Du Baoshuang, Wang Shan, Zhu Song, Li Yue, Huang Dejian, Chen Shangwei
State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi 214122, China.
International Joint Laboratory on Food Safety, Jiangnan University, Wuxi 214122, China.
Foods. 2023 May 14;12(10):1986. doi: 10.3390/foods12101986.
Dihydromyricetin (DHM) is a phytochemical with multiple bioactivities. However, its poor liposolubility limits its application in the field. In this study, DHM was acylated with different fatty acid vinyl esters to improve its lipophilicity, and five DHM acylated derivatives with different carbon chain lengths (C2-DHM, C4-DHM, C6-DHM, C8-DHM, and C12-DHM) and different lipophilicity were synthesized. The relationship between the lipophilicity and antioxidant activities of DHM and its derivatives was evaluated with oil and emulsion models using chemical and cellular antioxidant activity (CAA) tests. The capacity of DHM derivatives to scavenge 1,1-diphenyl-2-picrylhydrazyl radical (DPPH•) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical (ABTS+•) was similar to that of DHM, except for C12-DHM. The antioxidant activity of DHM derivatives was lower than that of DHM in sunflower oil, while C4-DHM exhibited better antioxidant capacity in oil-in-water emulsion. In CAA tests, C8-DHM (median effective dose (EC) 35.14 μmol/L) exhibited better antioxidant activity than that of DHM (EC: 226.26 μmol/L). The results showed that in different antioxidant models, DHM derivatives with different lipophilicity had various antioxidant activities, which has guiding significance for the use of DHM and its derivatives.
二氢杨梅素（DHM）是一种具有多种生物活性的植物化学物质。然而，其较差的脂溶性限制了它在该领域的应用。在本研究中，二氢杨梅素与不同的脂肪酸乙烯酯进行酰化反应以提高其亲脂性，并合成了五种具有不同碳链长度（C2-DHM、C4-DHM、C6-DHM、C8-DHM和C12-DHM）和不同亲脂性的二氢杨梅素酰化衍生物。使用化学和细胞抗氧化活性（CAA）测试，通过油和乳液模型评估了二氢杨梅素及其衍生物的亲脂性与抗氧化活性之间的关系。除C12-DHM外，二氢杨梅素衍生物清除1,1-二苯基-2-苦基肼自由基（DPPH•）和2,2'-联氮-双-（3-乙基苯并噻唑啉-6-磺酸）自由基（ABTS+•）的能力与二氢杨梅素相似。在向日葵油中，二氢杨梅素衍生物的抗氧化活性低于二氢杨梅素，而C4-DHM在水包油乳液中表现出更好的抗氧化能力。在CAA测试中，C8-DHM（半数有效剂量（EC）为35.14 μmol/L）表现出比二氢杨梅素（EC：226.26 μmol/L）更好的抗氧化活性。结果表明，在不同的抗氧化模型中，具有不同亲脂性的二氢杨梅素衍生物具有不同的抗氧化活性，这对二氢杨梅素及其衍生物的使用具有指导意义。
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