Epoxinnamide: An Epoxy Cinnamoyl-Containing Nonribosomal Peptide from an Intertidal Mudflat-Derived Streptomyces sp.

Sangwook Kang, Jaeho Han, Sung Chul Jang, Joon Soo An, Ilnam Kang, Yun Kwon, Sang Jip Nam, Sang Hee Shim, Jang Cheon Cho, Sang Kook Lee, Dong Chan Oh

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

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, 3JHH 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 μM. It also exhibited effective antiangiogenesis activity in human umbilical vein endothelial cells (IC50 = 13.4 μM).

Original languageEnglish
Article number455
JournalMarine Drugs
Volume20
Issue number7
DOIs
StatePublished - Jul 2022

Bibliographical note

Publisher Copyright:
© 2022 by the authors.

Keywords

  • Streptomyces
  • angiogenesis
  • bifunctional thioesterase
  • biosynthetic gene cluster
  • cinnamoyl-containing nonribosomal peptide
  • quinone reductase

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