Bioactive Natural and Semisynthetic Latrunculins
Marine-derived macrolides latrunculins A and B, of the Red Sea sponge Negombata magnifica, are the first marine natural products that have been found to reversibly bind to actin monomers and to disrupt its organization. Latrunculins are structurally related to many antimicrobial and antiangiogenic m...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2006-02, Vol.69 (2), p.219-223 |
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| creator | El Sayed, Khalid A Youssef, Diaa T. A Marchetti, Dario |
| description | Marine-derived macrolides latrunculins A and B, of the Red Sea sponge Negombata magnifica, are the first marine natural products that have been found to reversibly bind to actin monomers and to disrupt its organization. Latrunculins are structurally related to many antimicrobial and antiangiogenic macrolides. Several grams of latrunculin B (1), together with a new latrunculin named latrunculin T (2), were isolated from a recent collection of N. magnifica. Semisynthetic modifications of 1, including acetylation, acetalization, and N-hydroxymethylation, afforded four new (4, 5, 7, 8) and two known (6 and 9) semisynthetic analogues. Specifically, 15-O-methyllatrunculin B (6) showed a promising antiangiogenic activity in a chick chorioallantoic membrane assay and antimigratory activity in Boyden's chamber assay. Moreover, latrunculin B (1) and the new N-acetyllatrunculin B (4) displayed potent antimigratory activity in a wound-healing assay. Natural and semisynthetic latrunculins showed potent antimicrobial activity against Candida albicans, Saccharomyces cerevisiae, Staphylococcus aureus, and Bacillus cereus. Latrunculins are potential leads that can be developed as anticancer and antimicrobial agents. |
| doi_str_mv | 10.1021/np050372r |
| format | Article |
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A ; Marchetti, Dario</creator><creatorcontrib>El Sayed, Khalid A ; Youssef, Diaa T. A ; Marchetti, Dario</creatorcontrib><description>Marine-derived macrolides latrunculins A and B, of the Red Sea sponge Negombata magnifica, are the first marine natural products that have been found to reversibly bind to actin monomers and to disrupt its organization. Latrunculins are structurally related to many antimicrobial and antiangiogenic macrolides. Several grams of latrunculin B (1), together with a new latrunculin named latrunculin T (2), were isolated from a recent collection of N. magnifica. Semisynthetic modifications of 1, including acetylation, acetalization, and N-hydroxymethylation, afforded four new (4, 5, 7, 8) and two known (6 and 9) semisynthetic analogues. Specifically, 15-O-methyllatrunculin B (6) showed a promising antiangiogenic activity in a chick chorioallantoic membrane assay and antimigratory activity in Boyden's chamber assay. Moreover, latrunculin B (1) and the new N-acetyllatrunculin B (4) displayed potent antimigratory activity in a wound-healing assay. Natural and semisynthetic latrunculins showed potent antimicrobial activity against Candida albicans, Saccharomyces cerevisiae, Staphylococcus aureus, and Bacillus cereus. Latrunculins are potential leads that can be developed as anticancer and antimicrobial agents.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np050372r</identifier><identifier>PMID: 16499319</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Anti-Infective Agents - chemical synthesis ; Anti-Infective Agents - chemistry ; Anti-Infective Agents - isolation & purification ; Anti-Infective Agents - pharmacology ; antiangiogenic activity ; antibacterial properties ; anticarcinogenic activity ; antifungal properties ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - isolation & purification ; Antineoplastic Agents - pharmacology ; Bacillus cereus ; Bacillus cereus - drug effects ; Biological and medical sciences ; Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis ; Bridged Bicyclo Compounds, Heterocyclic - chemistry ; Bridged Bicyclo Compounds, Heterocyclic - isolation & purification ; Bridged Bicyclo Compounds, Heterocyclic - pharmacology ; Candida albicans ; Candida albicans - drug effects ; chemical structure ; cultured cells ; cytotoxicity ; General pharmacology ; Indian Ocean ; latrunculin ; macrolides ; Macrolides - chemical synthesis ; Macrolides - chemistry ; Macrolides - isolation & purification ; Macrolides - pharmacology ; Medical sciences ; mice ; Microbial Sensitivity Tests ; Molecular Structure ; Negombata magnifica ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Porifera ; Porifera - chemistry ; Saccharomyces cerevisiae ; Saccharomyces cerevisiae - drug effects ; spectral analysis ; Staphylococcus aureus ; Staphylococcus aureus - drug effects ; stereochemistry ; thiazoles ; Thiazoles - chemical synthesis ; Thiazoles - chemistry ; Thiazoles - isolation & purification ; Thiazoles - pharmacology ; Thiazolidines ; Tumor Cells, Cultured ; Wound Healing - drug effects</subject><ispartof>Journal of natural products (Washington, D.C.), 2006-02, Vol.69 (2), p.219-223</ispartof><rights>Copyright © 2006 American Chemical Society and American Society of Pharmacognosy</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a405t-5f92f42a1a3dd98be10ccc896c497e956b3540fd8b5a44e1f87a77f4d259c7cc3</citedby><cites>FETCH-LOGICAL-a405t-5f92f42a1a3dd98be10ccc896c497e956b3540fd8b5a44e1f87a77f4d259c7cc3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np050372r$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np050372r$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27074,27922,27923,56736,56786</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17581612$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16499319$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>El Sayed, Khalid A</creatorcontrib><creatorcontrib>Youssef, Diaa T. A</creatorcontrib><creatorcontrib>Marchetti, Dario</creatorcontrib><title>Bioactive Natural and Semisynthetic Latrunculins</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Marine-derived macrolides latrunculins A and B, of the Red Sea sponge Negombata magnifica, are the first marine natural products that have been found to reversibly bind to actin monomers and to disrupt its organization. Latrunculins are structurally related to many antimicrobial and antiangiogenic macrolides. Several grams of latrunculin B (1), together with a new latrunculin named latrunculin T (2), were isolated from a recent collection of N. magnifica. Semisynthetic modifications of 1, including acetylation, acetalization, and N-hydroxymethylation, afforded four new (4, 5, 7, 8) and two known (6 and 9) semisynthetic analogues. Specifically, 15-O-methyllatrunculin B (6) showed a promising antiangiogenic activity in a chick chorioallantoic membrane assay and antimigratory activity in Boyden's chamber assay. Moreover, latrunculin B (1) and the new N-acetyllatrunculin B (4) displayed potent antimigratory activity in a wound-healing assay. Natural and semisynthetic latrunculins showed potent antimicrobial activity against Candida albicans, Saccharomyces cerevisiae, Staphylococcus aureus, and Bacillus cereus. Latrunculins are potential leads that can be developed as anticancer and antimicrobial agents.</description><subject>Animals</subject><subject>Anti-Infective Agents - chemical synthesis</subject><subject>Anti-Infective Agents - chemistry</subject><subject>Anti-Infective Agents - isolation & purification</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>antiangiogenic activity</subject><subject>antibacterial properties</subject><subject>anticarcinogenic activity</subject><subject>antifungal properties</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - isolation & purification</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Bacillus cereus</subject><subject>Bacillus cereus - drug effects</subject><subject>Biological and medical sciences</subject><subject>Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis</subject><subject>Bridged Bicyclo Compounds, Heterocyclic - chemistry</subject><subject>Bridged Bicyclo Compounds, Heterocyclic - isolation & purification</subject><subject>Bridged Bicyclo Compounds, Heterocyclic - pharmacology</subject><subject>Candida albicans</subject><subject>Candida albicans - drug effects</subject><subject>chemical structure</subject><subject>cultured cells</subject><subject>cytotoxicity</subject><subject>General pharmacology</subject><subject>Indian Ocean</subject><subject>latrunculin</subject><subject>macrolides</subject><subject>Macrolides - chemical synthesis</subject><subject>Macrolides - chemistry</subject><subject>Macrolides - isolation & purification</subject><subject>Macrolides - pharmacology</subject><subject>Medical sciences</subject><subject>mice</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Negombata magnifica</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Porifera</subject><subject>Porifera - chemistry</subject><subject>Saccharomyces cerevisiae</subject><subject>Saccharomyces cerevisiae - drug effects</subject><subject>spectral analysis</subject><subject>Staphylococcus aureus</subject><subject>Staphylococcus aureus - drug effects</subject><subject>stereochemistry</subject><subject>thiazoles</subject><subject>Thiazoles - chemical synthesis</subject><subject>Thiazoles - chemistry</subject><subject>Thiazoles - isolation & purification</subject><subject>Thiazoles - pharmacology</subject><subject>Thiazolidines</subject><subject>Tumor Cells, Cultured</subject><subject>Wound Healing - drug effects</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E1vEzEQBmALgWgoHPgDkAtIHLbM-HN9JBX9QKEgpZW4WROvDVs2u8HeRfTf1yhRc-lpDn70euZl7DXCCQLHj_0WFAjD0xM2Q8Wh0sDVUzYD1KIStZZH7EXOtwAgwKrn7Ai1tFagnTFYtAP5sf0b5lc0Tom6OfXNfBU2bb7rx19hbP18SWOaej91bZ9fsmeRuhxe7ecxuzn7fH16US2_nV-eflpWJEGNlYqWR8kJSTSNrdcBwXtfW-2lNcEqvRZKQmzqtSIpA8bakDFRNlxZb7wXx-z9Lnebhj9TyKMrG_nQddSHYcpOG22VRFHghx30acg5hei2qd1QunMI7n897qGeYt_sQ6f1JjQHue-jgHd7QNlTFxP1vs0HZ1SNGnlx1c61eQz_Ht4p_S6LCaPc9feVO198MVc_Fsp9Lf7tzkcaHP1MJfNmxQEFIGiFtj78TD6722FKfWn3kRPuAZJTkIY</recordid><startdate>20060201</startdate><enddate>20060201</enddate><creator>El Sayed, Khalid A</creator><creator>Youssef, Diaa T. A</creator><creator>Marchetti, Dario</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><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>20060201</creationdate><title>Bioactive Natural and Semisynthetic Latrunculins</title><author>El Sayed, Khalid A ; Youssef, Diaa T. A ; Marchetti, Dario</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a405t-5f92f42a1a3dd98be10ccc896c497e956b3540fd8b5a44e1f87a77f4d259c7cc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Animals</topic><topic>Anti-Infective Agents - chemical synthesis</topic><topic>Anti-Infective Agents - chemistry</topic><topic>Anti-Infective Agents - isolation & purification</topic><topic>Anti-Infective Agents - pharmacology</topic><topic>antiangiogenic activity</topic><topic>antibacterial properties</topic><topic>anticarcinogenic activity</topic><topic>antifungal properties</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - isolation & purification</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Bacillus cereus</topic><topic>Bacillus cereus - drug effects</topic><topic>Biological and medical sciences</topic><topic>Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis</topic><topic>Bridged Bicyclo Compounds, Heterocyclic - chemistry</topic><topic>Bridged Bicyclo Compounds, Heterocyclic - isolation & purification</topic><topic>Bridged Bicyclo Compounds, Heterocyclic - pharmacology</topic><topic>Candida albicans</topic><topic>Candida albicans - drug effects</topic><topic>chemical structure</topic><topic>cultured cells</topic><topic>cytotoxicity</topic><topic>General pharmacology</topic><topic>Indian Ocean</topic><topic>latrunculin</topic><topic>macrolides</topic><topic>Macrolides - chemical synthesis</topic><topic>Macrolides - chemistry</topic><topic>Macrolides - isolation & purification</topic><topic>Macrolides - pharmacology</topic><topic>Medical sciences</topic><topic>mice</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Negombata magnifica</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Porifera</topic><topic>Porifera - chemistry</topic><topic>Saccharomyces cerevisiae</topic><topic>Saccharomyces cerevisiae - drug effects</topic><topic>spectral analysis</topic><topic>Staphylococcus