Bioactive Compounds from the Aerial Parts of Evolvulus linarioides
Three new caryophyllane-type sesquiterpenoids, linariophyllenes A–C (1–3), two new hamamelitol derivatives, linaritols A (4) and B (5), two new chromones, linariosides A (6) and B (7), and three known chromones, cnidimol C (8), monnieriside A (9), and undulatoside A (10), were identified from the ae...
Gespeichert in:
| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2020-05, Vol.83 (5), p.1515-1523 |
|---|---|
| Hauptverfasser: | , , , , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1523 |
|---|---|
| container_issue | 5 |
| container_start_page | 1515 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 83 |
| creator | Pereira, Laiane C. O Abreu, Lucas S Silva, Joanda P. R. e Machado, Francisca S. V. L Queiroga, Cinthia S do Espı́rito-Santo, Renan F Agnelo-Silva, Diego F. de Villarreal, Cristiane F Agra, Maria de F Scotti, Marcus T Costa, Vicente C. de O Tavares, Josean F Silva, Marcelo S. da |
| description | Three new caryophyllane-type sesquiterpenoids, linariophyllenes A–C (1–3), two new hamamelitol derivatives, linaritols A (4) and B (5), two new chromones, linariosides A (6) and B (7), and three known chromones, cnidimol C (8), monnieriside A (9), and undulatoside A (10), were identified from the aerial parts of Evolvulus linarioides. The structures of these compounds were elucidated by NMR, MS, and IR data. The absolute configurations of compounds 1–5 and 7 were established via electronic circular dichroism data. The anti-inflammatory potential of compounds 1–5 and 7–10 was evaluated by determining their ability to inhibit the production of nitric oxide (NO) and proinflammatory cytokine IL-1β by stimulated J774 macrophages. Compounds tested at noncytotoxic concentrations inhibited NO production by macrophages, exhibiting IC50 values between 17.8 and 66.2 μM, and inhibited IL-1β production by stimulated macrophages by 72.7–96.2%. |
| doi_str_mv | 10.1021/acs.jnatprod.9b01189 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2398618584</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2398618584</sourcerecordid><originalsourceid>FETCH-LOGICAL-a348t-c95154a70624bf58b5c34efe057443d62fc15fd099dbe2f1669d8b9fced5878d3</originalsourceid><addsrcrecordid>eNp9kDtPwzAUhS0EoqXwDxDyyJLid-yxVOUhVYIBZsvxQ6RK4mInlfj3BNoyMt3lO-fqfABcYzTHiOA7Y_N805l-m6KbqwphLNUJmGJOUCEQ4adgirCgBZWCTcBFzhuEEEWKn4MJJVSwkpZTcH9fR2P7eufhMrbbOHQuw5BiC_sPDxc-1aaBryb1GcYAV7vY7IZmyLCpO5PqWDufL8FZME32V4c7A-8Pq7flU7F-eXxeLtaFoUz2hVUcc2ZKJAirApcVt5T54BEvGaNOkGAxDw4p5SpPAhZCOVmpYL3jspSOzsDtvndc_Dn43Ou2ztY3jel8HLImVEmBJZdsRNketSnmnHzQ21S3Jn1pjPSPPT3a00d7-mBvjN0cPgxV691f6KhrBNAe-I3HIXXj4P87vwHvp39Y</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2398618584</pqid></control><display><type>article</type><title>Bioactive Compounds from the Aerial Parts of Evolvulus linarioides</title><source>ACS Publications</source><creator>Pereira, Laiane C. O ; Abreu, Lucas S ; Silva, Joanda P. R. e ; Machado, Francisca S. V. L ; Queiroga, Cinthia S ; do Espı́rito-Santo, Renan F ; Agnelo-Silva, Diego F. de ; Villarreal, Cristiane F ; Agra, Maria de F ; Scotti, Marcus T ; Costa, Vicente C. de O ; Tavares, Josean F ; Silva, Marcelo S. da</creator><creatorcontrib>Pereira, Laiane C. O ; Abreu, Lucas S ; Silva, Joanda P. R. e ; Machado, Francisca S. V. L ; Queiroga, Cinthia S ; do Espı́rito-Santo, Renan F ; Agnelo-Silva, Diego F. de ; Villarreal, Cristiane F ; Agra, Maria de F ; Scotti, Marcus T ; Costa, Vicente C. de O ; Tavares, Josean F ; Silva, Marcelo S. da</creatorcontrib><description>Three new caryophyllane-type sesquiterpenoids, linariophyllenes A–C (1–3), two new hamamelitol derivatives, linaritols A (4) and B (5), two new chromones, linariosides A (6) and B (7), and three known chromones, cnidimol C (8), monnieriside A (9), and undulatoside A (10), were identified from the aerial parts of Evolvulus linarioides. The structures of these compounds were elucidated by NMR, MS, and IR data. The absolute configurations of compounds 1–5 and 7 were established via electronic circular dichroism data. The anti-inflammatory potential of compounds 1–5 and 7–10 was evaluated by determining their ability to inhibit the production of nitric oxide (NO) and proinflammatory cytokine IL-1β by stimulated J774 macrophages. Compounds tested at noncytotoxic concentrations inhibited NO production by macrophages, exhibiting IC50 values between 17.8 and 66.2 μM, and inhibited IL-1β production by stimulated macrophages by 72.7–96.2%.