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Brasilamides A-D: Sesquiterpenoids from the Plant Endophytic Fungus Paraconiothyrium brasiliense
New tricyclic sesquiterpenoids brasilamides A–D (1–4) and the known pinthunamide (5) have been isolated from cultures of the plant endophytic fungus Paraconiothyrium brasiliense Verkley. Their structures were elucidated primarily by NMR spectroscopy, and the structure of 1 was further confirmed by X...
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| Published in: | European Journal of Organic Chemistry 2010-06, Vol.2010 (17), p.3302-3306 |
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| Main Authors: | , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c3574-e0187ad4e06bc3fc84a0b17a3d1c6f1ae5b74af86aa862e1658eece1d8629ec23 |
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| cites | cdi_FETCH-LOGICAL-c3574-e0187ad4e06bc3fc84a0b17a3d1c6f1ae5b74af86aa862e1658eece1d8629ec23 |
| container_end_page | 3306 |
| container_issue | 17 |
| container_start_page | 3302 |
| container_title | European Journal of Organic Chemistry |
| container_volume | 2010 |
| creator | Liu, Ling Gao, Hao Chen, Xulin Cai, Xiaoyue Yang, Leilei Guo, Liangdong Yao, Xinsheng Che, Yongsheng |
| description | New tricyclic sesquiterpenoids brasilamides A–D (1–4) and the known pinthunamide (5) have been isolated from cultures of the plant endophytic fungus Paraconiothyrium brasiliense Verkley. Their structures were elucidated primarily by NMR spectroscopy, and the structure of 1 was further confirmed by X‐ray crystallography. The absolute configuration of the C‐5 tertiary alcohol in 2 was assigned by analogy to 1 and confirmed by observing the circular dichroism of in situ generated [Rh2(OCOCF3)4] complex. Compounds 2–4 showed modest inhibitory effects on HIV‐1 replication in C8166 cells. Compounds 1 and 2 possess an unprecedented4‐oxatricyclo‐[3.3.1.02,7]nonane skeleton.
Paraconiothyrium brasiliense produced four new tricyclic sesquiterpenoids namedbrasilamides A–D (1–4); compounds 1 and 2 possess an unprecedented 4‐oxatricyclo[3.3.1.02,7]nonane skeleton. Compounds 2–4 showed modest inhibitory effects on HIV‐1 replication in C8166 cells. |
| doi_str_mv | 10.1002/ejoc.201000284 |
| format | article |
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Paraconiothyrium brasiliense produced four new tricyclic sesquiterpenoids namedbrasilamides A–D (1–4); compounds 1 and 2 possess an unprecedented 4‐oxatricyclo[3.3.1.02,7]nonane skeleton. Compounds 2–4 showed modest inhibitory effects on HIV‐1 replication in C8166 cells.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201000284</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids ; Antiviral agents ; Biological activity ; Chemistry ; Configuration determination ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Natural products ; Organic chemistry ; Preparations and properties ; Structure elucidation ; Terpenoids</subject><ispartof>European Journal of Organic Chemistry, 2010-06, Vol.2010 (17), p.3302-3306</ispartof><rights>Copyright © 2010 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3574-e0187ad4e06bc3fc84a0b17a3d1c6f1ae5b74af86aa862e1658eece1d8629ec23</citedby><cites>FETCH-LOGICAL-c3574-e0187ad4e06bc3fc84a0b17a3d1c6f1ae5b74af86aa862e1658eece1d8629ec23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>313,314,780,784,792,27922,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22912036$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Ling</creatorcontrib><creatorcontrib>Gao, Hao</creatorcontrib><creatorcontrib>Chen, Xulin</creatorcontrib><creatorcontrib>Cai, Xiaoyue</creatorcontrib><creatorcontrib>Yang, Leilei</creatorcontrib><creatorcontrib>Guo, Liangdong</creatorcontrib><creatorcontrib>Yao, Xinsheng</creatorcontrib><creatorcontrib>Che, Yongsheng</creatorcontrib><title>Brasilamides A-D: Sesquiterpenoids from the Plant Endophytic Fungus Paraconiothyrium brasiliense</title><title>European Journal of Organic Chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>New tricyclic sesquiterpenoids brasilamides A–D (1–4) and the known pinthunamide (5) have been isolated from cultures of the plant endophytic fungus Paraconiothyrium brasiliense Verkley. Their structures were elucidated primarily by NMR spectroscopy, and the structure of 1 was further confirmed by X‐ray crystallography. The absolute configuration of the C‐5 tertiary alcohol in 2 was assigned by analogy to 1 and confirmed by observing the circular dichroism of in situ generated [Rh2(OCOCF3)4] complex. Compounds 2–4 showed modest inhibitory effects on HIV‐1 replication in C8166 cells. Compounds 1 and 2 possess an unprecedented4‐oxatricyclo‐[3.3.1.02,7]nonane skeleton.
