Abstract
The resinous wood of Aquilaria sinensis, known as agarwood (Chen Xiang in Chinese), is traditionally used for the treatment of abdominal pain, vomiting, circulatory disorders, and dyspnea. Four new 2-(2-phenylethyl)-4H-chromen-4-one derivatives, namely 7-methoxy-2-[2-(4′-hydroxy-phenyl)ethyl]chromone (1), 7-hydroxy-2-[2-(4′-methoxyphenyl)ethyl]chromone (2), 5,6-dihydroxy- 2-[2-(3′-hydroxy-4′-methoxyphenyl)ethyl]chromone (3), and 6-hydroxy-5-methoxy-2-(2-phenyl-ethyl)chromone (4), have been isolated from the resinous wood of A. sinensis, together with nine known compounds. The structures of these compounds were determined through spectroscopic and MS analyses. Among the isolated compounds, neopetasan, 7-methoxy-2-(2-phenylethyl)-chromone, 6,7-dimethoxy-2-(2-phenylethyl)chromone, and 6,7-dimethoxy-2-[2-(4′-methoxy-phenyl)ethyl]chromone inhibited NF-κB activation in LPS-stimulated RAW 264.7 macrophages with relative luciferase activity values of 0.55 ± 0.09, 0.54 ± 0.03, 0.31 ± 0.05, and 0.38 ± 0.14, respectively, versus that of vehicle control (1.03 ± 0.02). In addition, 5,6-dihydroxy-2-[2-(3′-hydroxy-4′-methoxyphenyl)ethyl]chromone, 7-methoxy-2-(2-phenylethyl)chromone, 7-dimethoxy-2-(2-phenylethyl)chromone, and 6,7-dimethoxy-2-[2-(4′-methoxyphenyl)ethyl]chromone could suppress LPS-induced NO production in RAW 264.7 cells and did not induce cytotoxicity against RAW 264.7 cells after 24-h treatment.
Highlights
Aquilaria sinensis (Lour.) Gilg. (Thymelaeaceae) is an evergreen tree endemic to China
Four new 2-(2-phenylethyl)-4H-chromen-4-one derivatives, namely 7-methoxy-2-[2-(40 -hydroxyphenyl)ethyl]chromone (1), 7-hydroxy-2-[2-(40 -methoxyphenyl)ethyl]chromone (2), 5,6-dihydroxy-2-[2-(30 hydroxy-40 -methoxyphenyl)ethyl]chromone (3), and 6-hydroxy-5-methoxy-2-(2-phenylethyl)chromone (4), and nine known compounds 5–13 have been isolated from the resinous wood of
This paper describes the structural elucidation of the compounds numbered 1 through 4 and the inhibitory activities of all isolates on LPS-induced Nuclear factor κB (NF-κB) activation of macrophages
Summary
Aquilaria sinensis (Lour.) Gilg. (Thymelaeaceae) is an evergreen tree endemic to China. Various benzenoids [2], flavonoids [2,3], 2-(2-phenylethyl)chromones [2,4,5,6,7], sesquiterpenes [8], steroids [2,7], triterpenoids [5], and their derivatives were isolated from this plant in previous studies Many of these compounds exhibit anti-acetylcholinesterase [8], anti-inflammatory [2,7], antitumor [3], and cytotoxic [6] activities. In our studies on the anti-inflammatory constituents of Formosan plants and Chinese herbal medicines, many species have been screened for in vitro inhibitory activity against NF-κB, a key transcriptional activator of pro-inflammatory molecules in LPS-activated macrophages, and A. sinensis was found to be an active species. This paper describes the structural elucidation of the compounds numbered 1 through 4 and the inhibitory activities of all isolates on LPS-induced NF-κB activation of macrophages
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