New enantiomeric lignans and new meroterpenoids with nitric oxide release inhibitory activity from Piper puberulum

被引:15
作者
Zheng, Yuan-kun [1 ]
Wang, Ya-qi [1 ]
Su, Bao-jun [1 ]
Wang, Heng-shan [1 ]
Liao, Hai-bing [1 ]
Liang, Dong [1 ]
机构
[1] Guangxi Normal Univ, Collaborat Innovat Ctr Guangxi Ethn Med, Sch Chem & Pharmaceut Sci, State Key Lab Chem & Mol Engn Med Resources, Guilin 541004, Peoples R China
关键词
Piper puberulum; Lignan; Meroterpenoid; Anti-neuroinflammatory; SESQUITERPENOIDS; ALKALOIDS; PHYTOCHEMISTRY; NEOLIGNANS; STEMS;
D O I
10.1016/j.bioorg.2021.105522
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Six new lignans with various type of linkage between two C6-C3 fragments (1a, 1b, 2a, 2b, 3, 4), two new meroterpenoids (5, 6) and 24 known compounds (7-30) were isolated from an EtOH extract of the stems and leaves of Piper puberulum. The absolute configurations of enantiomers 1a and 1b were determined by single crystal X-ray diffraction analysis, 2a and 2b were determined by comparing their calculated and experimental ECD spectra. Biogenetically, all the new lignans may come from the polymerization of two molecules of hydroxychavicol (30). In the anti-neuroinflammation activity assay, the IC50 values of fifteen compounds were lower than those of the positive control minocycline, and compound 1a showed good activity, but its enantiomer 1b showed no activity. Compound 1a have notable anti-neuroinflammatory activity, and can significantly decrease mRNA levels of proinflammatory cytokines (IL-1 beta, IL-6, TNF-alpha) in a dose-dependent manner.
引用
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页数:9
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