Novel Diterpenoids Incorporating Rearranged Labdanes from the Chinese Liverwort Anastrophyllum joergensenii and Their Anti-inflammatory Activity.
Mingzhu ZhuYinghui GaoYi LiFeng XieJinchuan ZhouLintao XuDongxue LvXinyu ZhangZe-Jun XuTing DongTao ShenJiaozhen ZhangHong-Xiang LouPublished in: Journal of agricultural and food chemistry (2023)
Liverworts provide valuable ecological services to improve the sustainability of agriculture, encompassing soil health maintenance and natural pest management. Some liverworts have potential applications in medicine and as food additives. Twenty-two novel diterpenoids (anajoerins A-V), of which anajoerins B-G are rearranged labdanes featuring an unprecedented 6/5 fused ring system, were isolated from the Chinese liverwort Anastrophyllum joergensenii Schiffn. The absolute configurations of all compounds were identified based on high-resolution electrospray ionization mass spectroscopy data, NMR spectra, and ECD calculations. Plausible biogenetic pathways for unprecedented rearranged labdanes were proposed. Seven diterpenoids exhibited anti-inflammatory activity by reducing nitric oxide production in LPS-stimulated RAW264.7 murine macrophages in a dose-dependent manner with IC 50 s between 9.71 and 56.56 μM. All tested compounds showed no cytotoxicity at the tested concentrations. Western blot analyses of NF-κB p65 downregulation showed that anajoerin L could inhibit the NF-κB signaling pathway. Furthermore, anajoerin L also suppressed the secretion of the ConA-induced proinflammatory cytokines IFN-γ, TNF-α, and IL-6.
Keyphrases
- signaling pathway
- high resolution
- human health
- pi k akt
- nitric oxide
- climate change
- healthcare
- density functional theory
- risk assessment
- mental health
- epithelial mesenchymal transition
- induced apoptosis
- lps induced
- public health
- mass spectrometry
- inflammatory response
- high glucose
- solid state
- rheumatoid arthritis
- primary care
- molecular dynamics
- magnetic resonance
- oxidative stress
- diabetic rats
- cell proliferation
- south africa
- dendritic cells
- electronic health record
- big data
- hydrogen peroxide
- immune response
- nuclear factor
- nitric oxide synthase
- endothelial cells
- health information
- ionic liquid
- tandem mass spectrometry
- machine learning
- social media
- monte carlo
- plant growth
- high speed