title: Unexpected talaroenamine derivatives and an undescribed polyester from the fungus Talaromyces stipitatus ATCC10500.
abstract: Chemical investigation of the fungus Talaromyces stipitatus ATCC 10500, whose genome has been sequenced, led to the isolation of four undescribed talaroenamines B-E along with the known talaroenamine A. Their structures were elucidated on the basis of spectroscopic studies including mass spectrometry, extensive 2D NMR and electronic circular dichroism (ECD). Interestingly, talaroenamine A had previously been isolated from the strain of T. stipitatus Δtrop C, a strain knocked out for the gene encoding a non-heme Fe(II)-dependent dioxygenase catalyzing the oxidative ring expansion leading to the tropolone, but never from a wild-type strain. All talaroenamines were evaluated for their antiplasmodial activity and Talaroenamine D exhibited the best inhibition against the chloroquine-resistant Plasmodium falciparum (FcB1 strain) without noticeable toxicity on HeLa and preadipose cell lines. In the course of the chemical investigation of T. stipitatus, an undescribed polyester was also isolated and its absolute configuration was determined by hydrolysis and transesterification followed by gas chromatography on chiral column.
authors.affiliation: Molécules de Communication et Adaptation des Micro-organismes, UMR 7245 CNRS/MNHN, Muséum National d'Histoire Naturelle, 57 rue Cuvier (CP54), 75231 Paris Cedex 05, France.
authors.forename: Yi
authors.initials: Y
authors.lastname: Zang
authors.affiliation: Laboratoire de Pharmacognosie, UMR 8638 CNRS, Faculté des Sciences Pharmaceutiques et Biologiques, Paris Descartes University, Sorbonne Paris Cité, 4 Avenue de l'Observatoire, 75006 Paris, France.
authors.forename: Grégory
authors.initials: G
authors.lastname: Genta-Jouve
authors.affiliation: Molécules de Communication et Adaptation des Micro-organismes, UMR 7245 CNRS/MNHN, Muséum National d'Histoire Naturelle, 57 rue Cuvier (CP54), 75231 Paris Cedex 05, France.
authors.forename: Tithnara Anthony
authors.initials: TA
authors.lastname: Sun
authors.affiliation: Molécules de Communication et Adaptation des Micro-organismes, UMR 7245 CNRS/MNHN, Muséum National d'Histoire Naturelle, 57 rue Cuvier (CP54), 75231 Paris Cedex 05, France.
authors.forename: Xuwen
authors.initials: X
authors.lastname: Li
authors.affiliation: Molécules de Communication et Adaptation des Micro-organismes, UMR 7245 CNRS/MNHN, Muséum National d'Histoire Naturelle, 57 rue Cuvier (CP54), 75231 Paris Cedex 05, France.
authors.forename: Buisson
authors.initials: B
authors.lastname: Didier
authors.affiliation: Molécules de Communication et Adaptation des Micro-organismes, UMR 7245 CNRS/MNHN, Muséum National d'Histoire Naturelle, 57 rue Cuvier (CP54), 75231 Paris Cedex 05, France.
authors.forename: Stéphane
authors.initials: S
authors.lastname: Mann
authors.affiliation: Molécules de Communication et Adaptation des Micro-organismes, UMR 7245 CNRS/MNHN, Muséum National d'Histoire Naturelle, 57 rue Cuvier (CP54), 75231 Paris Cedex 05, France.
authors.forename: Elisabeth
authors.initials: E
authors.lastname: Mouray
authors.affiliation: Cancer Biology and Therapeutics, Centre de Recherche Saint-Antoine, Institut Universitaire de Cancérologie, Université Pierre et Marie Curie, Sorbonne Universités et Institut National de la Santé et de la Recherche Médicale (INSERM) UMR 938, Hôpital Sant-Antoine, 184 rue du Faubourg Saint Antoine, 75571 Paris Cedex 12, France.
authors.forename: Annette K
authors.initials: AK
authors.lastname: Larsen
authors.affiliation: Cancer Biology and Therapeutics, Centre de Recherche Saint-Antoine, Institut Universitaire de Cancérologie, Université Pierre et Marie Curie, Sorbonne Universités et Institut National de la Santé et de la Recherche Médicale (INSERM) UMR 938, Hôpital Sant-Antoine, 184 rue du Faubourg Saint Antoine, 75571 Paris Cedex 12, France.
authors.forename: Alexandre E
authors.initials: AE
authors.lastname: Escargueil
authors.affiliation: Molécules de Communication et Adaptation des Micro-organismes, UMR 7245 CNRS/MNHN, Muséum National d'Histoire Naturelle, 57 rue Cuvier (CP54), 75231 Paris Cedex 05, France. Electronic address: bnay@mnhn.fr.
authors.forename: Bastien
authors.initials: B
authors.lastname: Nay
authors.affiliation: Molécules de Communication et Adaptation des Micro-organismes, UMR 7245 CNRS/MNHN, Muséum National d'Histoire Naturelle, 57 rue Cuvier (CP54), 75231 Paris Cedex 05, France. Electronic address: sprado@mnhn.fr.
authors.forename: Soizic
authors.initials: S
authors.lastname: Prado
mesh_terms: D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001555:Benzene Derivatives / Q000737:chemistry / Q000302:isolation & purification*; D002738:Chloroquine / Q000494:pharmacology*; D002942:Circular Dichroism; D049308:Dioxygenases / Q000378:metabolism; D004351:Drug Resistance; D006367:HeLa Cells; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010963:Plasmodium falciparum / Q000187:drug effects*; D011091:Polyesters / Q000737:chemistry / Q000302:isolation & purification; D061065:Polyketides / Q000737:chemistry / Q000302:isolation & purification*; D032901:Talaromyces / Q000737:chemistry*
chemical_list: D000962:Antimalarials; D001555:Benzene Derivatives; D011091:Polyesters; D061065:Polyketides; D002738:Chloroquine; D049308:Dioxygenases
keywords: Fungal natural products; Polyesters; Polyketides; Talaromyces stipitatus