| 引用本文: | 孙梦璇,于良民,刘振霞,王璇,姜晓辉.兼具酚酸及辣素活性结构化合物的合成及其应用性能研究[J].材料科学与工艺,2025,33(6):12-22.DOI:10.11951/j.issn.1005-0299.20240042. |
| SUN Mengxuan,YU Liangmin,LIU Zhenxia,WANG Xuan,JIANG Xiaohui.Synthesis and performance study of structured compounds with dual phenolic and capsaicin activities[J].Materials Science and Technology,2025,33(6):12-22.DOI:10.11951/j.issn.1005-0299.20240042. |
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| 兼具酚酸及辣素活性结构化合物的合成及其应用性能研究 |
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孙梦璇1, 于良民1,2, 刘振霞1, 王璇1, 姜晓辉1,2
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(1. 海洋化学理论与技术教育部重点实验室(中国海洋大学 化学化工学院),山东 青岛266100; 2.中国海洋大学 三亚海洋研究所 海南省海洋观测与信息重点实验室,海南 三亚 572024)
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| 摘要: |
| 辣椒素是辣椒中的活性成分,因其良好的抗菌、抗氧化和防污特性而备受关注。酚酸是一类同时含有羟基和羧基的化合物,具有清除自由基和抗氧化等生理活性。合成了兼具1到3个酚羟基和酰胺活性基团的2,6-二丙烯酰胺甲基-3,4,5-三羟基羧基苯甲酸(A),3,5-二丙烯酰胺甲基-2,6-二羟基苯甲酸(B),2,6-二丙烯酰胺甲基-3,5-二羟基苯甲酸(C),N-(2-苯甲酸-2,4-二羟基-5-苯甲酰胺甲基苄基)苯甲酰胺(D)、 N-(2,3,4-三羟基-5-丙烯酰胺甲基苄基)丙烯酰胺(E)、3,5-二丙烯酰胺甲基-2,6-二羟基苯乙酮(F)和 2,4-二丙烯酰胺甲基-6-叔丁基间甲酚(G)等7种辣素衍生物,并通过红外光谱、1H NMR和13C NMR进行表征。化合物的抗氧化活性通过还原力测试和DPPH自由基清除能力测试进行评估,抑菌活性通过测定对大肠杆菌的抑制作用进行评估。结果表明,7种辣椒素衍生物均具有一定的抗氧化和抗菌活性,其中,酚酸辣素衍生物A的抗氧化活性与维生素C相似,抑制率EC50为7.953 μg/mL,质量浓度为3 mg/mL时的抑菌率为99.18%。酚酸辣椒素衍生物在食品、医药和化妆品领域具有更大的发展潜力。 |
| 关键词: 辣素衍生物 合成 酚酸 抗氧化活性 抑菌活性 |
| DOI：10.11951/j.issn.1005-0299.20240042 |
| 分类号:TQ283,TS202 |
| 文献标识码:A |
| 基金项目:中国博士后科学基金(2023M733337);青岛博士后科学基金(QDBSH20230102075). |
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| Synthesis and performance study of structured compounds with dual phenolic and capsaicin activities |
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SUN Mengxuan1, YU Liangmin1,2, LIU Zhenxia1, WANG Xuan1, JIANG Xiaohui1,2
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(1.Key Laboratory of Marine Chemistry Theory and Technology(College of Chemistry and Chemical Engineering, Ocean University of China), Ministry of Education, Qingdao 266100, China;2.Key Laboratory of Ocean Observation and Information of Hainan Province, Sanya Oceanographic Institution, Ocean University of China, Sanya 572024, China)
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| Abstract: |
| Capsaicin, as an active ingredient in chili peppers, has garnered significant attention because of its excellent physiological activities such as antimicrobial, antioxidant and antifouling properties. Phenolic acids are a class of compounds containing both hydroxyl and carboxyl groups, which have physiological activities such as free radical scavenging and antioxidantactivity. In this study, a total of seven capsaicin derivatives 2,6-Diacrylamidomethyl-3,4,5-trihydroxycarboxybenzoic acid (A), 3,5-Diacrylamidomethyl-2,6-dihydroxybenzoic acid (B), 2,6-Diacrylamidomethyl-3,5-dihydroxybenzoic acid (C), N-(2-Benzoic acid-2,4-dihydroxy-5-benzamidomethylbenzyl)benzamide (D), N-(2,3,4-Trihydroxy-5-acrylamidomethylbenzyl) acrylamide (E), 3,5-Diacrylamidomethyl-2,6-dihydroxyacetophenone (F), and 2,4-Diacrylamidomethyl-6-tert-butyl-m-cresol (G) with one to three phenolic hydroxyl and amide reactive groups were synthesized, each containing 1 to 3 phenolic hydroxyl and amide active groups. These capsaicin derivatives were characterized by IR, 1H NMR and 13C NMR. The antioxidant activity of the compounds was evaluated by reducing power test and DPPH radical scavenging capacity test. The bacteriostatic activity was evaluated by the determination of E.coli bacterial inhibition. From the results, all seven capsaicin derivatives possess certain levels of antioxidant and antibacterial activities. Among them, the phenolic acid capsaicin derivative A shows antioxidant activity similar to VC with an EC50 of 7.953 μg/mL and a bacterial inhibition rate of 99.18% at a mass concentration of 3 mg/mL. Phenolic acid capsaicin derivatives have significant potential for development in the food, pharmaceutical and cosmetic fields. |
| Key words: capsaicin derivatives synthesis phenolic acids antioxidant activity antibacterial activity |
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