Seongsanamides A-D: Antiallergic Bicyclic Peptides from Bacillus safensis KCTC 12796BP

Org Lett. 2018 Dec 7;20(23):7539-7543. doi: 10.1021/acs.orglett.8b03293. Epub 2018 Nov 20.

Abstract

Six seongsanamides were isolated from the culture broth of Bacillus safensis KCTC 12796BP, and their structures were elucidated by spectroscopic data analysis combined with Marfey's method, electronic circular dichroism calculations, and biosynthetic gene cluster analysis. Compounds 1-4 were bicyclic peptides with isodityrosine residues; 5 and 6 were monocyclic peptides. Only the bicyclic seongsanamides inhibited degranulation and LTC4/PGD2 generation in IgE/Ag-stimulated bone marrow-derived mast cells. Oral administration of 1 suppressed mast cell-dependent passive cutaneous anaphylaxis reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Allergic Agents / chemistry
  • Anti-Allergic Agents / isolation & purification
  • Anti-Allergic Agents / pharmacology*
  • Bacillus / chemistry*
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology*
  • Leukotriene C4 / antagonists & inhibitors
  • Leukotriene C4 / biosynthesis
  • Mast Cells / drug effects
  • Mast Cells / metabolism
  • Mice
  • Molecular Structure
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification
  • Peptides, Cyclic / pharmacology*
  • Prostaglandin D2 / antagonists & inhibitors
  • Prostaglandin D2 / biosynthesis
  • Structure-Activity Relationship
  • beta-N-Acetylhexosaminidases / antagonists & inhibitors*
  • beta-N-Acetylhexosaminidases / metabolism

Substances

  • Anti-Allergic Agents
  • Enzyme Inhibitors
  • Peptides, Cyclic
  • Leukotriene C4
  • beta-N-Acetylhexosaminidases
  • Prostaglandin D2