Sadopeptins A and B, Sulfoxide- and Piperidone-Containing Cyclic Heptapeptides with Proteasome Inhibitory Activity from a Streptomyces sp.
- 주제(기타) Plant Sciences; Chemistry, Medicinal; Pharmacology & Pharmacy
- 설명문(일반) [Park, Jiyoon; Hwang, Sunghoon; Du, Young Eun; Oh, Dong-Chan] Seoul Natl Univ, Nat Prod Res Inst, Coll Pharm, Seoul 08826, South Korea; [Kim, Jiseong; Lee, Min Jae] Seoul Natl Univ, Coll Med, Dept Biomed Sci, Seoul 03080, South Korea; [Oh, Daehyun; Park, Hyeung-geun] Seoul Natl Univ, Res Inst Pharmaceut Sci, Seoul 08826, South Korea; [Oh, Daehyun; Park, Hyeung-geun] Seoul Natl Univ, Coll Pharm, Seoul 08826, South Korea; [Nam, Sang-Jip] Ewha Womans Univ, Dept Chem & Nanosci, Seoul 03760, South Korea
- 등재 SCIE, SCOPUS
- 발행기관 AMER CHEMICAL SOC
- 발행년도 2023
- 총서유형 Journal
- URI http://www.dcollection.net/handler/ewha/000000204324
- 본문언어 영어
- Published As https://doi.org/10.1021/acs.jnatprod.2c00978
초록/요약
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.
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