满江红全草化学成分研究

Chemical constituents from whole herbs of Azolla imbricata

目的研究满江红Azolla imbricata全草的化学成分。方法采用硅胶、ODS、Sephadex LH-20凝胶柱色谱和半制备HPLC等方法分离与纯化,运用NMR、MS等波谱技术鉴定化合物结构。结果从满江红全草95%乙醇提取物中分离得到20个化合物,分别鉴定为绿原酸甲酯(1)、4-O-咖啡酰基奎宁酸(2)、3,4-O-双咖啡酰基奎宁酸甲酯(3)、3,4,5-O-三咖啡酰基奎宁酸甲酯(4)、(-)-N-[3′,4′-双羟基-(E)-肉桂酰基]-3-羟基-L-酪氨酸(5)、(-)-N-[3′,4′-双羟基-(E)-肉桂酰基]-L-酪氨酸(6)、(-)-N-[3′,4′-双羟基-(E)-肉桂酰基]-L-酪氨酸甲酯(7)、(-)-N-[4′-羟基-(E)-肉桂酰基]-L-酪氨酸(8)、brainicin(9)、槲皮素-3-O-β-D-葡萄糖苷(10)、柚皮素-7-O-β-D-葡萄糖苷(11)、山柰酚-3-O-(6″-O-咖啡酰基)-β-D-葡萄糖苷(12)、咖啡酸(13)、表白色杜鹃素(14)、myzodendrone(15)、反式阿魏酸-β-D-葡萄糖苷(16)、5,7-二羟基色原酮-2-羧酸(17)、松脂素-4-O-β-D-葡萄糖苷(18)、植醇(19)和反式-12-氧-(10Z,15Z)-植物二烯酸(20)。结论化合物1~12、14~18和20为首次从满江红属植物中分离得到,化合物19为首次从满江红中分离得到。化合物1~7、10、12和13具显著抗氧化活性。

Objective To investigate the chemical constituents from whole herbs of Azolla imbricata. Methods The chemical constituents were separated and purified by various chromatographic techniques of silica gel, ODS, Sephadex LH-20 gel, and semi-preparative HPLC. Their structures were identified by NMR and MS spectroscopic methods. Results Twenty compounds were isolated from A. imbricata and identified as chlorogenic acid methyl ester(1), 4-O-caffeoylquinic acid(2), 3,4-O-dicaffeoylquinic acid methyl ester(3), 3,4,5-O-tricaffeoylquinic acid methyl ester(4),(-)-N-[3′,4′-dihydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine(5),(-)-N-[3′,4′-dihydroxy-(E)-cinnamoyl]-L-tyrosine(6),(-)-N-[3′,4′-dihydroxy-(E)-cinnamoyl]-L-tyrosine methyl ester(7),(-)-N-[4′-hydroxy-(E)-cinnamoyl)]-L-tyrosine(8), brainicin(9), quercetin-3-O-β-D-glucoside(10), naringenin-7-O-β-D-glucoside(11), kaempferol-3-O-(6″-O-caffeoyl)-β-D-glucoside(12), caffeic acid(13), epirhododendrin(14), myzodendrone(15), trans-ferulic acid-β-D-glucoside(16), 5,7-dihydroxychromone-2-carboxylic acid(17), pinoresinol-4-O-β-D-glucoside(18), phytol(19) and trans-12-oxo-(10 Z,15 Z)-phytodienoic acid(20). Conclusion Compounds 1—12, 14—18, and 20 are isolated from the genus Azolla for the first time and compound 19 is isolated from A. imbricata for the first time. Compounds 1—7, 10, 12, and 13 exhibit good antioxidant activity.