Anti-inflammatory Chromones from Agarwood Produced Via Whole-Tree Agarwood-Inducing Technique of Aquilaria sinensis
YU Zhang-xin1, WANG Can-hong1, ZHENG Wei1, CHEN De-li1, YANG Yu1, LIU Yang-yang1*, WEI Jian-he1,2*
1. Hainan Provincial Key Laboratory of Resources Conservation and Development of Southern Medicine & Key Laboratory of State Administration of Traditional Chinese Medicine for Agarwood Sustainable Utilization, Hainan Branch of the Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Haikou 570311, China; 2. Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education & National Engineering Laboratory for Breeding of Endangered Medicinal Materials, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100193, China
Abstract：OBJECTIVE To investigate the chromones and anti-inflammation effect of agarwood produced via whole-tree agarwood-inducing technique (Agar-Wit) from A. sinensis. METHODS The constituents were isolated and purified by chromatographic technique and semi-preparation HPLC. RAW264.7 cell model induced by lipopolysaccharide was used to evaluate the anti-inflammatory activity of some compounds, and the secretion level of TNF-α was detected by ELISA. RESULTS A new 2-(2-phenylethyl) chromone, (7′R)-2-[2-(7′-hydroxyphenyl)ethyl] chromone (1), along with nine analogues (2-10) were isolated from the agarwood produced by Agar-Wit, their structures were identified on the basis of physicochemical characteristics and spectroscopic data analysis as 6,7-dimethoxy-2-[2-(7′-hydroxyphenyl)ethyl] chromone (2), 6-hydroxy-2-[2-(7′-hydroxyphenyl)ethyl] chromone (3), 8-chloro-6-hydroxy-2-(2-phenylethyl)chromen-4-one (4), 8-chloro-6-hydroxy-2-[2-(4′-methoxyphenyl)ethyl] chromone (5), 8-chloro-6-hydroxy-2-[2-(3′-hydroxy-4′-methoxyphenyl)ethyl] chromone (6), 7-hydroxy-6-methoxy-2-(2-phenylethyl) chromone (7), 6-hydroxy-7-dimethoxy-2-[2-(4′-hydroxyethyl)] chromone (8), 6-hydroxy-2-[2-(3′-methoxy-4′-hydroxy)ethyl] chromone (9), 6-hydroxy-2-[2-(3′-hydroxy-4′-methoxyphenyl)ethyl] chromone (10). The results showed that compounds 1, 4, 6, 9 significantly inhibited the release of TNF-α inflammatory factors in RAW264.7 cells induced by LPS, with IC50 values of 13.30, 8.53, 7.72, and 10.87 μg·mL-1, respectively. CONCLUSION Compound 1 is a new compound. The crystal structure of compound 4 is reported for the first time. Compounds 1, 4, 6, 9 show significant anti-inflammation activities.
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2019, Vol. 54 
