Effects of Various Isoquinoline Alkaloids on In Vitro 3H-Dopamine Uptake by Rat Striatal Synaptosomes
Various alkaloids having an isoquinoline skeleton from different species of the Annonaceae, Fumariacae, and Aristolochiacae (aporphine, cularine, benzylisoquinoline, and bisbenzylisoquinoline derivatives) were tested for their ability to inhibit in vitro 3H-dopamine uptake by rat striatal dopamine D...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 1995-10, Vol.58 (10), p.1475-1484 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Protais, Philippe Arbaoui, Jeannette Bakkali, El-Hassan Bermejo, Almudena Cortes, Diego |
| description | Various alkaloids having an isoquinoline skeleton from different species of the Annonaceae, Fumariacae, and Aristolochiacae (aporphine, cularine, benzylisoquinoline, and bisbenzylisoquinoline derivatives) were tested for their ability to inhibit in vitro 3H-dopamine uptake by rat striatal dopamine D1 3H-SCH 23390 AND D2 3H-raclopride binding sites. Except for some aporphine derivatives (anonaine [1], norstephalagine [2], isopiline [3]) and some bisbenzylisoquinoline alkaloids (dimethylgrisabine [27], antioquine [28], obaberine [29], isotetrandrine [30]) that displayed affinities of the same order as the reference compounds (nomifensine [38], amineptine [39], dexamphetamine [40]), the other tested products had low, or no, affinity on the 3H-dopamine uptake since, in comparison, its affinity at dopamine D1 3H-SCH 23390 and D2 3H-raclopride binding sites was low. These data suggest that it could be possible to synthesize anonaine-like products displaying intense dopamine-uptake inhibitory properties, which could lead to a potential antidepressant activity. |
| doi_str_mv | 10.1021/np50124a001 |
| format | Article |
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Except for some aporphine derivatives (anonaine [1], norstephalagine [2], isopiline [3]) and some bisbenzylisoquinoline alkaloids (dimethylgrisabine [27], antioquine [28], obaberine [29], isotetrandrine [30]) that displayed affinities of the same order as the reference compounds (nomifensine [38], amineptine [39], dexamphetamine [40]), the other tested products had low, or no, affinity on the 3H-dopamine uptake since, in comparison, its affinity at dopamine D1 3H-SCH 23390 and D2 3H-raclopride binding sites was low. These data suggest that it could be possible to synthesize anonaine-like products displaying intense dopamine-uptake inhibitory properties, which could lead to a potential antidepressant activity.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np50124a001</identifier><identifier>PMID: 8676127</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>ALCALOIDE QUINOLIQUE ; ALCALOIDES DE LA QUINOLINA ; Alkaloids - metabolism ; Animals ; ANNONACEAE ; ARISTOLOCHIACEAE ; BARK ; Benzazepines - metabolism ; BINDING SITE ; Binding, Competitive ; BIOASSAYS ; Biological and medical sciences ; CHEMICAL COMPOSITION ; COMPOSICION QUIMICA ; COMPOSITION CHIMIQUE ; Corpus Striatum - metabolism ; CORTEZA ; DERIVATIVES ; DOPAMINA ; DOPAMINE ; Dopamine - metabolism ; Dopamine Antagonists - metabolism ; DOSAGE BIOLOGIQUE ; DRUG PLANTS ; ECORCE ; ENSAYO BIOLOGICO ; FEUILLE ; FUMARIACEAE ; General pharmacology ; HOJAS ; In Vitro Techniques ; INHIBICION ; INHIBITION ; LEAVES ; Male ; Medical sciences ; MOLECULAR CONFORMATION ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; PLANTAS MEDICINALES ; PLANTE MEDICINALE ; QUINOLINE ALKALOIDS ; Raclopride ; RAT ; RATA ; RATS ; Rats, Wistar ; Salicylamides - metabolism ; Synaptosomes - metabolism ; Tritium</subject><ispartof>Journal of natural products (Washington, D.C.), 1995-10, Vol.58 (10), p.1475-1484</ispartof><rights>1996 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/np50124a001$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np50124a001$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2941180$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/8676127$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Protais, Philippe</creatorcontrib><creatorcontrib>Arbaoui, Jeannette</creatorcontrib><creatorcontrib>Bakkali, El-Hassan</creatorcontrib><creatorcontrib>Bermejo, Almudena</creatorcontrib><creatorcontrib>Cortes, Diego</creatorcontrib><title>Effects of Various Isoquinoline Alkaloids on In Vitro 3H-Dopamine Uptake by Rat Striatal Synaptosomes</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Various alkaloids