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

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
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DOI:
10.1055/a-0645-1437
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发表时间:
2018-06
期刊:
影响因子:
2.7
通讯作者:
Sin-Ling Wang;Hsiang‐Ruei Liao;M. Cheng;Chih-Wen Shu;Chun-Lin Chen;M. Chung;Jih-Jung Chen
Sin-Ling Wang;Hsiang‐Ruei Liao;M. Cheng;Chih-Wen Shu;Chun-Lin Chen;M. Chung;Jih-Jung Chen
中科院分区:
医学3区
文献类型:
--
作者:
Sin-Ling Wang;Hsiang‐Ruei Liao;M. Cheng;Chih-Wen Shu;Chun-Lin Chen;M. Chung;Jih-Jung Chen

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摘要四个新的2-(2-苯乙基)-4H-苯并吡喃-4-酮衍生物,6-羟基-5-甲氧基-2-[2-(4′-甲氧基苯基)乙基]色酮(1),6,7-二甲氧基-2-[2-(2′-羟基苯基)乙基]色酮(2),5-羟基-6-甲氧基-2-[2-(3′-甲氧基苯基)乙基]-色酮(3)和7-氯-8-羟基-2-[2-(2-甲氧基苯基)乙基]-色酮(3),从白木香(Aquilariasinensis)中分离得到一个新的化合物[4′-(4′-甲氧基苯基)乙基]色酮(4),以及16个已知化合物(5-20)。其中7-甲氧基-2-[2-(4′-甲氧基苯基)乙基]色酮(5)为首次从天然来源中分离得到。新化合物的结构经波谱分析(1D和2D NMR,HR-ESI-MS,IR,UV)确定。包括1种化合物在内的9种化合物对人中性粒细胞响应50 µM的甲酰-L-甲硫氨酰-L-亮氨酰-L-苯丙氨酸产生超氧阴离子的抑制率超过80%。
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 (5–20). 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.