Preparation of phytosteryl ornithine ester hydrochloride and improvement of its bioaccessibility and cholesterol-reducing activity in vitro.
In this work, synthesis of phytosteryl ornithine ester hydrochloride was studied for the first time using an intermediate phytosteryl N,N'-bis[tert-butoloxycarbonyl(BOC)]-ornithine ester. This method also involved esterification of phytosterols with N,N'-bis(BOC)-ornithine and deprotection. The maximum yield was 90% and deprotection of BOC group was more than 99% using the HCl/ethyl acetate method. As a result, thermal stability and water solubility as well as emulsifying activity and stability of phytosterols were improved through coupling with ornithine, which is favorable for their application in water-based food systems. We also observed increased bioaccessibility of phytosteryl ornithine hydrochloride (4.5%) and 65% of phytosteryl ornithine hydrochloride was hydrolyzed in vitro. These results indicated that ornithine phytosteryl ester hydrochloride can reduce dissolution capacity of cholesterol in vitro, representing improved cholesterol-reducing activity, which will further expand the applications of phytosteryl ornithine ester hydrochloride.
['Jia|Chengsheng|C|', 'Xia|Xue|X|', 'Wang|Huiqi|H|', 'Bertrand|Muhoza|M|', 'Chen|Gang|G|', 'Zhang|Xiaoming|X|']
D000085:Acetates D000924:Anticholesteremic Agents D001682:Biological Availability D002784:Cholesterol D004063:Digestion D045703:Emulsifying Agents D004951:Esterification D006801:Humans D006868:Hydrolysis D009682:Magnetic Resonance Spectroscopy D009952:Ornithine D010840:Phytosterols D012995:Solubility D013024:Soybean Oil D017550:Spectroscopy, Fourier Transform Infrared D014867:Water
Ornithine Bioaccessibility Cholesterol-reducing Esterification Phytosterols