Spirograterpene A, a Tetracyclic Spiro-Diterpene with a Fused 5/5/5/5 Ring System from the Deep-Sea-Derived Fungus Penicillium granulatum MCCC 3A00475

A novel spiro-tetracyclic diterpene, spirograterpene A (1), was isolated from the deep-sea-derived fungus Penicillium granulatum MCCC 3A00475, together with two biosynthetically related cyclopianes, conidiogenone I (2) and conidiogenone C (3). The relative configuration of 1 was elucidated by extens...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of natural products (Washington, D.C.) D.C.), 2017-07, Vol.80 (7), p.2174-2177
Hauptverfasser: Niu, Siwen, Fan, Zuo-Wang, Xie, Chun-Lan, Liu, Qingmei, Luo, Zhu-Hua, Liu, Guangming, Yang, Xian-Wen
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 2177
container_issue 7
container_start_page 2174
container_title Journal of natural products (Washington, D.C.)
container_volume 80
creator Niu, Siwen
Fan, Zuo-Wang
Xie, Chun-Lan
Liu, Qingmei
Luo, Zhu-Hua
Liu, Guangming
Yang, Xian-Wen
description A novel spiro-tetracyclic diterpene, spirograterpene A (1), was isolated from the deep-sea-derived fungus Penicillium granulatum MCCC 3A00475, together with two biosynthetically related cyclopianes, conidiogenone I (2) and conidiogenone C (3). The relative configuration of 1 was elucidated by extensive spectroscopic analyses, and the absolute structure was established by the modified Mosher’s method. Compound 1 is the second example of a diterpene featuring a 5/5/5/5 spirocyclic carbon skeleton. It showed modest antiallergic activity.
doi_str_mv 10.1021/acs.jnatprod.7b00475
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1917963744</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1917963744</sourcerecordid><originalsourceid>FETCH-LOGICAL-a348t-623be91aa7c503db81ec97bd564a2ea436a4f281279ecd5474b1bfad40e0a24d3</originalsourceid><addsrcrecordid>eNp9kcluFDEQhi0EIpPAGyDkIwd64q2346iHCUhBiTLh3Kp2V08c9YYX0LwIz4szC0dUB9fh-6tU_gj5wNmSM8GvQbvl8wh-tlO7zBvGVJ6-IgueCpZkTKSvyYLxTCayyNQFuXTumTEmWZm-JReiyEohcrEgf7azsdPOgkc744h09ZkCfURvQe91bzQ9AMnanIHfxj9FZBMctjS9PhR9MOOObvfO40A7Ow3UPyFdI87JFiFZozW_Ir0J4y44eo-j0abvTRho3DyGHnxsv1dVReXqcMg78qaD3uH703tFfmy-PFZfk9u7m2_V6jYBqQqfZEI2WHKAXKdMtk3BUZd506aZAoGgZAaqEwUXeYm6TVWuGt500CqGDIRq5RX5dJwbf_FnQOfrwTiNfQ8jTsHVvOR5mclcqYiqI6rt5JzFrp6tGcDua87qFyN1NFKfjdQnIzH28bQhNAO2_0JnBRFgR-AQn4Id48H_n_kXSsqaeg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1917963744</pqid></control><display><type>article</type><title>Spirograterpene A, a Tetracyclic Spiro-Diterpene with a Fused 5/5/5/5 Ring System from the Deep-Sea-Derived Fungus Penicillium granulatum MCCC 3A00475</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Niu, Siwen ; Fan, Zuo-Wang ; Xie, Chun-Lan ; Liu, Qingmei ; Luo, Zhu-Hua ; Liu, Guangming ; Yang, Xian-Wen</creator><creatorcontrib>Niu, Siwen ; Fan, Zuo-Wang ; Xie, Chun-Lan ; Liu, Qingmei ; Luo, Zhu-Hua ; Liu, Guangming ; Yang, Xian-Wen</creatorcontrib><description>A novel spiro-tetracyclic diterpene, spirograterpene A (1), was isolated from the deep-sea-derived fungus Penicillium granulatum MCCC 3A00475, together with two biosynthetically related cyclopianes, conidiogenone I (2) and conidiogenone C (3). The relative configuration of 1 was elucidated by extensive spectroscopic analyses, and the absolute structure was established by the modified Mosher’s method. Compound 1 is the second example of a diterpene featuring a 5/5/5/5 spirocyclic carbon skeleton. It showed modest antiallergic activity.