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High-speed counter-current chromatography (HSCCC) was successfully applied for the first time to isolate and purify four cis-trans isomers of coumaroylspermidine analogs from Safflower. HSCCC separation was achieved with a two-phase solvent system composed of chloroform-methanol-water (1:1:1, v/v/v) with the upper phase as the mobile phase. In a single run, a total of 1.3mg of N(1), N(5), N(10)-(E)-tri-p-coumaroylspermidine (EEE), 4.4mg of N(1)(E)-N(5)-(Z)-N(10)-(E)-tri-p-coumaroylspermidine (EZE), 7.2mg of N(1)(Z)-N(5)-(Z)-N(10)-(E)-tri-p-coumaroylspermidine (ZZE), and 11.5mg of N(1),N(5),N(10)-(Z)-tri-p-coumaroylspermidine (ZZZ) were obtained from 100mg of crude sample. High Performance Liquid Chromatography (HPLC) analysis showed that the purities of these four components are 95.5%, 98.1%, 97.5% and 96.2%, respectively. The chemical structures were identified by ESI-MS, (1)H NMR and (13)C NMR.
Two novel organic amide alkaloids, 4-[(<i>E</i>)-<i>p</i>-coumaroylamino]butan-1-ol (<b>1</b>) and 4-[(<i>Z</i>)-<i>p</i>-coumaroylamino]butan-1-ol (<b>2</b>), together with a rare pyridoindole alkaloid, hippophamide (<b>3</b>), were isolated from the seed residue of <i>Hippophae rhamnoides</i> Linn. subsp. <i>sinensis</i> Rousi. Their structures were determined by spectroscopic means. The results show that compounds <b>1</b> and <b>2</b> are (<i>E</i>/<i>Z</i>)<i>-</i>isomers, compound <b>3</b>, a pyridoindole alkaloid concerted with <i>γ</i>-lactam ring.