Anti-inflammatory bicyclic polyprenylated acylphloroglucinols with diverse architectures including an unprecedented 6/6/6 tricyclic core from Garcinia yunnanensis

doi:10.1016/j.bioorg.2024.107864

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	Anti-inflammatory bicyclic polyprenylated acylphloroglucinols with diverse architectures including an unprecedented 6/6/6 tricyclic core from Garcinia yunnanensis
	Hu, Xin-Yue; Luo, Hui-Juan; Wei, Xin; Wang, Yu-Zhuo; Ye, Yan-Song; Wan, Shi-Jie; Zheng, Dan; Zhou, Yu; Xu, Hong-Xi; Li, Xing-Ren; Lin, Li-Gen; Xu, Gang
	2024
发表期刊	BIOORGANIC CHEMISTRY
ISSN	0045-2068
卷号	153 页码:107864
摘要	Garciyunnanol A (1), an unprecedented 1,2-seco-bicyclic polyprenylated acylphloroglucinol (BPAP) possessing a unique 6/6/6 tricyclic core, was characterized from Garcinia yunnanensis together with 16 BPAPs, including eight new compounds (garciyunnanols B-I, 2-9). Biogenetically, the bicyclo[3.3.1]nonane-2,4,9-trione moiety of 12 reconstructed the bicyclic 6-lactone core of 2 through Norrish type I cleavage and cyclization, followed by a cyclization of two side chains to form an intriguing 6/6/6 tricyclic core of 1. Their structures were elucidated through analysis of spectroscopic data, calculation and comparison of ECD spectra. Bioactivity evaluation manifested that compounds 1, 2, 5, 6 and 14 demonstrated superior inhibition of NO production compared to the positive control dexamethasone. Notably, compound 5 exhibited a dose-dependent inhibitory effect on NO production, with an IC50 value of 0.25 +/- 0.87 mu M. Furthermore, experiments involving ELISA, Western blotting, and immunofluorescence staining revealed that 5 effectively reduced the secretion of interleukin-1/3 in LPS plus nigericin-stimulated THP-1 macrophages by inhibiting the activation of the NLRP3 inflammasome.
DOI	10.1016/j.bioorg.2024.107864
WOS记录号	WOS:001335199400001
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/76184
专题	中国科学院昆明植物研究所
推荐引用方式 GB/T 7714	Hu, Xin-Yue,Luo, Hui-Juan,Wei, Xin,et al. Anti-inflammatory bicyclic polyprenylated acylphloroglucinols with diverse architectures including an unprecedented 6/6/6 tricyclic core from Garcinia yunnanensis[J]. BIOORGANIC CHEMISTRY,2024,153:107864.
APA	Hu, Xin-Yue.,Luo, Hui-Juan.,Wei, Xin.,Wang, Yu-Zhuo.,Ye, Yan-Song.,...&Xu, Gang.(2024).Anti-inflammatory bicyclic polyprenylated acylphloroglucinols with diverse architectures including an unprecedented 6/6/6 tricyclic core from Garcinia yunnanensis.BIOORGANIC CHEMISTRY,153,107864.
MLA	Hu, Xin-Yue,et al."Anti-inflammatory bicyclic polyprenylated acylphloroglucinols with diverse architectures including an unprecedented 6/6/6 tricyclic core from Garcinia yunnanensis".BIOORGANIC CHEMISTRY 153(2024):107864.

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