Publication Details

Category Text Publication
Reference Category Journals
DOI 10.1021/acs.jnatprod.5b01018
Title (Primary) Chilenopeptins A and B, peptaibols from the Chilean Sepedonium aff. chalcipori KSH 883
Author Otto, A.; Laub, A.; Wendt, L.; Porzel, A.; Schmidt, J.; Palfner, G.; Becerra, J.; Krüger, D.; Stadler, M.; Wessjohann, L.; Westermann, B.; Arnold, N.
Source Titel Journal of Natural Products
Year 2016
Department BOOEK
Volume 79
Issue 4
Page From 929
Page To 938
Language englisch
UFZ wide themes 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.
Persistent UFZ Identifier
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 10.1021/acs.jnatprod.5b01018