Grandisines C−G, Indolizidine Alkaloids from the Australian Rainforest Tree Elaeocarpus grandis
Five new indolizidine alkaloids, grandisines C, D, E, F, and G (4−8), and one known indolizidine alkaloid, (−)-isoelaeocarpiline (3), were isolated from the leaves of Elaeocarpus grandis and their structures determined by 1D and 2D NMR spectroscopy. Grandisine C (4) is isomeric with the known compou...
Gespeichert in:
| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2006-09, Vol.69 (9), p.1295-1299 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1299 |
|---|---|
| container_issue | 9 |
| container_start_page | 1295 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 69 |
| creator | Katavic, Peter L Venables, Debra A Forster, Paul I Guymer, Gordon Carroll, Anthony R |
| description | Five new indolizidine alkaloids, grandisines C, D, E, F, and G (4−8), and one known indolizidine alkaloid, (−)-isoelaeocarpiline (3), were isolated from the leaves of Elaeocarpus grandis and their structures determined by 1D and 2D NMR spectroscopy. Grandisine C (4) is isomeric with the known compound rudrakine (1). The absolute configuration of grandisine D (5) was deduced by its conversion to (−)-isoelaeocarpiline. Grandisine E (6) contains a novel tetracyclic ring system. Grandisine F (7) is the 14-amino analogue of grandisine C. Grandisine G (8) contains the novel combination of a piperidine attached to an indolizidine. Grandisines C, D, F, and G and (−)-isoelaeocarpiline showed receptor binding affinity for the human δ-opioid receptor with IC50 values of 14.6, 1.65, 1.55, 75.4, and 9.9 μM, respectively. |
| doi_str_mv | 10.1021/np060179c |
| format | Article |
| fullrecord | <record><control><sourceid>acs_pubme</sourceid><recordid>TN_cdi_pubmed_primary_16989522</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>a069580748</sourcerecordid><originalsourceid>FETCH-LOGICAL-a331t-ccb14deeb4855f2889b6ba8794c647364e81d1dc055b5a317e5229e3fc46a81a3</originalsourceid><addsrcrecordid>eNpFkc1O3DAUhS3Uqgy0C16g9YZdU-6Nf-Is0QgGJEQrGDbdWDeOQw2ZZGRnpJYn6JpH5ElwNRRWVzr307k_h7EDhG8IJR4Na9CAVe122AxVCYWGUr1jM0AtCmG03GV7Kd0BgIBafWC7qGtTq7KcMVpEGtqQwuATnz_9fVx85edDO_bhIbRZ5Mf9PfVjaBPv4rji068sbdIUqQ808CsKQzdGnya-jN7zk5786CiuN4nfbp0_svcd9cl_eqn77Ob0ZDk_Ky6-L87nxxcFCYFT4VyDsvW-kUaprjSmbnRDpqql07ISWnqDLbYOlGoUCax83r_2onNSk0ES--zz1ne9aVa-tesYVhT_2P-3ZuDwBaDkqO_yei6kN86gqGSNmSu2XEiT__3ap3hvdSUqZZc_ru2ZuISfUl3aRea_bPmORku3MXveXJeAAhBBlhrfJpNL9m7cxCE_wiLYf-nZ1_TEM-41h4M</addsrcrecordid><sourcetype>Index Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Grandisines C−G, Indolizidine Alkaloids from the Australian Rainforest Tree Elaeocarpus grandis</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Katavic, Peter L ; Venables, Debra A ; Forster, Paul I ; Guymer, Gordon ; Carroll, Anthony R</creator><creatorcontrib>Katavic, Peter L ; Venables, Debra A ; Forster, Paul I ; Guymer, Gordon ; Carroll, Anthony R</creatorcontrib><description>Five new indolizidine alkaloids, grandisines C, D, E, F, and G (4−8), and one known indolizidine alkaloid, (−)-isoelaeocarpiline (3), were isolated from the leaves of Elaeocarpus grandis and their structures determined by 1D and 2D NMR spectroscopy. Grandisine C (4) is isomeric with the known compound rudrakine (1). The absolute configuration of grandisine D (5) was deduced by its conversion to (−)-isoelaeocarpiline. Grandisine E (6) contains a novel tetracyclic ring system. Grandisine F (7) is the 14-amino analogue of grandisine C. Grandisine G (8) contains the novel combination of a piperidine attached to an indolizidine. Grandisines C, D, F, and G and (−)-isoelaeocarpiline showed receptor binding affinity for the human δ-opioid receptor with IC50 values of 14.6, 1.65, 1.55, 75.4, and 9.9 μM, respectively.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np060179c</identifier><identifier>PMID: 16989522</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alkaloids - chemistry ; Alkaloids - isolation & purification ; Alkaloids - pharmacology ; Australia ; bioactive properties ; Biological and medical sciences ; chemical constituents of plants ; chemical structure ; Elaeocarpaceae - chemistry ; Elaeocarpus ; Elaeocarpus grandis ; forest trees ; General pharmacology ; grandisine ; Humans ; indolizidine alkaloids ; Indolizines - chemistry ; Indolizines - isolation & purification ; Indolizines - pharmacology ; Inhibitory Concentration 50 ; isoelaeocarpiline ; ligands ; Medical sciences ; Molecular Structure ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Plant Leaves - chemistry ; Plants, Medicinal - chemistry ; Pyridines - chemistry ; Pyridines - isolation & purification ; Pyridines - pharmacology ; rain forests ; receptors ; Receptors, Opioid - drug effects ; spectral analysis ; Trees - chemistry</subject><ispartof>Journal of natural products (Washington, D.C.), 2006-09, Vol.69 (9), p.1295-1299</ispartof><rights>Copyright © 2006 American Chemical Society and American Society of Pharmacognosy</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np060179c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np060179c$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18137491$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16989522$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Katavic, Peter L</creatorcontrib><creatorcontrib>Venables, Debra A</creatorcontrib><creatorcontrib>Forster, Paul I</creatorcontrib><creatorcontrib>Guymer, Gordon</creatorcontrib><creatorcontrib>Carroll, Anthony R</creatorcontrib><title>Grandisines C−G, Indolizidine Alkaloids from the Australian Rainforest Tree Elaeocarpus grandis</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Five new indolizidine alkaloids, grandisines C, D, E, F, and G (4−8), and one known indolizidine alkaloid, (−)-isoelaeocarpiline (3), were isolated from the leaves of Elaeocarpus grandis and their structures determined by 1D and 2D NMR spectroscopy. Grandisine C (4) is isomeric with the known compound rudrakine (1). The absolute configuration of grandisine D (5) was deduced by its conversion to (−)-isoelaeocarpiline. Grandisine E (6) contains a novel tetracyclic ring system. Grandisine F (7) is the 14-amino analogue of grandisine C. Grandisine G (8) contains the novel combination of a piperidine attached to an indolizidine. Grandisines C, D, F, and G and (−)-isoelaeocarpiline showed receptor binding affinity for the human δ-opioid receptor with IC50 values of 14.6, 1.65, 1.55, 75.4, and 9.9 μM, respectively.</description><subject>Alkaloids - chemistry</subject><subject>Alkaloids - isolation & purification</subject><subject>Alkaloids - pharmacology</subject><subject>Australia</subject><subject>bioactive properties</subject><subject>Biological and medical sciences</subject><subject>chemical constituents of plants</subject><subject>chemical structure</subject><subject>Elaeocarpaceae - chemistry</subject><subject>Elaeocarpus</subject><subject>Elaeocarpus grandis</subject><subject>forest trees</subject><subject>General pharmacology</subject><subject>grandisine</subject><subject>Humans</subject><subject>indolizidine alkaloids</subject><subject>Indolizines - chemistry</subject><subject>Indolizines - isolation & purification</subject><subject>Indolizines - pharmacology</subject><subject>Inhibitory Concentration 50</subject><subject>isoelaeocarpiline</subject><subject>ligands</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plant Leaves - chemistry</subject><subject>Plants, Medicinal - chemistry</subject><subject>Pyridines - chemistry</subject><subject>Pyridines - isolation & purification</subject><subject>Pyridines - pharmacology</subject><subject>rain forests</subject><subject>receptors</subject><subject>Receptors, Opioid - drug effects</subject><subject>spectral analysis</subject><subject>Trees - chemistry</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>eNpFkc1O3DAUhS3Uqgy0C16g9YZdU-6Nf-Is0QgGJEQrGDbdWDeOQw2ZZGRnpJYn6JpH5ElwNRRWVzr307k_h7EDhG8IJR4Na9CAVe122AxVCYWGUr1jM0AtCmG03GV7Kd0BgIBafWC7qGtTq7KcMVpEGtqQwuATnz_9fVx85edDO_bhIbRZ5Mf9PfVjaBPv4rji068sbdIUqQ808CsKQzdGnya-jN7zk5786CiuN4nfbp0_svcd9cl_eqn77Ob0ZDk_Ky6-L87nxxcFCYFT4VyDsvW-kUaprjSmbnRDpqql07ISWnqDLbYOlGoUCax83r_2onNSk0ES--zz1ne9aVa-tesYVhT_2P-3ZuDwBaDkqO_yei6kN86gqGSNmSu2XEiT__3ap3hvdSUqZZc_ru2ZuISfUl3aRea_bPmORku3MXveXJeAAhBBlhrfJpNL9m7cxCE_wiLYf-nZ1_TEM-41h4M</recordid><startdate>20060922</startdate><enddate>20060922</enddate><creator>Katavic, Peter L</creator><creator>Venables, Debra A</creator><creator>Forster, Paul I</creator><creator>Guymer, Gordon</creator><creator>Carroll, Anthony R</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>20060922</creationdate><title>Grandisines C−G, Indolizidine Alkaloids from the Australian Rainforest Tree Elaeocarpus grandis</title><author>Katavic, Peter L ; Venables, Debra A ; Forster, Paul I ; Guymer, Gordon ; Carroll, Anthony R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a331t-ccb14deeb4855f2889b6ba8794c647364e81d1dc055b5a317e5229e3fc46a81a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Alkaloids - chemistry</topic><topic>Alkaloids - isolation & purification</topic><topic>Alkaloids - pharmacology</topic><topic>Australia</topic><topic>bioactive properties</topic><topic>Biological and medical sciences</topic><topic>chemical constituents of plants</topic><topic>chemical structure</topic><topic>Elaeocarpaceae - chemistry</topic><topic>Elaeocarpus</topic><topic>Elaeocarpus grandis</topic><topic>forest trees</topic><topic>General pharmacology</topic><topic>grandisine</topic><topic>Humans</topic><topic>indolizidine alkaloids</topic><topic>Indolizines - chemistry</topic><topic>Indolizines - isolation & purification</topic><topic>Indolizines - pharmacology</topic><topic>Inhibitory Concentration 50</topic><topic>isoelaeocarpiline</topic><topic>ligands</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plant Leaves - chemistry</topic><topic>Plants, Medicinal - chemistry</topic><topic>Pyridines - chemistry</topic><topic>Pyridines - isolation & purification</topic><topic>Pyridines - pharmacology</topic><topic>rain forests</topic><topic>receptors</topic><topic>Receptors, Opioid - drug effects</topic><topic>spectral analysis</topic><topic>Trees - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Katavic, Peter L</creatorcontrib><creatorcontrib>Venables, Debra A</creatorcontrib><creatorcontrib>Forster, Paul I</creatorcontrib><creatorcontrib>Guymer, Gordon</creatorcontrib><creatorcontrib>Carroll, Anthony R</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>Katavic, Peter L</au><au>Venables, Debra A</au><au>Forster, Paul I</au><au>Guymer, Gordon</au><au>Carroll, Anthony R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Grandisines C−G, Indolizidine Alkaloids from the Australian Rainforest Tree Elaeocarpus grandis</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2006-09-22</date><risdate>2006</risdate><volume>69</volume><issue>9</issue><spage>1295</spage><epage>1299</epage><pages>1295-1299</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Five new indolizidine alkaloids, grandisines C, D, E, F, and G (4−8), and one known indolizidine alkaloid, (−)-isoelaeocarpiline (3), were isolated from the leaves of Elaeocarpus grandis and their structures determined by 1D and 2D NMR spectroscopy. Grandisine C (4) is isomeric with the known compound rudrakine (1). The absolute configuration of grandisine D (5) was deduced by its conversion to (−)-isoelaeocarpiline. Grandisine E (6) contains a novel tetracyclic ring system. Grandisine F (7) is the 14-amino analogue of grandisine C. Grandisine G (8) contains the novel combination of a piperidine attached to an indolizidine. Grandisines C, D, F, and G and (−)-isoelaeocarpiline showed receptor binding affinity for the human δ-opioid receptor with IC50 values of 14.6, 1.65, 1.55, 75.4, and 9.9 μM, respectively.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>16989522</pmid><doi>10.1021/np060179c</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2006-09, Vol.69 (9), p.1295-1299 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_pubmed_primary_16989522 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Alkaloids - chemistry Alkaloids - isolation & purification Alkaloids - pharmacology Australia bioactive properties Biological and medical sciences chemical constituents of plants chemical structure Elaeocarpaceae - chemistry Elaeocarpus Elaeocarpus grandis forest trees General pharmacology grandisine Humans indolizidine alkaloids Indolizines - chemistry Indolizines - isolation & purification Indolizines - pharmacology Inhibitory Concentration 50 isoelaeocarpiline ligands Medical sciences Molecular Structure Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plant Leaves - chemistry Plants, Medicinal - chemistry Pyridines - chemistry Pyridines - isolation & purification Pyridines - pharmacology rain forests receptors Receptors, Opioid - drug effects spectral analysis Trees - chemistry |
| title | Grandisines C−G, Indolizidine Alkaloids from the Australian Rainforest Tree Elaeocarpus grandis |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-22T22%3A39%3A12IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Grandisines%20C%E2%88%92G,%20Indolizidine%20Alkaloids%20from%20the%20Australian%20Rainforest%20Tree%20Elaeocarpus%20grandis&rft.jtitle=Journal%20of%20natural%20products%20(Washington,%20D.C.)&rft.au=Katavic,%20Peter%20L&rft.date=2006-09-22&rft.volume=69&rft.issue=9&rft.spage=1295&rft.epage=1299&rft.pages=1295-1299&rft.issn=0163-3864&rft.eissn=1520-6025&rft.coden=JNPRDF&rft_id=info:doi/10.1021/np060179c&rft_dat=%3Cacs_pubme%3Ea069580748%3C/acs_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/16989522&rfr_iscdi=true |