title: Unguiculin A and Ptilomycalins E-H, Antimalarial Guanidine Alkaloids from the Marine Sponge Monanchora unguiculata.
abstract: Chemical study of the CH2Cl2-MeOH (1:1) extract from the sponge Monanchora unguiculata collected in Madagascar highlighted five new compounds, one acyclic guanidine alkaloid, unguiculin A (1) and four pentacyclic alkaloids, ptilomycalins E-H (2-5), along with four known compounds: crambescidin 800 (6) and crambescidin 359 (7), crambescidic acid (8), and fromiamycalin (9). Their structures were elucidated by 1D and 2D NMR spectra and HRESIMS data. All compounds were evaluated for their cytotoxicity against KB cells and their antiplasmodial activity. The new ptilomycalin E (2) and the mixture of the new ptilomycalins G (4) and H (5) showed promising cytotoxicity against KB cells with IC50values of 0.85 and 0.92 μM, respectively. Ptilomycalin F (3) and fromiamycalin (9) exhibited promising activity against Plasmodium falciparum with IC50values of 0.23 and 0.24 μM, respectively.
authors.affiliation: Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments, Faculté des Sciences et Technologies, Université de La Réunion , 15 Avenue René Cassin, CS 92003, 97744 Saint-Denis Cedex 9, La Réunion, France.
authors.forename: Pierre-Eric
authors.initials: PE
authors.lastname: Campos
authors.affiliation: School of Pharmaceutical Sciences, EPGL, University of Geneva, University of Lausanne , Quai Ernest-Ansermet 30, CH-1211 Geneva 4, Switzerland.
authors.forename: Jean-Luc
authors.initials: JL
authors.lastname: Wolfender
authors.affiliation: School of Pharmaceutical Sciences, EPGL, University of Geneva, University of Lausanne , Quai Ernest-Ansermet 30, CH-1211 Geneva 4, Switzerland.
authors.forename: Emerson F
authors.identifier: 0000-0001-9567-1664
authors.initials: EF
authors.lastname: Queiroz
authors.affiliation: School of Pharmaceutical Sciences, EPGL, University of Geneva, University of Lausanne , Quai Ernest-Ansermet 30, CH-1211 Geneva 4, Switzerland.
authors.forename: Laurence
authors.initials: L
authors.lastname: Marcourt
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay , 1, av. de la Terrasse, 91198 Gif-sur-Yvette, France.
authors.forename: Ali
authors.identifier: 0000-0002-1762-6910
authors.initials: A
authors.lastname: Al-Mourabit
authors.affiliation: Laboratory of Pharmacognosy, Department of Pharmacy, CIRM, University of Liége B36 , 4000 Liège, Belgium.
authors.forename: Michel
authors.initials: M
authors.lastname: Frederich
authors.affiliation: Laboratory of Pharmacognosy, Department of Pharmacy, CIRM, University of Liége B36 , 4000 Liège, Belgium.
authors.forename: Annélise
authors.initials: A
authors.lastname: Bordignon
authors.affiliation: Naturalis Biodiversity Center , Darwinweg 2, 2333 CR Leiden, Netherlands.
authors.forename: Nicole
authors.initials: N
authors.lastname: De Voogd
authors.affiliation: Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments, Faculté des Sciences et Technologies, Université de La Réunion , 15 Avenue René Cassin, CS 92003, 97744 Saint-Denis Cedex 9, La Réunion, France.
authors.forename: Bertrand
authors.initials: B
authors.lastname: Illien
authors.affiliation: Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments, Faculté des Sciences et Technologies, Université de La Réunion , 15 Avenue René Cassin, CS 92003, 97744 Saint-Denis Cedex 9, La Réunion, France.
authors.forename: Anne
authors.identifier: 0000-0001-5188-0704
authors.initials: A
authors.lastname: Gauvin-Bialecki
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity; D000818:Animals; D000962:Antimalarials / Q000494:pharmacology*; D019791:Guanidine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology / Q000633:toxicity; D006146:Guanidines / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity; D006801:Humans; D020128:Inhibitory Concentration 50; D007624:KB Cells; D008270:Madagascar; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010963:Plasmodium falciparum / Q000737:chemistry / Q000187:drug effects*; D013141:Spiro Compounds / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity
chemical_list: D000470:Alkaloids; D000962:Antimalarials; D006146:Guanidines; D013141:Spiro Compounds; C505319:crambescidic acid; C449038:crambescidin 359; C490355:crambescidin 800; C000622144:ptilomycalin E; C000622146:ptilomycalin G; C000622148:ptilomycalin H; C000622142:unguiculin A; D019791:Guanidine