title: MDN-0104, an antiplasmodial betaine lipid from Heterospora chenopodii.
abstract: Bioassay-guided fractionation of the crude fermentation extract of Heterospora chenopodii led to the isolation of a novel monoacylglyceryltrimethylhomoserine (1). The structure of this new betaine lipid was elucidated by detailed spectroscopic analysis using one- and two-dimensional NMR experiments and high-resolution mass spectrometry. Compound 1 displayed moderate in vitro antimalarial activity against Plasmodium falciparum, with an IC50 value of 7 μM. This betaine lipid is the first monoacylglyceryltrimethylhomoserine ever reported in the Fungi, and its acyl moiety also represents a novel natural 3-keto fatty acid. The new compound was isolated during a drug discovery program aimed at the identification of new antimalarial leads from a natural product library of microbial extracts. Interestingly, the related fungus Heterospora dimorphospora was also found to produce compound 1, suggesting that species of this genus may be a promising source of monoacylglyceryltrimethylhomoserines.
authors.affiliation: Fundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía , Avenida del Conocimiento 34, Parque Tecnológico de Ciencias de la Salud, E-18016, Granada, Spain.
authors.forename: Jesús
authors.initials: J
authors.lastname: Martín
authors.forename: Gloria
authors.initials: G
authors.lastname: Crespo
authors.forename: Víctor
authors.initials: V
authors.lastname: González-Menéndez
authors.forename: Guiomar
authors.initials: G
authors.lastname: Pérez-Moreno
authors.forename: Paula
authors.initials: P
authors.lastname: Sánchez-Carrasco
authors.forename: Ignacio
authors.initials: I
authors.lastname: Pérez-Victoria
authors.forename: Luis M
authors.initials: LM
authors.lastname: Ruiz-Pérez
authors.forename: Dolores
authors.initials: D
authors.lastname: González-Pacanowska
authors.forename: Francisca
authors.initials: F
authors.lastname: Vicente
authors.forename: Olga
authors.initials: O
authors.lastname: Genilloud
authors.forename: Gerald F
authors.initials: GF
authors.lastname: Bills
authors.forename: Fernando
authors.initials: F
authors.lastname: Reyes
mesh_terms: D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001622:Betaine / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D008288:Malaria / Q000188:drug therapy; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010936:Plant Extracts / Q000737:chemistry; D010963:Plasmodium falciparum / Q000187:drug effects*; D014280:Triglycerides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D000962:Antimalarials; C000594633:MDN-0104; D010936:Plant Extracts; D014280:Triglycerides; D001622:Betaine