new antimalarial quassinoid from Simaba orinocensis
A new antimalarial quassinoid, namely, orinocinolide (1), was isolated from the root bark of Simaba orinocensis, together with the previously reported simalikalactone D (2). The structure of 1 was determined primarily from 1D and 2D NMR analysis, as well as by chemical derivatization. Compound 1 was...
Gespeichert in:
| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2004-05, Vol.67 (5), p.772-777 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 777 |
|---|---|
| container_issue | 5 |
| container_start_page | 772 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 67 |
| creator | Muhammad, I Bedir, E Khan, S.I Tekwani, B.L Khan, I.A Takamatsu, S Pelletier, J Walker, L.A |
| description | A new antimalarial quassinoid, namely, orinocinolide (1), was isolated from the root bark of Simaba orinocensis, together with the previously reported simalikalactone D (2). The structure of 1 was determined primarily from 1D and 2D NMR analysis, as well as by chemical derivatization. Compound 1 was found to be as equally potent as 2 against Plasmodium falciparum clones D6 and W2 (IC(50) 3.27 and 8.53 ng/mL vs 3.0 and 3.67 ng/mL, respectively), but was 4- and 28-fold less toxic than 2 against VERO cells (IC(50) 10 vs 2.3 microg/mL) and HL-60 (IC(50) 0.7 vs 0.025 microg/mL), respectively. In addition, 2 was >46- and >31-fold more potent than pentamidine and amphotericin B (IC(50) 0.035 vs 1.6 and 1.1 microg/mL) against Leishmania donovani, while 1 was inactive. Orinocinolide (1) inhibited growth of human cancer cells SK-MEL, KB, BT-549, and SK-OV-3, but was less potent than 2 (IC(50) 0.8-1.9 vs 0.3-1.0 microg/mL) against these cells. |
| doi_str_mv | 10.1021/np030524n |
| format | Article |
| fullrecord | <record><control><sourceid>istex_pubme</sourceid><recordid>TN_cdi_pubmed_primary_15165136</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>ark_67375_TPS_4TSXH0HK_M</sourcerecordid><originalsourceid>FETCH-LOGICAL-f299t-8a291f5a246c3a28da7dee33bea174cd82a2bf081110f9b936075eb57b7ed63d3</originalsourceid><addsrcrecordid>eNpN0MFKw0AQBuBFFFurB19Ac_EYnd3J7iZHKWrEikJa8BYmya5E06Tutqhv70KreBqY_-NnGMZOOVxyEPyqXwGCFEm_x8ZcCogVCLnPxsAVxpiqZMSOvH8DCCyTh2zEJVeSoxoz7M1nRP26XVJHrqUu-tiQ920_tE1k3bCMihBVFA0u7GrT-9YfswNLnTcnuzlhi9ub-TSPZ09399PrWWxFlq3jlETGrSSRqBpJpA3pxhjEyhDXSd2kgkRlIeWcg82qDBVoaSqpK20ahQ1O2Nm2d7WplqYpVy6c4r7L3-sDuNgB8jV11lFft_6f0xkiiODirWv92nz95eTeS6VRy3L-XJTJvHjJIX8oH4M_33pLQ0mvLnQuCgEcIbw7lanAH9-aavU</addsrcrecordid><sourcetype>Index Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>new antimalarial quassinoid from Simaba orinocensis</title><source>MEDLINE</source><source>ACS Publications</source><creator>Muhammad, I ; Bedir, E ; Khan, S.I ; Tekwani, B.L ; Khan, I.A ; Takamatsu, S ; Pelletier, J ; Walker, L.A</creator><creatorcontrib>Muhammad, I ; Bedir, E ; Khan, S.I ; Tekwani, B.L ; Khan, I.A ; Takamatsu, S ; Pelletier, J ; Walker, L.A</creatorcontrib><description>A new antimalarial quassinoid, namely, orinocinolide (1), was isolated from the root bark of Simaba orinocensis, together with the previously reported simalikalactone D (2). The structure of 1 was determined primarily from 1D and 2D NMR analysis, as well as by chemical derivatization. Compound 1 was found to be as equally potent as 2 against Plasmodium falciparum clones D6 and W2 (IC(50) 3.27 and 8.53 ng/mL vs 3.0 and 3.67 ng/mL, respectively), but was 4- and 28-fold less toxic than 2 against VERO cells (IC(50) 10 vs 2.3 microg/mL) and HL-60 (IC(50) 0.7 vs 0.025 microg/mL), respectively. In addition, 2 was >46- and >31-fold more potent than pentamidine and amphotericin B (IC(50) 0.035 vs 1.6 and 1.1 microg/mL) against Leishmania donovani, while 1 was inactive. Orinocinolide (1) inhibited growth of human cancer cells SK-MEL, KB, BT-549, and SK-OV-3, but was less potent than 2 (IC(50) 0.8-1.9 vs 0.3-1.0 microg/mL) against these cells.