Biologically Active Aspidofractinine Alkaloids from Kopsia singapurensis
Ten new indole alkaloids of the aspidofractinine type, in addition to several recently reported indole alkaloids and 20 other known alkaloids, were obtained from the leaf and stem-bark extract of the Malayan Kopsia singapurensis, viz., kopsimalines A−E (1−5), kopsinicine (6), kopsofinone (7), and ko...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2008-01, Vol.71 (1), p.53-57 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Subramaniam, G Hiraku, Osamu Hayashi, Masahiko Koyano, Takashi Komiyama, Kanki Kam, Toh-Seok |
| description | Ten new indole alkaloids of the aspidofractinine type, in addition to several recently reported indole alkaloids and 20 other known alkaloids, were obtained from the leaf and stem-bark extract of the Malayan Kopsia singapurensis, viz., kopsimalines A−E (1−5), kopsinicine (6), kopsofinone (7), and kopsiloscines H−J (8−10). The structures of these alkaloids were determined using NMR and MS analysis. Kopsimalines A (1), B (2), C (3), D (4), and E (5) and kopsiloscine J (10) were found to reverse multidrug-resistance in vincristine-resistant KB cells, with 1 showing the highest potency. |
| doi_str_mv | 10.1021/np070401t |
| format | Article |
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The structures of these alkaloids were determined using NMR and MS analysis. Kopsimalines A (1), B (2), C (3), D (4), and E (5) and kopsiloscine J (10) were found to reverse multidrug-resistance in vincristine-resistant KB cells, with 1 showing the highest potency.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np070401t</identifier><identifier>PMID: 18078327</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>anticarcinogenic activity ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - isolation & purification ; Antineoplastic Agents, Phytogenic - pharmacology ; Apocynaceae ; Apocynaceae - chemistry ; aspidofractinine alkaloids ; Biological and medical sciences ; chemical structure ; cultured cells ; cytotoxicity ; Drug Resistance, Neoplasm - drug effects ; Drug Screening Assays, Antitumor ; General pharmacology ; Humans ; indole alkaloids ; Indole Alkaloids - chemistry ; Indole Alkaloids - isolation & purification ; Indole Alkaloids - pharmacology ; KB Cells ; Kopsia singapurensis ; kopsiloscine ; kopsimaline ; kopsinicine ; kopsofinone ; Malaysia ; Medical sciences ; Molecular Structure ; multiple drug resistance ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Plant Bark - chemistry ; Plant Leaves - chemistry ; Plants, Medicinal - chemistry ; spectral analysis ; Vincristine - pharmacology</subject><ispartof>Journal of natural products (Washington, D.C.), 2008-01, Vol.71 (1), p.53-57</ispartof><rights>Copyright © 2008 American Chemical Society and American Society of Pharmacognosy and std np</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a471t-28220e1ffb634768d8eeaf4c4403acc573f719225b2e87a61afefdf73339b4833</citedby><cites>FETCH-LOGICAL-a471t-28220e1ffb634768d8eeaf4c4403acc573f719225b2e87a61afefdf73339b4833</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/np070401t$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np070401t$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20032443$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18078327$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Subramaniam, G</creatorcontrib><creatorcontrib>Hiraku, Osamu</creatorcontrib><creatorcontrib>Hayashi, Masahiko</creatorcontrib><creatorcontrib>Koyano, Takashi</creatorcontrib><creatorcontrib>Komiyama, Kanki</creatorcontrib><creatorcontrib>Kam, Toh-Seok</creatorcontrib><title>Biologically Active Aspidofractinine Alkaloids from Kopsia singapurensis</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Ten new indole alkaloids of the aspidofractinine type, in addition to several recently reported indole alkaloids and 20 other known alkaloids, were obtained from the leaf and stem-bark extract of the Malayan Kopsia singapurensis, viz., kopsimalines A−E (1−5), kopsinicine (6), kopsofinone (7), and kopsiloscines H−J (8−10). The structures of these alkaloids were determined using NMR and MS analysis. Kopsimalines A (1), B (2), C (3), D (4), and E (5) and kopsiloscine J (10) were found to reverse multidrug-resistance in vincristine-resistant KB cells, with 1 showing the highest potency.</description><subject>anticarcinogenic activity</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - isolation & purification</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Apocynaceae</subject><subject>Apocynaceae - chemistry</subject><subject>aspidofractinine alkaloids</subject><subject>Biological and medical sciences</subject><subject>chemical structure</subject><subject>cultured cells</subject><subject>cytotoxicity</subject><subject>Drug Resistance, Neoplasm - drug effects</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General pharmacology</subject><subject>Humans</subject><subject>indole alkaloids</subject><subject>Indole Alkaloids - chemistry</subject><subject>Indole Alkaloids - isolation & purification</subject><subject>Indole Alkaloids - pharmacology</subject><subject>KB Cells</subject><subject>Kopsia singapurensis</subject><subject>kopsiloscine</subject><subject>kopsimaline</subject><subject>kopsinicine</subject><subject>kopsofinone</subject><subject>Malaysia</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>multiple