Cytotoxic cardenolides from the latex of Calotropis procera
[Display omitted] Three new cardenolides (3, 9 and 10), along with eight known ones, were isolated from the latex of Calotropis procera. The structural determination was accomplished by the 1D- and 2D-NMR spectra as well as HRESIMS analysis. The growth inhibitory activity of the latex and its sub-fr...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2015-10, Vol.25 (20), p.4615-4620 |
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| creator | Mohamed, Nadia H. Liu, Miaomiao Abdel-Mageed, Wael M. Alwahibi, Lamya H. Dai, Huanqin Ismail, Mady Ahmed Badr, Gamal Quinn, Ronald J. Liu, Xueting Zhang, Lixin Shoreit, Ahmed A.M. |
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Three new cardenolides (3, 9 and 10), along with eight known ones, were isolated from the latex of Calotropis procera. The structural determination was accomplished by the 1D- and 2D-NMR spectra as well as HRESIMS analysis. The growth inhibitory activity of the latex and its sub-fractions as well as isolated compounds was evaluated against human A549 and Hela cell lines. The results exhibited that latex had strong growth inhibitory activity with IC50s of (3.37μM, A-549) and (6.45μM, Hela). Among the four extracts (hexane, chloroform, ethyl acetate and aqueous), chloroform extract displayed the highest potential cytotoxic activity, with IC50s of (0.985μM, A-549) and (1.471μM, Hela). All the isolated compounds displayed various degrees of cytotoxic activity and the highest activity was observed by calactin (1) with IC50s values of (0.036μM, A-549) and (0.083μM, Hela). None of these isolated compounds exhibited good antimicrobial activity evaluated by determination of their MICs using the broth microdilution method against various infectious pathogens. The structure–activity relationships for cytotoxic activity were also discussed. |
| doi_str_mv | 10.1016/j.bmcl.2015.08.044 |
| format | Article |
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Three new cardenolides (3, 9 and 10), along with eight known ones, were isolated from the latex of Calotropis procera. The structural determination was accomplished by the 1D- and 2D-NMR spectra as well as HRESIMS analysis. The growth inhibitory activity of the latex and its sub-fractions as well as isolated compounds was evaluated against human A549 and Hela cell lines. The results exhibited that latex had strong growth inhibitory activity with IC50s of (3.37μM, A-549) and (6.45μM, Hela). Among the four extracts (hexane, chloroform, ethyl acetate and aqueous), chloroform extract displayed the highest potential cytotoxic activity, with IC50s of (0.985μM, A-549) and (1.471μM, Hela). All the isolated compounds displayed various degrees of cytotoxic activity and the highest activity was observed by calactin (1) with IC50s values of (0.036μM, A-549) and (0.083μM, Hela). None of these isolated compounds exhibited good antimicrobial activity evaluated by determination of their MICs using the broth microdilution method against various infectious pathogens. The structure–activity relationships for cytotoxic activity were also discussed.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2015.08.044</identifier><identifier>PMID: 26323871</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - isolation & purification ; Anti-Bacterial Agents - pharmacology ; Antifungal Agents - chemistry ; Antifungal Agents - isolation & purification ; Antifungal Agents - pharmacology ; Antimicrobial activity ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - isolation & purification ; Antineoplastic Agents, Phytogenic - pharmacology ; Asclepiadaceae ; Bacteria - drug effects ; Calotropis - chemistry ; Calotropis procera ; Cardenolides ; Cardenolides - chemistry ; Cardenolides - isolation & purification ; Cardenolides - pharmacology ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Cytotoxicity ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; Fungi - drug effects ; HeLa Cells ; Humans ; Latex - chemistry ; Microbial Sensitivity Tests ; Molecular Structure ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2015-10, Vol.25 (20), p.4615-4620</ispartof><rights>2015 Elsevier Ltd</rights><rights>Copyright © 2015 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c377t-6510f7a21b0f1dec124686bd2ab96a50fc019907d41af1f04772138a5d2b04c63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2015.08.044$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26323871$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mohamed, Nadia H.