Certain Norditerpenoid Alkaloids and Their Cardiovascular Action
Thirteen new derivatives of norditerpenoid alkaloids, namely, 8-deacetyl-8-p-aminobenzoyldelphinine (1), 8-deacetyl-8-anthranoyldelphinine (2), 8-deacetyl-8-(4-hydroxy-3-methoxycinnamoyl)delphinine (3), 16-demethoxy-15,16-didehydro-8-p-anisoyl-14-benzoyldelphonine (4), 6-acetylheteratisine N-oxide (...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 1998-06, Vol.61 (6), p.743-748 |
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| creator | Desai, Haridutt K Hart, Bradley P Caldwell, R. William Jianzhong-Huang Pelletier, S. William |
| description | Thirteen new derivatives of norditerpenoid alkaloids, namely, 8-deacetyl-8-p-aminobenzoyldelphinine (1), 8-deacetyl-8-anthranoyldelphinine (2), 8-deacetyl-8-(4-hydroxy-3-methoxycinnamoyl)delphinine (3), 16-demethoxy-15,16-didehydro-8-p-anisoyl-14-benzoyldelphonine (4), 6-acetylheteratisine N-oxide (6), 3,8-diacetylfalconerine (7), 8-stearoylfalconerine (8), 8-linolenylfalconerine (9), 13-acetylpyrodelphinine (11), 13-acetyldelphinine N-oxide (13), N-deacetyl-8,9-diacetyllappaconitine (14), 8,9-(methylenedioxy)lappaconine (15), and 16-epipyroaconitine N-oxide (17), were prepared, and their structures were established by analysis of spectroscopic data (1D and 2D NMR, HRFABMS). The preliminary in vivo cardiovascular action (hypotensive, bradycardic, and ventricular arrhythmias) of these new compounds was tested in male Sprague−Dawley rats. The results are reported herein. |
| doi_str_mv | 10.1021/np970499j |
| format | Article |
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William ; Jianzhong-Huang ; Pelletier, S. William</creator><creatorcontrib>Desai, Haridutt K ; Hart, Bradley P ; Caldwell, R. William ; Jianzhong-Huang ; Pelletier, S. William</creatorcontrib><description>Thirteen new derivatives of norditerpenoid alkaloids, namely, 8-deacetyl-8-p-aminobenzoyldelphinine (1), 8-deacetyl-8-anthranoyldelphinine (2), 8-deacetyl-8-(4-hydroxy-3-methoxycinnamoyl)delphinine (3), 16-demethoxy-15,16-didehydro-8-p-anisoyl-14-benzoyldelphonine (4), 6-acetylheteratisine N-oxide (6), 3,8-diacetylfalconerine (7), 8-stearoylfalconerine (8), 8-linolenylfalconerine (9), 13-acetylpyrodelphinine (11), 13-acetyldelphinine N-oxide (13), N-deacetyl-8,9-diacetyllappaconitine (14), 8,9-(methylenedioxy)lappaconine (15), and 16-epipyroaconitine N-oxide (17), were prepared, and their structures were established by analysis of spectroscopic data (1D and 2D NMR, HRFABMS). The preliminary in vivo cardiovascular action (hypotensive, bradycardic, and ventricular arrhythmias) of these new compounds was tested in male Sprague−Dawley rats. The results are reported herein.