drug resistance</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plant Bark - chemistry</subject><subject>Plant Leaves - chemistry</subject><subject>Plants, Medicinal - chemistry</subject><subject>spectral analysis</subject><subject>Vincristine - pharmacology</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM1uEzEURi1ERdPCgheA2YDEYsr1z9jOMrTQVm0FUtsNG-vGY0duJ-OpPYPat8dRorBhZdk--r57DyHvKZxQYPRrP4ACAXR8RWa0YVBLYM1rMgMqec21FIfkKOcHAOAwb96QQ6pBac7UjFx8C7GLq2Cx616qhR3DH1ct8hDa6BOWax_68tA9YhdDmyuf4rq6ikMOWOXQr3CYkutzyG_Jgccuu3e785jc__h-d3pRX_88vzxdXNcoFB1rphkDR71fSi6U1K12Dr2wQgBHaxvFvaJzxpolc1qhpOidb73inM-XQnN-TD5vc4cUnyaXR7MO2bquw97FKRsFTHAhaQG_bEGbYs7JeTOksMb0YiiYjTaz11bYD7vQabl27T9y56kAn3YA5qKqqOltyHuOFbNMiM109ZYLeXTP-39Mj0Yqrhpz9-vWnIH6fS5vzsxV4T9ueY_R4CqVzPtbBpQDaDXflO-b0WbzEKfUF7v_WeEvFECZGA</recordid><startdate>20080101</startdate><enddate>20080101</enddate><creator>Subramaniam, G</creator><creator>Hiraku, Osamu</creator><creator>Hayashi, Masahiko</creator><creator>Koyano, Takashi</creator><creator>Komiyama, Kanki</creator><creator>Kam, Toh-Seok</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>20080101</creationdate><title>Biologically Active Aspidofractinine Alkaloids from Kopsia singapurensis</title><author>Subramaniam, G ; Hiraku, Osamu ; Hayashi, Masahiko ; Koyano, Takashi ; Komiyama, Kanki ; Kam, Toh-Seok</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a471t-28220e1ffb634768d8eeaf4c4403acc573f719225b2e87a61afefdf73339b4833</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>anticarcinogenic activity</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - isolation & purification</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Apocynaceae</topic><topic>Apocynaceae - chemistry</topic><topic>aspidofractinine alkaloids</topic><topic>Biological and medical sciences</topic><topic>chemical structure</topic><topic>cultured cells</topic><topic>cytotoxicity</topic><topic>Drug Resistance, Neoplasm - drug effects</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General pharmacology</topic><topic>Humans</topic><topic>indole alkaloids</topic><topic>Indole Alkaloids - chemistry</topic><topic>Indole Alkaloids - isolation & purification</topic><topic>Indole Alkaloids - pharmacology</topic><topic>KB Cells</topic><topic>Kopsia singapurensis</topic><topic>kopsiloscine</topic><topic>kopsimaline</topic><topic>kopsinicine</topic><topic>kopsofinone</topic><topic>Malaysia</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>multiple drug resistance</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plant Bark - chemistry</topic><topic>Plant Leaves - chemistry</topic><topic>Plants, Medicinal - chemistry</topic><topic>spectral analysis</topic><topic>Vincristine - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Subramaniam, G</creatorcontrib><creatorcontrib>Hiraku, Osamu</creatorcontrib><creatorcontrib>Hayashi, Masahiko</creatorcontrib><creatorcontrib>Koyano, Takashi</creatorcontrib><creatorcontrib>Komiyama, Kanki</creatorcontrib><creatorcontrib>Kam, Toh-Seok</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>Subramaniam, G</au><au>Hiraku, Osamu</au><au>Hayashi, Masahiko</au><au>Koyano, Takashi</au><au>Komiyama, Kanki</au><au>Kam, Toh-Seok</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Biologically Active Aspidofractinine Alkaloids from Kopsia singapurensis</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2008-01-01</date><risdate>2008</risdate><volume>71</volume><issue>1</issue><spage>53</spage><epage>57</epage><pages>53-57</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Ten new indole alkaloids of the aspidofractinine type, in addition to several recently reported indole alkaloids and 20 other known alkaloids, were obtained from the leaf and stem-bark extract of the Malayan Kopsia singapurensis, viz., kopsimalines A−E (1−5), kopsinicine (6), kopsofinone (7), and kopsiloscines H−J (8−10). The structures of these alkaloids were determined using NMR and MS analysis. Kopsimalines A (1), B (2), C (3), D (4), and E (5) and kopsiloscine J (10) were found to reverse multidrug-resistance in vincristine-resistant KB cells, with 1 showing the highest potency.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>18078327</pmid><doi>10.1021/np070401t</doi><tpages>5</tpages></addata></record> |
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| subjects | anticarcinogenic activity Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - isolation & purification Antineoplastic Agents, Phytogenic - pharmacology Apocynaceae Apocynaceae - chemistry aspidofractinine alkaloids Biological and medical sciences chemical structure cultured cells cytotoxicity Drug Resistance, Neoplasm - drug effects Drug Screening Assays, Antitumor General pharmacology Humans indole alkaloids Indole Alkaloids - chemistry Indole Alkaloids - isolation & purification Indole Alkaloids - pharmacology KB Cells Kopsia singapurensis kopsiloscine kopsimaline kopsinicine kopsofinone Malaysia Medical sciences Molecular Structure multiple drug resistance Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plant Bark - chemistry Plant Leaves - chemistry Plants, Medicinal - chemistry spectral analysis Vincristine - pharmacology |
| title | Biologically Active Aspidofractinine Alkaloids from Kopsia singapurensis |
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