A series of meroterpenoids with rearranged skeletons from an endophytic fungus Penicillium sp. GDGJ-285
Under the guidance of MS/MS based molecular networking, five new meroterpenoids ( 1–5 ), including three novel skeleton meroterpenoids, peniclactones A–C ( 1–3 ), and two new isoaustinone analogues, 6-hydroxyisoaustinone ( 4 ) and 6-ketoisoaustinone ( 5 ), were isolated from the fungus Penicillium s...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2021-05, Vol.8 (10), p.2232-2241 |
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| creator | Mo, Tu-Xiang Huang, Xi-Shan Zhang, Wen-Xiu Schäberle, Till F. Qin, Jiang-Ke Zhou, De-Xiong Qin, Xiao-Ya Xu, Zhao-Long Li, Jun Yang, Rui-Yun |
| description | Under the guidance of MS/MS based molecular networking, five new meroterpenoids (
1–5
), including three novel skeleton meroterpenoids, peniclactones A–C (
1–3
), and two new isoaustinone analogues, 6-hydroxyisoaustinone (
4
) and 6-ketoisoaustinone (
5
), were isolated from the fungus
Penicillium
sp. GDGJ-285. Their structures were elucidated by HRMS and NMR spectroscopy, and their absolute configurations were determined by X-ray single-crystal diffraction analysis. Peniclactones A–C (
1–3
) represent the first meroterpenoids featuring a 6/5/6/6/5/6 (
1
), 6/5/6/6/5/5 (
2
), and 6/5/6/5/5/6 (
3
) hexacyclic ring system, respectively. Bioassays showed that compound
3
inhibited nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophage cells with an IC
50
value of 39.03 μM. |
| doi_str_mv | 10.1039/D1QO00173F |
| format | Article |
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1–5
), including three novel skeleton meroterpenoids, peniclactones A–C (
1–3
), and two new isoaustinone analogues, 6-hydroxyisoaustinone (
4
) and 6-ketoisoaustinone (
5
), were isolated from the fungus
Penicillium
sp. GDGJ-285. Their structures were elucidated by HRMS and NMR spectroscopy, and their absolute configurations were determined by X-ray single-crystal diffraction analysis. Peniclactones A–C (
1–3
) represent the first meroterpenoids featuring a 6/5/6/6/5/6 (
1
), 6/5/6/6/5/5 (
2
), and 6/5/6/5/5/6 (
3
) hexacyclic ring system, respectively. Bioassays showed that compound
3
inhibited nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophage cells with an IC
50
value of 39.03 μM.</description><identifier>ISSN: 2052-4129</identifier><identifier>ISSN: 2052-4110</identifier><identifier>EISSN: 2052-4129</identifier><identifier>EISSN: 2052-4110</identifier><identifier>DOI: 10.1039/D1QO00173F</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Bioassays ; Crystallography ; Endophytes ; Fungi ; Lipopolysaccharides ; Macrophages ; Magnetic resonance spectroscopy ; Nitric oxide ; NMR ; NMR spectroscopy ; Nuclear magnetic resonance ; Organic chemistry ; Penicillium ; Single crystals ; Spectrum analysis ; X-ray crystallography</subject><ispartof>Organic Chemistry Frontiers, 2021-05, Vol.8 (10), p.2232-2241</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c259t-e978c113978da5d69ff39b860cf34429695219d9dae11e4185fa8da4e4e264503</citedby><cites>FETCH-LOGICAL-c259t-e978c113978da5d69ff39b860cf34429695219d9dae11e4185fa8da4e4e264503</cites><orcidid>0000-0002-3306-4700 ; 0000-0001-9947-8079</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Mo, Tu-Xiang</creatorcontrib><creatorcontrib>Huang, Xi-Shan</creatorcontrib><creatorcontrib>Zhang, Wen-Xiu</creatorcontrib><creatorcontrib>Schäberle, Till F.</creatorcontrib><creatorcontrib>Qin, Jiang-Ke</creatorcontrib><creatorcontrib>Zhou, De-Xiong</creatorcontrib><creatorcontrib>Qin, Xiao-Ya</creatorcontrib><creatorcontrib>Xu, Zhao-Long</creatorcontrib><creatorcontrib>Li, Jun</creatorcontrib><creatorcontrib>Yang, Rui-Yun</creatorcontrib><title>A series of meroterpenoids with rearranged skeletons from an endophytic fungus Penicillium sp. GDGJ-285</title><title>Organic Chemistry Frontiers</title><description>Under the guidance of MS/MS based molecular networking, five new meroterpenoids (
1–5
), including three novel skeleton meroterpenoids, peniclactones A–C (
1–3
), and two new isoaustinone analogues, 6-hydroxyisoaustinone (
4
) and 6-ketoisoaustinone (
5
), were isolated from the fungus
Penicillium
sp. GDGJ-285. Their structures were elucidated by HRMS and NMR spectroscopy, and their absolute configurations were determined by X-ray single-crystal diffraction analysis. Peniclactones A–C (
1–3
) represent the first meroterpenoids featuring a 6/5/6/6/5/6 (
1
), 6/5/6/6/5/5 (
2
), and 6/5/6/5/5/6 (
3
) hexacyclic ring system, respectively. Bioassays showed that compound
3
inhibited nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophage cells with an IC
50
