title: Chilenopeptins A and B, Peptaibols from the Chilean Sepedonium aff. chalcipori KSH 883.
abstract: The Chilean Sepedonium aff. chalcipori strain KSH 883, isolated from the endemic Boletus loyo Philippi, was studied in a polythetic approach based on chemical, molecular, and biological data. A taxonomic study of the strain using molecular data of the ITS, EF1-α, and RPB2 barcoding genes confirmed the position of the isolated strain within the S. chalcipori clade, but also suggested the separation of this clade into three different species. Two new linear 15-residue peptaibols, named chilenopeptins A (1) and B (2), together with the known peptaibols tylopeptins A (3) and B (4) were isolated from the semisolid culture of strain KSH 883. The structures of 1 and 2 were elucidated on the basis of HRESIMS(n) experiments in conjunction with comprehensive 1D and 2D NMR analysis. Thus, the sequence of chilenopeptin A (1) was identified as Ac-Aib(1)-Ser(2)-Trp(3)-Aib(4)-Pro(5)-Leu(6)-Aib(7)-Aib(8)-Gln(9)-Aib(10)-Aib(11)-Gln(12)-Aib(13)-Leu(14)-Pheol(15), while chilenopeptin B (2) differs from 1 by the replacement of Trp(3) by Phe(3). Additionally, the total synthesis of 1 and 2 was accomplished by a solid-phase approach, confirming the absolute configuration of all chiral amino acids as l. Both the chilenopeptins (1 and 2) and tylopeptins (3 and 4) were evaluated for their potential to inhibit the growth of phytopathogenic organisms.
authors.affiliation: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry , Weinberg 3, D-06120 Halle (Saale), Germany.
authors.forename: Alexander
authors.initials: A
authors.lastname: Otto
authors.affiliation: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry , Weinberg 3, D-06120 Halle (Saale), Germany.
authors.forename: Annegret
authors.initials: A
authors.lastname: Laub
authors.affiliation: Department of Microbial Drugs, Helmholtz Centre for Infection Research , Inhoffenstrasse 7, D-38124 Braunschweig, Germany.
authors.forename: Lucile
authors.initials: L
authors.lastname: Wendt
authors.affiliation: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry , Weinberg 3, D-06120 Halle (Saale), Germany.
authors.forename: Andrea
authors.initials: A
authors.lastname: Porzel
authors.affiliation: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry , Weinberg 3, D-06120 Halle (Saale), Germany.
authors.forename: Jürgen
authors.initials: J
authors.lastname: Schmidt
authors.affiliation: Departamento de Botanica, Facultad de Ciencias Naturales y Oceanograficas, Universidad de Concepción , Casilla 160-C, Concepción, Chile.
authors.forename: Götz
authors.initials: G
authors.lastname: Palfner
authors.affiliation: Departamento de Botanica, Facultad de Ciencias Naturales y Oceanograficas, Universidad de Concepción , Casilla 160-C, Concepción, Chile.
authors.forename: José
authors.initials: J
authors.lastname: Becerra
authors.affiliation: Department of Soil Ecology, Helmholtz Centre for Environmental Research , Theodor-Lieser-Strasse 4, D-06120 Halle (Saale), Germany.
authors.forename: Dirk
authors.initials: D
authors.lastname: Krüger
authors.affiliation: Department of Microbial Drugs, Helmholtz Centre for Infection Research , Inhoffenstrasse 7, D-38124 Braunschweig, Germany.
authors.forename: Marc
authors.initials: M
authors.lastname: Stadler
authors.affiliation: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry , Weinberg 3, D-06120 Halle (Saale), Germany.|Institute of Chemistry, Faculty of Natural Sciences II, Martin Luther University Halle-Wittenberg , Kurt-Mothes-Strasse 2, D-06120 Halle (Saale), Germany.
authors.forename: Ludger
authors.initials: L
authors.lastname: Wessjohann
authors.affiliation: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry , Weinberg 3, D-06120 Halle (Saale), Germany.|Institute of Chemistry, Faculty of Natural Sciences II, Martin Luther University Halle-Wittenberg , Kurt-Mothes-Strasse 2, D-06120 Halle (Saale), Germany.
authors.forename: Bernhard
authors.initials: B
authors.lastname: Westermann
authors.affiliation: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry , Weinberg 3, D-06120 Halle (Saale), Germany.
authors.forename: Norbert
authors.initials: N
authors.lastname: Arnold
mesh_terms: D000595:Amino Acid Sequence; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001487:Basidiomycota / Q000378:metabolism; D002677:Chile; D006999:Hypocreales / Q000737:chemistry; D015394:Molecular Structure; D054848:Peptaibols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010455:Peptides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D014242:Trichoderma / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D054848:Peptaibols; D010455:Peptides; C000610472:chilenopeptin A; C000610473:chilenopeptin B; C403870:tylopeptin A; C403871:tylopeptin B