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

Jiyoon Park, Jiseong Kim, Sunghoon Hwang, Daehyun Oh, Young Eun Du, Sang Jip Nam, Hyeung Geun Park, Min Jae Lee, Dong Chan Oh

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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.

Original languageEnglish
Pages (from-to)612-620
Number of pages9
JournalJournal of Natural Products
Volume86
Issue number3
DOIs
StatePublished - 24 Mar 2023

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea grants funded by the Republic of Korean Government (Ministry of Science and ICT) (2020R1A2C2003518, 2021R1A4A2001251, 2021R1A2C2008023, and 2020R1A5A1019023).

Publisher Copyright:
© 2023 American Chemical Society and American Society of Pharmacognosy.

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