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/acs.jnatprod.9b01189</identifier><identifier>PMID: 32364737</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><ispartof>Journal of natural products (Washington, D.C.), 2020-05, Vol.83 (5), p.1515-1523</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a348t-c95154a70624bf58b5c34efe057443d62fc15fd099dbe2f1669d8b9fced5878d3</citedby><cites>FETCH-LOGICAL-a348t-c95154a70624bf58b5c34efe057443d62fc15fd099dbe2f1669d8b9fced5878d3</cites><orcidid>0000-0001-5620-8095 ; 0000-0003-0293-2605 ; 0000-0003-4863-8057 ; 0000-0002-0113-7864</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.9b01189$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jnatprod.9b01189$$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/32364737$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pereira, Laiane C. O</creatorcontrib><creatorcontrib>Abreu, Lucas S</creatorcontrib><creatorcontrib>Silva, Joanda P. R. e</creatorcontrib><creatorcontrib>Machado, Francisca S. V. L</creatorcontrib><creatorcontrib>Queiroga, Cinthia S</creatorcontrib><creatorcontrib>do Espı́rito-Santo, Renan F</creatorcontrib><creatorcontrib>Agnelo-Silva, Diego F. de</creatorcontrib><creatorcontrib>Villarreal, Cristiane F</creatorcontrib><creatorcontrib>Agra, Maria de F</creatorcontrib><creatorcontrib>Scotti, Marcus T</creatorcontrib><creatorcontrib>Costa, Vicente C. de O</creatorcontrib><creatorcontrib>Tavares, Josean F</creatorcontrib><creatorcontrib>Silva, Marcelo S. da</creatorcontrib><title>Bioactive Compounds from the Aerial Parts of Evolvulus linarioides</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Three new caryophyllane-type sesquiterpenoids, linariophyllenes A–C (1–3), two new hamamelitol derivatives, linaritols A (4) and B (5), two new chromones, linariosides A (6) and B (7), and three known chromones, cnidimol C (8), monnieriside A (9), and undulatoside A (10), were identified from the aerial parts of Evolvulus linarioides. The structures of these compounds were elucidated by NMR, MS, and IR data. The absolute configurations of compounds 1–5 and 7 were established via electronic circular dichroism data. The anti-inflammatory potential of compounds 1–5 and 7–10 was evaluated by determining their ability to inhibit the production of nitric oxide (NO) and proinflammatory cytokine IL-1β by stimulated J774 macrophages. Compounds tested at noncytotoxic concentrations inhibited NO production by macrophages, exhibiting IC50 values between 17.8 and 66.2 μM, and inhibited IL-1β production by stimulated macrophages by 72.7–96.2%.</description><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kDtPwzAUhS0EoqXwDxDyyJLid-yxVOUhVYIBZsvxQ6RK4mInlfj3BNoyMt3lO-fqfABcYzTHiOA7Y_N805l-m6KbqwphLNUJmGJOUCEQ4adgirCgBZWCTcBFzhuEEEWKn4MJJVSwkpZTcH9fR2P7eufhMrbbOHQuw5BiC_sPDxc-1aaBryb1GcYAV7vY7IZmyLCpO5PqWDufL8FZME32V4c7A-8Pq7flU7F-eXxeLtaFoUz2hVUcc2ZKJAirApcVt5T54BEvGaNOkGAxDw4p5SpPAhZCOVmpYL3jspSOzsDtvndc_Dn43Ou2ztY3jel8HLImVEmBJZdsRNketSnmnHzQ21S3Jn1pjPSPPT3a00d7-mBvjN0cPgxV691f6KhrBNAe-I3HIXXj4P87vwHvp39Y</recordid><startdate>20200522</startdate><enddate>20200522</enddate><creator>Pereira, Laiane C. O</creator><creator>Abreu, Lucas S</creator><creator>Silva, Joanda P. R. e</creator><creator>Machado, Francisca S. V. L</creator><creator>Queiroga, Cinthia S</creator><creator>do Espı́rito-Santo, Renan F</creator><creator>Agnelo-Silva, Diego F. de</creator><creator>Villarreal, Cristiane F</creator><creator>Agra, Maria de F</creator><creator>Scotti, Marcus T</creator><creator>Costa, Vicente C. de O</creator><creator>Tavares, Josean F</creator><creator>Silva, Marcelo S. da</creator><general>American Chemical Society and American Society of Pharmacognosy</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-5620-8095</orcidid><orcidid>https://orcid.org/0000-0003-0293-2605</orcidid><orcidid>https://orcid.org/0000-0003-4863-8057</orcidid><orcidid>https://orcid.org/0000-0002-0113-7864</orcidid></search><sort><creationdate>20200522</creationdate><title>Bioactive