Liu, Hui, He, Xiao-Zhi, Feng, Mi-Yan, Yuan-Zeng, Rauwolf, Tyler J., Shao, Li-Dong, Ni, Wei, Yan, Hui, Porco, John A., Hao, Xiao-Jiang, Qin, Xu-Jie, and Liu, Hai-Yang
• Eleven new acylphloroglucinols were isolated from the fruits of Eucalyptus robusta. • Their structures were established by extensive spectroscopic analysis. • 6 , 8 , 10 , and 11 were potent AChE inhibitors with IC 50 values of 3.22, 3.82, and 2.55 μΜ, respectively. • Possible interaction sites of 6 , 8 , 10 , and 11 with AChE were investigated by molecular docking. Eleven new acylphloroglucinols, including six new formylated phloroglucinol-monoterpene meroterpenoids, eucalyprobusals A–F (1 – 6), one monomeric acylphloroglucinol, eucalyprobusone B (7), and four dimeric acylphloroglucinols, eucalyprobusones C–F (8 – 11) were purified from the fruits of Eucalyptus robusta. The establishment of the structures of 1 – 11 was achieved by a combination of NMR and HRESIMS data analyses, electron circular dichroism (ECD), and single-crystal X-ray diffraction. Compounds 6 , 8 , and an inseparable mixture of 10 and 11 were found to be potent AChE inhibitors with IC 50 values of 3.22 ± 0.36, 3.82 ± 0.22, and 2.55 ± 0.28 μΜ, respectively. Possible interaction sites of 6 , 8 , 10 , and 11 with AChE were investigated by means of molecular docking studies, and the results revealed that AChE residues Asn87, Ser125, Thr83, Tyr133, Tyr124, Tyr337, and Tyr341 played crucial roles in the observed activity of the aforementioned compounds. [ABSTRACT FROM AUTHOR]