</creatorcontrib><creatorcontrib>Liu, Miaomiao</creatorcontrib><creatorcontrib>Abdel-Mageed, Wael M.</creatorcontrib><creatorcontrib>Alwahibi, Lamya H.</creatorcontrib><creatorcontrib>Dai, Huanqin</creatorcontrib><creatorcontrib>Ismail, Mady Ahmed</creatorcontrib><creatorcontrib>Badr, Gamal</creatorcontrib><creatorcontrib>Quinn, Ronald J.</creatorcontrib><creatorcontrib>Liu, Xueting</creatorcontrib><creatorcontrib>Zhang, Lixin</creatorcontrib><creatorcontrib>Shoreit, Ahmed A.M.</creatorcontrib><title>Cytotoxic cardenolides from the latex of Calotropis procera</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
Three new cardenolides (3, 9 and 10), along with eight known ones, were isolated from the latex of Calotropis procera. The structural determination was accomplished by the 1D- and 2D-NMR spectra as well as HRESIMS analysis. The growth inhibitory activity of the latex and its sub-fractions as well as isolated compounds was evaluated against human A549 and Hela cell lines. The results exhibited that latex had strong growth inhibitory activity with IC50s of (3.37μM, A-549) and (6.45μM, Hela). Among the four extracts (hexane, chloroform, ethyl acetate and aqueous), chloroform extract displayed the highest potential cytotoxic activity, with IC50s of (0.985μM, A-549) and (1.471μM, Hela). All the isolated compounds displayed various degrees of cytotoxic activity and the highest activity was observed by calactin (1) with IC50s values of (0.036μM, A-549) and (0.083μM, Hela). None of these isolated compounds exhibited good antimicrobial activity evaluated by determination of their MICs using the broth microdilution method against various infectious pathogens. The structure–activity relationships for cytotoxic activity were also discussed.</description><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - isolation & purification</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - isolation & purification</subject><subject>Antifungal Agents - pharmacology</subject><subject>Antimicrobial activity</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - isolation & purification</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Asclepiadaceae</subject><subject>Bacteria - drug effects</subject><subject>Calotropis - chemistry</subject><subject>Calotropis procera</subject><subject>Cardenolides</subject><subject>Cardenolides - chemistry</subject><subject>Cardenolides - isolation & purification</subject><subject>Cardenolides - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Cytotoxicity</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Fungi - drug effects</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>Latex - chemistry</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEtLxDAUhYMoOj7-gAvp0k3rvWmatuhGBl8guFFwF9LkBjO0kzHpiP57O4y6dHU33zmX8zF2ilAgoLxYFN1g-oIDVgU0BQixw2YopMhLAdUum0ErIW9a8XrADlNaAKCYoH12wGXJy6bGGbucf41hDJ_eZEZHS8vQe0spczEM2fhGWa9H-syCy-a6D2MMK5-yVQyGoj5me073iU5-7hF7ub15nt_nj093D_Prx9yUdT3mskJwtebYgUNLBrmQjews110rdQXOALYt1FagduhA1DXHstGV5R0II8sjdr7tnf6-rymNavDJUN_rJYV1Ulhj026mwYTyLWpiSCmSU6voBx2_FILaSFMLtZGmNtIUNGryMYXOfvrX3UD2L_JraQKutgBNKz88RZWMp6Uh6yOZUdng_-v_BjJHfKg</recordid><startdate>20151015</startdate><enddate>20151015</enddate><creator>Mohamed, Nadia H.</creator><creator>Liu, Miaomiao</creator><creator>Abdel-Mageed, Wael M.</creator><creator>Alwahibi, Lamya H.</creator><creator>Dai, Huanqin</creator><creator>Ismail, Mady Ahmed</creator><creator>Badr, Gamal</creator><creator>Quinn, Ronald J.</creator><creator>Liu, Xueting</creator><creator>Zhang, Lixin</creator><creator>Shoreit, Ahmed A.M.