The biosynthesis of β-carboline and quinolizidine alkaloids of Alangium lamarckii
The incorporation of tryptamine, dopamine, N-deacetylisoipecoside, N-deacetylipecoside into alangimarckine, deoxytubulosine and ankorine and of strictosidine and vincoside into alangimarckine and deoxytubulosine in young Alangium lamarckii Thw. (Alangiaceae) has been studied and specific utilisation...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2002-08, Vol.60 (8), p.853-859 |
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| container_title | Phytochemistry (Oxford) |
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| creator | Jain, Sudha Sinha, Archana Bhakuni, Dewan S |
| description | The incorporation of tryptamine, dopamine,
N-deacetylisoipecoside,
N-deacetylipecoside into alangimarckine, deoxytubulosine and ankorine and of strictosidine and vincoside into alangimarckine and deoxytubulosine in young
Alangium lamarckii Thw. (Alangiaceae) has been studied and specific utilisation of
N-deacetylisoipecoside demonstrated. Parallel experiments with nordeoxytubulosine and deoxytubulosine suggested that
O-methylation precedes condensation of protoemetine with tryptamine and further the reduction of ethylene side chain takes place before condensation. Hydroxylation at C-8 in the
trans-quinolizidine moiety is the terminal step in the biosynthesis of alangimarckine.
Incorporation of labelled precursors into
17,
20 and
6 in
Alangium lamarckii Thw. is reported. It is shown that
O-methylation precedes condensation of protoemetine nucleus with tryptamine, reduction of the ethylene side chain occurs before condensation and C-8 hydroxylation in transquinolizidine part is the terminal step in the biosynthesis of
17. |
| doi_str_mv | 10.1016/S0031-9422(02)00057-2 |
| format | Article |
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N-deacetylisoipecoside,
N-deacetylipecoside into alangimarckine, deoxytubulosine and ankorine and of strictosidine and vincoside into alangimarckine and deoxytubulosine in young
Alangium lamarckii Thw. (Alangiaceae) has been studied and specific utilisation of
N-deacetylisoipecoside demonstrated. Parallel experiments with nordeoxytubulosine and deoxytubulosine suggested that
O-methylation precedes condensation of protoemetine with tryptamine and further the reduction of ethylene side chain takes place before condensation. Hydroxylation at C-8 in the
trans-quinolizidine moiety is the terminal step in the biosynthesis of alangimarckine.
Incorporation of labelled precursors into
17,
20 and
6 in
Alangium lamarckii Thw. is reported. It is shown that
O-methylation precedes condensation of protoemetine nucleus with tryptamine, reduction of the ethylene side chain occurs before condensation and C-8 hydroxylation in transquinolizidine part is the terminal step in the biosynthesis of
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N-deacetylisoipecoside,
N-deacetylipecoside into alangimarckine, deoxytubulosine and ankorine and of strictosidine and vincoside into alangimarckine and deoxytubulosine in young
Alangium lamarckii Thw. (Alangiaceae) has been studied and specific utilisation of
N-deacetylisoipecoside demonstrated. Parallel experiments with nordeoxytubulosine and deoxytubulosine suggested that
O-methylation precedes condensation of protoemetine with tryptamine and further the reduction of ethylene side chain takes place before condensation. Hydroxylation at C-8 in the
trans-quinolizidine moiety is the terminal step in the biosynthesis of alangimarckine.
