Structurally diverse diterpenoids from the seeds of Caesalpinia minax Hance and their bioactivities

Phytochemistry. 2024 Sep:225:114189. doi: 10.1016/j.phytochem.2024.114189. Epub 2024 Jun 20.

Abstract

Eight previously undescribed diterpenoids, caesamins A-H (1-8), were separated and identified from the seeds of Caesalpinia minax Hance. Their structures were characterized by extensive spectroscopic data and X-ray crystallographic analysis. Structurally, caesamin A (1) is the first cassane-type diterpenoid with a C23 carbon skeleton containing an unusual isopropyl. Caesamin F (6) represents the first example of cleistanthane diterpenoid from the genus Caesalpinia. Caesamins B (2) and F (6) exhibited inhibitory activity against LPS-induced nitric oxide production in RAW 264.7 macrophages with IC50 values of 45.67 ± 0.92 and 42.99 ± 0.24 μM, comparable to positive control 43.69 ± 2.62 μM of NG-Monomethyl-L-arginine. Furthermore, the chemotaxonomic significance of the isolates was discussed.

Keywords: Caesalpinia minax Hance; Diterpenoid; Fabaceae; Nitric oxide (NO); α-Glucosidase.

MeSH terms

  • Animals
  • Caesalpinia* / chemistry
  • Diterpenes* / chemistry
  • Diterpenes* / isolation & purification
  • Diterpenes* / pharmacology
  • Dose-Response Relationship, Drug
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Mice
  • Molecular Structure
  • Nitric Oxide* / antagonists & inhibitors
  • Nitric Oxide* / biosynthesis
  • RAW 264.7 Cells
  • Seeds* / chemistry
  • Structure-Activity Relationship

Substances

  • Diterpenes
  • Nitric Oxide
  • Lipopolysaccharides