Zou Xinyue, Xu Ting, Zhao Tian, Xia Jing, Zhu Feifan, Hou Yu, Lu Baiyi, Zhang Yunfei, Yang Xuan
Department of Chemistry, China Agricultural University, Beijing, 100193, China.
College of Biosystems Engineering and Food Science, Key Laboratory for Quality Evaluation and Health Benefit of Agro-Products, Ministry of Agriculture and Rural Affair, Interdisciplinary Research Center on Optical Agricultural and Food Engineering, Zhejiang University, No. 866 Yuhangtang Road, Hangzhou, Zhejiang, 310058, China.
Curr Res Food Sci. 2024 Feb 26;8:100702. doi: 10.1016/j.crfs.2024.100702. eCollection 2024.
Phytosterol organic acid esters are important food resources and the components of biomembrane structure. Due to the lack of extraction and synthesis techniques, more research has been focused on phytosterols, and the research on phytosterol acid esters have encountered a bottleneck, but phytosterol acid esters confer substantial benefits to human health. In this study, stigmasteryl vanillate (VAN), stigmasteryl protocatechuate (PRO) and stigmasteryl sinapate (SIN) were prepared through the Steglich reaction. The processes are promotable and the products reach up to 95% purity. In addition, their stability was evaluated by differential scanning calorimetry and thermogravimetric analysis. HPLC analysis revealed an enhancement in water solubility after esterification with phenolic acid. In an digestion model, the bioaccessibility of stigmasteryl phenolates was significantly higher than that of stigmasterols (STIs). Regarding the anti-inflammatory properties, VAN, PRO, and SIN exhibit superior effects against TNF-α induced pro-inflammatory responses compared to STI. All stigmasteryl phenolates supplementation increased the ATP production, the basal, and maximal oxygen consumption rate in mitochondrial stress test. Overall, we present a synthesis method for stigmasteryl phenolates. It will contribute to the development and research of phytosterol acid ester analysis, functions and utilization in food. Moreover, the nutrient-stigmasterol hybrids tactic we have constructed is practical and can become a targeted mitochondrial delivery strategy with enhanced anti-inflammatory effects.
植物甾醇有机酸酯是重要的食物资源和生物膜结构的组成成分。由于缺乏提取和合成技术，更多的研究集中在植物甾醇上，而对植物甾醇酸酯的研究遇到了瓶颈，但植物甾醇酸酯对人体健康有诸多益处。在本研究中，通过施陶丁格反应制备了香草酸豆甾醇酯（VAN）、原儿茶酸豆甾醇酯（PRO）和芥子酸豆甾醇酯（SIN）。该工艺具有可推广性，产品纯度可达95%。此外，通过差示扫描量热法和热重分析对其稳定性进行了评估。高效液相色谱分析表明，与酚酸酯化后水溶性增强。在消化模型中，豆甾醇酚盐的生物可及性显著高于豆甾醇（STIs）。在抗炎特性方面，与STI相比，VAN、PRO和SIN对肿瘤坏死因子-α诱导的促炎反应表现出更优的效果。在线粒体应激试验中，所有豆甾醇酚盐补充剂均增加了ATP产量、基础耗氧率和最大耗氧率。总体而言，我们提出了一种豆甾醇酚盐的合成方法。这将有助于植物甾醇酸酯在食品中的分析、功能及利用方面的开发和研究。此外，我们构建的营养-豆甾醇杂交策略具有实用性，可成为一种具有增强抗炎作用的靶向线粒体递送策略。
