New short peptaibols from a marine Trichoderma strain

Abstract

The production of peptaibols by a marine-related Trichoderma longibrachiatum strain was studied using electrospray ionisation multiple-stage ion trap mass spectrometry (ESI-MSn-IT) and gas chromatography/electron impact mass spectrometry (GC/EI-MS). Two major groups of peptaibols were identified, those with long sequences (20 amino acids) and others with short sequences (11 amino acids). This paper describes the methodology used to establish the sequences of short peptaibols in a mixture without previous individual separation. Nine peptaibols were identified. Among them, eight are new, namely as trichobrachin A I-IV (Aib9-Pro10 sequence) and as trichobrachin B I-IV (Val9-Pro10 sequence). Original Pro6-Val7 and Val9-Pro10 sequences have to be noted.

Two Classes of New Peptaibols Are Synthesized by a Single Non-ribosomal Peptide Synthetase of Trichoderma virens

“…Methanol of HPLC quality grade was purchased from Baker (Deventer, Holland). Microheterogenous mixtures of peptaibols were sequenced using consecutive fragmentation in ESI-MS n , according to the method described previously (20,23).…”

“…An extensive survey of 28 Trichoderma/Hypocrea species for peptaibol production by intact-cell MALDI-TOF mass spectrometry (ICMS) revealed that peptaibols are produced by all strains with some producing up to five peptide families of different sizes (19). In addition to terrestrial strains, peptaibols have also been isolated from marine strains of Trichoderma (7,20,22,23).…”

Peptaibol profiles of Iranian Trichoderma isolates

“…The bioassay revealed that all examined isolates of T. viride, T. viridescens, T. asperellum, T. citrinoviride and T. longibrachiatum have bioactive compounds in their crude extracts. Peptaibols have the same chemical characteristics and molecular masses, therefore they cannot be completely separated by HPLC and are eluted together [28]. The complete separation of peptaibols is usually difficult but certain methods such as high energy collision, or collision-induced dissociation mass spectrometry were applicable to characterize peptaibols in crude extracts [34].…”

“…The complete separation of peptaibols is usually difficult but certain methods such as high energy collision, or collision-induced dissociation mass spectrometry were applicable to characterize peptaibols in crude extracts [34]. The ESI-IT-MS technology is a more simple method for the sequencing of peptaibols [28]. We used HPLC for separation and ESI-MS for sequencing and identification of peptaibol compounds.…”

Peptaibiomics: Towards a Myriad of Bioactive Peptides Containing Cα‐Dialkylamino Acids?

“…Selective inhibitory activity against PTEN-negative MDA468 tumor cells has been observed [187]. Furthermore, eight new eleven-residue peptaibols, trichobrachins A I -IV and B I -IV, as well as one trichorovin [110] were reported from T. longibrachiatum MMS 151, a marine strain that has been isolated from the cockle Mytilus edulis [188].…”