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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
- 남상집
- Issue Date
- 2023
- Journal Title
- Journal of Natural Products
- ISSN
- 0163-3864
- Citation
- Journal of Natural Products vol. 86, no. 3, pp. 612 - 620
- Publisher
- American Chemical Society
- Indexed
- SCIE; 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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