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Sadopeptins A and B, Sulfoxide- and Piperidone-Containing Cyclic Heptapeptides with Proteasome Inhibitory Activity from a Streptomyces sp.

Title
Sadopeptins A and B, Sulfoxide- and Piperidone-Containing Cyclic Heptapeptides with Proteasome Inhibitory Activity from a Streptomyces sp.
Authors
Park J.Kim J.Hwang S.Oh D.Du Y.E.Nam S.-J.Park H.-G.Lee M.J.Oh D.-C.
Ewha Authors
남상집
SCOPUS Author ID
남상집scopus
Issue Date
2023
Journal Title
Journal of Natural Products
ISSN
0163-3864JCR Link
Citation
Journal of Natural Products vol. 86, no. 3, pp. 612 - 620
Publisher
American Chemical Society
Indexed
SCIE; SCOPUS WOS scopus
Document Type
Article
Abstract
New sulfur-bearing natural products, sadopeptins A and B (1 and 2), were discovered from Streptomyces sp. YNK18 based on a targeted search using the characteristic isotopic signature of sulfur in mass spectrometry analysis. Compounds 1 and 2 were determined to be new cyclic heptapeptides, bearing methionine sulfoxide [Met(O)] and 3-amino-6-hydroxy-2-piperidone (Ahp), based on 1D and 2D NMR spectroscopy along with IR, UV, and MS. The configurations of sadopeptins A and B (1 and 2) were established via the analysis of the ROESY NMR correlation, oxidation, Marfey’s method, and circular dichroism (CD) spectroscopy. The bioinformatics analysis of the full Streptomyces sp. YNK18 genome identified a nonribosomal peptide synthetase (NRPS) biosynthetic gene cluster (BGC), and a putative biosynthetic pathway is proposed. Sadopeptins A and B displayed proteasome-inhibitory activity without affecting cellular autophagic flux. © 2023 American Chemical Society and American Society of Pharmacognosy.
DOI
10.1021/acs.jnatprod.2c00978
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
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