having an isoquinoline skeleton from different species of the Annonaceae, Fumariacae, and Aristolochiacae (aporphine, cularine, benzylisoquinoline, and bisbenzylisoquinoline derivatives) were tested for their ability to inhibit in vitro 3H-dopamine uptake by rat striatal dopamine D1 3H-SCH 23390 AND D2 3H-raclopride binding sites. Except for some aporphine derivatives (anonaine [1], norstephalagine [2], isopiline [3]) and some bisbenzylisoquinoline alkaloids (dimethylgrisabine [27], antioquine [28], obaberine [29], isotetrandrine [30]) that displayed affinities of the same order as the reference compounds (nomifensine [38], amineptine [39], dexamphetamine [40]), the other tested products had low, or no, affinity on the 3H-dopamine uptake since, in comparison, its affinity at dopamine D1 3H-SCH 23390 and D2 3H-raclopride binding sites was low. These data suggest that it could be possible to synthesize anonaine-like products displaying intense dopamine-uptake inhibitory properties, which could lead to a potential antidepressant activity.</description><subject>ALCALOIDE QUINOLIQUE</subject><subject>ALCALOIDES DE LA QUINOLINA</subject><subject>Alkaloids - metabolism</subject><subject>Animals</subject><subject>ANNONACEAE</subject><subject>ARISTOLOCHIACEAE</subject><subject>BARK</subject><subject>Benzazepines - metabolism</subject><subject>BINDING SITE</subject><subject>Binding, Competitive</subject><subject>BIOASSAYS</subject><subject>Biological and medical sciences</subject><subject>CHEMICAL COMPOSITION</subject><subject>COMPOSICION QUIMICA</subject><subject>COMPOSITION CHIMIQUE</subject><subject>Corpus Striatum - metabolism</subject><subject>CORTEZA</subject><subject>DERIVATIVES</subject><subject>DOPAMINA</subject><subject>DOPAMINE</subject><subject>Dopamine - metabolism</subject><subject>Dopamine Antagonists - metabolism</subject><subject>DOSAGE BIOLOGIQUE</subject><subject>DRUG PLANTS</subject><subject>ECORCE</subject><subject>ENSAYO BIOLOGICO</subject><subject>FEUILLE</subject><subject>FUMARIACEAE</subject><subject>General pharmacology</subject><subject>HOJAS</subject><subject>In Vitro Techniques</subject><subject>INHIBICION</subject><subject>INHIBITION</subject><subject>LEAVES</subject><subject>Male</subject><subject>Medical sciences</subject><subject>MOLECULAR CONFORMATION</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>PLANTAS MEDICINALES</subject><subject>PLANTE MEDICINALE</subject><subject>QUINOLINE ALKALOIDS</subject><subject>Raclopride</subject><subject>RAT</subject><subject>RATA</subject><subject>RATS</subject><subject>Rats, Wistar</subject><subject>Salicylamides - metabolism</subject><subject>Synaptosomes - metabolism</subject><subject>Tritium</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1995</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpNkc2P0zAQxS0EWsrCiRsSkg8ITgGP7djJcVUWttJKFPoBN2ua2MjbJA52KtH_HletVsxlDu83b_RmCHkN7CMwDp-GsWTAJTIGT8gMSs4KxXj5lMwYKFGISsnn5EVKD4wxweryilxVSivgekbsrXO2mRINjm4x-nBIdJHCn4MfQucHS2-6PXbBt5kY6GKgWz_FQMVd8TmM2J-IzTjh3tLdkf7Aia6m6HHCjq6OA45TSKG36SV55rBL9tWlX5PNl9v1_K64__Z1Mb-5LxA06MK12oGtULoWmqYG2arG7nQpubJc1SVrHUinhJaiYm1ldaurapdneMud5Uxck_dn3zHmCDZNpvepsV2Hg83JjM4lpeAZfHsBD7vetmaMvsd4NJe7ZP3dRcfUYOciDo1PjxivJUB12lecMZ8m-_dRxrg3SgtdmvVyZebL7a_18ieY75l_c-YdBoO_Y7bcrGoFJdQnsw9nEZtkHsIhDvlUBpg5Pdn892TxD6r2lGs</recordid><startdate>199510</startdate><enddate>199510</enddate><creator>Protais, Philippe</creator><creator>Arbaoui, Jeannette</creator><creator>Bakkali, El-Hassan</creator><creator>Bermejo, Almudena</creator><creator>Cortes, Diego</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>7X8</scope></search><sort><creationdate>199510</creationdate><title>Effects of Various Isoquinoline Alkaloids on In Vitro 3H-Dopamine Uptake by Rat Striatal Synaptosomes</title><author>Protais, Philippe ; Arbaoui, Jeannette ; Bakkali, El-Hassan ; Bermejo, Almudena ; Cortes, Diego</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a1717-fd7f1e8a4fd1cc914d6ceb75426e26950df14f6374380d8e7d788b7f12d2fe203</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1995</creationdate><topic>ALCALOIDE QUINOLIQUE</topic><topic>ALCALOIDES DE LA QUINOLINA</topic><topic>Alkaloids - metabolism</topic><topic>Animals</topic><topic>ANNONACEAE</topic><topic>ARISTOLOCHIACEAE</topic><topic>BARK</topic><topic>Benzazepines - metabolism</topic><topic>BINDING SITE</topic><topic>Binding, Competitive</topic><topic>BIOASSAYS</topic><topic>Biological and