title: Daldionin, an Unprecedented Binaphthyl Derivative, and Diverse Polyketide Congeners from a Fungal Orchid Endophyte.
abstract: Thailand possesses a rich diversity of orchid species that, in turn, live in symbiosis with a wide variety of fungi. Such endophytes have the potential to produce secondary metabolites with bioactivity against orchid and/or human pathogens. The orchid-associated fungal strain Daldinia eschscholtzii was found to produce a diverse range of aromatic polyketides including the new naphthalene derivatives daldionin, nodulones B and C, and daldinones F and G along with eight known compounds. Daldionin possesses an unprecedented oxane-linked binaphthyl ring system. These compounds demonstrate the high diversity of structural variations that are constructed during fungal biosynthesis, and the results include important observations concerning the biosynthesis of binaphthyl derivatives. Daldionin was found to have weak antiproliferative activity against HUVEC and K-562 cell lines. All but one of the isolated compounds showed moderate antimicrobial activity towards at least one of the four tested microbial strains.
authors.affiliation: Department of Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology (HKI), Beutenbergstr.11a, 07745, Jena, Germany.
authors.forename: Emma C
authors.initials: EC
authors.lastname: Barnes
authors.affiliation: Department of Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology (HKI), Beutenbergstr.11a, 07745, Jena, Germany.
authors.forename: Juangjun
authors.initials: J
authors.lastname: Jumpathong
authors.affiliation: Department of Biology, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand.
authors.forename: Saisamorn
authors.initials: S
authors.lastname: Lumyong
authors.affiliation: Jena Microbial Resource Collection, Leibniz Institute for Natural Product Research and Infection Biology (HKI), Beutenbergstr.11a, 07745, Jena, Germany.|Faculty of Biology and Pharmacy, Institute of Microbiology, University of Jena, Neugasse 25, 07743, Jena, Germany.
authors.forename: Kerstin
authors.initials: K
authors.lastname: Voigt
authors.affiliation: Department of Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology (HKI), Beutenbergstr.11a, 07745, Jena, Germany. Christian.Hertweck@hki-jena.de.|Chair of Natural Product Chemistry, Friedrich Schiller University, Jena, Germany. Christian.Hertweck@hki-jena.de.
authors.forename: Christian
authors.initials: C
authors.lastname: Hertweck
mesh_terms: D000890:Anti-Infective Agents / Q000737:chemistry* / Q000494:pharmacology*; D001688:Biological Products / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D002460:Cell Line; D060026:Endophytes / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D005658:Fungi / Q000737:chemistry* / Q000378:metabolism; D006574:Heterocyclic Compounds, 2-Ring / Q000737:chemistry* / Q000494:pharmacology*; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D009281:Naphthalenes / Q000737:chemistry*; D061065:Polyketides / Q000737:chemistry*; D013785:Thailand
chemical_list: D000890:Anti-Infective Agents; D001688:Biological Products; D006574:Heterocyclic Compounds, 2-Ring; D006575:Heterocyclic Compounds, 3-Ring; D009281:Naphthalenes; D061065:Polyketides; C532316:daldinin B; C532318:daldinin C
keywords: biosynthesis; drug discovery; natural products; polyketides; structure elucidation