value of 39.03 μM.</description><subject>Bioassays</subject><subject>Crystallography</subject><subject>Endophytes</subject><subject>Fungi</subject><subject>Lipopolysaccharides</subject><subject>Macrophages</subject><subject>Magnetic resonance spectroscopy</subject><subject>Nitric oxide</subject><subject>NMR</subject><subject>NMR spectroscopy</subject><subject>Nuclear magnetic resonance</subject><subject>Organic chemistry</subject><subject>Penicillium</subject><subject>Single crystals</subject><subject>Spectrum analysis</subject><subject>X-ray crystallography</subject><issn>2052-4129</issn><issn>2052-4110</issn><issn>2052-4129</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpNkE1LAzEYhIMoWGov_oKAN2FrPrebY2m1KoUq6HmJmzdt6m6yJrtI_71bKuhhmDk8zMAgdE3JlBKu7pb0dUMInfGHMzRiRLJMUKbO_-VLNElpTwaIyZzI2Qht5zhBdJBwsLiBGDqILfjgTMLfrtvhCDpG7bdgcPqEGrrgE7YxNFh7DN6EdnfoXIVt77d9wi_gXeXq2vUNTu0Ur5ar54wV8gpdWF0nmPz6GL0_3L8tHrP1ZvW0mK-ziknVZaBmRUUpH8xoaXJlLVcfRU4qy4VgKleSUWWU0UApCFpIqwdSgACWC0n4GN2cetsYvnpIXbkPffTDZMkkKwTjR43R7YmqYkgpgi3b6BodDyUl5fHL8u9L_gNExWVt</recordid><startdate>20210521</startdate><enddate>20210521</enddate><creator>Mo, Tu-Xiang</creator><creator>Huang, Xi-Shan</creator><creator>Zhang, Wen-Xiu</creator><creator>Schäberle, Till F.</creator><creator>Qin, Jiang-Ke</creator><creator>Zhou, De-Xiong</creator><creator>Qin, Xiao-Ya</creator><creator>Xu, Zhao-Long</creator><creator>Li, Jun</creator><creator>Yang, Rui-Yun</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0002-3306-4700</orcidid><orcidid>https://orcid.org/0000-0001-9947-8079</orcidid></search><sort><creationdate>20210521</creationdate><title>A series of meroterpenoids with rearranged skeletons from an endophytic fungus Penicillium sp. GDGJ-285</title><author>Mo, Tu-Xiang ; Huang, Xi-Shan ; Zhang, Wen-Xiu ; Schäberle, Till F. ; Qin, Jiang-Ke ; Zhou, De-Xiong ; Qin, Xiao-Ya ; Xu, Zhao-Long ; Li, Jun ; Yang, Rui-Yun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c259t-e978c113978da5d69ff39b860cf34429695219d9dae11e4185fa8da4e4e264503</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Bioassays</topic><topic>Crystallography</topic><topic>Endophytes</topic><topic>Fungi</topic><topic>Lipopolysaccharides</topic><topic>Macrophages</topic><topic>Magnetic resonance spectroscopy</topic><topic>Nitric oxide</topic><topic>NMR</topic><topic>NMR spectroscopy</topic><topic>Nuclear magnetic resonance</topic><topic>Organic chemistry</topic><topic>Penicillium</topic><topic>Single crystals</topic><topic>Spectrum analysis</topic><topic>X-ray crystallography</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mo, Tu-Xiang</creatorcontrib><creatorcontrib>Huang, Xi-Shan</creatorcontrib><creatorcontrib>Zhang, Wen-Xiu</creatorcontrib><creatorcontrib>Schäberle, Till F.</creatorcontrib><creatorcontrib>Qin, Jiang-Ke</creatorcontrib><creatorcontrib>Zhou, De-Xiong</creatorcontrib><creatorcontrib>Qin, Xiao-Ya</creatorcontrib><creatorcontrib>Xu, Zhao-Long</creatorcontrib><creatorcontrib>Li, Jun</creatorcontrib><creatorcontrib>Yang, Rui-Yun</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic Chemistry Frontiers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mo, Tu-Xiang</au><au>Huang, Xi-Shan</au><au>Zhang, Wen-Xiu</au><au>Schäberle, Till F.</au><au>Qin, Jiang-Ke</au><au>Zhou, De-Xiong</au><au>Qin, Xiao-Ya</au><au>Xu, Zhao-Long</au><au>Li, Jun</au><au>Yang, Rui-Yun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A series of meroterpenoids with rearranged skeletons from an endophytic fungus Penicillium sp. GDGJ-285</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2021-05-21</date><risdate>2021</risdate><volume>8</volume><issue>10</issue><spage>2232</spage><epage>2241</epage><pages>2232-2241</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>Under the guidance of MS/MS based molecular networking, five new meroterpenoids (
1–5
), including three novel skeleton meroterpenoids, peniclactones A–C (
1–3
), and two new isoaustinone analogues, 6-hydroxyisoaustinone (
4
) and 6-ketoisoaustinone (
5
), were isolated from the fungus
Penicillium
sp. GDGJ-285. Their structures were elucidated by HRMS and NMR spectroscopy, and their absolute configurations were determined by X-ray single-crystal diffraction analysis. Peniclactones A–C (
1–3
) represent the first meroterpenoids featuring a 6/5/6/6/5/6 (
1
), 6/5/6/6/5/5 (
2
), and 6/5/6/5/5/6 (
3
) hexacyclic ring system, respectively. Bioassays showed that compound
3
inhibited nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophage cells with an IC
50
value of 39.03 μM.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D1QO00173F</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-3306-4700</orcidid><orcidid>https://orcid.org/0000-0001-9947-8079</orcidid></addata></record> |
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| ispartof | Organic Chemistry Frontiers, 2021-05, Vol.8 (10), p.2232-2241 |
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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Bioassays Crystallography Endophytes Fungi Lipopolysaccharides Macrophages Magnetic resonance spectroscopy Nitric oxide NMR NMR spectroscopy Nuclear magnetic resonance Organic chemistry Penicillium Single crystals Spectrum analysis X-ray crystallography |
| title | A series of meroterpenoids with rearranged skeletons from an endophytic fungus Penicillium sp. GDGJ-285 |
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