Targeted Isolation of Monoterpene Indole Alkaloids from Palicourea sessilis
journal contributionposted on 09.11.2017, 18:20 by Luiz C. Klein-Júnior, Sylvian Cretton, Pierre-Marie Allard, Grégory Genta-Jouve, Carolina S. Passos, Juliana Salton, Pablo Bertelli, Marion Pupier, Damien Jeannerat, Yvan Vander Heyden, André L. Gasper, Jean-Luc Wolfender, Philippe Christen, Amélia T. Henriques
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.
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acetylcholinesterasemethyllyalosideMonoterpene Indole AlkaloidsTargeted IsolationHRMS4β-networkingLC-HRMS4α- hydroxyisodolichantosidepresencealkaloids allineapproachmethylmethyltryptamine5- oxodolichantosidesemipreparative HPLC50 μ M4- NcompoundPalicourea sessilisfragmentationNMRmonoterpene indole alkaloidsPalicourea sessilis Phytochemical investigationsilicoMSECD measurements