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Azetidine-Bearing Non-Ribosomal Peptides, Bonnevillamides D and E, Isolated from a Carrion Beetle-Associated Actinomycete

Title
Azetidine-Bearing Non-Ribosomal Peptides, Bonnevillamides D and E, Isolated from a Carrion Beetle-Associated Actinomycete
Authors
Shin, Yern-HyerkBan, Yeon HeeShin, JisuPark, In WookYoon, SoljeeKo, KeebeomShin, JongheonNam, Sang-JipWinter, Jaclyn M.Kim, YoungSooYoon, Yeo JoonOh, Dong-Chan
Ewha Authors
남상집
SCOPUS Author ID
남상집scopusscopus
Issue Date
2021
Journal Title
JOURNAL OF ORGANIC CHEMISTRY
ISSN
0022-3263JCR Link

1520-6904JCR Link
Citation
JOURNAL OF ORGANIC CHEMISTRY vol. 86, no. 16, pp. 11149 - 11159
Publisher
AMER CHEMICAL SOC
Indexed
SCIE; SCOPUS WOS
Document Type
Article
Abstract
Two new nonribosomal peptides, bonnevillamides D and E (1 and 2), have been discovered in Streptomyces sp. UTZ13 isolated from the carrion beetle, Nicrophorus concolor. Combinational analysis of the UV, MS, and NMR spectroscopic data revealed that their planar structures were comprised of dichlorinated linear peptides containing nonproteinogenic amino acid residues, such as 4-methylazetidinecarboxylic acid and 4-O-acetyl-5-methylproline. The configurations of bonnevillamides D and E (1 and 2) were determined based on ROESY correlations, the advanced Marfey's method, phenylglycine methyl ester derivatization, molecular modeling, and circular dichroism spectroscopy. The nonribosomal peptide synthetase biosynthetic pathway of bonnevillamides D and E has been proposed using bioinformatic analysis of the whole-genome sequence data of Streptomyces sp. UTZ13. Their biological activity toward the aggregation of amyloid-beta, which is one of the key pathogenic proteins in Alzheimer's disease, was evaluated using a thioflavin T assay and gel electrophoresis. Bonnevillamides D and E reversed the fibril formation by inducing the monomerization of amyloid-beta aggregates.
DOI
10.1021/acs.joc.1c00360
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자연과학대학 > 화학·나노과학전공 > Journal papers
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