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Penicisulfuranols A–F, Alkaloids from the Mangrove Endophytic Fungus Penicillium janthinellum HDN13-309
Six new epipolythiodioxopiperazine (ETP) alkaloids, penicisulfuranols A–F (1–6), were isolated from the mangrove endophytic fungus Penicillium janthinellum HDN13-309. All structures including absolute configurations were elucidated on the basis of comprehensive spectroscopic data and ECD calculation...
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| Published in: | Journal of natural products (Washington, D.C.) D.C.), 2017-01, Vol.80 (1), p.71-75 |
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| Main Authors: | , , , , , , , , |
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| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-a414t-3ed44f49d4a11858ff8f249407dcef5c06b07e39b53611545031e47264ac5203 |
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| cites | cdi_FETCH-LOGICAL-a414t-3ed44f49d4a11858ff8f249407dcef5c06b07e39b53611545031e47264ac5203 |
| container_end_page | 75 |
| container_issue | 1 |
| container_start_page | 71 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 80 |
| creator | Zhu, Meilin Zhang, Xiaomin Feng, Huimin Dai, Jiajia Li, Jing Che, Qian Gu, Qianqun Zhu, Tianjiao Li, Dehai |
| description | Six new epipolythiodioxopiperazine (ETP) alkaloids, penicisulfuranols A–F (1–6), were isolated from the mangrove endophytic fungus Penicillium janthinellum HDN13-309. All structures including absolute configurations were elucidated on the basis of comprehensive spectroscopic data and ECD calculations. They belong to the unusual family of ETPs containing sulfur atoms on both α- and β-positions of amino acid residues and a rare 1,2-oxazadecaline core moiety. In addition, compounds 1–6 also possess a rare spiro-furan ring and 1–3 showed cytotoxicity with IC50 values ranging from 0.1 to 3.9 μM. |
| doi_str_mv | 10.1021/acs.jnatprod.6b00483 |
| format | article |
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All structures including absolute configurations were elucidated on the basis of comprehensive spectroscopic data and ECD calculations. They belong to the unusual family of ETPs containing sulfur atoms on both α- and β-positions of amino acid residues and a rare 1,2-oxazadecaline core moiety. 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Nat. Prod</addtitle><description>Six new epipolythiodioxopiperazine (ETP) alkaloids, penicisulfuranols A–F (1–6), were isolated from the mangrove endophytic fungus Penicillium janthinellum HDN13-309. All structures including absolute configurations were elucidated on the basis of comprehensive spectroscopic data and ECD calculations. They belong to the unusual family of ETPs containing sulfur atoms on both α- and β-positions of amino acid residues and a rare 1,2-oxazadecaline core moiety. In addition, compounds 1–6 also possess a rare spiro-furan ring and 1–3 showed cytotoxicity with IC50 values ranging from 0.1 to 3.9 μM.</description><subject>Alkaloids - chemistry</subject><subject>Alkaloids - isolation & purification</subject><subject>Citrinin - chemistry</subject><subject>Citrinin - isolation & purification</subject><subject>Crystallography, X-Ray</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Oxazines - chemistry</subject><subject>Penicillium - chemistry</subject><subject>Piperazines - chemistry</subject><subject>Piperazines - isolation & purification</subject><subject>Rhizophoraceae - chemistry</subject><subject>Rhizophoraceae - microbiology</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp9kM1OGzEUha0KVELaN6gqL1l0wvXfZGYZpQkg8dMF-5EzYxOnHjvY40rZ9R14Q54EQwJLVldXOufcez6EfhCYEKDkXLZxsnFy2AbfTcoVAK_YFzQigkJRAhVHaASkZAWrSn6CTmPcAACDWnxFJ3Ra15RUbITMH-VMa2KyOgXpvI149vz_afkLz-xfab3pItbB93hYK3wj3UPw_xReuM5v17vBtHiZ3EOKeB9jrUk93kg3rI1T1ubl8vctyU9A_Q0da2mj-n6YY3S_XNzPL4vru4ur-ey6kJzwoWCq41zzuuOSkEpUWlea8prDtGuVFi3kqlPF6pVgJSGCC2BE8SktuWxzdTZGZ_vYzOUxqTg0vYlt_kU65VNsciahVS0EzVK-l7bBxxiUbrbB9DLsGgLNK-MmM27eGTcHxtn283AhrXrVfZjeoWYB7AVvdp-Cy30_z3wBHuaL_A</recordid><startdate>20170127</startdate><enddate>20170127</enddate><creator>Zhu, Meilin</creator><creator>Zhang, Xiaomin</creator><creator>Feng, Huimin</creator><creator>Dai, Jiajia</creator><creator>Li, Jing</creator><creator>Che, Qian</creator><creator>Gu, Qianqun</creator><creator>Zhu, Tianjiao</creator><creator>Li, Dehai</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></search><sort><creationdate>20170127</creationdate><title>Penicisulfuranols A–F, Alkaloids from the Mangrove Endophytic Fungus Penicillium janthinellum HDN13-309</title><author>Zhu, Meilin ; Zhang, Xiaomin ; Feng, Huimin ; Dai, Jiajia ; Li, Jing ; Che, Qian ; Gu, Qianqun ; Zhu, Tianjiao ; Li, Dehai</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a414t-3ed44f49d4a11858ff8f249407dcef5c06b07e39b53611545031e47264ac5203</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Alkaloids - chemistry</topic><topic>Alkaloids - isolation & purification</topic><topic>Citrinin - chemistry</topic><topic>Citrinin - isolation & purification</topic><topic>Crystallography, X-Ray</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Oxazines - chemistry</topic><topic>Penicillium - chemistry</topic><topic>Piperazines - chemistry</topic><topic>Piperazines - isolation & purification</topic><topic>Rhizophoraceae - chemistry</topic><topic>Rhizophoraceae - microbiology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhu, Meilin</creatorcontrib><creatorcontrib>Zhang, Xiaomin</creatorcontrib><creatorcontrib>Feng, Huimin</creatorcontrib><creatorcontrib>Dai, Jiajia</creatorcontrib><creatorcontrib>Li, Jing</creatorcontrib><creatorcontrib>Che, Qian</creatorcontrib><creatorcontrib>Gu, Qianqun</creatorcontrib><creatorcontrib>Zhu, Tianjiao</creatorcontrib><creatorcontrib>Li, Dehai</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>Zhu, Meilin</au><au>Zhang, Xiaomin</au><au>Feng, Huimin</au><au>Dai, Jiajia</au><au>Li, Jing</au><au>Che, Qian</au><au>Gu, Qianqun</au><au>Zhu, Tianjiao</au><au>Li, Dehai</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Penicisulfuranols A–F, Alkaloids from the Mangrove Endophytic Fungus Penicillium janthinellum HDN13-309</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2017-01-27</date><risdate>2017</risdate><volume>80</volume><issue>1</issue><spage>71</spage><epage>75</epage><pages>71-75</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>Six new epipolythiodioxopiperazine (ETP) alkaloids, penicisulfuranols A–F (1–6), were isolated from the mangrove endophytic fungus Penicillium janthinellum HDN13-309. All structures including absolute configurations were elucidated on the basis of comprehensive spectroscopic data and ECD calculations. They belong to the unusual family of ETPs containing sulfur atoms on both α- and β-positions of amino acid residues and a rare 1,2-oxazadecaline core moiety. 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| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2017-01, Vol.80 (1), p.71-75 |
| issn | 0163-3864 1520-6025 |
| language | eng |
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| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Alkaloids - chemistry Alkaloids - isolation & purification Citrinin - chemistry Citrinin - isolation & purification Crystallography, X-Ray Molecular Structure Nuclear Magnetic Resonance, Biomolecular Oxazines - chemistry Penicillium - chemistry Piperazines - chemistry Piperazines - isolation & purification Rhizophoraceae - chemistry Rhizophoraceae - microbiology |
| title | Penicisulfuranols A–F, Alkaloids from the Mangrove Endophytic Fungus Penicillium janthinellum HDN13-309 |
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