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/acs.jnatprod.7b00475</identifier><identifier>PMID: 28692272</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Anti-Allergic Agents - chemistry ; Anti-Allergic Agents - isolation &amp; purification ; Anti-Allergic Agents - pharmacology ; Diterpenes - chemistry ; Diterpenes - isolation &amp; purification ; Diterpenes - pharmacology ; Marine Biology ; Molecular Structure ; Penicillium - chemistry ; Spiro Compounds</subject><ispartof>Journal of natural products (Washington, D.C.), 2017-07, Vol.80 (7), p.2174-2177</ispartof><rights>Copyright © 2017 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a348t-623be91aa7c503db81ec97bd564a2ea436a4f281279ecd5474b1bfad40e0a24d3</citedby><cites>FETCH-LOGICAL-a348t-623be91aa7c503db81ec97bd564a2ea436a4f281279ecd5474b1bfad40e0a24d3</cites><orcidid>0000-0002-8689-0504 ; 0000-0002-4967-0844</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.jnatprod.7b00475$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jnatprod.7b00475$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28692272$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Niu, Siwen</creatorcontrib><creatorcontrib>Fan, Zuo-Wang</creatorcontrib><creatorcontrib>Xie, Chun-Lan</creatorcontrib><creatorcontrib>Liu, Qingmei</creatorcontrib><creatorcontrib>Luo, Zhu-Hua</creatorcontrib><creatorcontrib>Liu, Guangming</creatorcontrib><creatorcontrib>Yang, Xian-Wen</creatorcontrib><title>Spirograterpene A, a Tetracyclic Spiro-Diterpene with a Fused 5/5/5/5 Ring System from the Deep-Sea-Derived Fungus Penicillium granulatum MCCC 3A00475</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>A novel spiro-tetracyclic diterpene, spirograterpene A (1), was isolated from the deep-sea-derived fungus Penicillium granulatum MCCC 3A00475, together with two biosynthetically related cyclopianes, conidiogenone I (2) and conidiogenone C (3). The relative configuration of 1 was elucidated by extensive spectroscopic analyses, and the absolute structure was established by the modified Mosher’s method. Compound 1 is the second example of a diterpene featuring a 5/5/5/5 spirocyclic carbon skeleton. It showed modest antiallergic activity.</description><subject>Anti-Allergic Agents - chemistry</subject><subject>Anti-Allergic Agents - isolation &amp; purification</subject><subject>Anti-Allergic Agents - pharmacology</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - isolation &amp; purification</subject><subject>Diterpenes - pharmacology</subject><subject>Marine Biology</subject><subject>Molecular Structure</subject><subject>Penicillium - chemistry</subject><subject>Spiro Compounds</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kcluFDEQhi0EIpPAGyDkIwd64q2346iHCUhBiTLh3Kp2V08c9YYX0LwIz4szC0dUB9fh-6tU_gj5wNmSM8GvQbvl8wh-tlO7zBvGVJ6-IgueCpZkTKSvyYLxTCayyNQFuXTumTEmWZm-JReiyEohcrEgf7azsdPOgkc744h09ZkCfURvQe91bzQ9AMnanIHfxj9FZBMctjS9PhR9MOOObvfO40A7Ow3UPyFdI87JFiFZozW_Ir0J4y44eo-j0abvTRho3DyGHnxsv1dVReXqcMg78qaD3uH703tFfmy-PFZfk9u7m2_V6jYBqQqfZEI2WHKAXKdMtk3BUZd506aZAoGgZAaqEwUXeYm6TVWuGt500CqGDIRq5RX5dJwbf_FnQOfrwTiNfQ8jTsHVvOR5mclcqYiqI6rt5JzFrp6tGcDua87qFyN1NFKfjdQnIzH28bQhNAO2_0JnBRFgR-AQn4Id48H_n_kXSsqaeg</recordid><startdate>20170728</startdate><enddate>20170728</enddate><creator>Niu, Siwen</creator><creator>Fan, Zuo-Wang</creator><creator>Xie, Chun-Lan</creator><creator>Liu, Qingmei</creator><creator>Luo, Zhu-Hua</creator><creator>Liu, Guangming</creator><creator>Yang, Xian-Wen</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><orcidid>https://orcid.org/0000-0002-8689-0504</orcidid><orcidid>https://orcid.org/0000-0002-4967-0844</orcidid></search><sort><creationdate>20170728</creationdate><title>Spirograterpene A, a Tetracyclic Spiro-Diterpene with a Fused 5/5/5/5 Ring System from the Deep-Sea-Derived Fungus Penicillium granulatum MCCC 3A00475</title><author>Niu, Siwen ; Fan, Zuo-Wang ; Xie, Chun-Lan ; Liu, Qingmei ; Luo, Zhu-Hua ; Liu, Guangming ; Yang, Xian-Wen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a348t-623be91aa7c503db81ec97bd564a2ea436a4f281279ecd5474b1bfad40e0a24d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Anti-Allergic Agents - chemistry</topic><topic>Anti-Allergic Agents - isolation &amp; purification</topic><topic>Anti-Allergic Agents - pharmacology</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - isolation &amp; purification</topic><topic>Diterpenes - pharmacology</topic><topic>Marine Biology</topic><topic>Molecular Structure</topic><topic>Penicillium - chemistry</topic><topic>Spiro Compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Niu, Siwen</creatorcontrib><creatorcontrib>Fan, Zuo-Wang</creatorcontrib><creatorcontrib>Xie, Chun-Lan</creatorcontrib><creatorcontrib>Liu, Qingmei</creatorcontrib><creatorcontrib>Luo, Zhu-Hua</creatorcontrib><creatorcontrib>Liu, Guangming</creatorcontrib><creatorcontrib>Yang, Xian-Wen</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>Niu, Siwen</au><au>Fan, Zuo-Wang</au><au>Xie, Chun-Lan</au><au>Liu, Qingmei</au><au>Luo, Zhu-Hua</au><au>Liu, Guangming</au><au>Yang, Xian-Wen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Spirograterpene A, a Tetracyclic Spiro-Diterpene with a Fused 5/5/5/5 Ring System from the Deep-Sea-Derived Fungus Penicillium granulatum MCCC 3A00475</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2017-07-28</date><risdate>2017</risdate><volume>80</volume><issue>7</issue><spage>2174</spage><epage>2177</epage><pages>2174-2177</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>A novel spiro-tetracyclic diterpene, spirograterpene A (1), was isolated from the deep-sea-derived fungus Penicillium granulatum MCCC 3A00475, together with two biosynthetically related cyclopianes, conidiogenone I (2) and conidiogenone C (3). The relative configuration of 1 was elucidated by extensive spectroscopic analyses, and the absolute structure was established by the modified Mosher’s method. Compound 1 is the second example of a diterpene featuring a 5/5/5/5 spirocyclic carbon skeleton. It showed modest antiallergic activity.</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>28692272</pmid><doi>10.1021/acs.jnatprod.7b00475</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-8689-0504</orcidid><orcidid>https://orcid.org/0000-0002-4967-0844</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0163-3864
ispartof Journal of natural products (Washington, D.C.), 2017-07, Vol.80 (7), p.2174-2177
issn 0163-3864
1520-6025
language eng
recordid cdi_proquest_miscellaneous_1917963744
source MEDLINE; American Chemical Society Journals
subjects Anti-Allergic Agents - chemistry
Anti-Allergic Agents - isolation & purification
Anti-Allergic Agents - pharmacology
Diterpenes - chemistry
Diterpenes - isolation & purification
Diterpenes - pharmacology
Marine Biology
Molecular Structure
Penicillium - chemistry
Spiro Compounds
title Spirograterpene A, a Tetracyclic Spiro-Diterpene with a Fused 5/5/5/5 Ring System from the Deep-Sea-Derived Fungus Penicillium granulatum MCCC 3A00475
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-02T08%3A45%3A09IST&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=Spirograterpene%20A,%20a%20Tetracyclic%20Spiro-Diterpene%20with%20a%20Fused%205/5/5/5%20Ring%20System%20from%20the%20Deep-Sea-Derived%20Fungus%20Penicillium%20granulatum%20MCCC%203A00475&rft.jtitle=Journal%20of%20natural%20products%20(Washington,%20D.C.)&rft.au=Niu,%20Siwen&rft.date=2017-07-28&rft.volume=80&rft.issue=7&rft.spage=2174&rft.epage=2177&rft.pages=2174-2177&rft.issn=0163-3864&rft.eissn=1520-6025&rft_id=info:doi/10.1021/acs.jnatprod.7b00475&rft_dat=%3Cproquest_cross%3E1917963744%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=1917963744&rft_id=info:pmid/28692272&rfr_iscdi=true