目的 研究通体结香技术产沉香中的2-(2-苯乙基)色酮类成分及其抗炎活性。方法 综合运用多种现代色谱分离方法对提取物进行分离,并通过理化常数和波谱分析鉴定化合物结构;结合脂多糖介导的RAW 264.7细胞模型评价部分化合物的抗炎活性,同时通过酶联免疫方法检测TNF-α的分泌水平。结果 从通体香中分离得到1个新化合物(7′R)-2-[2-(7′-羟基苯基)乙基]色酮 (1), 此外还有9个类似物,分别鉴定为: 6,7-二甲氧基-2-[2-(7′-羟基苯基)乙基]色酮 (2), 6-羟基-2-[2-(7′-羟基苯基)乙基]色酮 (3), 8-氯-6-羟基-2-(2-苯基乙基)色酮 (4), 8-氯-6-羟基-2-[2-(4′-甲氧基苯基)乙基]色酮 (5), 8-氯-6-羟基-2-[2-(3′-羟基-4′-甲氧基苯基)乙基]色酮 (6), 7-羟基-6-甲氧基-2-(2-苯基乙基)色酮 (7), 6-羟基-7-甲氧基-2-[2-(4′-羟基苯基)乙基]色酮 (8), 6-羟基-2-[2-(3′-甲氧基-4′-羟基苯基)乙基]色酮(9), 6-羟基-2-[2-(3′-羟基-4′-甲氧基苯基)乙基]色酮 (10)。活性实验结果发现,化合物1, 4, 6, 9对 LPS 诱导RAW264.7 细胞释放TNF-α炎症因子具有显著抑制作用,IC50值分别为13.30,8.53,7.72和10.87 μg·mL-1。结论 化合物1为新化合物,首次报道化合物4的晶体结构;化合物1, 4, 6, 9具有显著抗炎作用。
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.
关键词
白木香 /
通体结香技术 /
沉香 /
色酮 /
抗炎活性
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Key words
Aquilaria sinensis /
whole-tree agarwood-inducing technique /
agarwood /
chromone /
anti-inflammation
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中图分类号：
R932
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参考文献
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脚注
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基金
海南省自然科学基金项目资助(219QN342);国家重点研发计划项目资助(2018YFC1706400);中国医学科学院医学与健康科技创新工程项目资助(2016-I2M-2-003);中组部“万人计划”项目资助(99950534);海南省自然科学基金创新团队项目资助(2017CXTD022)
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