Paraconiothyrium brasiliense produced four new tricyclic sesquiterpenoids namedbrasilamides A–D (1–4); compounds 1 and 2 possess an unprecedented 4‐oxatricyclo[3.3.1.02,7]nonane skeleton. Compounds 2–4 showed modest inhibitory effects on HIV‐1 replication in C8166 cells.</description><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Antiviral agents</subject><subject>Biological activity</subject><subject>Chemistry</subject><subject>Configuration determination</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Natural products</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Structure elucidation</subject><subject>Terpenoids</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNqFkL1PwzAUxCMEEqWwMnthTLHj1EnYSj-BilZqEWzmxXmhLmlS7FSQ_56UoIqN6d2T7ncnneNcMtphlHrXuC5Ux6O1pl7oHzktRqPIpSKix7X2ue-yiL-cOmfWrmtPJARrOa-3BqzOYKMTtKTnDm7IAu3HTpdotpgXOrEkNcWGlCsk8wzykgzzpNiuqlIrMtrlbztL5mBAFbkuylVl9G5D4p9QjbnFc-ckhczixe9tO0-j4bI_caez8V2_N3UV7wa-i5SFASQ-UhErnqrQBxqzAHjClEgZYDcOfEhDARAKD5nohogKWVJ_ESqPt51Ok6tMYa3BVG6N3oCpJKNyv4_c7yMP-9TAVQNswSrIUgO50vZAeV7EPMpF7Ysa36fOsPonVQ7vZ_2_HW7Dalvi14EF8y5FwIOufH4cy-n8gS-Wg4kc8W-FcYhv</recordid><startdate>201006</startdate><enddate>201006</enddate><creator>Liu, Ling</creator><creator>Gao, Hao</creator><creator>Chen, Xulin</creator><creator>Cai, Xiaoyue</creator><creator>Yang, Leilei</creator><creator>Guo, Liangdong</creator><creator>Yao, Xinsheng</creator><creator>Che, Yongsheng</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201006</creationdate><title>Brasilamides A-D: Sesquiterpenoids from the Plant Endophytic Fungus Paraconiothyrium brasiliense</title><author>Liu, Ling ; Gao, Hao ; Chen, Xulin ; Cai, Xiaoyue ; Yang, Leilei ; Guo, Liangdong ; Yao, Xinsheng ; Che, Yongsheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3574-e0187ad4e06bc3fc84a0b17a3d1c6f1ae5b74af86aa862e1658eece1d8629ec23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Antiviral agents</topic><topic>Biological activity</topic><topic>Chemistry</topic><topic>Configuration determination</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Natural products</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Structure elucidation</topic><topic>Terpenoids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Ling</creatorcontrib><creatorcontrib>Gao, Hao</creatorcontrib><creatorcontrib>Chen, Xulin</creatorcontrib><creatorcontrib>Cai, Xiaoyue</creatorcontrib><creatorcontrib>Yang, Leilei</creatorcontrib><creatorcontrib>Guo, Liangdong</creatorcontrib><creatorcontrib>Yao, Xinsheng</creatorcontrib><creatorcontrib>Che, Yongsheng</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Ling</au><au>Gao, Hao</au><au>Chen, Xulin</au><au>Cai, Xiaoyue</au><au>Yang, Leilei</au><au>Guo, Liangdong</au><au>Yao, Xinsheng</au><au>Che, Yongsheng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Brasilamides A-D: Sesquiterpenoids from the Plant Endophytic Fungus Paraconiothyrium brasiliense</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2010-06</date><risdate>2010</risdate><volume>2010</volume><issue>17</issue><spage>3302</spage><epage>3306</epage><pages>3302-3306</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>New tricyclic sesquiterpenoids brasilamides A–D (1–4) and the known pinthunamide (5) have been isolated from cultures of the plant endophytic fungus Paraconiothyrium brasiliense Verkley. Their structures were elucidated primarily by NMR spectroscopy, and the structure of 1 was further confirmed by X‐ray crystallography. The absolute configuration of the C‐5 tertiary alcohol in 2 was assigned by analogy to 1 and confirmed by observing the circular dichroism of in situ generated [Rh2(OCOCF3)4] complex. Compounds 2–4 showed modest inhibitory effects on HIV‐1 replication in C8166 cells. Compounds 1 and 2 possess an unprecedented4‐oxatricyclo‐[3.3.1.02,7]nonane skeleton.
Paraconiothyrium brasiliense produced four new tricyclic sesquiterpenoids namedbrasilamides A–D (1–4); compounds 1 and 2 possess an unprecedented 4‐oxatricyclo[3.3.1.02,7]nonane skeleton. Compounds 2–4 showed modest inhibitory effects on HIV‐1 replication in C8166 cells.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201000284</doi><tpages>5</tpages></addata></record> |
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| ispartof | European Journal of Organic Chemistry, 2010-06, Vol.2010 (17), p.3302-3306 |
| issn | 1434-193X 1099-0690 |
| language | eng |
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| source | Wiley-Blackwell Read & Publish Collection |
| subjects | Alicyclic compounds, terpenoids, prostaglandins, steroids Antiviral agents Biological activity Chemistry Configuration determination Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Natural products Organic chemistry Preparations and properties Structure elucidation Terpenoids |
| title | Brasilamides A-D: Sesquiterpenoids from the Plant Endophytic Fungus Paraconiothyrium brasiliense |
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