aureus</topic><topic>Staphylococcus aureus - drug effects</topic><topic>stereochemistry</topic><topic>thiazoles</topic><topic>Thiazoles - chemical synthesis</topic><topic>Thiazoles - chemistry</topic><topic>Thiazoles - isolation & purification</topic><topic>Thiazoles - pharmacology</topic><topic>Thiazolidines</topic><topic>Tumor Cells, Cultured</topic><topic>Wound Healing - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>El Sayed, Khalid A</creatorcontrib><creatorcontrib>Youssef, Diaa T. A</creatorcontrib><creatorcontrib>Marchetti, Dario</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><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>El Sayed, Khalid A</au><au>Youssef, Diaa T. A</au><au>Marchetti, Dario</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bioactive Natural and Semisynthetic Latrunculins</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2006-02-01</date><risdate>2006</risdate><volume>69</volume><issue>2</issue><spage>219</spage><epage>223</epage><pages>219-223</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Marine-derived macrolides latrunculins A and B, of the Red Sea sponge Negombata magnifica, are the first marine natural products that have been found to reversibly bind to actin monomers and to disrupt its organization. Latrunculins are structurally related to many antimicrobial and antiangiogenic macrolides. Several grams of latrunculin B (1), together with a new latrunculin named latrunculin T (2), were isolated from a recent collection of N. magnifica. Semisynthetic modifications of 1, including acetylation, acetalization, and N-hydroxymethylation, afforded four new (4, 5, 7, 8) and two known (6 and 9) semisynthetic analogues. Specifically, 15-O-methyllatrunculin B (6) showed a promising antiangiogenic activity in a chick chorioallantoic membrane assay and antimigratory activity in Boyden's chamber assay. Moreover, latrunculin B (1) and the new N-acetyllatrunculin B (4) displayed potent antimigratory activity in a wound-healing assay. Natural and semisynthetic latrunculins showed potent antimicrobial activity against Candida albicans, Saccharomyces cerevisiae, Staphylococcus aureus, and Bacillus cereus. Latrunculins are potential leads that can be developed as anticancer and antimicrobial agents.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>16499319</pmid><doi>10.1021/np050372r</doi><tpages>5</tpages></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 2006-02, Vol.69 (2), p.219-223 |
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| subjects | Animals Anti-Infective Agents - chemical synthesis Anti-Infective Agents - chemistry Anti-Infective Agents - isolation & purification Anti-Infective Agents - pharmacology antiangiogenic activity antibacterial properties anticarcinogenic activity antifungal properties Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - isolation & purification Antineoplastic Agents - pharmacology Bacillus cereus Bacillus cereus - drug effects Biological and medical sciences Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis Bridged Bicyclo Compounds, Heterocyclic - chemistry Bridged Bicyclo Compounds, Heterocyclic - isolation & purification Bridged Bicyclo Compounds, Heterocyclic - pharmacology Candida albicans Candida albicans - drug effects chemical structure cultured cells cytotoxicity General pharmacology Indian Ocean latrunculin macrolides Macrolides - chemical synthesis Macrolides - chemistry Macrolides - isolation & purification Macrolides - pharmacology Medical sciences mice Microbial Sensitivity Tests Molecular Structure Negombata magnifica Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Porifera Porifera - chemistry Saccharomyces cerevisiae Saccharomyces cerevisiae - drug effects spectral analysis Staphylococcus aureus Staphylococcus aureus - drug effects stereochemistry thiazoles Thiazoles - chemical synthesis Thiazoles - chemistry Thiazoles - isolation & purification Thiazoles - pharmacology Thiazolidines Tumor Cells, Cultured Wound Healing - drug effects |
| title | Bioactive Natural and Semisynthetic Latrunculins |
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