</creator><general>Elsevier Ltd</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>20151015</creationdate><title>Cytotoxic cardenolides from the latex of Calotropis procera</title><author>Mohamed, Nadia H. ; Liu, Miaomiao ; Abdel-Mageed, Wael M. ; Alwahibi, Lamya H. ; Dai, Huanqin ; Ismail, Mady Ahmed ; Badr, Gamal ; Quinn, Ronald J. ; Liu, Xueting ; Zhang, Lixin ; Shoreit, Ahmed A.M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c377t-6510f7a21b0f1dec124686bd2ab96a50fc019907d41af1f04772138a5d2b04c63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - isolation & purification</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - isolation & purification</topic><topic>Antifungal Agents - pharmacology</topic><topic>Antimicrobial activity</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - isolation & purification</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Asclepiadaceae</topic><topic>Bacteria - drug effects</topic><topic>Calotropis - chemistry</topic><topic>Calotropis procera</topic><topic>Cardenolides</topic><topic>Cardenolides - chemistry</topic><topic>Cardenolides - isolation & purification</topic><topic>Cardenolides - pharmacology</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Cytotoxicity</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Fungi - drug effects</topic><topic>HeLa Cells</topic><topic>Humans</topic><topic>Latex - chemistry</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mohamed, Nadia H.</creatorcontrib><creatorcontrib>Liu, Miaomiao</creatorcontrib><creatorcontrib>Abdel-Mageed, Wael M.</creatorcontrib><creatorcontrib>Alwahibi, Lamya H.</creatorcontrib><creatorcontrib>Dai, Huanqin</creatorcontrib><creatorcontrib>Ismail, Mady Ahmed</creatorcontrib><creatorcontrib>Badr, Gamal</creatorcontrib><creatorcontrib>Quinn, Ronald J.</creatorcontrib><creatorcontrib>Liu, Xueting</creatorcontrib><creatorcontrib>Zhang, Lixin</creatorcontrib><creatorcontrib>Shoreit, Ahmed A.M.</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>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mohamed, Nadia H.</au><au>Liu, Miaomiao</au><au>Abdel-Mageed, Wael M.</au><au>Alwahibi, Lamya H.</au><au>Dai, Huanqin</au><au>Ismail, Mady Ahmed</au><au>Badr, Gamal</au><au>Quinn, Ronald J.</au><au>Liu, Xueting</au><au>Zhang, Lixin</au><au>Shoreit, Ahmed A.M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cytotoxic cardenolides from the latex of Calotropis procera</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2015-10-15</date><risdate>2015</risdate><volume>25</volume><issue>20</issue><spage>4615</spage><epage>4620</epage><pages>4615-4620</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
Three new cardenolides (3, 9 and 10), along with eight known ones, were isolated from the latex of Calotropis procera. The structural determination was accomplished by the 1D- and 2D-NMR spectra as well as HRESIMS analysis. The growth inhibitory activity of the latex and its sub-fractions as well as isolated compounds was evaluated against human A549 and Hela cell lines. The results exhibited that latex had strong growth inhibitory activity with IC50s of (3.37μM, A-549) and (6.45μM, Hela). Among the four extracts (hexane, chloroform, ethyl acetate and aqueous), chloroform extract displayed the highest potential cytotoxic activity, with IC50s of (0.985μM, A-549) and (1.471μM, Hela). All the isolated compounds displayed various degrees of cytotoxic activity and the highest activity was observed by calactin (1) with IC50s values of (0.036μM, A-549) and (0.083μM, Hela). None of these isolated compounds exhibited good antimicrobial activity evaluated by determination of their MICs using the broth microdilution method against various infectious pathogens. The structure–activity relationships for cytotoxic activity were also discussed.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>26323871</pmid><doi>10.1016/j.bmcl.2015.08.044</doi><tpages>6</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 2015-10, Vol.25 (20), p.4615-4620 |
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| subjects | Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - isolation & purification Anti-Bacterial Agents - pharmacology Antifungal Agents - chemistry Antifungal Agents - isolation & purification Antifungal Agents - pharmacology Antimicrobial activity Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - isolation & purification Antineoplastic Agents, Phytogenic - pharmacology Asclepiadaceae Bacteria - drug effects Calotropis - chemistry Calotropis procera Cardenolides Cardenolides - chemistry Cardenolides - isolation & purification Cardenolides - pharmacology Cell Line, Tumor Cell Proliferation - drug effects Cytotoxicity Dose-Response Relationship, Drug Drug Screening Assays, Antitumor Fungi - drug effects HeLa Cells Humans Latex - chemistry Microbial Sensitivity Tests Molecular Structure Structure-Activity Relationship |
| title | Cytotoxic cardenolides from the latex of Calotropis procera |
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