Syringenes A-L: Bioactive dimeric eremophilane sesquiterpenoids from Syringa pinnatifolia.

Bioorg Chem

State Key Laboratory Breeding Base of Dao-di Herbs, National Resource Center for Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700, PR China. Electronic address:

Published: August 2022

A phytochemical investigation guided by H NMR and LC-MS data on the ethanol extract of Syringa pinnatifolia stems led to the isolation of 11 new dimeric eremophilane sesquiterpenoids, namely, syringenes A-K (1-11) and one known analog (12, syringene L). These structures were elucidated by extensive analysis of spectroscopic data, single-crystal X-ray diffraction, and computational methods. Biological assays revealed that 1-12 exhibited different degrees of anti-inflammatory effects, and 5 and 6 showed significant cytotoxicity against human hepatoma HepG2 cells with IC values of 12.3 and 12.9 μM, respectively. Furthermore, flow cytometry assays and western blot analysis revealed that 5 and 6 promoted the apoptosis of HepG2 cells by activating ERK. Finally, the molecular docking analysis implied that the carbonyl and hydroxy groups at the C-11/C-6' of 5 and 6 had a good binding affinity with ERK.

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http://dx.doi.org/10.1016/j.bioorg.2022.105879DOI Listing

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