Targeted Isolation of Monoterpene Indole Alkaloids from Palicourea sessilis
Phytochemical investigation of the alkaloid extract of Palicourea sessilis by LC-HRMS/MS using molecular networking and an in silico MS/MS fragmentation approach suggested the presence of several new monoterpene indole alkaloids. These compounds were isolated by semipreparative HPLC, and their struc...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2017-11, Vol.80 (11), p.3032-3037 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Klein-Júnior, Luiz C Cretton, Sylvian Allard, Pierre-Marie Genta-Jouve, Grégory Passos, Carolina S Salton, Juliana Bertelli, Pablo Pupier, Marion Jeannerat, Damien Heyden, Yvan Vander Gasper, André L Wolfender, Jean-Luc Christen, Philippe Henriques, Amélia T |
| description | Phytochemical investigation of the alkaloid extract of Palicourea sessilis by LC-HRMS/MS using molecular networking and an in silico MS/MS fragmentation approach suggested the presence of several new monoterpene indole alkaloids. These compounds were isolated by semipreparative HPLC, and their structures confirmed by means of HRMS, NMR, and ECD measurements as 4-N-methyllyaloside (3), 4-N-methyl-3,4-dehydrostrictosidine (4), 4β-hydroxyisodolichantoside (6), and 4α-hydroxyisodolichantoside (7), as well as the known alkaloids alline (1), N-methyltryptamine (2), isodolichantoside (5), and 5-oxodolichantoside (8). In addition, the acetylcholinesterase inhibitory activity of the compounds was evaluated up to 50 μM. |
| doi_str_mv | 10.1021/acs.jnatprod.7b00681 |
| format | Article |
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Nat. Prod</addtitle><description>Phytochemical investigation of the alkaloid extract of Palicourea sessilis by LC-HRMS/MS using molecular networking and an in silico MS/MS fragmentation approach suggested the presence of several new monoterpene indole alkaloids. These compounds were isolated by semipreparative HPLC, and their structures confirmed by means of HRMS, NMR, and ECD measurements as 4-N-methyllyaloside (3), 4-N-methyl-3,4-dehydrostrictosidine (4), 4β-hydroxyisodolichantoside (6), and 4α-hydroxyisodolichantoside (7), as well as the known alkaloids alline (1), N-methyltryptamine (2), isodolichantoside (5), and 5-oxodolichantoside (8). In addition, the acetylcholinesterase inhibitory activity of the compounds was evaluated up to 50 μM.</description><subject>Acetylcholinesterase - drug effects</subject><subject>Brazil</subject><subject>Cholinesterase Inhibitors - chemistry</subject><subject>Cholinesterase Inhibitors - isolation & purification</subject><subject>Cholinesterase Inhibitors - pharmacology</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Plant Leaves - chemistry</subject><subject>Rubiaceae - chemistry</subject><subject>Secologanin Tryptamine Alkaloids - chemistry</subject><subject>Secologanin Tryptamine Alkaloids - isolation & purification</subject><subject>Tryptamines - chemistry</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kD1PwzAQhi0EoqXwDxDKyJJydhzHGSvER0URDGW2nPiCUpy42MnAv8fQlpHpbnje93QPIZcU5hQYvdF1mG96PWy9M_OiAhCSHpEpzRmkAlh-TKZARZZmUvAJOQthAwAZlPkpmbCSMhCcTcnTWvt3HNAky-CsHlrXJ65Jnl3vBvRb7DFZ9sZZTBb2Q1vXmpA03nXJq7Zt7UaPOgkYQmvbcE5OGm0DXuznjLzd361vH9PVy8PydrFKdcblkMpayoblwAEqXrDcaMhNZWoW97rROSux0abSUqBmrDBcSmYo55RWlCPybEaud73x9c8Rw6C6NtRore7RjUHRUmSsEKzIIsp3aO1dCB4btfVtp_2XoqB-NKqoUR00qr3GGLvaXxirDs1f6OAtArADfuNRQx8f_r_zGzeHgoM</recordid><startdate>20171122</startdate><enddate>20171122</enddate><creator>Klein-Júnior, Luiz C</creator><creator>Cretton, Sylvian</creator><creator>Allard, Pierre-Marie</creator><creator>Genta-Jouve, Grégory</creator><creator>Passos, Carolina S</creator><creator>Salton, Juliana</creator><creator>Bertelli, Pablo</creator><creator>Pupier, Marion</creator><creator>Jeannerat, Damien</creator><creator>Heyden, Yvan Vander</creator><creator>Gasper, André L</creator><creator>Wolfender, Jean-Luc</creator><creator>Christen, Philippe</creator><creator>Henriques, Amélia T</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><orcidid>https://orcid.org/0000-0002-0125-952X</orcidid><orcidid>https://orcid.org/0000-0003-2243-1701</orcidid></search><sort><creationdate>20171122</creationdate><title>Targeted Isolation of Monoterpene Indole Alkaloids from Palicourea sessilis</title><author>Klein-Júnior, Luiz C ; 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| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2017-11, Vol.80 (11), p.3032-3037 |
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| source | ACS Publications; MEDLINE |
| subjects | Acetylcholinesterase - drug effects Brazil Cholinesterase Inhibitors - chemistry Cholinesterase Inhibitors - isolation & purification Cholinesterase Inhibitors - pharmacology Molecular Structure Nuclear Magnetic Resonance, Biomolecular Plant Leaves - chemistry Rubiaceae - chemistry Secologanin Tryptamine Alkaloids - chemistry Secologanin Tryptamine Alkaloids - isolation & purification Tryptamines - chemistry |
| title | Targeted Isolation of Monoterpene Indole Alkaloids from Palicourea sessilis |
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