Sulfur and nitrogen-containing compounds from the whole bodies of Blaps japanensis

Bioorg Chem. 2020 Sep:102:104086. doi: 10.1016/j.bioorg.2020.104086. Epub 2020 Jul 10.

Abstract

Pipajiains H-J (1-3), three new phenolic derivatives with an unusual sulfone group, pipajiamides A-C (4-6), three new amide derivatives, pipajiaine A (7), one new imidazole analogue, and pipajiaine B (8), a pair of new pyrrolidine derivatives, along with three known compounds were isolated from the insect Blaps japanensis. Their structures were identified by spectroscopic and computational methods. Chiral HPLC was used to separate the (-)- and (+)-antipodes of 4 and 8. Biological activities of all the new compounds against extracellular matrix in rat renal proximal tubular cells, human cancer cells (A549, Huh-7, and K562), COX-2, ROCK1, and JAK3 were evaluated. The results show that compounds 2, (+)-4, and (-)-4 are active against kidney fibrosis, whereas, compound 9 is active toward human cancer cells, inflammation, and JAK3 kinase.

Keywords: Blaps japanensis; Insects; Nitrogenous compounds; Renal protection; Sulfur compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cells, Cultured
  • Coleoptera / chemistry*
  • Density Functional Theory
  • Dose-Response Relationship, Drug
  • Fibrosis / drug therapy
  • Humans
  • Janus Kinase 3 / antagonists & inhibitors
  • Janus Kinase 3 / metabolism
  • Molecular Structure
  • Nitrogen Compounds / chemistry
  • Nitrogen Compounds / isolation & purification
  • Nitrogen Compounds / pharmacology*
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / isolation & purification
  • Protein Kinase Inhibitors / pharmacology*
  • Rats
  • Structure-Activity Relationship
  • Sulfur / chemistry
  • Sulfur / isolation & purification
  • Sulfur / pharmacology*
  • rho-Associated Kinases / antagonists & inhibitors
  • rho-Associated Kinases / metabolism

Substances

  • Nitrogen Compounds
  • Protein Kinase Inhibitors
  • Sulfur
  • JAK3 protein, human
  • Janus Kinase 3
  • ROCK1 protein, human
  • rho-Associated Kinases