黔产剑叶凤尾蕨的化学成分研究

Chemical constituents of Pteris ensiformis from Guizhou

关键词:  剑叶凤尾蕨, 化学成分, 结构鉴定, 抗肿瘤活性, 抗凝血活性

Key words:  Pteris ensiformis, chemical constituent, structural identification, anti-tumor activity, anticoagulant activity

摘要:

为研究剑叶凤尾蕨(Pteris ensiformis)的化学成分,该研究选用硅胶、凝胶、MCI、C₁₈等柱色谱进行分离纯化,结合¹H-NMR、¹³C-NMR、MS、IR等波谱数据鉴定化合物结构,并通过MTS和APTT、PT以及TT等方法对所分离得到的部分单体化合物进行抗肿瘤和抗凝血活性筛选。结果表明:(1)从剑叶凤尾蕨中分离得到15个化合物,分别为2-羟基-乙酰基吡咯(1)、N-(3-羧丙基)-2-乙酰基吡咯(2)、3-羟基-2-甲基吡啶(3)、N-甲基羟胺(4)、pterosin S 13-O-glucoside(5)、obtupterosin C(6)、ent-11α-hydroxy-15-oxokauran-19-oic acid(7)、ent-11α-hydroxy-15-oxokaur-16-en-19-oic acid(8)、β-谷甾醇(9)、ent-11α-hydroxy-15-oxokaur-16-en-19-oic acid-O-glucopyranoside(10)、5, 5'-二丁氧基-2, 2'-双环呋喃(11)、5, 5'-二(2-乙基-己氧基)-2, 2'-双环呋喃(12)、黑麦草内酯(13)、丁二酸(14)、富马酸(15)。化合物1为新的吡咯生物碱类天然产物,化合物1-7、10-15为首次从剑叶凤尾蕨中分离得到,化合物1、3、4为首次从凤尾蕨属植物中分离得到。(2)活性测试结果表明,在浓度为40 μmol·L^-1时,化合物1、2、3、5、6、10对肿瘤细胞HL-60、A549、SMMC-7721、MDA-MB-231及SW480的体外肿瘤生长有抑制作用; 在样品浓度为2.0 mmol·L^-1时,化合物1、2、3、6对APTT有缩短作用,化合物1、5、6对PT有延长作用。该研究结果丰富了黔产剑叶凤尾蕨的化学成分,为抗肿瘤药物的研发提供了物质基础。

Abstract:

To study the chemical constituents of Pteris ensiformis, silica gel, gel, MCI, C₁₈ and other column chromatography were used for separation and purification, and their structures were identified by ¹H-NMR, ¹³C-NMR, MS, IR and othe spectral data; the anti-tumor and anti-coagulation activities of some monomers were screened by MTS, APTT, PT and TT. The results were as follows:(1)A total of 15 compounds were isolated from P. ensiformis, the compounds were 2-hydroxy-acetylpyrrole(1), N-(3-carboxypropyl)-2-acetylpyrrole(2), 3-hydroxy-2-methylpyridine(3), N-methylhydroxylamine(4), pterosin S 13-O-glucoside(5), obtupterosin C(6), ent-11α-hydroxy-15-oxokauran-19-oic acid(7), ent-11α-hydroxy-15-oxokaur-16-en-19-oic acid(8), β-sitosterol(9), ent-11α-hydroxy-15-oxokaur-16-en-19-oic acid-O-glucopyranoside(10), 5, 5'-dibutoxy-2, 2'-bifuran(11), 5, 5'-di(2-ethyl-hexyloxy)-2, 2'-bifuran(12),(-)-loliolide(13), succinic acid(14), fumaric acid(15). Compound 1 is a new natural product of pyrrole alkaloids. Compounds 1-7, 10-15 were isolated from P. ensiformis for the first time, and compounds 1, 3, 4 were isolated from Pteris for the first time.(2)The results of activity test showed that compounds 1, 2, 3, 5, 6 and 10 inhibited the growth of tumor cells HL-60, A549, SMMC-7721, MDA-MB-231 and SW480 in vitro at a concentration of 40 μmol·L^-1, At the concentration of 2.0 mmol·L^-1, compounds 1, 2, 3 and 6 shortened APTT and compounds 1, 5 and 6 prolonged PT. The study enriches the chemical constituents of P. ensiformis from Guizhou and provides a material basis for the development of anti-tumor drugs.