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np970499j</identifier><identifier>PMID: 9644057</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>ACONITUM ; ALCALOIDE ; ALCALOIDES ; ALKALOIDS ; Alkaloids - chemical synthesis ; Alkaloids - pharmacology ; Animals ; Anti-Arrhythmia Agents - chemical synthesis ; Anti-Arrhythmia Agents - pharmacology ; Antihypertensive agents ; Antihypertensive Agents - chemical synthesis ; Antihypertensive Agents - pharmacology ; ARRHYTHMIA ; Biological and medical sciences ; BLOOD PRESSURE ; BRADYCARDIA ; CARDIAC RHYTHM ; CARDIOVASCULAR AGENTS ; Cardiovascular Agents - chemical synthesis ; Cardiovascular Agents - pharmacology ; CARDIOVASCULAR DISEASES ; Cardiovascular system ; CHEMICAL COMPOSITION ; CHEMICAL STRUCTURE ; COMPOSICION QUIMICA ; COMPOSITION CHIMIQUE ; DELPHINIUM ; Diterpenes - chemical synthesis ; Diterpenes - pharmacology ; DITERPENOIDE ; DITERPENOIDS ; DITERPENOS ; ENFERMEDADES CARDIOVASCULARES ; ESPECTROMETRIA ; ESTRUCTURA QUIMICA ; EXTRACTOS VEGETALES ; EXTRAIT D'ORIGINE VEGETALE ; FRECUENCIA CARDIACA ; FREQUENCE CARDIAQUE ; HEART RATE ; Hemodynamics - drug effects ; HYPOTENSION ; MALADIE CARDIOVASCULAIRE ; Male ; Medical sciences ; MEDICAMENTOS CARDIOVASCULARES ; MEDICINAL PROPERTIES ; MODIFICATEUR CARDIOVASCULAIRE ; Pharmacology. Drug treatments ; PLANT EXTRACTS ; Plants, Medicinal - chemistry ; PRESION SANGUINEA ; PRESSION SANGUINE ; PROPIEDADES MEDICINALES ; PROPRIETE PHARMACOLOGIQUE ; Rats ; Rats, Inbred SHR ; Rats, Sprague-Dawley ; SPECTRAL ANALYSIS ; SPECTROMETRIE ; SPECTROMETRY ; STRUCTURE CHIMIQUE</subject><ispartof>Journal of natural products (Washington, D.C.), 1998-06, Vol.61 (6), p.743-748</ispartof><rights>Copyright © 1998 American Chemical Society and American Society of Pharmacognosy</rights><rights>1998 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a399t-d7a422d739f811f9acc8abce705d33b26a183a2754bfd8850d43b363c9a88f6d3</citedby><cites>FETCH-LOGICAL-a399t-d7a422d739f811f9acc8abce705d33b26a183a2754bfd8850d43b363c9a88f6d3</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/np970499j$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np970499j$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2764,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2307375$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9644057$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Desai, Haridutt K</creatorcontrib><creatorcontrib>Hart, Bradley P</creatorcontrib><creatorcontrib>Caldwell, R. William</creatorcontrib><creatorcontrib>Jianzhong-Huang</creatorcontrib><creatorcontrib>Pelletier, S. William</creatorcontrib><title>Certain Norditerpenoid Alkaloids and Their Cardiovascular Action</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Thirteen new derivatives of norditerpenoid alkaloids, namely, 8-deacetyl-8-p-aminobenzoyldelphinine (1), 8-deacetyl-8-anthranoyldelphinine (2), 8-deacetyl-8-(4-hydroxy-3-methoxycinnamoyl)delphinine (3), 16-demethoxy-15,16-didehydro-8-p-anisoyl-14-benzoyldelphonine (4), 6-acetylheteratisine N-oxide (6), 3,8-diacetylfalconerine (7), 8-stearoylfalconerine (8), 8-linolenylfalconerine (9), 13-acetylpyrodelphinine (11), 13-acetyldelphinine N-oxide (13), N-deacetyl-8,9-diacetyllappaconitine (14), 8,9-(methylenedioxy)lappaconine (15), and 16-epipyroaconitine N-oxide (17), were prepared, and their structures were established by analysis of spectroscopic data (1D and 2D NMR, HRFABMS). The preliminary in vivo cardiovascular action (hypotensive, bradycardic, and ventricular arrhythmias) of these new compounds was tested in male Sprague−Dawley rats. The results are reported herein.