Bridged Epipolythiodiketopiperazines from Penicillium raciborskii, an Endophytic Fungus of Rhododendron tomentosum Harmaja
Three new epithiodiketopiperazine natural products [outovirin A (1), outovirin B (2), and outovirin C (3)] resembling the antifungal natural product gliovirin have been identified in extracts of Penicillium raciborskii, an endophytic fungus isolated from Rhododendron tomentosum. The compounds are un...
Gespeichert in:
| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2016-04, Vol.79 (4), p.685-690 |
|---|---|
| Hauptverfasser: | , , , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 690 |
|---|---|
| container_issue | 4 |
| container_start_page | 685 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 79 |
| creator | Kajula, Marena Ward, Joshua M Turpeinen, Ari Tejesvi, Mysore V Hokkanen, Juho Tolonen, Ari Häkkänen, Heikki Picart, Pere Ihalainen, Janne Sahl, Hans-Georg Pirttilä, Anna Maria Mattila, Sampo |
| description | Three new epithiodiketopiperazine natural products [outovirin A (1), outovirin B (2), and outovirin C (3)] resembling the antifungal natural product gliovirin have been identified in extracts of Penicillium raciborskii, an endophytic fungus isolated from Rhododendron tomentosum. The compounds are unusual for their class in that they possess sulfide bridges between α- and β-carbons rather than the typical α–α bridging. To our knowledge, outovirin A represents the first reported naturally produced epimonothiodiketopiperazine, and antifungal outovirin C is the first reported trisulfide gliovirin-like compound. This report describes the identification and structural elucidation of the compounds by LC-MS/MS and NMR. |
| doi_str_mv | 10.1021/np500822k |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1794500772</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1783917381</sourcerecordid><originalsourceid>FETCH-LOGICAL-a414t-5a9ea3df0ccd8c6074792216a7608aece2afc14dec7978525cc438e13cc48ed33</originalsourceid><addsrcrecordid>eNqNkcFO3DAURa2qqEwHFv2ByptKVCLwbCexs2zRUJCQQAjWkbFfGM8kdmoni5mvJ9VMZ8WC1dWTzruLewj5xuCCAWeXvi8AFOfrT2TGCg5ZCbz4TGbASpEJVebH5GtKKwAQUBVfyDGXUMiyghnZ_o7OvqKli971od0MSxesW-MQphuj3jqPiTYxdPQBvTOubd3Y0aiNewkxrZ07p9rThbehX24GZ-j16F_HRENDH5fBBovexuDpEDr0Q0jT842OnV7pE3LU6Dbh6T7n5Pl68XR1k93d_7m9-nWX6ZzlQ1boCrWwDRhjlSlB5rLinJValqA0GuS6MSy3aGQlVcELY3KhkIkpFVoh5uRs19vH8HfENNSdSwbbVnsMY6qZrPJpPyn5B1AlKiaFYhP6c4eaGFKK2NR9dJ2Om5pB_c9KfbAysd_3teNLh_ZA_tcwAT92gDapXoUx-mmQd4reABwilmY</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1783917381</pqid></control><display><type>article</type><title>Bridged Epipolythiodiketopiperazines from Penicillium raciborskii, an Endophytic Fungus of Rhododendron tomentosum Harmaja</title><source>ACS Publications</source><source>MEDLINE</source><creator>Kajula, Marena ; Ward, Joshua M ; Turpeinen, Ari ; Tejesvi, Mysore V ; Hokkanen, Juho ; Tolonen, Ari ; Häkkänen, Heikki ; Picart, Pere ; Ihalainen, Janne ; Sahl, Hans-Georg ; Pirttilä, Anna Maria ; Mattila, Sampo</creator><creatorcontrib>Kajula, Marena ; Ward, Joshua M ; Turpeinen, Ari ; Tejesvi, Mysore V ; Hokkanen, Juho ; Tolonen, Ari ; Häkkänen, Heikki ; Picart, Pere ; Ihalainen, Janne ; Sahl, Hans-Georg ; Pirttilä, Anna Maria ; Mattila, Sampo</creatorcontrib><description>Three new epithiodiketopiperazine natural products [outovirin A (1), outovirin B (2), and outovirin C (3)] resembling the antifungal natural product gliovirin have been identified in extracts of Penicillium raciborskii, an endophytic fungus isolated from Rhododendron tomentosum. The compounds are unusual for their class in that they possess sulfide bridges between α- and β-carbons rather than the typical α–α bridging. To our knowledge, outovirin A represents the first reported naturally produced epimonothiodiketopiperazine, and antifungal outovirin C is the first reported trisulfide gliovirin-like compound. This report describes the identification and structural elucidation of the compounds by LC-MS/MS and NMR.