豆甾醇鸟氨酸酯的制备及性质研究
首发时间:2019-03-15
摘要:以N, N\'-bis(BOC)-鸟氨酸为底物通过复合化学催化法与豆甾醇,制备豆甾醇鸟氨酸酯盐酸盐,包括豆甾醇的酯化和BOC基团的脱保护。用红外光谱(FT-IR),质谱(MS)和核磁共振(NMR)等分析手段对中间体和终产物进行结构表征。当以N,N\'-二环己基碳二亚胺(DCC),1-羟基苯甲酰基三唑(HOBt),4-二甲基氨基吡啶(DMAP)为复合催化剂时,产率可达90%。此外,脱BOC保护基采取HCl/乙酸乙酯脱保护法,脱保护率可达99%以上,副产物较少,终产物是豆甾醇鸟氨酸酯盐酸盐。经体外消化实验测定可得,豆甾醇鸟氨酸酯盐酸盐的生物利用度为4.5%,其中,多达65%的豆甾醇鸟氨酸酯盐酸盐能够被分解。
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Preparation and properties of stigmasteryl ornithine ester
Abstract:N,N\'-bis(BOC)-ornithine as substrate with stigmasterol through chemical method to prepare stigmasteryl ornithine ester hydrochloride. This method involved esterification ofstigmasterol with N,N\'-bis(BOC)-ornithine and deprotection of BOC group. The structure of intermediate and final product stigmasterylornithine ester hydrochloride were determined by Fourier Transform Infrared (FT-IR), Mass Spectrometry(MS) and Nuclear Magnetic Resonance(NMR). The maximum esterification yield of over 90% was obtained when the catalysts were the mixtures of N, N\'-dicyclohexylcarbodiimide(DCC), 1-hydroxybenzoyl triazole(HOBt), 4-dimethylaminopyridine (DMAP). In addition, over 99% of BOC group deprotection degree was achieved using HCl/ethyl acetate deprotection method with less by-products. And, the final product wasstigmasterylornithine ester hydrochloride. In vitro digestion, bioaccessibility of stigmasteryl ornithine ester hydrochloride was found to be 4.5% and 65% of stigmasteryl ornithine ester hydrochloride could be hydrolyzed.
Keywords: Stigmasterol Ornithine Stigmasterylornithine ester Bioaccessibility
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