Syringenes M - Q, Eremophilane Sesquiterpenoid Dimers from the Peeled Stems of Syringa pinnatifolia

As a part of systematic studies on Syringa pinnatifolia, a continued phytochemical investigation guided by H-1-NMR and LC/MS data on the ethanol extract afforded five new dimeric eremophilane sesquiterpenoids, namely syringenes M-Q (1-5). These structures were elucidated by extensive analysis of spectroscopic data, including infrared (IR), high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), nuclear magnetic resonance (NMR), quantum-mechanics-based computational analysis of NMR chemical shifts, and single-crystal X-ray diffraction. Compounds 4 and 5 showed inhibitory activities against NO production induced by lipopolysaccharide in RAW264.7 macrophage cells, with IC50 values of 5.1 and 9.3 mu M, compared to positive control indomethacin (IC50 33.6 mu M). These dimeric eremophilane sesquiterpenoids may be potential markers for discriminating this species from the genus Syringa and the Oleaceae family.