Rhazinilam–Leuconolam–Leuconoxine Alkaloids from Leuconotis griffithii
Eight new indole alkaloids (1–8) belonging to the rhazinilam–leuconolam–leuconoxine group, in addition to 52 other alkaloids, were isolated from the stem-bark extract of Leuconotis griffithii, viz., nor-rhazinicine (1), 5,21-dihydrorhazinilam-N-oxide (2), 3,14-dehydroleuconolam (3), and leuconodines...
Gespeichert in:
| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2013-05, Vol.76 (5), p.957-964 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 964 |
|---|---|
| container_issue | 5 |
| container_start_page | 957 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 76 |
| creator | Gan, Chew-Yan Low, Yun-Yee Thomas, Noel F Kam, Toh-Seok |
| description | Eight new indole alkaloids (1–8) belonging to the rhazinilam–leuconolam–leuconoxine group, in addition to 52 other alkaloids, were isolated from the stem-bark extract of Leuconotis griffithii, viz., nor-rhazinicine (1), 5,21-dihydrorhazinilam-N-oxide (2), 3,14-dehydroleuconolam (3), and leuconodines A–E (4–8). The structures of these alkaloids were determined using NMR and MS analyses and in some instances confirmed by X-ray diffraction analyses. Alkaloids 1, 5, and 7 showed only moderate to weak cytotoxicity toward KB cells (IC50 12–18 μg/mL), while 8 showed moderate activity in reversing MDR in vincristine-resistant KB cells. |
| doi_str_mv | 10.1021/np400214y |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1355480761</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1355480761</sourcerecordid><originalsourceid>FETCH-LOGICAL-a315t-c554d5db1ed0421e75a1fbf5c38ee0ac472c1d1fd79ca05da2c181602a05cae23</originalsourceid><addsrcrecordid>eNptkM1KAzEUhYMotlYXvoB0I-hi9N5JMjNdSvGXgiC6HtL82NSZSU1mwLryHXxDn8RIa0FwdTjcj3M5h5BDhDOEFM-bBYOobLlF-shTSDJI-TbpA2Y0oUXGemQvhDkAUBjxXdJLacZyVuR9cvcwE--2sZWovz4-J7qTrnF_zJtt9PCiehGVsyoMjXf1cH1qbRg-e2uMbWfW7pMdI6qgD9Y6IE9Xl4_jm2Ryf307vpgkgiJvE8k5U1xNUStgKeqcCzRTwyUttAYhWZ5KVGhUPpICuBLRFhgbRSOFTumAnKxyF969djq0ZW2D1FUlGu26UCKNHwrIM4zo6QqV3oXgtSkX3tbCL0uE8me6cjNdZI_Wsd201mpD_m4VgeMVIGQo567zTWz5T9A3q894fw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1355480761</pqid></control><display><type>article</type><title>Rhazinilam–Leuconolam–Leuconoxine Alkaloids from Leuconotis griffithii</title><source>MEDLINE</source><source>ACS Publications</source><creator>Gan, Chew-Yan ; Low, Yun-Yee ; Thomas, Noel F ; Kam, Toh-Seok</creator><creatorcontrib>Gan, Chew-Yan ; Low, Yun-Yee ; Thomas, Noel F ; Kam, Toh-Seok</creatorcontrib><description>Eight new indole alkaloids (1–8) belonging to the rhazinilam–leuconolam–leuconoxine group, in addition to 52 other alkaloids, were isolated from the stem-bark extract of Leuconotis griffithii, viz., nor-rhazinicine (1), 5,21-dihydrorhazinilam-N-oxide (2), 3,14-dehydroleuconolam (3), and leuconodines A–E (4–8). The structures of these alkaloids were determined using NMR and MS analyses and in some instances confirmed by X-ray diffraction analyses. Alkaloids 1, 5, and 7 showed only moderate to weak cytotoxicity toward KB cells (IC50 12–18 μg/mL), while 8 showed moderate activity in reversing MDR in vincristine-resistant KB cells.