[关键词]
[摘要]
目的 研究彝药双参Triplostegia glandulifera干燥块根的化学成分,并评价其体外抗炎活性。方法 综合运用硅胶、SephadexLH-20、ODS及半制备型高效液相色谱技术等进行分离纯化;通过理化性质与波谱数据鉴定化合物结构;采用CCK-8法与Griess法分别测定化合物的细胞毒性及对一氧化氮(NO)释放的抑制作用。结果 从双参干燥块根的乙醇提取物中分离得到24个化合物,分别鉴定为3,4-二甲氧基苯甲醇-O-[β-D-呋喃芹糖基(1→6)-β-D-吡喃葡萄糖苷](1)、sysamarin B(2)、primulagenin A(3)、齐墩果酸-3-O-[α-L-吡喃鼠李糖基-(1→3)-β-D-吡喃木糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖苷](4)、齐墩果酸-3-O-α-L-吡喃阿拉伯糖苷(5)、咖啡酸(6)、咖啡酸乙酯(7)、(2'R,3'R)-2',3'-二羟基- 4'-甲氧基咖啡酰丁酸酯(8)、5-O-[(E)-咖啡酰基]-奎宁酸(9)、4,5-二-O-咖啡酰奎宁酸甲酯(10)、丁香酚基-O-β-D-吡喃葡萄糖苷(11)、(2α,3β)-7-O-甲基雪松素(12)、(7S,8R)-赤式-7,9,9'-三羟基-3,3'-二甲氧基-8-O-4'-新木脂素-4-O-β-D-吡喃葡萄糖苷(13)、(+)-松脂醇(14)、(-)-松脂醇(15)、(+)-丁香脂素-O-β-D-双吡喃葡萄糖苷(16)、原儿茶酸乙酯(17)、橘皮素(18)、橙皮苷(19)、(1S,3S)-1-甲基-1,2,3,4-四氢-β-咔啉-3-羧酸(20)、诺宁生物碱B(21)、士的宁灵碱(22)、1-(β-D-ribofuranosyl)-1H-1,2,4-triazone(23)、肌苷(24)。化合物2、4、5、19可显著抑制NO释放,其中化合物4、5的半数抑制浓度(median inhibition concentration,IC50)分别为(23.76±1.22)、(23.87±0.23)μmol/L。结论 化合物1为新化合物,命名为双参酚苷A(triplostegia phenolic glycoside A);化合物2~5、7~24均为首次从双参属植物中分离得到;化合物2、4、5和19具有较强体外抗炎活性。
[Key word]
[Abstract]
Objective To systematically investigate the chemical constituents and in vitro anti-inflammatory activities of the dried tuberous roots of Triplostegia glandulifera. Method Compounds were isolated and purified by silica gel, Sephadex LH-20, ODS column chromatography and semi-preparative HPLC. Their structures were identified by physicochemical properties and spectroscopic data. The cytotoxicity and inhibitory effects on nitric oxide (NO) production were evaluated by CCK-8 assay and Griess method, respectively. Results Twenty-four compounds were isolated and identified as 3,4-dimethoxybenzyl alcohol-O-[β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside] (1), sysamarin B (2), primulagenin A (3), oleanolic acid-3-O-[α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside] (4), oleanolic acid-3-O-α-L-arabinopyranoside (5), caffeic acid (6), ethyl caffeate (7), (2'R,3'R)-2',3'-dihydroxy-4'-methoxy caffeoyl butyrate (8), 5-O-[(E)-caffeoyl]-quinic acid (9), methyl 4,5-di-O-caffeoyl quinate (10), eugenyl-O-β-D-gucopyranoside (11), rel-(2α,3β)-7-O-methylcedrusin (12), (7S,8R)-erythro-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-β-D-glucopyranoside (13), (+)-pinoresinol (14), (-)-pinoresinol (15), (+)-syringaresinol-O-β-D-diglucopyranoside (16), ethyl protocatechuate (17), tangeretin (18), hesperidin (19), (1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (20), nonialkaloid B (21), strych-novoline (22), 1-(β-D-ribofuranosyl)-1H-1,2,4-triazone (23), and inosine (24). Compounds 2, 4, 5 and 19 showed significant inhibitory activities against NO production. The IC50 values of compounds 4 and 5 were (23.76 ± 1.22) and (23.87 ± 0.23) μmol/L, respectively, which were comparable to that of dexamethasone. Conclusion Compound 1 is a new compound. Compounds 2-5 and 7-24 were isolated from the genus Triplostegia for the first time. Compounds 2, 4, 5 and 19 possess potent in vitro anti-inflammatory activities.
[中图分类号]
R284.1
[基金项目]
国家自然科学基金项目(82260758);国家自然科学基金项目(31860092);BK-高等教育“121”工程专项-云南省一流学科-中药学(30271109904);云南省高层次人才培养支持计划“青年拔尖人才”专项项目(YNWR-QNBJ-2020-255)