Cytotoxic Activity of Some Phenanthroindolizidine N-Oxide Alkaloids from Cynanchum vincetoxicum
Two previously known phenanthroindolizidine alkaloids, (-)-10beta-antofine N-oxide (1) and (-)-10beta, 13aalpha-14beta-hydroxyantofine N-oxide (2), and a novel alkaloid, (-)-10beta,13aalpha-secoantofine N-oxide (3), were isolated from aerial parts of Cynanchum vincetoxicum. Their structures were est...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2000-11, Vol.63 (11), p.1584-1586 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | STæRK, Dan CHRISTENSEN, Jette LEMMICH, Else DUUS, Jens Ø. OLSEN, Carl Erik JAROSZEWSKI, Jerzy W. |
| description | Two previously known phenanthroindolizidine alkaloids, (-)-10beta-antofine N-oxide (1) and (-)-10beta, 13aalpha-14beta-hydroxyantofine N-oxide (2), and a novel alkaloid, (-)-10beta,13aalpha-secoantofine N-oxide (3), were isolated from aerial parts of Cynanchum vincetoxicum. Their structures were established by means of NMR methods, including COSY, NOESY, HSQC, and HMBC experiments, as well as from their CD spectra. Cytotoxic activity of the alkaloids was assessed in vitro using both a drug-sensitive KB-3-1 and a multi-drug-resistant KB-V1 cancer cell line. The antofine derivatives (1 and 2) showed pronounced cytotoxicity against the drug-sensitive cell line (IC(50) values about 100 nM), whereas the secoantofine derivative (3) was considerably less active. The KB-V1 cell line showed a marginal resistance against all alkaloids, demonstrating that these compounds are poor substrates for the P-glycoprotein (P-170) efflux pump. |
| doi_str_mv | 10.1021/np0003443 |
| format | Article |
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Their structures were established by means of NMR methods, including COSY, NOESY, HSQC, and HMBC experiments, as well as from their CD spectra. Cytotoxic activity of the alkaloids was assessed in vitro using both a drug-sensitive KB-3-1 and a multi-drug-resistant KB-V1 cancer cell line. The antofine derivatives (1 and 2) showed pronounced cytotoxicity against the drug-sensitive cell line (IC(50) values about 100 nM), whereas the secoantofine derivative (3) was considerably less active. The KB-V1 cell line showed a marginal resistance against all alkaloids, demonstrating that these compounds are poor substrates for the P-glycoprotein (P-170) efflux pump.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np0003443</identifier><identifier>PMID: 11087617</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alkaloids - isolation & purification ; Alkaloids - pharmacology ; Antineoplastic Agents, Phytogenic - isolation & purification ; Antineoplastic Agents, Phytogenic - pharmacology ; Biological and medical sciences ; Circular Dichroism ; Drug Screening Assays, Antitumor ; General pharmacology ; Humans ; Indolizines ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Medical sciences ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Phenanthrenes - isolation & purification ; Phenanthrenes - pharmacology ; Plant Leaves - chemistry ; Plants, Medicinal - chemistry ; Spectrophotometry, Ultraviolet ; Tumor Cells, Cultured</subject><ispartof>Journal of natural products (Washington, D.C.), 2000-11, Vol.63 (11), p.1584-1586</ispartof><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=830854$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11087617$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>STæRK, Dan</creatorcontrib><creatorcontrib>CHRISTENSEN, Jette</creatorcontrib><creatorcontrib>LEMMICH, Else</creatorcontrib><creatorcontrib>DUUS, Jens Ø.</creatorcontrib><creatorcontrib>OLSEN, Carl Erik</creatorcontrib><creatorcontrib>JAROSZEWSKI, Jerzy W.</creatorcontrib><title>Cytotoxic Activity of Some Phenanthroindolizidine N-Oxide Alkaloids from Cynanchum vincetoxicum</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Two previously known phenanthroindolizidine alkaloids, (-)-10beta-antofine N-oxide (1) and (-)-10beta, 13aalpha-14beta-hydroxyantofine N-oxide (2), and a novel alkaloid, (-)-10beta,13aalpha-secoantofine N-oxide (3), were isolated from aerial parts of Cynanchum vincetoxicum. Their structures were established by means of NMR methods, including COSY, NOESY, HSQC, and HMBC experiments, as well as from their CD spectra. Cytotoxic activity of the alkaloids was assessed in vitro using both a drug-sensitive KB-3-1 and a multi-drug-resistant KB-V1 cancer cell line. The antofine derivatives (1 and 2) showed pronounced cytotoxicity against the drug-sensitive cell line (IC(50) values about 100 nM), whereas the secoantofine derivative (3) was considerably less active. The KB-V1 cell line showed a marginal resistance against all alkaloids, demonstrating that these compounds are poor substrates for the P-glycoprotein (P-170) efflux pump.