title: Revisiting Previously Investigated Plants: A Molecular Networking-Based Study of Geissospermum laeve.
abstract: Three new monoterpene indole alkaloids (1-3) have been isolated from the bark of Geissospermum laeve, together with the known alkaloids (-)-leuconolam (4), geissolosimine (5), and geissospermine (6). The structures of 1-3 were elucidated by analysis of their HRMS and NMR spectroscopic data. The absolute configuration of geissolaevine (1) was deduced from the comparison of experimental and theoretically calculated ECD spectra. The isolation workflow was guided by a molecular networking-based dereplication strategy using an in-house database of monoterpene indole alkaloids. In addition, five known compounds previously undescribed in the Geissospermum genus were dereplicated from the G. laeve alkaloid extract network and were assigned with various levels of identification confidence. The antiparasitic activities against Plasmodium falciparum and Leishmania donovani as well as the cytotoxic activity against the MRC-5 cell line were determined for compounds 1-5.
authors.affiliation: Équipe "Pharmacognosie-Chimie des Substances Naturelles" BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay , 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, France.
authors.forename: Alexander E
authors.initials: AE
authors.lastname: Fox Ramos
authors.affiliation: Équipe "Pharmacognosie-Chimie des Substances Naturelles" BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay , 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, France.
authors.forename: Charlotte
authors.initials: C
authors.lastname: Alcover
authors.affiliation: Équipe "Pharmacognosie-Chimie des Substances Naturelles" BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay , 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, France.
authors.forename: Laurent
authors.initials: L
authors.lastname: Evanno
authors.affiliation: Équipe "Pharmacognosie-Chimie des Substances Naturelles" BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay , 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, France.
authors.forename: Alexandre
authors.initials: A
authors.lastname: Maciuk
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, Université Paris-Saclay , 21 Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
authors.forename: Marc
authors.identifier: 0000-0002-0877-8234
authors.initials: M
authors.lastname: Litaudon
authors.affiliation: CNRS, UMR8172 EcoFoG, AgroParisTech, Cirad, INRA, Université des Antilles, Université de Guyane , 23 Avenue Pasteur, 97300 Cayenne, France.
authors.forename: Christophe
authors.initials: C
authors.lastname: Duplais
authors.affiliation: Équipe "Molécules Fluorées et Chimie Médicinale" BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay , 5 rue J.-B. Clément, 92290 Châtenay-Malabry, France.
authors.forename: Guillaume
authors.identifier: 0000-0001-8955-0364
authors.initials: G
authors.lastname: Bernadat
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, Université Paris-Saclay , 21 Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Gallard
authors.affiliation: Équipe "Pharmacognosie-Chimie des Substances Naturelles" BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay , 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, France.
authors.forename: Jean-Christophe
authors.initials: JC
authors.lastname: Jullian
authors.affiliation: Unité Molécules de Communication et Adaptation des Microorganismes (MCAM, UMR 7245), Muséum National d'Histoire Naturelle, CNRS, Sorbonne Universités, CP52 , 57 Rue Cuvier, 75005 Paris, France.
authors.forename: Elisabeth
authors.initials: E
authors.lastname: Mouray
authors.affiliation: Unité Molécules de Communication et Adaptation des Microorganismes (MCAM, UMR 7245), Muséum National d'Histoire Naturelle, CNRS, Sorbonne Universités, CP52 , 57 Rue Cuvier, 75005 Paris, France.
authors.forename: Philippe
authors.initials: P
authors.lastname: Grellier
authors.affiliation: Équipe "Chimiothérapie Antiparasitaire" BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay , 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, France.
authors.forename: Philippe M
authors.initials: PM
authors.lastname: Loiseau
authors.affiliation: Équipe "Chimiothérapie Antiparasitaire" BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay , 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, France.
authors.forename: Sébastien
authors.initials: S
authors.lastname: Pomel
authors.affiliation: Équipe "Pharmacognosie-Chimie des Substances Naturelles" BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay , 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, France.
authors.forename: Erwan
authors.initials: E
authors.lastname: Poupon
authors.affiliation: Équipe "Pharmacognosie-Chimie des Substances Naturelles" BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay , 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, France.
authors.forename: Pierre
authors.initials: P
authors.lastname: Champy
authors.affiliation: Équipe "Pharmacognosie-Chimie des Substances Naturelles" BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay , 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, France.
authors.forename: Mehdi A
authors.identifier: 0000-0003-2153-4290
authors.initials: MA
authors.lastname: Beniddir
mesh_terms: D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000977:Antiparasitic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D029062:Apocynaceae / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D005616:French Guiana; D006801:Humans; D026121:Indole Alkaloids / Q000737:chemistry; D007893:Leishmania donovani / Q000187:drug effects; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D021261:Parasitic Sensitivity Tests; D018515:Plant Leaves / Q000737:chemistry*; D010963:Plasmodium falciparum / Q000187:drug effects; D046948:Secologanin Tryptamine Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000962:Antimalarials; D000977:Antiparasitic Agents; D026121:Indole Alkaloids; C000621471:O-methylgeissolaevine; D046948:Secologanin Tryptamine Alkaloids; C000621470:geissolaevine; C561024:geissospermine