2-(2-Phenylethyl)-4H-chromen-4-one Derivatives from the Resinous Wood of Aquilaria sinensis with Anti-Inflammatory Effects in LPS-Induced Macrophages

  • Molecules. 2018 Jan 30;23(2):289. doi: 10.3390/molecules23020289.
Sin-Ling Wang  1 ,  Yun-Chen Tsai  2 ,  Shu-Ling Fu  3 ,  Ming-Jen Cheng  4 ,  Mei-Ing Chung  5 ,  Jih-Jung Chen  6  7
Affiliations
  • 1. School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan. [email protected].
  • 2. Institute of Traditional Medicine, National Yang-Ming University, Taipei 112, Taiwan.
  • 3. Institute of Traditional Medicine, National Yang-Ming University, Taipei 112, Taiwan. [email protected].
  • 4. Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, Taiwan. [email protected].
  • 5. School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan. [email protected].
  • 6. Faculty of Pharmacy, School of Pharmaceutical Sciences, National Yang-Ming University, Taipei 112, Taiwan. [email protected].
  • 7. Department of Medical Research, China Medical University Hospital, China Medical University, Taichung 404, Taiwan. [email protected].
PMID: 29385754 DOI: 10.3390/molecules23020289
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.

Keywords
2-(2-phenylethyl)-4H-chromen-4-one; Aquilaria sinensis; Thymelaeaceae; anti-inflammatory activity; resinous wood; structure elucidation.
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