F</creatorcontrib><creatorcontrib>Kalinovsky, Anatoly I</creatorcontrib><creatorcontrib>Pushilin, Michael A</creatorcontrib><creatorcontrib>Glazunov, Valeriy P</creatorcontrib><creatorcontrib>Khudyakova, Yuliya V</creatorcontrib><creatorcontrib>Kirichuk, Natalya N</creatorcontrib><creatorcontrib>Ermakova, Svetlana P</creatorcontrib><creatorcontrib>Dyshlovoy, Sergey A</creatorcontrib><creatorcontrib>Yurchenko, Ekaterina A</creatorcontrib><creatorcontrib>Afiyatullov, Shamil Sh</creatorcontrib><title>Oxirapentyns F–K from the Marine-Sediment-Derived Fungus Isaria felina KMM 4639</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Six new highly oxygenated chromene derivatives, oxirapentyns F–K (2–7), one new polyketide (8), one new benzofurane (9), and two known cyclodepsipeptides, isoisariin B and isaridin E, were isolated from the lipophilic extract of the marine-derived fungus Isaria felina KMM 4639. The structures of compounds 2–9 were determined using spectroscopic methods. The relative configurations of compounds 2–7 were established through a combination of NOE data and spin coupling constants, and these results were confirmed by X-ray crystallographic analysis of 4. The absolute structures of all oxirapentyns were assumed based on their biogenetic relationship and confirmed using the modified Mosher’s method on 2 and 7. 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Nat. Prod</addtitle><date>2014-06-27</date><risdate>2014</risdate><volume>77</volume><issue>6</issue><spage>1321</spage><epage>1328</epage><pages>1321-1328</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>Six new highly oxygenated chromene derivatives, oxirapentyns F–K (2–7), one new polyketide (8), one new benzofurane (9), and two known cyclodepsipeptides, isoisariin B and isaridin E, were isolated from the lipophilic extract of the marine-derived fungus Isaria felina KMM 4639. The structures of compounds 2–9 were determined using spectroscopic methods. The relative configurations of compounds 2–7 were established through a combination of NOE data and spin coupling constants, and these results were confirmed by X-ray crystallographic analysis of 4. The absolute structures of all oxirapentyns were assumed based on their biogenetic relationship and confirmed using the modified Mosher’s method on 2 and 7. Isariketide (8) showed moderate cytotoxicity toward HL-60 cells.</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>24911656</pmid><doi>10.1021/np500014m</doi><tpages>8</tpages></addata></record> |
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| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2014-06, Vol.77 (6), p.1321-1328 |
| issn | 0163-3864 1520-6025 |
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| source | MEDLINE; ACS Publications |
| subjects | Alkynes - chemistry Alkynes - isolation & purification Alkynes - pharmacology Antineoplastic Agents - chemistry Antineoplastic Agents - isolation & purification Antineoplastic Agents - pharmacology Benzopyrans - chemistry Benzopyrans - isolation & purification Benzopyrans - pharmacology Cell Survival - drug effects Crystallography, X-Ray Depsipeptides - chemistry Depsipeptides - isolation & purification Drug Screening Assays, Antitumor Geologic Sediments - chemistry HL-60 Cells Humans Hypocreales - chemistry Marine Biology Microbial Sensitivity Tests Molecular Conformation Molecular Structure Nuclear Magnetic Resonance, Biomolecular Oceans and Seas |
| title | Oxirapentyns F–K from the Marine-Sediment-Derived Fungus Isaria felina KMM 4639 |
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