Sesquiterpenoids and 2-(2-Phenylethyl)chromone Derivatives from the Resinous Heartwood of Aquilaria sinensis
Shuya Wei, Dong‐Bao Hu, Mengyuan Xia, Ji‐Feng Luo, Hui Yan, Jing‐Hua Yang, Yun-Song Wang, Yue‐Hu Wang
Abstract
Abstract One novel spirolactone, aquilarisinolide ( 1 ), three new sesquiterpenoids, (2 R ,4 S ,5 R ,7 R )-2-hydroxyeremophila-9,11-dien-8-one ( 2 ), (1 R ,4 S ,5 S ,7 R ,11 R )-13-hydroxyepidaphnauran-9-en-8-one ( 3 ), and (4 R ,5 S ,7 R ,8 S ,10 S ,13 R )-8,13-dihydroxyrotunda-1,11-dien-3-one ( 4 ), together with 13 known compounds ( 5 – 17 ) were isolated from the resinous heartwood of Aquilaria sinensis (Thymelaeaceae). The structures of the new compounds were elucidated based on the analysis of NMR and MS data and theoretical calculations their ECD spectra. The isolated compounds were evaluated for their protective activities against PC12 cell injury induced by corticosterone (CORT) and 1-methyl-4-phenylpyridine ion (MPP + ), as well as inhibitory activities against BACE1. Compound 4 , 5,6-dihydroxy-2-(2-phenylethyl)chromone ( 5 ), daphnauranol B ( 7 ), 6-methoxy-2-[2-(3-methyoxyphenyl)ethyl]chromone ( 10 ), isoagarotetrol ( 14 ), and 1-hydroxy-1,5-diphenylpentan-3-one ( 16 ) showed significant protective effects on CORT-induced injury in PC12 cells at a concentration of 20 μM ( P < 0.001). Isoagarotetrol ( 14 ) showed a significant protective effect on MPP + -induced injury in PC12 cells at a concentration of 20 μM ( P < 0.001), while compound 4 showed a moderate activity ( P < 0.01). The BACE1-inhibitory activities of all tested compounds were very weak with less than 30% inhibition at a concentration of 20 μM. Graphic Abstract