Isolation, Characterization, and Antiproliferative Activity of Terpenoids from the Tropical Plant Turraea delphinensis
The isolation, structure determination, and biological evaluation of constituents from the organic extract of Turraea delphinensis Wahlert (Meliaceae) resulted in the isolation of 51 secondary metabolites, including 14 new terpenoids (six cycloartanes, four tirucallanes/euphanes, three limonoids, an...
Gespeichert in:
Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2024-07, Vol.87 (7), p.1763-1777 |
---|---|
Hauptverfasser: | , , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 1777 |
---|---|
container_issue | 7 |
container_start_page | 1763 |
container_title | Journal of natural products (Washington, D.C.) |
container_volume | 87 |
creator | Kouno, Hayato Amuti, Saidanxia Saito, Yohei Fukuyoshi, Shuichi Miyake, Katsunori Goto, Masuo Newman, David J. O’Keefe, Barry R. Lee, Kuo-Hsiung Nakagawa-Goto, Kyoko |
description | The isolation, structure determination, and biological evaluation of constituents from the organic extract of Turraea delphinensis Wahlert (Meliaceae) resulted in the isolation of 51 secondary metabolites, including 14 new terpenoids (six cycloartanes, four tirucallanes/euphanes, three limonoids, and a 7-keto sterol). Among the new compounds, 1 is the first triterpenoid with a trioxaspiro[4.4]nonane side chain, while 11–13 are the first 17-γ-lactone tetranortriterpenoids with four oxygenated functional groups at C-1, -3, -6, and -7. The isolated compounds were evaluated for antiproliferative activity against five human tumor cell lines, including a vinblastine-resistant cell line. |
doi_str_mv | 10.1021/acs.jnatprod.4c00313 |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_3153742746</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3153742746</sourcerecordid><originalsourceid>FETCH-LOGICAL-a260t-691ad17af49f5a54df2425f5f3464c86fcfe5138a78d30a61e2e9af0e1c05ab83</originalsourceid><addsrcrecordid>eNqFkU1v1DAQhi0EotuPf4CQjxzI1t9JjqtVgUqV4LCco6kz1rrK2sF2KrW_HtPdcoTTSKPnnfH4IeQDZ2vOBL8Gm9cPAcqc4rhWljHJ5Ruy4lqwxjCh35IV40Y2sjPqjJzn_MAqw3r9npzJrm-ZZmpFHm9znKD4GD7T7R4S2ILJP586EEa6CcXXHZN3mGr7EenG1uLLE42O7jDNGKIfM3UpHmjZI92lOHsLE_0xQSh0t6QECHTEad77gCH7fEneOZgyXp3qBfn55Wa3_dbcff96u93cNSAMK43pOYy8Bad6p0Gr0QkltNNOKqNsZ5x1qLnsoO1GycBwFNiDY8gt03DfyQvy6Ti3XvBrwVyGg88Wp_owjEseJNeyVaJV5v8oa40SQmlZUXVEbYo5J3TDnPwB0tPA2fBHzlDlDK9yhpOcGvt42rDcH3D8G3q1UQF2BF7icUmh_s2_Z_4GvO-g2A</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3076422453</pqid></control><display><type>article</type><title>Isolation, Characterization, and Antiproliferative Activity of Terpenoids from the Tropical Plant Turraea delphinensis</title><source>American Chemical Society Journals</source><creator>Kouno, Hayato ; Amuti, Saidanxia ; Saito, Yohei ; Fukuyoshi, Shuichi ; Miyake, Katsunori ; Goto, Masuo ; Newman, David J. ; O’Keefe, Barry R. ; Lee, Kuo-Hsiung ; Nakagawa-Goto, Kyoko</creator><creatorcontrib>Kouno, Hayato ; Amuti, Saidanxia ; Saito, Yohei ; Fukuyoshi, Shuichi ; Miyake, Katsunori ; Goto, Masuo ; Newman, David J. ; O’Keefe, Barry R. ; Lee, Kuo-Hsiung ; Nakagawa-Goto, Kyoko</creatorcontrib><description>The isolation, structure determination, and biological evaluation of constituents from the organic extract of Turraea delphinensis Wahlert (Meliaceae) resulted in the isolation of 51 secondary metabolites, including 14 new terpenoids (six cycloartanes, four tirucallanes/euphanes, three limonoids, and a 7-keto sterol). Among the new compounds, 1 is the first triterpenoid with a trioxaspiro[4.4]nonane side chain, while 11–13 are the first 17-γ-lactone tetranortriterpenoids with four oxygenated functional groups at C-1, -3, -6, and -7. The isolated compounds were evaluated for antiproliferative activity against five human tumor cell lines, including a vinblastine-resistant cell line.