Dimeric eremophilane-type sesquiterpenoids from the peeled stems of Syringa pinnatifolia

Abstract

A continued phytochemical investigation guided by ¹H NMR and LC-MS data on the ethanol extract from the peeled stems of Syringa pinnatifolia Hemsl. led to the isolation of 16 undescribed dimeric eremophilane sesquiterpenoids, namely syringenes R-Z (1-9) and A₁-G₁ (10-16). These structures were elucidated by extensive analysis of spectroscopic data, including HRESIMS, NMR, quantum-mechanics-based computational analysis of NMR chemical shifts, and single-crystal X-ray diffraction analyses, and a concise rule for determination of relative configuration of angular methyl was proposed. The results of the cardioprotective assay demonstrated that 3 exhibits a protective effect against hypoxia-induced injuries in H9c2 cells. This effect was observed at a concentration of 10 μM, with a protective rate of 28.43 ± 11.80%.

Keywords: Cardioprotective activity; Eremophilane sesquiterpenoid dimers; Oleaceae; Syringa pinnatifolia Hemsl.; Syringenes.