College of Food Science and Technology, Shanghai Ocean University, Shanghai 201306, China.
Fujian Province─Indonesia Marine Food Joint Research and Development Center, Fujian Polytechnic Normal University, Fuqing 350300, China.
J Agric Food Chem. 2023 Aug 16;71(32):12280-12288. doi: 10.1021/acs.jafc.3c01584. Epub 2023 Aug 8.
In this study, we investigated the inhibitory effects of three soybean isoflavones and two soybean phytosterols on the formation of 3-chloropropane-1,2-diol fatty acid esters (3-MCPDE) and aldehydes in heated soybean oil model. 0.4 mM of genistin, genistein, daidzein, stigmasterol, and β-sitosterol significantly reduced 3-MCPDE formation by 25.7, 51.4, 21.4, 61.6, and 55.7%, and total aldehydes formation by 42.03, 43.94, 28.36, 54.74, and 39.23%, respectively. Further study showed that stigmasterol reduced the content of glycidyl esters (GEs) and glycidol, two key intermediates of 3-MCPDE, and prevented fatty acids degradation in the oils. Moreover, the effects of continuous frying time on the content of stigmasterol and the migration of stigmasterol were evaluated in the fried dough sticks model system. The content of stigmasterol in soybean oil was found to be significantly decreased with prolonged heating time. The concentrations of stigmasterol in fried dough sticks and the migration rates of stigmasterol from soybean oil to fried dough sticks decreased with repeated frying sessions. In addition, stigmasterol undergoes oxidative changes during heat treatment, and the oxidation products including 5,6α-epoxystigmasterol, 5,6β-epoxystigmasterol, 7α-hydroxystigmasterol, 7β-hydroxystigmasterol, stigmasterlol-3β,5α,6β-triol, and 7-ketostigmasterol were identified in the frying oils but not in the fried dough sticks. Overall, stigmasterol could be added to soybean oil to reduce 3-MCPDE and aldehydes formation, and reacting with GEs/glycidol and protection of lipid acids from oxidation may be the mechanism of action of stigmasterol.
在这项研究中，我们研究了三种大豆异黄酮和两种大豆甾醇对加热大豆油模型中 3-氯-1,2-丙二醇脂肪酸酯（3-MCPDE）和醛形成的抑制作用。0.4mM 的染料木素、染料木黄酮、大豆苷元和豆甾醇、β-谷甾醇分别显著降低 3-MCPDE 的形成 25.7%、51.4%、21.4%、61.6%和 55.7%，总醛形成 42.03%、43.94%、28.36%、54.74%和 39.23%。进一步的研究表明，豆甾醇降低了缩水甘油酯（GEs）和缩水甘油这两种 3-MCPDE 的关键中间体的含量，并防止了油中脂肪酸的降解。此外，在油条模型体系中评估了连续油炸时间对豆甾醇含量和豆甾醇迁移的影响。研究发现，随着加热时间的延长，大豆油中的豆甾醇含量显著降低。随着油炸次数的增加，油条中的豆甾醇浓度和豆甾醇从大豆油向油条的迁移率均降低。此外，豆甾醇在热处理过程中发生氧化变化，鉴定出 5,6α-环氧豆甾醇、5,6β-环氧豆甾醇、7α-羟基豆甾醇、7β-羟基豆甾醇、豆甾醇-3β,5α,6β-三醇和 7-酮豆甾醇等氧化产物，但在油条中未检出。总的来说，豆甾醇可以添加到大豆油中以减少 3-MCPDE 和醛的形成，与 GEs/glycidol 反应和保护脂酸免受氧化可能是豆甾醇的作用机制。
