Isolation and structure elucidation of two new cassane derivatives from the seed kernels of Caesalpinia sinensis

J Asian Nat Prod Res. 2022 Oct;24(10):979-986. doi: 10.1080/10286020.2021.2004130. Epub 2021 Nov 18.

Abstract

Two new cassane-type derivatives (1-2), together with three known compounds (3-5), were isolated from the seed kernels of Caesalpinia sinensis. Their structures were elucidated on the basis of interpretation of comprehensive spectroscopic data, including HRESIMS and 1D/2D NMR spectroscopy, and the absolute configuration were established by means of ECD calculation. Compound 2, possessing a 16-degradative cassane skeleton, was rarely encountered in cassane diterpenoids isolated from the genus Caesalpinia. All compounds were evaluated for their anti-inflammatory activities against the overproduction of NO in LPS-stimulated RAW 264.7 macrophages, and compounds 1-5 could inhibit production of NO at the concentration of 50 μM.

Keywords: Caesalpinia sinensis; Leguminasae; anti-inflammatory activity; cassane diterpenoids.

MeSH terms

  • Anti-Inflammatory Agents / pharmacology
  • Caesalpinia* / chemistry
  • Diterpenes* / chemistry
  • Diterpenes* / pharmacology
  • Molecular Structure
  • Seeds / chemistry

Substances

  • Diterpenes
  • Anti-Inflammatory Agents