</description><subject>ACONITUM</subject><subject>ALCALOIDE</subject><subject>ALCALOIDES</subject><subject>ALKALOIDS</subject><subject>Alkaloids - chemical synthesis</subject><subject>Alkaloids - pharmacology</subject><subject>Animals</subject><subject>Anti-Arrhythmia Agents - chemical synthesis</subject><subject>Anti-Arrhythmia Agents - pharmacology</subject><subject>Antihypertensive agents</subject><subject>Antihypertensive Agents - chemical synthesis</subject><subject>Antihypertensive Agents - pharmacology</subject><subject>ARRHYTHMIA</subject><subject>Biological and medical sciences</subject><subject>BLOOD PRESSURE</subject><subject>BRADYCARDIA</subject><subject>CARDIAC RHYTHM</subject><subject>CARDIOVASCULAR AGENTS</subject><subject>Cardiovascular Agents - chemical synthesis</subject><subject>Cardiovascular Agents - pharmacology</subject><subject>CARDIOVASCULAR DISEASES</subject><subject>Cardiovascular system</subject><subject>CHEMICAL COMPOSITION</subject><subject>CHEMICAL STRUCTURE</subject><subject>COMPOSICION QUIMICA</subject><subject>COMPOSITION CHIMIQUE</subject><subject>DELPHINIUM</subject><subject>Diterpenes - chemical synthesis</subject><subject>Diterpenes - pharmacology</subject><subject>DITERPENOIDE</subject><subject>DITERPENOIDS</subject><subject>DITERPENOS</subject><subject>ENFERMEDADES CARDIOVASCULARES</subject><subject>ESPECTROMETRIA</subject><subject>ESTRUCTURA QUIMICA</subject><subject>EXTRACTOS VEGETALES</subject><subject>EXTRAIT D'ORIGINE VEGETALE</subject><subject>FRECUENCIA CARDIACA</subject><subject>FREQUENCE CARDIAQUE</subject><subject>HEART RATE</subject><subject>Hemodynamics - drug effects</subject><subject>HYPOTENSION</subject><subject>MALADIE CARDIOVASCULAIRE</subject><subject>Male</subject><subject>Medical sciences</subject><subject>MEDICAMENTOS CARDIOVASCULARES</subject><subject>MEDICINAL PROPERTIES</subject><subject>MODIFICATEUR CARDIOVASCULAIRE</subject><subject>Pharmacology. Drug treatments</subject><subject>PLANT EXTRACTS</subject><subject>Plants, Medicinal - chemistry</subject><subject>PRESION SANGUINEA</subject><subject>PRESSION SANGUINE</subject><subject>PROPIEDADES MEDICINALES</subject><subject>PROPRIETE PHARMACOLOGIQUE</subject><subject>Rats</subject><subject>Rats, Inbred SHR</subject><subject>Rats, Sprague-Dawley</subject><subject>SPECTRAL ANALYSIS</subject><subject>SPECTROMETRIE</subject><subject>SPECTROMETRY</subject><subject>STRUCTURE CHIMIQUE</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkF1P2zAUhq2JiRW2C34AUi4YEhfZ_JHY8R1VgA6JdZMo0u6sE9sZLmnc2Qli_x5XrcoNV8fS8-g9xy9CJwR_I5iS7_1aClxIufyAJqSkOOeYlgdogglnOat48QkdxbjEGDMsy0N0KHlR4FJM0GVtwwCuz-Y-GDfYsLa9dyabdk_QpUfMoDfZ4tG6kNWQFP8MUY8dhGyqB-f7z-hjC120X3bzGD3cXC_qH_ndr9ltPb3LgUk55EZAQakRTLYVIa0ErStotBW4NIw1lAOpGFBRFk1rqqrEpmAN40xLqKqWG3aMzre56-D_jTYOauWitl0HvfVjVEJKzqUoknixFXXwMQbbqnVwKwj_FcFq05bat5Xc013o2Kys2Zu7ehI_2_H0aejaAL12ca9RhgUTZdLyrebiYF_2GMKT4htBLX7fqz9XP-nNbI5V_ba2Ba_gb0iRD_dEpquEpJQk_nXLQUe19GPoU7PvnP8Kcz6VHw</recordid><startdate>19980626</startdate><enddate>19980626</enddate><creator>Desai, Haridutt