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Epoxinnamide: An Epoxy Cinnamoyl-Containing Nonribosomal Peptide from an Intertidal Mudflat-Derived Streptomyces sp.
- Title
- Epoxinnamide: An Epoxy Cinnamoyl-Containing Nonribosomal Peptide from an Intertidal Mudflat-Derived Streptomyces sp.
- Authors
- Kang, Sangwook; Han, Jaeho; Jang, Sung Chul; An, Joon Soo; Kang, Ilnam; Kwon, Yun; Nam, Sang-Jip; Shim, Sang Hee; Cho, Jang-Cheon; Lee, Sang Kook; Oh, Dong-Chan
- Ewha Authors
- 남상집
- SCOPUS Author ID
- 남상집
- Issue Date
- 2022
- Journal Title
- MARINE DRUGS
- ISSN
- 1660-3397
- Citation
- MARINE DRUGS vol. 20, no. 7
- Keywords
- cinnamoyl-containing nonribosomal peptide; Streptomyces; biosynthetic gene cluster; bifunctional thioesterase; quinone reductase; angiogenesis
- Publisher
- MDPI
- Indexed
- SCIE; SCOPUS
- Document Type
- Article
- Abstract
- Cinnamoyl-containing nonribosomal peptides (CCNPs) form a unique family of actinobacterial secondary metabolites and display various biological activities. A new CCNP named epoxinnamide (1) was discovered from intertidal mudflat-derived Streptomyces sp. OID44. The structure of 1 was determined by the analysis of one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) data along with a mass spectrum. The absolute configuration of 1 was assigned by the combination of advanced Marfey's method, (3)J(HH) and rotating-frame overhauser effect spectroscopy (ROESY) analysis, DP4 calculation, and genomic analysis. The putative biosynthetic pathway of epoxinnamide (1) was identified through the whole-genome sequencing of Streptomyces sp. OID44. In particular, the thioesterase domain in the nonribosomal peptide synthetase (NRPS) biosynthetic gene cluster was proposed as a bifunctional enzyme, which catalyzes both epimerization and macrocyclization. Epoxinnamide (1) induced quinone reductase (QR) activity in murine Hepa-1c1c7 cells by 1.6-fold at 5 mu M. It also exhibited effective antiangiogenesis activity in human umbilical vein endothelial cells (IC50 = 13.4 mu M).
- DOI
- 10.3390/md20070455
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
- Files in This Item:
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marinedrugs-20-00455-v3.pdf(3.41 MB)
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