Purification of honokiol derivatives from one-pot synthesis by high-performance counter-current chromatography.
This paper describes the application of high-performance counter-current chromatography (HPCCC) as a fast, useful and economic alternative for the separation and purification of seven honokiol derivatives (two of them are isomers), which were synthesized by a one-pot procedure. Five honokiol derivatives were successfully separated by n-hexane-ethyl acetate-methanol-water solvent system at three different volume ratios in a step-gradient elution. Two derivatives were obtained through a cycle elution mode. The whole separation process produced 366.3 mg, 323.6 mg, 242.8 mg, 216.2 mg, 203.5 mg, 185.8 mg and 279.3 mg of 3'-formylhonokiol (1), 2'-methoxy-3'-formylhonokiol (2), 2'-methoxyhonokiol (3), 4-methoxyhonokiol (4), 3',5-diformylhonokiol (5), 2',4-dimethoxy-3'-formylhonokiol (6) and 2',4-dimethoxyhonokiol (7) from crude sample of 3 g with purities of 98.7%, 99.3%, 98.6%, 98.2%, 99.0%, 98.4% and 99.2%, respectively. The purities and structural identification were determined by HPLC, (1)H NMR, (13)C NMR and mass spectroscopy.
Shi
Jie
J
State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, Gaopeng Street, Keyuan Road 4, Chengdu 610041, China.
Xu
Guobin
G
Peng
Aihua
A
Peng
Ming
M
Ye
Haoyu
H
Zhong
Shijie
S
He
Shichao
S
Li
Shucai
S
Luo
Youfu
Y
Wei
Yuquan
Y
Chen
Lijuan
L
D001713:Biphenyl Compounds / Q000737:chemistry / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D003377:Countercurrent Distribution / Q000379:methods*; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D000498:Allyl Compounds; D010636:Phenols
D001713:Biphenyl Compounds; D017705:Lignans; C005499:honokiol; D000498:Allyl Compounds; D010636:Phenols