[关键词]
[摘要]
目的 研究独蒜兰Pleione bulbocodioides假鳞茎的主要化学成分及抗炎活性。方法 通过LC-MS分析主要成分;使用硅胶柱、Sephadex LH-20凝胶柱色谱、制备薄层色谱、半制备液相色谱等分离技术进行分离纯化,通过波谱技术并结合文献对化合物进行结构鉴定;采用脂多糖(lipopolysaccharide,LPS)诱导的RAW264.7小鼠单核巨噬细胞体外炎症模型进行抗炎活性评价。结果 分离得到20个化合物,分别鉴定为对羟基苄基乙醚(1)、对羟基苯甲醛(2)、4-(甲氧基甲基)苯1,2-二醇(3)、3,4-二羟基苯甲醛(4)、对羟基苯乙醇(5)、反式阿魏酸(6)、山药素III(7)、3,3'-二羟基-5-甲氧基-2,6-二(对羟基苄基)联苄(8)、3',5-二羟基-3-甲氧基-2-(对羟基苄基)联苄(9)、3,3'-二羟基-5-甲氧基-2-(对羟基苄基)联苄(10)、bletistrin D(11)、4-烯丙基-2,6-二甲氧基苯基葡萄糖苷(12)、1-O-(4-羟甲基苯氧基)-2-O-反式肉桂酰-β-D-葡萄糖苷(13)、1-O-(4-羟甲基苯氧基)-6-O-反式肉桂酰-β-D-葡萄糖苷(14)、militarine(15)、bletistroside D(16)、天麻素(17)、1-[4'-O-(β-D-吡喃葡萄糖基)苄基]-2-O-(β-D-吡喃葡萄糖基)-4-{4''-O-[(3''''-O-反式阿魏酰基)-β-D-吡喃葡萄糖基]苄基}-(2R)-2-异丁基琥珀酸酯(18)、bletistroside C(19)和dactylorhin A(20)。对化合物7、8、15、16、18~20进行了抗炎活性筛选,化合物7、15、20在50 μmol/L时对NO的抑制率达到42.5%、23.1%和23.6%。结论 化合物18为新化合物,命名为白及琥珀酯苷M(bletistroside M),化合物8、11~14、16和19均是首次从该植物中分离得到;LC-MS显示独蒜兰的主要化学成分是山药素III(7)、militarine(15)和dactylorhin A(20)。此外,化合物7对LPS诱导的RAW264.7细胞炎症反应的抑制作用最好。
[Key word]
[Abstract]
Objective To study the main chemical constituents of Pleione bulbocodioides and the anti-inflammatory activities. Methods The main compounds were analyzed by LC-MS; Silica gel column, Sephadex LH-20 gel column chromatography, preparative thin-layer chromatography and semi-preparative liquid chromatography were used to isolate and purify these compounds. The structures of the isolated compounds were identified by spectroscopy (MS and NMR) methods; All the isolates were tested for the anti-inflammatory activities using the lipopolysaccharide (LPS)-activated of RAW264.7 cells. Results A total of 20 compounds were isolated and identified as p-hydroxybenzyl ethyl ether (1), p-hydroxybenzaldehyde (2), 4-(methoxymethyl)benzene-1,2-diol (3), 3,4-dihydroxybenzaldehyde (4), p-hydroxylbenzyl alcohol (5), (E)-ferulic acid (6), batatasin Ⅲ (7), 3,3'-dihydroxy-5-methoxy-2,6-bis(p-hydroxybenzyl)bibenzyl (8), 3',5-dihydroxy-3-methoxy-2-(p-hydroxybenzyl)bibenzyl (9), 3,3'-dihydroxy-5-methoxy-2-(p-hydroxybenzyl)bibenzyl (10), bletistrin D (11), 4-allyl-2,6-dimethoxyphenyl glucoside (12), 1-O-(4-hydroxymethylphenoxy)-2-O-trans-cinnamoyl-β-D-glucoside (13), 1-O-(4-hydroxymethylphenoxy)-6-O-trans-cinnamoyl-β-D-glucoside (14), militarine (15), bletistroside D (16), gastrodin (17), 1-[4'-O-(β-D-glucopyranosyloxy) benzyl)-2-O-(β-D-glucopyranosyloxy)-4-{4''-O-[(3''''-O-(E)-feruloyl)-β-D-glucopyranosyloxy] benzyl}-(2R)-2-isobutylsuccinate (18), bletistroside C (19) and dactylorhin A (20). Compounds 7, 8, 15, 16, 18—20 are screened for anti-inflammatory activity. Compounds 7, 15 and 20 showed 42.5 %, 23.1 % and 23.6 % inhibition of NO at 50 μmol/L. Conclusion Compound 18 is identified as a novel compound and named bletistroside M; Compounds 8, 11—14, 16 and 19 are obtained from this plant for the first time; LC-MS showed that the main chemical constituents were batatasin III (7), militarine (15) and dactylorhin A (20). In addition, compound 7 showed the best anti-inflammatory effects.
[中图分类号]
R284.1
[基金项目]
国家自然科学基金面上项目(32170407)