New biphenantherene and nervogenic acid derivatives from Liparis regnieri Finet and their inhibitory activities against NF-κB activation

• Published in: Tetrahedron 2017-03, Vol.73 (12), p.1611-1617
• Main Authors: Ren, Jie, Fan, Chao, Guo, Yi-Gong, Yan, Shi-Kai, Ye, Richard D., Zhang, Yan, Jin, Hui-Zi, Zhang, Wei-Dong
• Format: Article
• Language: English
• Subjects: Biphenantherene; Liparis regnieri Finet; Nervogenic acid derivative; NF-κB; Orchidaceae; Phenanthrene
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2017.02.004

A phytochemical investigation of the whole plant of Liparis regnieri Finet led to the isolation of one new biphenantherene (1) and ten new nervogenic acid derivatives (2–11), together with nine known compounds. Their structures were elucidated mainly by extensive analyses of 1D and 2D NMR spectroscopic data and chemical reactions. Additionally, for the first time a previously unreported biphenantherene was discovered to effectively suppress TNF-α induced expression of NF-κB-Luc in Hela cells with the IC50 value of 1.80 μM and the structure-activity relationshipwas also discussed. [Display omitted] •One unreported biphenantherene and ten new nervogenic acid derivatives were isolated from Liparis regnieri Finet.•Their structures were elucidated by NMR spectroscopic data and chemical reactions.•Biphenantherenes significantly inhibit TNF-α induced expression of NF-κB-Luc in Hela cells.•Dihydrophenanthrene dimers might be crucial chemical framework for the inhibitory activities against NF-κB activation.