Novel Diterpenoids Incorporating Rearranged Labdanes from the Chinese Liverwort Anastrophyllum joergensenii and Their Anti-inflammatory Activity

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 anaj...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2023-12, Vol.71 (49), p.19551-19567
Main Authors: Zhu, Mingzhu, Gao, Yinghui, Li, Yi, Xie, Feng, Zhou, Jinchuan, Xu, Lintao, Lv, Dongxue, Zhang, Xinyu, Xu, Zejun, Dong, Ting, Shen, Tao, Zhang, Jiaozhen, Lou, Hongxiang
Format: Article
Language:English
Subjects:
Animals
Anti-Inflammatory Agents - pharmacology
Bioactive Constituents, Metabolites, and Functions
China
Cytokines - metabolism
Diterpenes
Hepatophyta - metabolism
Lipopolysaccharides - pharmacology
Mice
NF-kappa B - metabolism
Nitric Oxide - metabolism
RAW 264.7 Cells
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Summary: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 IC50s 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.
ISSN:0021-8561
1520-5118
DOI:10.1021/acs.jafc.3c06235