一种新型的亲水性植物甾醇衍生物的化学酶法合成。
A novel chemo-enzymatic synthesis of hydrophilic phytosterol derivatives.
作者信息
He Wen-Sen, Hu Di, Wang Yu, Chen Xue-Yan, Jia Cheng-Sheng, Ma Hai-Le, Feng Biao
机构信息
School of Food and Biological Engineering, Jiangsu University, 301 Xuefu Road, Zhenjiang 212013, Jiangsu, China.
School of Food and Biological Engineering, Jiangsu University, 301 Xuefu Road, Zhenjiang 212013, Jiangsu, China.
出版信息
Food Chem. 2016 Feb 1;192:557-65. doi: 10.1016/j.foodchem.2015.07.047. Epub 2015 Jul 11.
In this study, a novel method was developed for chemo-enzymatic synthesis of hydrophilic phytosterol derivatives, phytosteryl polyethylene glycol succinate (PPGS), through an intermediate phytosteryl hemisuccinate (PSHS), which was first chemically prepared and subsequently coupled with polyethylene glycol (PEG) through lipase-catalyzed esterification. The chemical structure of intermediate and goal product were finally confirmed to be PSHS and PPGS by FT-IR, MS and NMR, suggesting that hydrophilic phytosterol derivatives were successfully synthesized. The effects of various parameters on the conversion of PSHS to PPGS were investigated and the highest conversion (>78%) was obtained under the selected conditions: 75 mmol/L PSHS, 1:2M ratio of PSHS to PEG, 50 g/L Novozym 435, 120 g/L 3 Å molecular sieves in tert-butanol, 55 °C, 96 h and 200 rpm. The solubility of phytosterols in water was significantly improved by coupling with PEG, facilitating the incorporation into a variety of foods containing water.
在本研究中，开发了一种新的化学酶法合成亲水性植物甾醇衍生物——植物甾醇聚乙二醇琥珀酸酯（PPGS）的方法，该方法通过中间体半琥珀酸植物甾醇（PSHS）进行，PSHS首先通过化学方法制备，随后通过脂肪酶催化的酯化反应与聚乙二醇（PEG）偶联。通过傅里叶变换红外光谱（FT-IR）、质谱（MS）和核磁共振（NMR）最终确认中间体和目标产物的化学结构分别为PSHS和PPGS，这表明成功合成了亲水性植物甾醇衍生物。研究了各种参数对PSHS转化为PPGS的影响，在选定条件下获得了最高转化率（>78%）：75 mmol/L PSHS、PSHS与PEG的摩尔比为1:2、50 g/L诺维信435、在叔丁醇中120 g/L 3 Å分子筛、55 °C、96 h和200 rpm。通过与PEG偶联，植物甾醇在水中的溶解度显著提高，便于其掺入各种含水食品中。
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