Two unprecedented neuroprotective 2-(2-phenylethyl)chromone derivatives from cultivated "Qi-Nan" agarwood of Aquilaria sinensis.

Two unprecedented 2-(2-phenylethyl)chromone derivatives, (R)-2-[2-hydroxy-2-(3-hydroxy-4-methoxyphenyl)ethyl]chromone (1) and (R)-1-hydroxy-5-(4-hydroxyphenyl)-1-phenylpentane-3-one (2), with one known compound were isolated from cultivated "Qi-Nan" agarwood of Aquilaria sinensis. Their structures were elucidated by analysis of 1D and 2D NMR as well as HRESIMS. TDDFT-ECD calculation was used to determine the absolute configuration. At 50 μM, compounds 1 and 3 exhibited significant neuroprotective effect, enhancing the cell vitality of human neuroblastoma SH-SY5Y cells induced by H 2 O 2 to 73.24 ± 0.43% and 74.71 ± 5.24%, respectively. [Display omitted] • Two 2-(2-phenylethyl)chromone derivatives were isolated from cultivated "Qi-Nan" agarwood. • Compound 2 was a crucial precursor of 2-(2-phenylethyl)chromone with C 6 –C 5 –C 6 scaffold. • Compound 1 demonstrated neuroprotective effect on H 2 O 2 induced damage in human neuroblastoma SH-SY5Y cells. [ABSTRACT FROM AUTHOR]