Details zur Publikation

Referenztyp Zeitschriften
DOI / URL Link
Titel (primär) Chilenopeptins A and B, peptaibols from the Chilean Sepedonium aff. chalcipori KSH 883
Autor Otto, A.; Laub, A.; Wendt, L.; Porzel, A.; Schmidt, J.; Palfner, G.; Becerra, J.; Krüger, D.; Stadler, M.; Wessjohann, L.; Westermann, B.; Arnold, N.;
Journal / Serie Journal of Natural Products
Erscheinungsjahr 2016
Department BOOEK;
Band/Volume 79
Heft 4
Sprache englisch;
POF III (gesamt) T12;
UFZ Querschnittsthemen RU1
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 HRESIMSn experiments in conjunction with comprehensive 1D and 2D NMR analysis. Thus, the sequence of chilenopeptin A (1) was identified as Ac-Aib1-Ser2-Trp3-Aib4-Pro5-Leu6-Aib7-Aib8-Gln9-Aib10-Aib11-Gln12-Aib13-Leu14-Pheol15, while chilenopeptin B (2) differs from 1 by the replacement of Trp3 by Phe3. 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.
ID 17477
dauerhafte UFZ-Verlinkung
Otto, A., Laub, A., Wendt, L., Porzel, A., Schmidt, J., Palfner, G., Becerra, J., Krüger, D., Stadler, M., Wessjohann, L., Westermann, B., Arnold, N. (2016):
Chilenopeptins A and B, peptaibols from the Chilean Sepedonium aff. chalcipori KSH 883
J. Nat. Prod. 79 (4), 929 - 938