Planta Med 2018; 84(18): 1340-1347
DOI: 10.1055/a-0645-1437
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Four New 2-(2-Phenylethyl)-4H-chromen-4-one Derivatives from the Resinous Wood of Aquilaria sinensis and Their Inhibitory Activities on Neutrophil Pro-Inflammatory Responses

Sin-Ling Wang
1   School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan
,
Hsiang-Ruei Liao
2   Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan, Taiwan
,
Ming-Jen Cheng
3   Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu, Taiwan
,
Chih-Wen Shu
4   Department of Medical Education and Research, Kaohsiung Veterans General Hospital, Kaohsiung, Taiwan
,
Chun-Lin Chen
5   Department of Biological Sciences, National Sun Yat-Sen University, Kaohsiung, Taiwan
,
Mei-Ing Chung
1   School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan
,
Jih-Jung Chen
6   Faculty of Pharmacy, School of Pharmaceutical Sciences, National Yang-Ming University, Taipei, Taiwan
7   Department of Medical Research, China Medical University Hospital, China Medical University, Taichung, Taiwan
› Author Affiliations
Further Information

Publication History

received 16 February 2018
revised 31 May 2018

accepted 14 June 2018

Publication Date:
28 June 2018 (online)

Abstract

Four new 2-(2-phenylethyl)-4H-chromen-4-one derivatives, 6-hydroxy-5-methoxy-2-[2-(4′-methoxyphenyl)ethyl]chromone (1), 6,7-dimethoxy-2-[2-(2′-hydroxyphenyl)ethyl]chromone (2), 5-hydroxy-6-methoxy-2-[2-(3′-methoxyphenyl)ethyl]-chromone (3), and 7-chloro-8-hydroxy-2-[2-(4′-methoxyphenyl)ethyl]chromone (4), have been isolated from the resinous wood of Aquilaria sinensis, together with 16 known compounds (520). Among these, 7-methoxy-2-[2-(4′-methoxyphenyl)ethyl]chromone (5) was isolated from a natural source for the first time. The structures of the new compounds were established by spectroscopic analyses (1D and 2D NMR, HR-ESI-MS, IR, UV). Nine compounds, including 1 showed more than 80% inhibition of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine at 50 µM.

Supporting Information

 
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