血见愁中1个新的倍半萜类化合物

A new sesquiterpenoid from Teucrium viscidum

目的研究血见愁Teucrium viscidum地上干燥部分的化学成分,发现抗氧化活性化合物。方法利用硅胶柱色谱、凝胶、ODS柱色谱等色谱技术方法进行分离纯化,并综合运用IR、HR-ESI-MS、^(1)H-NMR、^(13)C-NMR、HSQC、HMBC、COSY等方法鉴定化合物的结构,利用超氧阴离子自由基清除实验评价其抗氧化活性;结果从血见愁乙醇提取物醋酸乙酯萃取部分分离得到1个倍半萜类化合物(1)和6个苯丙素类化合物(2~7),分别鉴定为9-羟基-6,7-去环氧-茎点霉甜菜烯酮(1)、迷迭香酸(2)、迷迭香酸甲酯(3)、迷迭香酸乙酯(4)、反式咖啡酸(5)、反式咖啡酸乙酯(6)、反式咖啡酸乙烯酯(7),化合物2、3、5~7表现出一定的超氧阴离子清除活性,半数效应浓度(median effect concentration,EC_(50))分别为(2.07±1.22)、(0.95±0.26)、(0.84±0.18)、(1.98±1.12)和(5.39±0.89)μg/mL。结论化合物1为新化合物,命名为血见愁酮A;化合物2~4为血见愁植物中首次分离得到;化合物2、3、5~7具有一定的抗氧化活性。

Objective To study the chemical constituents of the aerial parts of Teucrium viscidum and discover bioactive compounds with antioxidant effects.Methods Separation and purification of chemical constituents were conducted by comprehensive chromatographic methods(including silica gel column chromatography,Sephadex LH-20,ODS column chromatography and other chromatographic techniques).The structures of the isolated compounds were determined on the basis of spectroscopic analysis including IR,HR-ESI-MS,^(1)H-NMR,^(13)C-NMR,HSQC,HMBC,COSY and other spectrum.Superoxide anion scavenging assay was used to evaluate the antioxidant activities of them.Results One sesquiterpenoid,named 9-hydroxy-6,7-de-epoxyphomenone(1),and six phenylpropanoids,named rosmarinic acid(2),methyl rosmarinate(3),ethyl rosmarinate(4),trans-caffeic acid(5),trans-caffeic acid ethyl ester(6),and trans-caffeic acid ethylene ester(7)were isolated and identified.Compounds 2,3 and 5−7 exhibited superoxide anion scavenging effects with median effect concentration(EC_(50))values of(2.07±1.22),(0.95±0.26),(0.84±0.18),(1.98±1.12)and(5.39±0.89)μg/mL,respectively.Conclusion Compound 1 is a new compound named teuvisone A,and compounds 2−4 are first isolated within this species.The results of the activity screening test indicate that compounds 2,3 and 5−7 exhibit certain antioxidant activity.