title: Unprecedented 17-residue peptaibiotics produced by marine-derived Trichoderma atroviride.
abstract: In the course of investigations on marine-derived toxigenic fungi, five strains of Trichoderma atroviride were studied for their production of peptaibiotics. While these five strains were found to produce classical 19-residue peptaibols, three of them exhibited unusual peptidic sodium-adduct [M + 2 Na](2+) ion peaks at m/z between 824 and 854. The sequencing of these peptides led to two series of unprecedented 17-residue peptaibiotics based on the model Ac-XXX-Ala-Ala-XXX-XXX-Gln-Aib-Aib-Aib-Ala/Ser-Lxx-Aib-Pro-XXX-Aib-Lxx-[C(129) ]. The C-terminus of these new peptides was common to all of them, and its elemental formula C5 H9 N2 O2 was established by HR-MS. It could correspond to the cyclized form of N(δ) -hydroxyornithine which has already been observed at the C-terminus of various peptidic siderophores. The comparison of the sequences of 17- and 19-residue peptides showed similarities for positions 1-16. This observation seems to indicate a common biosynthesis pathway. Both new 17-residue peptaibiotics and 19-residue peptaibols exhibited weak in vitro cytotoxicities against KB cells.
authors.affiliation: University of Nantes, LUNAM, Faculty of Pharmacy, MMS, F-44000 Nantes.
authors.forename: Angélique
authors.initials: A
authors.lastname: Carroux
authors.forename: Anne-Isaline
authors.initials: AI
authors.lastname: Van Bohemen
authors.forename: Catherine
authors.initials: C
authors.lastname: Roullier
authors.forename: Thibaut
authors.initials: T
authors.lastname: Robiou du Pont
authors.forename: Marieke
authors.initials: M
authors.lastname: Vansteelandt
authors.forename: Arnaud
authors.initials: A
authors.lastname: Bondon
authors.forename: Aurore
authors.initials: A
authors.lastname: Zalouk-Vergnoux
authors.forename: Yves François
authors.initials: YF
authors.lastname: Pouchus
authors.forename: Nicolas
authors.initials: N
authors.lastname: Ruiz
mesh_terms: D000595:Amino Acid Sequence; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D020128:Inhibitory Concentration 50; D007624:KB Cells; D008969:Molecular Sequence Data; D015394:Molecular Structure; D054848:Peptaibols / Q000737:chemistry* / Q000235:genetics / Q000494:pharmacology; D010455:Peptides / Q000737:chemistry / Q000235:genetics / Q000494:pharmacology; D014242:Trichoderma / Q000737:chemistry* / Q000145:classification
chemical_list: D000900:Anti-Bacterial Agents; D054848:Peptaibols; D010455:Peptides