</description><subject>Alkaloids - isolation & purification</subject><subject>Alkaloids - pharmacology</subject><subject>Antineoplastic Agents, Phytogenic - isolation & purification</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Circular Dichroism</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General pharmacology</subject><subject>Humans</subject><subject>Indolizines</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Medical sciences</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Phenanthrenes - isolation & purification</subject><subject>Phenanthrenes - pharmacology</subject><subject>Plant Leaves - chemistry</subject><subject>Plants, Medicinal - chemistry</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Tumor Cells, Cultured</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9z1FPwjAUBeDGaATRB_-AaeLztO3d2vKIi4KRAAn4vHRrGyrbSrZBmL_eKcjTfThfTs5F6J6SJ0oYfS63hBAIQ7hAfRoxEnDCokvUJ5RDAJKHPXRT11-_iAyja9SjlEjBqeijJG4b3_iDy_Aoa9zeNS32Fi99YfBibUpVNuvKu1L73H077UqDZ8H84LTBo3yjcu90jW3lCxy3Hc7WuwLvXZmZv85dcYuurMprc3e6A_T59rqKJ8F0Pn6PR9PAASVNAMOQCmNlCpGyXIdhpihQkXIjNWOKWalYKjnXNmUgYShAUiUiAmBkyjmBAXo49m53aWF0sq1coao2-f-0A48noOpM5bbqxrr67CQQGYWdCo7K1Y05nFNVbRIuQETJarFM-MeMTMZynLzADxLicMY</recordid><startdate>20001101</startdate><enddate>20001101</enddate><creator>STæRK, Dan</creator><creator>CHRISTENSEN, Jette</creator><creator>LEMMICH, Else</creator><creator>DUUS, Jens Ø.</creator><creator>OLSEN, Carl Erik</creator><creator>JAROSZEWSKI, Jerzy W.</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><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>20001101</creationdate><title>Cytotoxic Activity of Some Phenanthroindolizidine N-Oxide Alkaloids from Cynanchum vincetoxicum</title><author>STæRK, Dan ; CHRISTENSEN, Jette ; LEMMICH, Else ; DUUS, Jens Ø. ; OLSEN, Carl Erik ; JAROSZEWSKI, Jerzy W.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i310t-39417ef8b35af6d44ca1317b6e8d22a2f8a2b866dfb238397381a75033e8b6603</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Alkaloids - isolation & purification</topic><topic>Alkaloids - pharmacology</topic><topic>Antineoplastic Agents, Phytogenic - isolation & purification</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Circular Dichroism</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General pharmacology</topic><topic>Humans</topic><topic>Indolizines</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Medical sciences</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Phenanthrenes - isolation & purification</topic><topic>Phenanthrenes - pharmacology</topic><topic>Plant Leaves - chemistry</topic><topic>Plants, Medicinal - chemistry</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>STæRK, Dan</creatorcontrib><creatorcontrib>CHRISTENSEN, Jette</creatorcontrib><creatorcontrib>LEMMICH, Else</creatorcontrib><creatorcontrib>DUUS, Jens Ø.</creatorcontrib><creatorcontrib>OLSEN, Carl Erik</creatorcontrib><creatorcontrib>JAROSZEWSKI, Jerzy W.</creatorcontrib><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>STæRK, Dan</au><au>CHRISTENSEN, Jette</au><au>LEMMICH, Else</au><au>DUUS, Jens Ø.</au><au>OLSEN, Carl Erik</au><au>JAROSZEWSKI, Jerzy W.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cytotoxic Activity of Some Phenanthroindolizidine N-Oxide Alkaloids from Cynanchum vincetoxicum</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2000-11-01</date><risdate>2000</risdate><volume>63</volume><issue>11</issue><spage>1584</spage><epage>1586</epage><pages>1584-1586</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Two previously known phenanthroindolizidine alkaloids, (-)-10beta-antofine N-oxide (1) and (-)-10beta, 13aalpha-14beta-hydroxyantofine N-oxide (2), and a novel alkaloid, (-)-10beta,13aalpha-secoantofine N-oxide (3), were isolated from aerial parts of Cynanchum vincetoxicum. Their structures were established by means of NMR methods, including COSY, NOESY, HSQC, and HMBC experiments, as well as from their CD spectra. Cytotoxic activity of the alkaloids was assessed in vitro using both a drug-sensitive KB-3-1 and a multi-drug-resistant KB-V1 cancer cell line. The antofine derivatives (1 and 2) showed pronounced cytotoxicity against the drug-sensitive cell line (IC(50) values about 100 nM), whereas the secoantofine derivative (3) was considerably less active. The KB-V1 cell line showed a marginal resistance against all alkaloids, demonstrating that these compounds are poor substrates for the P-glycoprotein (P-170) efflux pump.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>11087617</pmid><doi>10.1021/np0003443</doi><tpages>3</tpages></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 2000-11, Vol.63 (11), p.1584-1586 |
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| source | MEDLINE; ACS Publications |
| subjects | Alkaloids - isolation & purification Alkaloids - pharmacology Antineoplastic Agents, Phytogenic - isolation & purification Antineoplastic Agents, Phytogenic - pharmacology Biological and medical sciences Circular Dichroism Drug Screening Assays, Antitumor General pharmacology Humans Indolizines Magnetic Resonance Spectroscopy Mass Spectrometry Medical sciences Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Phenanthrenes - isolation & purification Phenanthrenes - pharmacology Plant Leaves - chemistry Plants, Medicinal - chemistry Spectrophotometry, Ultraviolet Tumor Cells, Cultured |
| title | Cytotoxic Activity of Some Phenanthroindolizidine N-Oxide Alkaloids from Cynanchum vincetoxicum |
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