Highly oxygenated clerodane furanoditerpenoids from the leaves and twigs of Croton yunnanensis

Chin J Nat Med. 2024 Oct;22(10):945-954. doi: 10.1016/S1875-5364(24)60722-3.

Abstract

The phytochemical investigation of the leaves and twigs of Croton yunnanensis resulted in the isolation of eight new clerodane furanoditerpenoids, named croyunfuranoids A-H (1-8), along with three known analogs (9-11). The structures of these compounds were elucidated using spectroscopic analyses, and their absolute configurations were determined through a combination of electronic circular dichroism (ECD) calculations and single-crystal X-ray diffraction. Notably, Croyunfuranoid D (4) is identified as a rare 18,19-dinor-clerodane diterpenoid. Additionally, the structure of a previously reported diterpenoid, crotonyunnan B, was revised. All isolated compounds were evaluated for their inhibitory activities on nitric oxide (NO) production in LPS-induced RAW 264.7 macrophages. Among them, compounds 5 and 6 demonstrated significant inhibitory effects, with IC50 values of 20.33 ± 2.31 and 22.80 ± 1.31 μmol·L-1, respectively.

Keywords: Clerodane furanoditerpenoid; Croton yunnanensis; Euphorbiaceae; NO inhibitory activity.

MeSH terms

  • Animals
  • Croton* / chemistry
  • Diterpenes / chemistry
  • Diterpenes / pharmacology
  • Diterpenes, Clerodane* / chemistry
  • Diterpenes, Clerodane* / pharmacology
  • Macrophages* / drug effects
  • Mice
  • Molecular Structure
  • Nitric Oxide*
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Plant Leaves* / chemistry
  • Plant Stems / chemistry
  • RAW 264.7 Cells

Substances

  • Nitric Oxide
  • Diterpenes, Clerodane
  • Plant Extracts
  • Diterpenes