Kim Yeong A, Kim Hyung Kwoun
Department of Biotechnology, The Catholic University of Korea, Bucheon 14662, Republic of Korea.
J Microbiol Biotechnol. 2025 Feb 14;35:e2410055. doi: 10.4014/jmb.2410.10055.
Phytosterols are naturally found in lipid-rich plant foods and oils. These compounds exhibit various pharmacological effects, including anti-inflammatory, antimicrobial, antioxidant, and cholesterol-lowering properties. However, their industrial application has been limited due to their high melting points and poor solubility in both water and oil. Some unsaturated fatty acids can enhance phytosterols' oil solubility while exhibiting antimicrobial activities against various bacterial strains. In this study, we synthesized a linolenic acid stigmasterol ester (LASE) to improve oil and emulsion solubility of stigmasterol, a phytosterol known for its beneficial physiological effects in humans. LASE was synthesized with lipase A through a transesterification reaction using stigmasterol and α-linolenic acid-rich linseed oil as substrates. The reaction was conducted at 50°C in isooctane with 20 mM of both stigmasterol and linseed oil. Following synthesis, LASE was purified using preparative liquid chromatography. The purified LASE demonstrated a 20-fold improvement in solubility in tricaprylin (TCN) compared to stigmasterol. Additionally, its antibacterial activities against specific food spoilage bacteria were confirmed using a TCN-based emulsion system.
植物甾醇天然存在于富含脂质的植物性食物和油脂中。这些化合物具有多种药理作用，包括抗炎、抗菌、抗氧化和降胆固醇特性。然而，由于它们的高熔点以及在水和油中的低溶解性，其工业应用受到限制。一些不饱和脂肪酸可以提高植物甾醇的油溶性，同时对各种细菌菌株表现出抗菌活性。在本研究中，我们合成了一种亚麻酸豆甾醇酯（LASE），以提高豆甾醇（一种对人体具有有益生理作用的植物甾醇）的油溶性和乳液溶解性。以豆甾醇和富含α-亚麻酸的亚麻籽油为底物，通过脂肪酶A催化的酯交换反应合成了LASE。反应在50°C下于异辛烷中进行，豆甾醇和亚麻籽油的浓度均为20 mM。合成后，使用制备型液相色谱法对LASE进行纯化。与豆甾醇相比，纯化后的LASE在三辛酸甘油酯（TCN）中的溶解度提高了20倍。此外，使用基于TCN的乳液系统证实了其对特定食品腐败细菌的抗菌活性。
