栽培奇楠沉香化学成分及其抗炎活性研究

Chemical constituents from cultivated“Qi-Nan”agarwood and their anti-inflammatory activity

目的研究栽培奇楠沉香Aquilariae Lignum Resinatum的化学成分及其抗炎活性。方法采用硅胶、Sephadex LH-20凝胶等多种柱色谱分离技术分离化合物,并通过质谱、核磁共振等现代波谱学方法鉴定其结构,采用Griess法测试化合物的抗炎活性。结果从栽培奇楠沉香的乙醇提取物中分离得到17个化合物,分别为2-[(4-甲氧基苯甲酰氧基)甲基]色酮(1)、2-(2-苯乙基)色酮(2)、2-[2-(3-羟基-4-甲氧基苯)乙基]色酮(3)、2-[2-(3-甲氧基-4-羟基苯)乙基]色酮(4)、2-[2-(4-甲氧基苯)乙基]色酮(5)、2-[2-(2-羟基苯)乙基]色酮(6)、2-[2-(4-羟基苯)乙基]色酮(7)、6-羟基-2-[2-(3-羟基-4-甲氧基苯)乙基]色酮(8)、6-甲氧基-2-[2-(4-甲氧基苯)乙基)]色酮(9)、(R)-2-[2-羟基-2-(4-羟基苯)乙基]色酮(10)、(S)-2-[2-羟基-2-(4-羟基苯)乙基]色酮(11)、4-羟基苯甲酸甲酯(12)、4-丙烯基苯甲醚(13)、7β-H-9(10)-烯-11,12-环氧-8-氧艾里莫芬烷(14)、(5S,7S,9S,10S)-(-)-9-羟基-芹子烷-3,11-二烯-14-醛(15)、β-榄香烯-9β-醇(16)、角鲨烯(17)。结论化合物1为新化合物,化合物16首次在沉香中发现。体外抗炎活性测试结果表明,化合物8具有抑制脂多糖诱导小鼠单核巨噬细胞RAW264.7产生NO的活性,半数抑制浓度(median inhibition concentration,IC50)值为(27.81±2.34)μmol/L。

Objective To investigate the chemical constituents from cultivated“Qi-Nan”agarwood and their anti-inflammatory activity.Methods Various chromatographic techniques,such as Sephadex LH-20 and silica gel were used for separation.Their structures were elucidated based on mass spectrometry(MS),nuclear magnetic resonance(NMR)and other modern spectroscopic methods.The anti-inflammatory activity of these compounds was screened by Griess method.Results Seventeen compounds were isolated from ethanol extract of cultivated“Qi-Nan”agarwood,which were 2-[(4-methoxybenzoyloxy)methyl]chromone(1),2-(2-phenylethyl)chromone(2),2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]chromone(3),2-[2-(3-methoxy-4-hydroxyphenyl)ethyl]chromone(4),2-[2-(4-methoxyphenyl)ethyl]chromone(5),2-[2-(2-hydroxyphenyl)ethyl]chromone(6),2-[2-(4-hydroxyphenyl)ethyl]chromone(7),6-hydroxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]chromone(8),6-methoxy-2-[2-(4-methoxyphenyl)ethyl]chromone(9),(R)-2-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]chromone(10),(S)-2-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]chromone(11),methyl 4-hydroxybenzoate(12),anethole(13),7β-H-9(10)-ene-11,12-epoxy-8-oxoeremophilane(14),(5S,7S,9S,10S)-(-)-9-hydroxy-selina-3,11-dien-14-al(15),β-elemen-9β-ol(16),squalene(17).Conclusion Compound 1 was a new compound,compound 16 was identified from agarwood for the first time.In vitro anti-inflammatory assay results showed that compound 8 inhibits the NO production in mouse mononuclear macrophages RAW264.7 induced by LPS with IC50 value of(27.81±2.34)μmol/L.