Chilenopeptins A and B, Peptaibols from the Chilean Sepedonium aff. chalcipori KSH 883

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• 作者：Alexander Otto ; Annegret Laub ; Lucile Wendt ; Andrea Porzel ; Jürgen Schmidt ; Götz Palfner ; José Becerra ; Dirk Krüger ; Marc Stadler ; Ludger Wessjohann ; Bernhard Westermann ; Norbert Arnold
• 刊名：Journal of Natural Products
• 出版年：2016
• 出版时间：April 22, 2016
• 年：2016
• 卷：79
• 期：4
• 页码：929-938
• 全文大小：659K
• 年卷期：0
• ISSN：1520-6025

文摘

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.