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np400214y</identifier><identifier>PMID: 23647487</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Alkaloids - chemistry ; Alkaloids - isolation & purification ; Alkaloids - pharmacology ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - isolation & purification ; Antineoplastic Agents, Phytogenic - pharmacology ; Apocynaceae - chemistry ; Azepines - chemistry ; Crystallography, X-Ray ; Drug Resistance, Neoplasm - drug effects ; Drug Screening Assays, Antitumor ; Heterocyclic Compounds, 4 or More Rings - chemistry ; Humans ; Indolizines - chemistry ; KB Cells ; Lactams - chemistry ; Malaysia ; Molecular Conformation ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Plant Bark - chemistry ; Vincristine - pharmacology</subject><ispartof>Journal of natural products (Washington, D.C.), 2013-05, Vol.76 (5), p.957-964</ispartof><rights>Copyright © 2013 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-c554d5db1ed0421e75a1fbf5c38ee0ac472c1d1fd79ca05da2c181602a05cae23</citedby><cites>FETCH-LOGICAL-a315t-c554d5db1ed0421e75a1fbf5c38ee0ac472c1d1fd79ca05da2c181602a05cae23</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/np400214y$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np400214y$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23647487$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gan, Chew-Yan</creatorcontrib><creatorcontrib>Low, Yun-Yee</creatorcontrib><creatorcontrib>Thomas, Noel F</creatorcontrib><creatorcontrib>Kam, Toh-Seok</creatorcontrib><title>Rhazinilam–Leuconolam–Leuconoxine Alkaloids from Leuconotis griffithii</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Eight new indole alkaloids (1–8) belonging to the rhazinilam–leuconolam–leuconoxine group, in addition to 52 other alkaloids, were isolated from the stem-bark extract of Leuconotis griffithii, viz., nor-rhazinicine (1), 5,21-dihydrorhazinilam-N-oxide (2), 3,14-dehydroleuconolam (3), and leuconodines A–E (4–8). The structures of these alkaloids were determined using NMR and MS analyses and in some instances confirmed by X-ray diffraction analyses. Alkaloids 1, 5, and 7 showed only moderate to weak cytotoxicity toward KB cells (IC50 12–18 μg/mL), while 8 showed moderate activity in reversing MDR in vincristine-resistant KB cells.</description><subject>Alkaloids - chemistry</subject><subject>Alkaloids - isolation & purification</subject><subject>Alkaloids - pharmacology</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - isolation & purification</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Apocynaceae - chemistry</subject><subject>Azepines - chemistry</subject><subject>Crystallography, X-Ray</subject><subject>Drug Resistance, Neoplasm - drug effects</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Heterocyclic Compounds, 4 or More Rings - chemistry</subject><subject>Humans</subject><subject>Indolizines - chemistry</subject><subject>KB Cells</subject><subject>Lactams - chemistry</subject><subject>Malaysia</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Plant Bark - chemistry</subject><subject>Vincristine - pharmacology</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM1KAzEUhYMotlYXvoB0I-hi9N5JMjNdSvGXgiC6HtL82NSZSU1mwLryHXxDn8RIa0FwdTjcj3M5h5BDhDOEFM-bBYOobLlF-shTSDJI-TbpA2Y0oUXGemQvhDkAUBjxXdJLacZyVuR9cvcwE--2sZWovz4-J7qTrnF_zJtt9PCiehGVsyoMjXf1cH1qbRg-e2uMbWfW7pMdI6qgD9Y6IE9Xl4_jm2Ryf307vpgkgiJvE8k5U1xNUStgKeqcCzRTwyUttAYhWZ5KVGhUPpICuBLRFhgbRSOFTumAnKxyF969djq0ZW2D1FUlGu26UCKNHwrIM4zo6QqV3oXgtSkX3tbCL0uE8me6cjNdZI_Wsd201mpD_m4VgeMVIGQo567zTWz5T9A3q894fw</recordid><startdate>20130524</startdate><enddate>20130524</enddate><creator>Gan, Chew-Yan</creator><creator>Low, Yun-Yee</creator><creator>Thomas, Noel F</creator><creator>Kam, Toh-Seok</creator><general>American Chemical Society and American Society of Pharmacognosy</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>20130524</creationdate><title>Rhazinilam–Leuconolam–Leuconoxine Alkaloids from Leuconotis griffithii</title><author>Gan, Chew-Yan ; Low, Yun-Yee ; Thomas, Noel F ; Kam, Toh-Seok</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a315t-c554d5db1ed0421e75a1fbf5c38ee0ac472c1d1fd79ca05da2c181602a05cae23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Alkaloids - chemistry</topic><topic>Alkaloids - isolation & purification</topic><topic>Alkaloids - pharmacology</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - isolation & purification</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Apocynaceae - chemistry</topic><topic>Azepines - chemistry</topic><topic>Crystallography, X-Ray</topic><topic>Drug Resistance, Neoplasm - drug effects</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Heterocyclic Compounds, 4 or More Rings - chemistry</topic><topic>Humans</topic><topic>Indolizines - chemistry</topic><topic>KB Cells</topic><topic>Lactams - chemistry</topic><topic>Malaysia</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Plant Bark - chemistry</topic><topic>Vincristine - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gan, Chew-Yan</creatorcontrib><creatorcontrib>Low, Yun-Yee</creatorcontrib><creatorcontrib>Thomas, Noel F</creatorcontrib><creatorcontrib>Kam, Toh-Seok</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>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gan, Chew-Yan</au><au>Low, Yun-Yee</au><au>Thomas, Noel F</au><au>Kam, Toh-Seok</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rhazinilam–Leuconolam–Leuconoxine Alkaloids from Leuconotis griffithii</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2013-05-24</date><risdate>2013</risdate><volume>76</volume><issue>5</issue><spage>957</spage><epage>964</epage><pages>957-964</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>Eight new indole alkaloids (1–8) belonging to the rhazinilam–leuconolam–leuconoxine group, in addition to 52 other alkaloids, were isolated from the stem-bark extract of Leuconotis griffithii, viz., nor-rhazinicine (1), 5,21-dihydrorhazinilam-N-oxide (2), 3,14-dehydroleuconolam (3), and leuconodines A–E (4–8). The structures of these alkaloids were determined using NMR and MS analyses and in some instances confirmed by X-ray diffraction analyses. Alkaloids 1, 5, and 7 showed only moderate to weak cytotoxicity toward KB cells (IC50 12–18 μg/mL), while 8 showed moderate activity in reversing MDR in vincristine-resistant KB cells.</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>23647487</pmid><doi>10.1021/np400214y</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2013-05, Vol.76 (5), p.957-964 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1355480761 |
| source | MEDLINE; ACS Publications |
| subjects | Alkaloids - chemistry Alkaloids - isolation & purification Alkaloids - pharmacology Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - isolation & purification Antineoplastic Agents, Phytogenic - pharmacology Apocynaceae - chemistry Azepines - chemistry Crystallography, X-Ray Drug Resistance, Neoplasm - drug effects Drug Screening Assays, Antitumor Heterocyclic Compounds, 4 or More Rings - chemistry Humans Indolizines - chemistry KB Cells Lactams - chemistry Malaysia Molecular Conformation Molecular Structure Nuclear Magnetic Resonance, Biomolecular Plant Bark - chemistry Vincristine - pharmacology |
| title | Rhazinilam–Leuconolam–Leuconoxine Alkaloids from Leuconotis griffithii |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-12T22%3A44%3A18IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Rhazinilam%E2%80%93Leuconolam%E2%80%93Leuconoxine%20Alkaloids%20from%20Leuconotis%20griffithii&rft.jtitle=Journal%20of%20natural%20products%20(Washington,%20D.C.)&rft.au=Gan,%20Chew-Yan&rft.date=2013-05-24&rft.volume=76&rft.issue=5&rft.spage=957&rft.epage=964&rft.pages=957-964&rft.issn=0163-3864&rft.eissn=1520-6025&rft_id=info:doi/10.1021/np400214y&rft_dat=%3Cproquest_cross%3E1355480761%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1355480761&rft_id=info:pmid/23647487&rfr_iscdi=true |