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np030524n</identifier><identifier>PMID: 15165136</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Antimalarials - chemistry ; Antimalarials - isolation & purification ; Antimalarials - pharmacology ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - isolation & purification ; Antineoplastic Agents, Phytogenic - pharmacology ; Biological and medical sciences ; Drug Screening Assays, Antitumor ; General pharmacology ; Humans ; Inhibitory Concentration 50 ; Medical sciences ; Molecular Structure ; Peru ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Plants, Medicinal - chemistry ; Plasmodium falciparum - drug effects ; Quassins - chemistry ; Quassins - isolation & purification ; Quassins - pharmacology ; Simaroubaceae - chemistry ; Tumor Cells, Cultured</subject><ispartof>Journal of natural products (Washington, D.C.), 2004-05, Vol.67 (5), p.772-777</ispartof><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15793302$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15165136$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Muhammad, I</creatorcontrib><creatorcontrib>Bedir, E</creatorcontrib><creatorcontrib>Khan, S.I</creatorcontrib><creatorcontrib>Tekwani, B.L</creatorcontrib><creatorcontrib>Khan, I.A</creatorcontrib><creatorcontrib>Takamatsu, S</creatorcontrib><creatorcontrib>Pelletier, J</creatorcontrib><creatorcontrib>Walker, L.A</creatorcontrib><title>new antimalarial quassinoid from Simaba orinocensis</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>A new antimalarial quassinoid, namely, orinocinolide (1), was isolated from the root bark of Simaba orinocensis, together with the previously reported simalikalactone D (2). The structure of 1 was determined primarily from 1D and 2D NMR analysis, as well as by chemical derivatization. Compound 1 was found to be as equally potent as 2 against Plasmodium falciparum clones D6 and W2 (IC(50) 3.27 and 8.53 ng/mL vs 3.0 and 3.67 ng/mL, respectively), but was 4- and 28-fold less toxic than 2 against VERO cells (IC(50) 10 vs 2.3 microg/mL) and HL-60 (IC(50) 0.7 vs 0.025 microg/mL), respectively. In addition, 2 was >46- and >31-fold more potent than pentamidine and amphotericin B (IC(50) 0.035 vs 1.6 and 1.1 microg/mL) against Leishmania donovani, while 1 was inactive. Orinocinolide (1) inhibited growth of human cancer cells SK-MEL, KB, BT-549, and SK-OV-3, but was less potent than 2 (IC(50) 0.8-1.9 vs 0.3-1.0 microg/mL) against these cells.</description><subject>Animals</subject><subject>Antimalarials - chemistry</subject><subject>Antimalarials - isolation & purification</subject><subject>Antimalarials - pharmacology</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - isolation & purification</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General pharmacology</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Peru</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plants, Medicinal - chemistry</subject><subject>Plasmodium falciparum - drug effects</subject><subject>Quassins - chemistry</subject><subject>Quassins - isolation & purification</subject><subject>Quassins - pharmacology</subject><subject>Simaroubaceae - chemistry</subject><subject>Tumor Cells, Cultured</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpN0MFKw0AQBuBFFFurB19Ac_EYnd3J7iZHKWrEikJa8BYmya5E06Tutqhv70KreBqY_-NnGMZOOVxyEPyqXwGCFEm_x8ZcCogVCLnPxsAVxpiqZMSOvH8DCCyTh2zEJVeSoxoz7M1nRP26XVJHrqUu-tiQ920_tE1k3bCMihBVFA0u7GrT-9YfswNLnTcnuzlhi9ub-TSPZ09399PrWWxFlq3jlETGrSSRqBpJpA3pxhjEyhDXSd2kgkRlIeWcg82qDBVoaSqpK20ahQ1O2Nm2d7WplqYpVy6c4r7L3-sDuNgB8jV11lFft_6f0xkiiODirWv92nz95eTeS6VRy3L-XJTJvHjJIX8oH4M_33pLQ0mvLnQuCgEcIbw7lanAH9-aavU</recordid><startdate>20040501</startdate><enddate>20040501</enddate><creator>Muhammad, I</creator><creator>Bedir, E</creator><creator>Khan, S.I</creator><creator>Tekwani, B.L</creator><creator>Khan, I.A</creator><creator>Takamatsu, S</creator><creator>Pelletier, J</creator><creator>Walker, L.A</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></search><sort><creationdate>20040501</creationdate><title>new antimalarial quassinoid from Simaba orinocensis</title><author>Muhammad, I ; Bedir, E ; Khan, S.I ; Tekwani, B.L ; Khan, I.A ; Takamatsu, S ; Pelletier, J ; Walker, L.A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-f299t-8a291f5a246c3a28da7dee33bea174cd82a2bf081110f9b936075eb57b7ed63d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Animals</topic><topic>Antimalarials - chemistry</topic><topic>Antimalarials - isolation & purification</topic><topic>Antimalarials - pharmacology</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - isolation & purification</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General pharmacology</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Peru</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plants, Medicinal - chemistry</topic><topic>Plasmodium falciparum - drug effects</topic><topic>Quassins - chemistry</topic><topic>Quassins - isolation & purification</topic><topic>Quassins - pharmacology</topic><topic>Simaroubaceae - chemistry</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Muhammad, I</creatorcontrib><creatorcontrib>Bedir, E</creatorcontrib><creatorcontrib>Khan, S.I</creatorcontrib><creatorcontrib>Tekwani, B.L</creatorcontrib><creatorcontrib>Khan, I.A</creatorcontrib><creatorcontrib>Takamatsu, S</creatorcontrib><creatorcontrib>Pelletier, J</creatorcontrib><creatorcontrib>Walker, L.A</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><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Muhammad, I</au><au>Bedir, E</au><au>Khan, S.I</au><au>Tekwani, B.L</au><au>Khan, I.A</au><au>Takamatsu, S</au><au>Pelletier, J</au><au>Walker, L.A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>new antimalarial quassinoid from Simaba orinocensis</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2004-05-01</date><risdate>2004</risdate><volume>67</volume><issue>5</issue><spage>772</spage><epage>777</epage><pages>772-777</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>A new antimalarial quassinoid, namely, orinocinolide (1), was isolated from the root bark of Simaba orinocensis, together with the previously reported simalikalactone D (2). The structure of 1 was determined primarily from 1D and 2D NMR analysis, as well as by chemical derivatization. Compound 1 was found to be as equally potent as 2 against Plasmodium falciparum clones D6 and W2 (IC(50) 3.27 and 8.53 ng/mL vs 3.0 and 3.67 ng/mL, respectively), but was 4- and 28-fold less toxic than 2 against VERO cells (IC(50) 10 vs 2.3 microg/mL) and HL-60 (IC(50) 0.7 vs 0.025 microg/mL), respectively. In addition, 2 was >46- and >31-fold more potent than pentamidine and amphotericin B (IC(50) 0.035 vs 1.6 and 1.1 microg/mL) against Leishmania donovani, while 1 was inactive. Orinocinolide (1) inhibited growth of human cancer cells SK-MEL, KB, BT-549, and SK-OV-3, but was less potent than 2 (IC(50) 0.8-1.9 vs 0.3-1.0 microg/mL) against these cells.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>15165136</pmid><doi>10.1021/np030524n</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2004-05, Vol.67 (5), p.772-777 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_pubmed_primary_15165136 |
| source | MEDLINE; ACS Publications |
| subjects | Animals Antimalarials - chemistry Antimalarials - isolation & purification Antimalarials - pharmacology Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - isolation & purification Antineoplastic Agents, Phytogenic - pharmacology Biological and medical sciences Drug Screening Assays, Antitumor General pharmacology Humans Inhibitory Concentration 50 Medical sciences Molecular Structure Peru Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plants, Medicinal - chemistry Plasmodium falciparum - drug effects Quassins - chemistry Quassins - isolation & purification Quassins - pharmacology Simaroubaceae - chemistry Tumor Cells, Cultured |
| title | new antimalarial quassinoid from Simaba orinocensis |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-20T05%3A59%3A59IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-istex_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=new%20antimalarial%20quassinoid%20from%20Simaba%20orinocensis&rft.jtitle=Journal%20of%20natural%20products%20(Washington,%20D.C.)&rft.au=Muhammad,%20I&rft.date=2004-05-01&rft.volume=67&rft.issue=5&rft.spage=772&rft.epage=777&rft.pages=772-777&rft.issn=0163-3864&rft.eissn=1520-6025&rft.coden=JNPRDF&rft_id=info:doi/10.1021/np030524n&rft_dat=%3Cistex_pubme%3Eark_67375_TPS_4TSXH0HK_M%3C/istex_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/15165136&rfr_iscdi=true |