New cassane- and norcassane-type diterpenoids from the seed kernels of Caesalpinia sinensis and their anti-inflammatory activity in vitro

Fitoterapia. 2021 Sep:153:104978. doi: 10.1016/j.fitote.2021.104978. Epub 2021 Jun 24.

Abstract

The first investigation of phytochemistry on the seed kernels of Caesalpinia sinensis led to the isolation and characterization of six new compounds including three tricyclic-type cassane diterpenoids (1--3) and three norcassane-type diterpenoids (4-6), together with three know compounds (7-9). Compounds 1-9 represented the first discovery of cassane-type diterpenoids from C. sinensis. Their structures were elucidated by a combination of spectroscopic analysis, single-crystal X-ray diffraction experiment and ECD calculation. The characters for compounds 4 and 5 possessing the 15,16-degradative cassane skeleton were observed, which was extremely rare structural type in the genus Caesalpinia. The anti-inflammatory activities of all isolates were evaluated via examining their inhibitory effects against NO production in LPS-simulated RAW 264.7 cells. The results demonstrated that compound 1 exhibited the most significantly inhibitory efficacy with inhibition rate 67.3% at 10 μM. The iNOS enzyme activity assay further revealed that compound 1 showed potent NO inhibitory effect by reducing the enzymatic activity of iNOS.

Keywords: Anti-inflammation; Caesalpinia sinensis; Cassane diterpenoids; iNOS enzyme activity.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Caesalpinia / chemistry*
  • China
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology*
  • Mice
  • Molecular Structure
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology
  • RAW 264.7 Cells
  • Seeds / chemistry

Substances

  • Anti-Inflammatory Agents
  • Diterpenes
  • Phytochemicals