1. Six unprecedented 2-(2-phenethyl)chromone dimers from agarwood of Aquilaria filaria.
- Author
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Wei, Yuan, Dong, Wen-Hua, Li, Wei, Zeng, Jun, Chen, Hui-Qin, Huang, Sheng-Zhuo, Yang, Li, Mei, Wen-Li, Wang, Ya-Li, Guo, Zhi-Yong, Dai, Hao-Fu, and Wang, Hao
- Subjects
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CHROMONES , *IN vitro studies , *ANTI-inflammatory agents , *LIQUID chromatography-mass spectrometry , *NUCLEAR magnetic resonance spectroscopy , *NITRIC oxide , *PHYTOCHEMICALS , *DESCRIPTIVE statistics , *PLANT extracts , *BARK , *CELL lines , *MEDICINAL plants , *MOLECULAR structure , *OXIDOREDUCTASES , *ANIMAL experimentation , *COMPARATIVE studies , *PHARMACODYNAMICS , *CHEMICAL inhibitors - Abstract
Six new dimeric 2-(2-phenylethyl)chromones (1 – 6) were successfully isolated from the ethanol extract of agarwood of Aquilaria filaria from Philippines under HPLC-MS guidance. Compounds 1 – 6 are all dimers formed by linking 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromone and flindersia 2-(2-phenylethyl)chromone via a single ether bond, and the linkage site (C5-O-C8′′) of compound 2 is extremely rare. A variety of spectroscopic methods were used to ascertain their structures, including extensive 1D and 2D NMR spectroscopic analysis, HRESIMS, and comparison with literature. The in vitro tyrosinase inhibitory and anti-inflammatory activities of each isolate were assessed. Among these compounds, compound 2 had a tyrosinase inhibition effect with an IC 50 value of 27.71 ± 2.60 μM, and compound 4 exhibited moderate inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells with an IC 50 value of 35.40 ± 1.04 μM. [Display omitted] • Six new 2-(2-phenethyl)chromone dimers were isolated from agarwood of Aquilaria filaria. • Compound 2 had tyrosinase inhibition effect with an IC 50 value of 27.71 ± 2.60 μM. • Compound 4 exhibited anti-inflammatory activity with an IC 50 value of 35.40 ± 1.04 μM. [ABSTRACT FROM AUTHOR]
- Published
- 2024
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