大八角枝叶化学成分研究

Studies on chemical constituents from twigs and leaves of Illicium majus

目的研究大八角Illicius majus枝叶的化学成分。方法采用反复硅胶柱色谱、羟丙基葡聚糖凝胶(Sephadex LH-20)、中压快速制备色谱和反相制备HPLC等技术进行化合物的分离和纯化,利用电喷雾质谱(ESI-MS)、一维和二维核磁共振等波谱数据鉴定其结构。通过MTT比色法评价化合物的细胞毒活性。结果从大八角枝叶提取物中分离得到14个化合物,分别鉴定为3′-甲氧基山柰酚-3-O-吡喃鼠李糖苷(1)、槲皮素-3-O-阿拉伯糖苷(2)、山柰酚-3-O-阿拉伯糖苷(3)、8′-氧代-6-羟基-二氢红花菜豆酸(4)、4-O-methylcedrusin(5)、左旋马尾松树脂醇(6)、(7S,8R)-4,9,9′-三羟基-3,3′,5-三甲氧基二氢苯并呋喃木脂素(7)、vladinol F(8)、9,9′-二羟基-3,3′-二甲氧基二氢苯并呋喃木脂素-4-O-吡喃鼠李糖苷(9)、槲皮素-3-O-吡喃鼠李糖苷(10)、山柰酚-3-O-吡喃鼠李糖苷(11)、牡荆素(12)、3,5,7-三羟基色原酮-3-O-葡萄糖苷(13)和苯甲醇-O-β-D-吡喃葡萄糖苷(14)。14个化合物对人结肠癌细胞HCT-8、人肝癌细胞Bel-7402、人胃癌细胞BGC-823以及人肺癌细胞A549的IC50值均大于10μmol/L。结论 14个化合物均为首次从该植物中分离得到,其中化合物2、3、5、7~9和14为该属植物中首次分离得到。化合物1~14均未表现出明显的细胞毒活性。

Objective To study the chemical constituents from the twigs and leaves of Illicius majus. Methods The compounds were isolated by column chromatography over silica gel, Sephadex LH-20, and flash chromatography coupled with preparative HPLC. The structures were elucidated by spectroscopic analysis including ESI-MS, 1 D-NMR, and 2 D-NMR. The cytotoxic activities were assessed by MTT assay. Results Compounds 1—14 were isolated from the twigs and leaves of I. majus, and identified as 3′-methoxy-kaempferol-3-O-α-L-rhamnopyranoside（1）, quercetin-3-O-arabinoside（2）, kaempferol-3-O-arabinoside（3）, 8′-oxo-6-hydroxy-dihydrophaseic acid（4）, 4-O-methylcedrusin（5）,（-）-massoniresinol（6）,（7 S,8 R）-3,3′,5-trimethoxy-4′,7-epoxy-8,5′-neolignan-4,9,9′-triol（7）, vladinol F（8）, 2,3-dihydro-2-（4′-α-L-rhamnopyranosyl-3′-methoxyphenyl）-3-hydroxymethyl-7-methoxy-5-benzofuranpropanol（9）, quercetin-3-O-α-L-rhamnopyranoside（10）, kaempferol-3-O-α-L-rhamnopyranoside（11）, vitexin（12）, 3,5,7-trihydroxychromone-3-O-glucopyranoside（13）, and benzyl alcohol O-β-D-glucopyranoside（14）. Compounds 1—14 exhibited the cytotoxic activity against HCT-8, Bel-7402, BGC-823, and A549 with IC50 values of over 10 μmol/L, respectively. Conclusion Compounds 1—14 are all obtained from I. majus for the first time, and compounds 2, 3, 5, 7, 8, 9, and 14 are obtained from the genus of Illicium for the first time. All compounds show no significant cytotoxic activities against HCT-8, Bel-7402, BGC-823, and A549 cancer cell.