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Enzymatic Synthesis of a Novel Antioxidant Octacosanol Lipoate and Its Antioxidant Potency in Sunflower Oil
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-09-17 , DOI: 10.1021/acs.jafc.4c07240 Wen-Sen He 1, 2 , Liying Zhao 1 , Jiawei Sui 1 , Xian Li 1 , Shouhe Huang 2 , Huafang Ding 2 , Hanyue Zhu 2, 3 , Zhen-Yu Chen 2
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-09-17 , DOI: 10.1021/acs.jafc.4c07240 Wen-Sen He 1, 2 , Liying Zhao 1 , Jiawei Sui 1 , Xian Li 1 , Shouhe Huang 2 , Huafang Ding 2 , Hanyue Zhu 2, 3 , Zhen-Yu Chen 2
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α-Lipoic acid possesses remarkable antioxidant activity; however, its poor lipid solubility greatly restricts its practical utilization. The present study was the first (i) to synthesize a novel lipophilic antioxidant of octacosanol lipoate and (ii) to assess its antioxidant potency in sunflower oil by hydrogen nuclear magnetic resonance (1H NMR) spectroscopy. In brief, octacosanol lipoate was successfully synthesized using octacosanol and lipoic acid as substrates and Candida sp. 99–125 lipase as a catalyst. The conversion of octacosanol lipoate could reach as high as 98.1% within merely 2 h, with an overall yield of 87.9%. The hydrophobicity of lipoic acid was significantly enhanced upon esterification with octacosanol. Interestingly, both traditional methods and 1H NMR analysis consistently indicated that octacosanol lipoate exhibited superior antioxidant activity compared with butyl hydroxytoluene at high temperatures. It was concluded that octacosanol lipoate has the potential to be developed into a safe and efficient natural antioxidant which can be utilized not only in daily cooking oils but also in frying oils.
中文翻译：
新型抗氧化剂二十二烷醇硫辛酸酯的酶法合成及其在葵花籽油中的抗氧化功效
α-硫辛酸具有显着的抗氧化活性；然而，其脂溶性差极大地限制了其实际应用。本研究首次 (i) 合成了一种新型亲脂性抗氧化剂二十二烷醇硫辛酸酯，并 (ii) 通过氢核磁共振 ( 1 H NMR) 光谱评估了其在葵花籽油中的抗氧化功效。总之，以二十八醇和硫辛酸为底物，假丝酵母菌成功合成了二十八醇硫辛酸。 99–125脂肪酶作为催化剂。硫辛酸二十二烷醇的转化率在短短2小时内即可达到98.1%，总收率为87.9%。与二十八醇酯化后，硫辛酸的疏水性显着增强。有趣的是，传统方法和1 H NMR 分析一致表明，与丁基羟基甲苯相比，硫辛酸二十二烷醇在高温下表现出优异的抗氧化活性。结论表明，二十二烷醇硫辛酸酯有潜力发展成为一种安全、高效的天然抗氧化剂，不仅可用于日常食用油，还可用于煎炸油。
更新日期：2024-09-17
中文翻译：
新型抗氧化剂二十二烷醇硫辛酸酯的酶法合成及其在葵花籽油中的抗氧化功效
α-硫辛酸具有显着的抗氧化活性；然而，其脂溶性差极大地限制了其实际应用。本研究首次 (i) 合成了一种新型亲脂性抗氧化剂二十二烷醇硫辛酸酯，并 (ii) 通过氢核磁共振 ( 1 H NMR) 光谱评估了其在葵花籽油中的抗氧化功效。总之，以二十八醇和硫辛酸为底物，假丝酵母菌成功合成了二十八醇硫辛酸。 99–125脂肪酶作为催化剂。硫辛酸二十二烷醇的转化率在短短2小时内即可达到98.1%，总收率为87.9%。与二十八醇酯化后，硫辛酸的疏水性显着增强。有趣的是，传统方法和1 H NMR 分析一致表明，与丁基羟基甲苯相比，硫辛酸二十二烷醇在高温下表现出优异的抗氧化活性。结论表明，二十二烷醇硫辛酸酯有潜力发展成为一种安全、高效的天然抗氧化剂，不仅可用于日常食用油，还可用于煎炸油。
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