K</creator><creator>Hart, Bradley P</creator><creator>Caldwell, R. William</creator><creator>Jianzhong-Huang</creator><creator>Pelletier, S. William</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>19980626</creationdate><title>Certain Norditerpenoid Alkaloids and Their Cardiovascular Action</title><author>Desai, Haridutt K ; Hart, Bradley P ; Caldwell, R. William ; Jianzhong-Huang ; Pelletier, S. William</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a399t-d7a422d739f811f9acc8abce705d33b26a183a2754bfd8850d43b363c9a88f6d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><topic>ACONITUM</topic><topic>ALCALOIDE</topic><topic>ALCALOIDES</topic><topic>ALKALOIDS</topic><topic>Alkaloids - chemical synthesis</topic><topic>Alkaloids - pharmacology</topic><topic>Animals</topic><topic>Anti-Arrhythmia Agents - chemical synthesis</topic><topic>Anti-Arrhythmia Agents - pharmacology</topic><topic>Antihypertensive agents</topic><topic>Antihypertensive Agents - chemical synthesis</topic><topic>Antihypertensive Agents - pharmacology</topic><topic>ARRHYTHMIA</topic><topic>Biological and medical sciences</topic><topic>BLOOD PRESSURE</topic><topic>BRADYCARDIA</topic><topic>CARDIAC RHYTHM</topic><topic>CARDIOVASCULAR AGENTS</topic><topic>Cardiovascular Agents - chemical synthesis</topic><topic>Cardiovascular Agents - pharmacology</topic><topic>CARDIOVASCULAR DISEASES</topic><topic>Cardiovascular system</topic><topic>CHEMICAL COMPOSITION</topic><topic>CHEMICAL STRUCTURE</topic><topic>COMPOSICION QUIMICA</topic><topic>COMPOSITION CHIMIQUE</topic><topic>DELPHINIUM</topic><topic>Diterpenes - chemical synthesis</topic><topic>Diterpenes - pharmacology</topic><topic>DITERPENOIDE</topic><topic>DITERPENOIDS</topic><topic>DITERPENOS</topic><topic>ENFERMEDADES CARDIOVASCULARES</topic><topic>ESPECTROMETRIA</topic><topic>ESTRUCTURA QUIMICA</topic><topic>EXTRACTOS VEGETALES</topic><topic>EXTRAIT D'ORIGINE VEGETALE</topic><topic>FRECUENCIA CARDIACA</topic><topic>FREQUENCE CARDIAQUE</topic><topic>HEART RATE</topic><topic>Hemodynamics - drug effects</topic><topic>HYPOTENSION</topic><topic>MALADIE CARDIOVASCULAIRE</topic><topic>Male</topic><topic>Medical sciences</topic><topic>MEDICAMENTOS CARDIOVASCULARES</topic><topic>MEDICINAL PROPERTIES</topic><topic>MODIFICATEUR CARDIOVASCULAIRE</topic><topic>Pharmacology. Drug treatments</topic><topic>PLANT EXTRACTS</topic><topic>Plants, Medicinal - chemistry</topic><topic>PRESION SANGUINEA</topic><topic>PRESSION SANGUINE</topic><topic>PROPIEDADES MEDICINALES</topic><topic>PROPRIETE PHARMACOLOGIQUE</topic><topic>Rats</topic><topic>Rats, Inbred SHR</topic><topic>Rats, Sprague-Dawley</topic><topic>SPECTRAL ANALYSIS</topic><topic>SPECTROMETRIE</topic><topic>SPECTROMETRY</topic><topic>STRUCTURE CHIMIQUE</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Desai, Haridutt K</creatorcontrib><creatorcontrib>Hart, Bradley P</creatorcontrib><creatorcontrib>Caldwell, R. William</creatorcontrib><creatorcontrib>Jianzhong-Huang</creatorcontrib><creatorcontrib>Pelletier, S. William</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>Desai, Haridutt