medical sciences</topic><topic>CHEMICAL COMPOSITION</topic><topic>COMPOSICION QUIMICA</topic><topic>COMPOSITION CHIMIQUE</topic><topic>Corpus Striatum - metabolism</topic><topic>CORTEZA</topic><topic>DERIVATIVES</topic><topic>DOPAMINA</topic><topic>DOPAMINE</topic><topic>Dopamine - metabolism</topic><topic>Dopamine Antagonists - metabolism</topic><topic>DOSAGE BIOLOGIQUE</topic><topic>DRUG PLANTS</topic><topic>ECORCE</topic><topic>ENSAYO BIOLOGICO</topic><topic>FEUILLE</topic><topic>FUMARIACEAE</topic><topic>General pharmacology</topic><topic>HOJAS</topic><topic>In Vitro Techniques</topic><topic>INHIBICION</topic><topic>INHIBITION</topic><topic>LEAVES</topic><topic>Male</topic><topic>Medical sciences</topic><topic>MOLECULAR CONFORMATION</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>PLANTAS MEDICINALES</topic><topic>PLANTE MEDICINALE</topic><topic>QUINOLINE ALKALOIDS</topic><topic>Raclopride</topic><topic>RAT</topic><topic>RATA</topic><topic>RATS</topic><topic>Rats, Wistar</topic><topic>Salicylamides - metabolism</topic><topic>Synaptosomes - metabolism</topic><topic>Tritium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Protais, Philippe</creatorcontrib><creatorcontrib>Arbaoui, Jeannette</creatorcontrib><creatorcontrib>Bakkali, El-Hassan</creatorcontrib><creatorcontrib>Bermejo, Almudena</creatorcontrib><creatorcontrib>Cortes, Diego</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>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>Protais, Philippe</au><au>Arbaoui, Jeannette</au><au>Bakkali, El-Hassan</au><au>Bermejo, Almudena</au><au>Cortes, Diego</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Effects of Various Isoquinoline Alkaloids on In Vitro 3H-Dopamine Uptake by Rat Striatal Synaptosomes</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>1995-10</date><risdate>1995</risdate><volume>58</volume><issue>10</issue><spage>1475</spage><epage>1484</epage><pages>1475-1484</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Various alkaloids having an isoquinoline skeleton from different species of the Annonaceae, Fumariacae, and Aristolochiacae (aporphine, cularine, benzylisoquinoline, and bisbenzylisoquinoline derivatives) were tested for their ability to inhibit in vitro 3H-dopamine uptake by rat striatal dopamine D1 3H-SCH 23390 AND D2 3H-raclopride binding sites. Except for some aporphine derivatives (anonaine [1], norstephalagine [2], isopiline [3]) and some bisbenzylisoquinoline alkaloids (dimethylgrisabine [27], antioquine [28], obaberine [29], isotetrandrine [30]) that displayed affinities of the same order as the reference compounds (nomifensine [38], amineptine [39], dexamphetamine [40]), the other tested products had low, or no, affinity on the 3H-dopamine uptake since, in comparison, its affinity at dopamine D1 3H-SCH 23390 and D2 3H-raclopride binding sites was low. These data suggest that it could be possible to synthesize anonaine-like products displaying intense dopamine-uptake inhibitory properties, which could lead to a potential antidepressant activity.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>8676127</pmid><doi>10.1021/np50124a001</doi><tpages>10</tpages></addata></record> |
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| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 1995-10, Vol.58 (10), p.1475-1484 |
| issn | 0163-3864 1520-6025 |
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| source | ACS Publications; MEDLINE |
| subjects | ALCALOIDE QUINOLIQUE ALCALOIDES DE LA QUINOLINA Alkaloids - metabolism Animals ANNONACEAE ARISTOLOCHIACEAE BARK Benzazepines - metabolism BINDING SITE Binding, Competitive BIOASSAYS Biological and medical sciences CHEMICAL COMPOSITION COMPOSICION QUIMICA COMPOSITION CHIMIQUE Corpus Striatum - metabolism CORTEZA DERIVATIVES DOPAMINA DOPAMINE Dopamine - metabolism Dopamine Antagonists - metabolism DOSAGE BIOLOGIQUE DRUG PLANTS ECORCE ENSAYO BIOLOGICO FEUILLE FUMARIACEAE General pharmacology HOJAS In Vitro Techniques INHIBICION INHIBITION LEAVES Male Medical sciences MOLECULAR CONFORMATION Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments PLANTAS MEDICINALES PLANTE MEDICINALE QUINOLINE ALKALOIDS Raclopride RAT RATA RATS Rats, Wistar Salicylamides - metabolism Synaptosomes - metabolism Tritium |
| title | Effects of Various Isoquinoline Alkaloids on In Vitro 3H-Dopamine Uptake by Rat Striatal Synaptosomes |
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