Compounds from the Aerial Parts of Evolvulus linarioides</title><author>Pereira, Laiane C. O ; Abreu, Lucas S ; Silva, Joanda P. R. e ; Machado, Francisca S. V. L ; Queiroga, Cinthia S ; do Espı́rito-Santo, Renan F ; Agnelo-Silva, Diego F. de ; Villarreal, Cristiane F ; Agra, Maria de F ; Scotti, Marcus T ; Costa, Vicente C. de O ; Tavares, Josean F ; Silva, Marcelo S. da</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a348t-c95154a70624bf58b5c34efe057443d62fc15fd099dbe2f1669d8b9fced5878d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pereira, Laiane C. O</creatorcontrib><creatorcontrib>Abreu, Lucas S</creatorcontrib><creatorcontrib>Silva, Joanda P. R. e</creatorcontrib><creatorcontrib>Machado, Francisca S. V. L</creatorcontrib><creatorcontrib>Queiroga, Cinthia S</creatorcontrib><creatorcontrib>do Espı́rito-Santo, Renan F</creatorcontrib><creatorcontrib>Agnelo-Silva, Diego F. de</creatorcontrib><creatorcontrib>Villarreal, Cristiane F</creatorcontrib><creatorcontrib>Agra, Maria de F</creatorcontrib><creatorcontrib>Scotti, Marcus T</creatorcontrib><creatorcontrib>Costa, Vicente C. de O</creatorcontrib><creatorcontrib>Tavares, Josean F</creatorcontrib><creatorcontrib>Silva, Marcelo S. da</creatorcontrib><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>Pereira, Laiane C. O</au><au>Abreu, Lucas S</au><au>Silva, Joanda P. R. e</au><au>Machado, Francisca S. V. L</au><au>Queiroga, Cinthia S</au><au>do Espı́rito-Santo, Renan F</au><au>Agnelo-Silva, Diego F. de</au><au>Villarreal, Cristiane F</au><au>Agra, Maria de F</au><au>Scotti, Marcus T</au><au>Costa, Vicente C. de O</au><au>Tavares, Josean F</au><au>Silva, Marcelo S. da</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bioactive Compounds from the Aerial Parts of Evolvulus linarioides</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2020-05-22</date><risdate>2020</risdate><volume>83</volume><issue>5</issue><spage>1515</spage><epage>1523</epage><pages>1515-1523</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>Three new caryophyllane-type sesquiterpenoids, linariophyllenes A–C (1–3), two new hamamelitol derivatives, linaritols A (4) and B (5), two new chromones, linariosides A (6) and B (7), and three known chromones, cnidimol C (8), monnieriside A (9), and undulatoside A (10), were identified from the aerial parts of Evolvulus linarioides. The structures of these compounds were elucidated by NMR, MS, and IR data. The absolute configurations of compounds 1–5 and 7 were established via electronic circular dichroism data. The anti-inflammatory potential of compounds 1–5 and 7–10 was evaluated by determining their ability to inhibit the production of nitric oxide (NO) and proinflammatory cytokine IL-1β by stimulated J774 macrophages. Compounds tested at noncytotoxic concentrations inhibited NO production by macrophages, exhibiting IC50 values between 17.8 and 66.2 μM, and inhibited IL-1β production by stimulated macrophages by 72.7–96.2%.</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>32364737</pmid><doi>10.1021/acs.jnatprod.9b01189</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-5620-8095</orcidid><orcidid>https://orcid.org/0000-0003-0293-2605</orcidid><orcidid>https://orcid.org/0000-0003-4863-8057</orcidid><orcidid>https://orcid.org/0000-0002-0113-7864</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2020-05, Vol.83 (5), p.1515-1523 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2398618584 |
| source | ACS Publications |
| title | Bioactive Compounds from the Aerial Parts of Evolvulus linarioides |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-05T21%3A26%3A10IST&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=Bioactive%20Compounds%20from%20the%20Aerial%20Parts%20of%20Evolvulus%20linarioides&rft.jtitle=Journal%20of%20natural%20products%20(Washington,%20D.C.)&rft.au=Pereira,%20Laiane%20C.%20O&rft.date=2020-05-22&rft.volume=83&rft.issue=5&rft.spage=1515&rft.epage=1523&rft.pages=1515-1523&rft.issn=0163-3864&rft.eissn=1520-6025&rft_id=info:doi/10.1021/acs.jnatprod.9b01189&rft_dat=%3Cproquest_cross%3E2398618584%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=2398618584&rft_id=info:pmid/32364737&rfr_iscdi=true |