K</au><au>Hart, Bradley P</au><au>Caldwell, R. William</au><au>Jianzhong-Huang</au><au>Pelletier, S. William</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Certain Norditerpenoid Alkaloids and Their Cardiovascular Action</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>1998-06-26</date><risdate>1998</risdate><volume>61</volume><issue>6</issue><spage>743</spage><epage>748</epage><pages>743-748</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Thirteen new derivatives of norditerpenoid alkaloids, namely, 8-deacetyl-8-p-aminobenzoyldelphinine (1), 8-deacetyl-8-anthranoyldelphinine (2), 8-deacetyl-8-(4-hydroxy-3-methoxycinnamoyl)delphinine (3), 16-demethoxy-15,16-didehydro-8-p-anisoyl-14-benzoyldelphonine (4), 6-acetylheteratisine N-oxide (6), 3,8-diacetylfalconerine (7), 8-stearoylfalconerine (8), 8-linolenylfalconerine (9), 13-acetylpyrodelphinine (11), 13-acetyldelphinine N-oxide (13), N-deacetyl-8,9-diacetyllappaconitine (14), 8,9-(methylenedioxy)lappaconine (15), and 16-epipyroaconitine N-oxide (17), were prepared, and their structures were established by analysis of spectroscopic data (1D and 2D NMR, HRFABMS). The preliminary in vivo cardiovascular action (hypotensive, bradycardic, and ventricular arrhythmias) of these new compounds was tested in male Sprague−Dawley rats. The results are reported herein.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>9644057</pmid><doi>10.1021/np970499j</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 1998-06, Vol.61 (6), p.743-748 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_79966974 |
| source | MEDLINE; ACS Publications |
| subjects | ACONITUM ALCALOIDE ALCALOIDES ALKALOIDS Alkaloids - chemical synthesis Alkaloids - pharmacology Animals Anti-Arrhythmia Agents - chemical synthesis Anti-Arrhythmia Agents - pharmacology Antihypertensive agents Antihypertensive Agents - chemical synthesis Antihypertensive Agents - pharmacology ARRHYTHMIA Biological and medical sciences BLOOD PRESSURE BRADYCARDIA CARDIAC RHYTHM CARDIOVASCULAR AGENTS Cardiovascular Agents - chemical synthesis Cardiovascular Agents - pharmacology CARDIOVASCULAR DISEASES Cardiovascular system CHEMICAL COMPOSITION CHEMICAL STRUCTURE COMPOSICION QUIMICA COMPOSITION CHIMIQUE DELPHINIUM Diterpenes - chemical synthesis Diterpenes - pharmacology DITERPENOIDE DITERPENOIDS DITERPENOS ENFERMEDADES CARDIOVASCULARES ESPECTROMETRIA ESTRUCTURA QUIMICA EXTRACTOS VEGETALES EXTRAIT D'ORIGINE VEGETALE FRECUENCIA CARDIACA FREQUENCE CARDIAQUE HEART RATE Hemodynamics - drug effects HYPOTENSION MALADIE CARDIOVASCULAIRE Male Medical sciences MEDICAMENTOS CARDIOVASCULARES MEDICINAL PROPERTIES MODIFICATEUR CARDIOVASCULAIRE Pharmacology. Drug treatments PLANT EXTRACTS Plants, Medicinal - chemistry PRESION SANGUINEA PRESSION SANGUINE PROPIEDADES MEDICINALES PROPRIETE PHARMACOLOGIQUE Rats Rats, Inbred SHR Rats, Sprague-Dawley SPECTRAL ANALYSIS SPECTROMETRIE SPECTROMETRY STRUCTURE CHIMIQUE |
| title | Certain Norditerpenoid Alkaloids and Their Cardiovascular Action |
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