Four New Polyhydroxy Cyclohexanes from the Stems of Fissistigma tientangense

Chem Biodivers. 2023 May;20(5):e202300330. doi: 10.1002/cbdv.202300330. Epub 2023 Apr 26.

Abstract

Four undescribed polyhydroxy cyclohexanes, fissoxhydrylenes A-D (1-4), together with two known biogenetically related polyhydroxy cyclohexanes (5 and 6) were isolated from the stems of Fissistigma tientangense Tsiang et P. T. Li. Their structures were elucidated by detailed analysis of NMR, HR-ESI-MS, IR, UV and Optical rotations data. The absolute configuration of 1 was confirmed by X-ray crystallographic. The absolute configurations of 2-4 were confirmed by chemical reaction and optical rotations. Compound 4 represent the first example of a no substituent polyhydroxy cyclohexanes from natural products. All isolated compounds were evaluated for their anti-inflammatory activities against the lipopolysaccharide-induced nitric oxide (NO) production in mouse macrophage RAW 264.7 cells in vitro. Compounds 3 and 4 showed inhibitory activities with the IC50 values of 16.63±0.06 μM and 14.38±0.08 μM, respectively.

Keywords: Annonaceae; Fissistigma tientangense; anti-inflammatory; fissoxhydrylenes A-D; polyhydroxy cyclohexanes.

MeSH terms

  • Animals
  • Annonaceae* / chemistry
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Structure
  • Nitric Oxide
  • RAW 264.7 Cells

Substances

  • Anti-Inflammatory Agents
  • Nitric Oxide