Unprecedented 17-residue peptaibiotics produced by marine-derived Trichoderma atroviride.

Angélique Carroux , Anne-Isaline van Bohemen , Catherine Roullier , Thibaut Robiou Du Pont , Marieke Vansteelandt (1) , Arnaud Bondon (2, 3) , Aurore Zalouk-Vergnoux , Yves François Pouchus (1) , Nicolas Ruiz

1 MMS - Mer, molécules et santé EA 2160
2 PRISM - Plate-forme Rennaise d'Imagerie et Spectroscopie Structurale et Métabolique
3 IGDR - Institut de Génétique et Développement de Rennes

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.

Domains: Life Sciences [q-bio]; Biochemistry, Molecular Biology; Structural Biology [q-bio.BM]

Angélique Carroux, Anne-Isaline van Bohemen, Catherine Roullier, Thibaut Robiou Du Pont, Marieke Vansteelandt, et al.. Unprecedented 17-residue peptaibiotics produced by marine-derived Trichoderma atroviride.. Chemistry and Biodiversity, 2013, 10 (5), pp.772-86. ⟨10.1002/cbdv.201200398⟩. ⟨hal-00862780⟩