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np500822k</identifier><identifier>PMID: 27057690</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Antifungal Agents - chemistry ; Antifungal Agents - isolation & purification ; Antifungal Agents - pharmacology ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Penicillium ; Penicillium - chemistry ; Piperazines - chemistry ; Piperazines - isolation & purification ; Piperazines - pharmacology ; Rhododendron ; Rhododendron - microbiology</subject><ispartof>Journal of natural products (Washington, D.C.), 2016-04, Vol.79 (4), p.685-690</ispartof><rights>Copyright © 2016 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a414t-5a9ea3df0ccd8c6074792216a7608aece2afc14dec7978525cc438e13cc48ed33</citedby><cites>FETCH-LOGICAL-a414t-5a9ea3df0ccd8c6074792216a7608aece2afc14dec7978525cc438e13cc48ed33</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/np500822k$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np500822k$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27057690$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kajula, Marena</creatorcontrib><creatorcontrib>Ward, Joshua M</creatorcontrib><creatorcontrib>Turpeinen, Ari</creatorcontrib><creatorcontrib>Tejesvi, Mysore V</creatorcontrib><creatorcontrib>Hokkanen, Juho</creatorcontrib><creatorcontrib>Tolonen, Ari</creatorcontrib><creatorcontrib>Häkkänen, Heikki</creatorcontrib><creatorcontrib>Picart, Pere</creatorcontrib><creatorcontrib>Ihalainen, Janne</creatorcontrib><creatorcontrib>Sahl, Hans-Georg</creatorcontrib><creatorcontrib>Pirttilä, Anna Maria</creatorcontrib><creatorcontrib>Mattila, Sampo</creatorcontrib><title>Bridged Epipolythiodiketopiperazines from Penicillium raciborskii, an Endophytic Fungus of Rhododendron tomentosum Harmaja</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Three new epithiodiketopiperazine natural products [outovirin A (1), outovirin B (2), and outovirin C (3)] resembling the antifungal natural product gliovirin have been identified in extracts of Penicillium raciborskii, an endophytic fungus isolated from Rhododendron tomentosum. The compounds are unusual for their class in that they possess sulfide bridges between α- and β-carbons rather than the typical α–α bridging. To our knowledge, outovirin A represents the first reported naturally produced epimonothiodiketopiperazine, and antifungal outovirin C is the first reported trisulfide gliovirin-like compound. This report describes the identification and structural elucidation of the compounds by LC-MS/MS and NMR.</description><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - isolation & purification</subject><subject>Antifungal Agents - pharmacology</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Penicillium</subject><subject>Penicillium - chemistry</subject><subject>Piperazines - chemistry</subject><subject>Piperazines - isolation & purification</subject><subject>Piperazines - pharmacology</subject><subject>Rhododendron</subject><subject>Rhododendron - microbiology</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkcFO3DAURa2qqEwHFv2ByptKVCLwbCexs2zRUJCQQAjWkbFfGM8kdmoni5mvJ9VMZ8WC1dWTzruLewj5xuCCAWeXvi8AFOfrT2TGCg5ZCbz4TGbASpEJVebH5GtKKwAQUBVfyDGXUMiyghnZ_o7OvqKli971od0MSxesW-MQphuj3jqPiTYxdPQBvTOubd3Y0aiNewkxrZ07p9rThbehX24GZ-j16F_HRENDH5fBBovexuDpEDr0Q0jT842OnV7pE3LU6Dbh6T7n5Pl68XR1k93d_7m9-nWX6ZzlQ1boCrWwDRhjlSlB5rLinJValqA0GuS6MSy3aGQlVcELY3KhkIkpFVoh5uRs19vH8HfENNSdSwbbVnsMY6qZrPJpPyn5B1AlKiaFYhP6c4eaGFKK2NR9dJ2Om5pB_c9KfbAysd_3teNLh_ZA_tcwAT92gDapXoUx-mmQd4reABwilmY</recordid><startdate>20160422</startdate><enddate>20160422</enddate><creator>Kajula, Marena</creator><creator>Ward, Joshua M</creator><creator>Turpeinen, Ari</creator><creator>Tejesvi, Mysore V</creator><creator>Hokkanen, Juho</creator><creator>Tolonen, Ari</creator><creator>Häkkänen, Heikki</creator><creator>Picart, Pere</creator><creator>Ihalainen, Janne</creator><creator>Sahl, Hans-Georg</creator><creator>Pirttilä, Anna Maria</creator><creator>Mattila, Sampo</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><scope>M7N</scope></search><sort><creationdate>20160422</creationdate><title>Bridged Epipolythiodiketopiperazines from Penicillium raciborskii, an Endophytic Fungus of Rhododendron tomentosum Harmaja</title><author>Kajula, Marena ; Ward, Joshua M ; Turpeinen, Ari ; Tejesvi, Mysore V ; Hokkanen, Juho ; Tolonen, Ari ; Häkkänen, Heikki ; Picart, Pere ; Ihalainen, Janne ; Sahl, Hans-Georg ; Pirttilä, Anna Maria ; Mattila, Sampo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a414t-5a9ea3df0ccd8c6074792216a7608aece2afc14dec7978525cc438e13cc48ed33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - isolation & purification</topic><topic>Antifungal Agents - pharmacology</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Penicillium</topic><topic>Penicillium - chemistry</topic><topic>Piperazines - chemistry</topic><topic>Piperazines - isolation & purification</topic><topic>Piperazines - pharmacology</topic><topic>Rhododendron</topic><topic>Rhododendron - microbiology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kajula, Marena</creatorcontrib><creatorcontrib>Ward, Joshua M</creatorcontrib><creatorcontrib>Turpeinen, Ari</creatorcontrib><creatorcontrib>Tejesvi, Mysore V</creatorcontrib><creatorcontrib>Hokkanen, Juho</creatorcontrib><creatorcontrib>Tolonen, Ari</creatorcontrib><creatorcontrib>Häkkänen, Heikki</creatorcontrib><creatorcontrib>Picart, Pere</creatorcontrib><creatorcontrib>Ihalainen, Janne</creatorcontrib><creatorcontrib>Sahl, Hans-Georg</creatorcontrib><creatorcontrib>Pirttilä, Anna Maria</creatorcontrib><creatorcontrib>Mattila, Sampo</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><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kajula, Marena</au><au>Ward, Joshua M</au><au>Turpeinen, Ari</au><au>Tejesvi, Mysore V</au><au>Hokkanen, Juho</au><au>Tolonen, Ari</au><au>Häkkänen, Heikki</au><au>Picart, Pere</au><au>Ihalainen, Janne</au><au>Sahl, Hans-Georg</au><au>Pirttilä, Anna Maria</au><au>Mattila, Sampo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bridged Epipolythiodiketopiperazines from Penicillium raciborskii, an Endophytic Fungus of Rhododendron tomentosum Harmaja</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2016-04-22</date><risdate>2016</risdate><volume>79</volume><issue>4</issue><spage>685</spage><epage>690</epage><pages>685-690</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>Three new epithiodiketopiperazine natural products [outovirin A (1), outovirin B (2), and outovirin C (3)] resembling the antifungal natural product gliovirin have been identified in extracts of Penicillium raciborskii, an endophytic fungus isolated from Rhododendron tomentosum. The compounds are unusual for their class in that they possess sulfide bridges between α- and β-carbons rather than the typical α–α bridging. To our knowledge, outovirin A represents the first reported naturally produced epimonothiodiketopiperazine, and antifungal outovirin C is the first reported trisulfide gliovirin-like compound. This report describes the identification and structural elucidation of the compounds by LC-MS/MS and NMR.</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>27057690</pmid><doi>10.1021/np500822k</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2016-04, Vol.79 (4), p.685-690 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1794500772 |
| source | ACS Publications; MEDLINE |
| subjects | Antifungal Agents - chemistry Antifungal Agents - isolation & purification Antifungal Agents - pharmacology Molecular Structure Nuclear Magnetic Resonance, Biomolecular Penicillium Penicillium - chemistry Piperazines - chemistry Piperazines - isolation & purification Piperazines - pharmacology Rhododendron Rhododendron - microbiology |
| title | Bridged Epipolythiodiketopiperazines from Penicillium raciborskii, an Endophytic Fungus of Rhododendron tomentosum Harmaja |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-30T16%3A38%3A04IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Bridged%20Epipolythiodiketopiperazines%20from%20Penicillium%20raciborskii,%20an%20Endophytic%20Fungus%20of%20Rhododendron%20tomentosum%20Harmaja&rft.jtitle=Journal%20of%20natural%20products%20(Washington,%20D.C.)&rft.au=Kajula,%20Marena&rft.date=2016-04-22&rft.volume=79&rft.issue=4&rft.spage=685&rft.epage=690&rft.pages=685-690&rft.issn=0163-3864&rft.eissn=1520-6025&rft_id=info:doi/10.1021/np500822k&rft_dat=%3Cproquest_cross%3E1783917381%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1783917381&rft_id=info:pmid/27057690&rfr_iscdi=true |