Incorporation of labelled precursors into
17,
20 and
6 in
Alangium lamarckii Thw. is reported. It is shown that
O-methylation precedes condensation of protoemetine nucleus with tryptamine, reduction of the ethylene side chain occurs before condensation and C-8 hydroxylation in transquinolizidine part is the terminal step in the biosynthesis of
17.</description><subject>Alangiaceae</subject><subject>Alangiaceae - chemistry</subject><subject>Alangiaceae - metabolism</subject><subject>Alangimarckine</subject><subject>Alangium lamarckii Thw</subject><subject>Alkaloids</subject><subject>Alkaloids - biosynthesis</subject><subject>Alkaloids - chemistry</subject><subject>Ankorine</subject><subject>Antimicrobial</subject><subject>Biological and medical sciences</subject><subject>Biosynthesis</subject><subject>Carbolines - chemistry</subject><subject>Deoxytubulosine</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Metabolism</subject><subject>Metabolism. Physicochemical requirements</subject><subject>Molecular Structure</subject><subject>Plant physiology and development</subject><subject>Quinolizines - chemistry</subject><subject>Spectrum Analysis</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkNtKAzEQhoMoWg-PoOyNoherk2RPuZJSPEFB0Hod0uxEo9tdm3QFfSwfxGcy2y72UhgYJnwz-fkIOaRwToFmF48AnMYiYewU2BkApHnMNsiAFjmPeQ6wSQZ_yA7Z9f61g9Is2yY7lNEUCsoG5GHygtHUNv6zXrygtz5qTPTzHWvlpk1la4xUXUbz1tZh-rLl8qV6U1VjyyU7rFT9bNtZVKmZcvrN2n2yZVTl8aDve-Tp-moyuo3H9zd3o-E41lzQRSyypNRUlUZkNNcKQRQiS3MNjAmOqJgpgMGUQZIoo7kBlhiWcypEagQXgu-Rk9Xdd9fMW_QLObNeYxUCYdN6mVORp5zTAKYrULvGe4dGvjsbwn5KCrKTKZcyZWdKQqhOpmRh76j_oJ3OsFxv9fYCcNwDymtVGadqbf2a4wVLCuCBu1xxGHR8WHTSa4u1xtI61AtZNvafKL8LHJC6</recordid><startdate>20020801</startdate><enddate>20020801</enddate><creator>Jain, Sudha</creator><creator>Sinha, Archana</creator><creator>Bhakuni, Dewan S</creator><general>Elsevier Ltd</general><general>Elsevier</general><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>20020801</creationdate><title>The biosynthesis of β-carboline and quinolizidine alkaloids of Alangium lamarckii</title><author>Jain, Sudha ; Sinha, Archana ; Bhakuni, Dewan S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c391t-964dc1adf9617cae0989657c02293eea2f8020b2044afc3f024f2731995f93993</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Alangiaceae</topic><topic>Alangiaceae - chemistry</topic><topic>Alangiaceae - metabolism</topic><topic>Alangimarckine</topic><topic>Alangium lamarckii Thw</topic><topic>Alkaloids</topic><topic>Alkaloids - biosynthesis</topic><topic>Alkaloids - chemistry</topic><topic>Ankorine</topic><topic>Antimicrobial</topic><topic>Biological and medical sciences</topic><topic>Biosynthesis</topic><topic>Carbolines - chemistry</topic><topic>Deoxytubulosine</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Metabolism</topic><topic>Metabolism. Physicochemical requirements</topic><topic>Molecular Structure</topic><topic>Plant physiology and development</topic><topic>Quinolizines - chemistry</topic><topic>Spectrum Analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jain, Sudha</creatorcontrib><creatorcontrib>Sinha, Archana</creatorcontrib><creatorcontrib>Bhakuni, Dewan S</creatorcontrib><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>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jain, Sudha</au><au>Sinha, Archana</au><au>Bhakuni, Dewan S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The biosynthesis of β-carboline and quinolizidine alkaloids of Alangium lamarckii</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2002-08-01</date><risdate>2002</risdate><volume>60</volume><issue>8</issue><spage>853</spage><epage>859</epage><pages>853-859</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>The incorporation of tryptamine, dopamine,
N-deacetylisoipecoside,
N-deacetylipecoside into alangimarckine, deoxytubulosine and ankorine and of strictosidine and vincoside into alangimarckine and deoxytubulosine in young
Alangium lamarckii Thw. (Alangiaceae) has been studied and specific utilisation of
N-deacetylisoipecoside demonstrated. Parallel experiments with nordeoxytubulosine and deoxytubulosine suggested that
O-methylation precedes condensation of protoemetine with tryptamine and further the reduction of ethylene side chain takes place before condensation. Hydroxylation at C-8 in the
trans-quinolizidine moiety is the terminal step in the biosynthesis of alangimarckine.
Incorporation of labelled precursors into
17,
20 and
6 in
Alangium lamarckii Thw. is reported. It is shown that
O-methylation precedes condensation of protoemetine nucleus with tryptamine, reduction of the ethylene side chain occurs before condensation and C-8 hydroxylation in transquinolizidine part is the terminal step in the biosynthesis of
17.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>12150812</pmid><doi>10.1016/S0031-9422(02)00057-2</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Phytochemistry (Oxford), 2002-08, Vol.60 (8), p.853-859 |
| issn | 0031-9422 1873-3700 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_71975331 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Alangiaceae Alangiaceae - chemistry Alangiaceae - metabolism Alangimarckine Alangium lamarckii Thw Alkaloids Alkaloids - biosynthesis Alkaloids - chemistry Ankorine Antimicrobial Biological and medical sciences Biosynthesis Carbolines - chemistry Deoxytubulosine Fundamental and applied biological sciences. Psychology Metabolism Metabolism. Physicochemical requirements Molecular Structure Plant physiology and development Quinolizines - chemistry Spectrum Analysis |
| title | The biosynthesis of β-carboline and quinolizidine alkaloids of Alangium lamarckii |
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