</description><identifier>ISSN: 0163-3864</identifier><identifier>ISSN: 1520-6025</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/acs.jnatprod.4c00313</identifier><identifier>PMID: 38970504</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>biological assessment ; cell lines ; limonoids ; Meliaceae ; neoplasm cells ; secondary metabolites ; sterols ; tropical plants</subject><ispartof>Journal of natural products (Washington, D.C.), 2024-07, Vol.87 (7), p.1763-1777</ispartof><rights>2024 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-a260t-691ad17af49f5a54df2425f5f3464c86fcfe5138a78d30a61e2e9af0e1c05ab83</cites><orcidid>0000-0002-9659-1460 ; 0000-0003-0772-4856 ; 0000-0002-4959-2428 ; 0000-0002-6562-0070 ; 0000-0002-1642-6538</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.4c00313$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jnatprod.4c00313$$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/38970504$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kouno, Hayato</creatorcontrib><creatorcontrib>Amuti, Saidanxia</creatorcontrib><creatorcontrib>Saito, Yohei</creatorcontrib><creatorcontrib>Fukuyoshi, Shuichi</creatorcontrib><creatorcontrib>Miyake, Katsunori</creatorcontrib><creatorcontrib>Goto, Masuo</creatorcontrib><creatorcontrib>Newman, David J.</creatorcontrib><creatorcontrib>O’Keefe, Barry R.</creatorcontrib><creatorcontrib>Lee, Kuo-Hsiung</creatorcontrib><creatorcontrib>Nakagawa-Goto, Kyoko</creatorcontrib><title>Isolation, Characterization, and Antiproliferative Activity of Terpenoids from the Tropical Plant Turraea delphinensis</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>The isolation, structure determination, and biological evaluation of constituents from the organic extract of Turraea delphinensis Wahlert (Meliaceae) resulted in the isolation of 51 secondary metabolites, including 14 new terpenoids (six cycloartanes, four tirucallanes/euphanes, three limonoids, and a 7-keto sterol). Among the new compounds, 1 is the first triterpenoid with a trioxaspiro[4.4]nonane side chain, while 11–13 are the first 17-γ-lactone tetranortriterpenoids with four oxygenated functional groups at C-1, -3, -6, and -7. The isolated compounds were evaluated for antiproliferative activity against five human tumor cell lines, including a vinblastine-resistant cell line.</description><subject>biological assessment</subject><subject>cell lines</subject><subject>limonoids</subject><subject>Meliaceae</subject><subject>neoplasm cells</subject><subject>secondary metabolites</subject><subject>sterols</subject><subject>tropical plants</subject><issn>0163-3864</issn><issn>1520-6025</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkU1v1DAQhi0EotuPf4CQjxzI1t9JjqtVgUqV4LCco6kz1rrK2sF2KrW_HtPdcoTTSKPnnfH4IeQDZ2vOBL8Gm9cPAcqc4rhWljHJ5Ruy4lqwxjCh35IV40Y2sjPqjJzn_MAqw3r9npzJrm-ZZmpFHm9znKD4GD7T7R4S2ILJP586EEa6CcXXHZN3mGr7EenG1uLLE42O7jDNGKIfM3UpHmjZI92lOHsLE_0xQSh0t6QECHTEad77gCH7fEneOZgyXp3qBfn55Wa3_dbcff96u93cNSAMK43pOYy8Bad6p0Gr0QkltNNOKqNsZ5x1qLnsoO1GycBwFNiDY8gt03DfyQvy6Ti3XvBrwVyGg88Wp_owjEseJNeyVaJV5v8oa40SQmlZUXVEbYo5J3TDnPwB0tPA2fBHzlDlDK9yhpOcGvt42rDcH3D8G3q1UQF2BF7icUmh_s2_Z_4GvO-g2A</recordid><startdate>20240726</startdate><enddate>20240726</enddate><creator>Kouno, Hayato</creator><creator>Amuti, Saidanxia</creator><creator>Saito, Yohei</creator><creator>Fukuyoshi, Shuichi</creator><creator>Miyake, Katsunori</creator><creator>Goto, Masuo</creator><creator>Newman, David J.</creator><creator>O’Keefe, Barry R.</creator><creator>Lee, Kuo-Hsiung</creator><creator>Nakagawa-Goto, Kyoko</creator><general>American Chemical Society and American Society of Pharmacognosy</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><orcidid>https://orcid.org/0000-0002-9659-1460</orcidid><orcidid>https://orcid.org/0000-0003-0772-4856</orcidid><orcidid>https://orcid.org/0000-0002-4959-2428</orcidid><orcidid>https://orcid.org/0000-0002-6562-0070</orcidid><orcidid>https://orcid.org/0000-0002-1642-6538</orcidid></search><sort><creationdate>20240726</creationdate><title>Isolation, Characterization, and Antiproliferative Activity of Terpenoids from the Tropical Plant Turraea delphinensis</title><author>Kouno, Hayato ; Amuti, Saidanxia ; Saito, Yohei ; Fukuyoshi, Shuichi ; Miyake, Katsunori ; Goto, Masuo ; Newman, David J. ; O’Keefe, Barry R. ; Lee, Kuo-Hsiung ; Nakagawa-Goto, Kyoko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a260t-691ad17af49f5a54df2425f5f3464c86fcfe5138a78d30a61e2e9af0e1c05ab83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>biological assessment</topic><topic>cell lines</topic><topic>limonoids</topic><topic>Meliaceae</topic><topic>neoplasm cells</topic><topic>secondary metabolites</topic><topic>sterols</topic><topic>tropical plants</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kouno, Hayato</creatorcontrib><creatorcontrib>Amuti, Saidanxia</creatorcontrib><creatorcontrib>Saito, Yohei</creatorcontrib><creatorcontrib>Fukuyoshi, Shuichi</creatorcontrib><creatorcontrib>Miyake, Katsunori</creatorcontrib><creatorcontrib>Goto, Masuo</creatorcontrib><creatorcontrib>Newman, David J.</creatorcontrib><creatorcontrib>O’Keefe, Barry R.</creatorcontrib><creatorcontrib>Lee, Kuo-Hsiung</creatorcontrib><creatorcontrib>Nakagawa-Goto, Kyoko</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kouno, Hayato</au><au>Amuti, Saidanxia</au><au>Saito, Yohei</au><au>Fukuyoshi, Shuichi</au><au>Miyake, Katsunori</au><au>Goto, Masuo</au><au>Newman, David J.</au><au>O’Keefe, Barry R.</au><au>Lee, Kuo-Hsiung</au><au>Nakagawa-Goto, Kyoko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isolation, Characterization, and Antiproliferative Activity of Terpenoids from the Tropical Plant Turraea delphinensis</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2024-07-26</date><risdate>2024</risdate><volume>87</volume><issue>7</issue><spage>1763</spage><epage>1777</epage><pages>1763-1777</pages><issn>0163-3864</issn><issn>1520-6025</issn><eissn>1520-6025</eissn><abstract>The isolation, structure determination, and biological evaluation of constituents from the organic extract of Turraea delphinensis Wahlert (Meliaceae) resulted in the isolation of 51 secondary metabolites, including 14 new terpenoids (six cycloartanes, four tirucallanes/euphanes, three limonoids, and a 7-keto sterol). Among the new compounds, 1 is the first triterpenoid with a trioxaspiro[4.4]nonane side chain, while 11–13 are the first 17-γ-lactone tetranortriterpenoids with four oxygenated functional groups at C-1, -3, -6, and -7. The isolated compounds were evaluated for antiproliferative activity against five human tumor cell lines, including a vinblastine-resistant cell line.</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>38970504</pmid><doi>10.1021/acs.jnatprod.4c00313</doi><tpages>15</tpages><orcidid>https://orcid.org/0000-0002-9659-1460</orcidid><orcidid>https://orcid.org/0000-0003-0772-4856</orcidid><orcidid>https://orcid.org/0000-0002-4959-2428</orcidid><orcidid>https://orcid.org/0000-0002-6562-0070</orcidid><orcidid>https://orcid.org/0000-0002-1642-6538</orcidid></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0163-3864 |
ispartof | Journal of natural products (Washington, D.C.), 2024-07, Vol.87 (7), p.1763-1777 |
issn | 0163-3864 1520-6025 1520-6025 |
language | eng |
recordid | cdi_proquest_miscellaneous_3153742746 |
source | American Chemical Society Journals |
subjects | biological assessment cell lines limonoids Meliaceae neoplasm cells secondary metabolites sterols tropical plants |
title | Isolation, Characterization, and Antiproliferative Activity of Terpenoids from the Tropical Plant Turraea delphinensis |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-07T03%3A44%3A06IST&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=Isolation,%20Characterization,%20and%20Antiproliferative%20Activity%20of%20Terpenoids%20from%20the%20Tropical%20Plant%20Turraea%20delphinensis&rft.jtitle=Journal%20of%20natural%20products%20(Washington,%20D.C.)&rft.au=Kouno,%20Hayato&rft.date=2024-07-26&rft.volume=87&rft.issue=7&rft.spage=1763&rft.epage=1777&rft.pages=1763-1777&rft.issn=0163-3864&rft.eissn=1520-6025&rft_id=info:doi/10.1021/acs.jnatprod.4c00313&rft_dat=%3Cproquest_cross%3E3153742746%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=3076422453&rft_id=info:pmid/38970504&rfr_iscdi=true |