Abstract
Objective: This study focuses on exploring a more effective method of tetrahydrocurcumin synthesis. Methods: With vanillin and acethylacetone as starting materials, curcumin was prepared by Claisen condensation reaction under the condition of alkali, and then a hydrogenation reaction was conducted with palladium catalysis to obtain tetrahydrocurcumin. Its structural identification was confirmed by Ultraviolet and Visible Spectrophotometry (UV-VIS), Infrared Spectroscopy (IR) and Nuclear Magnetic Resonance Spectroscopy (1H-NMR, 13C-NMR). The antioxidant activity was evaluated by DPPH radical scavenging capacity, ABTS radical scavenging capacity and total antioxidant capacity. Results: The results showed that the total yield of this synthesis was 45.70%, and the purity was 97.68%. on the DPPH radical scavenging activity [IC50=(74.33±0.003) mg/L] of tetrahydrocurcumin was significantly higher than that of BHT; its ABTS radical scavenging activity [IC50=(17.15±0.004) mg/L] was significantly higher than that of VC, and the total antioxidant capacity and ferric reducing ability were stronger than BHT and VC. Conclusion: Compared with existing preparation methods, this method is more efficient which inclining a potential price advantage. The antioxidant capacity of tetrahydrocurcumin is mainly embodied in free radical scavenging and chemical reduction, showing a potential application prospect.
Publication Date
9-28-2021
First Page
168
Last Page
172,210
DOI
10.13652/j.issn.1003-5788.2021.09.027
Recommended Citation
Shu-xia, DU; Wang, SHAN; Li, XU; Xiao-huan, TENG; and Qi-kun, TAN
(2021)
"Characterization of synthetic tetrahydrocurcumin and its antioxidant activity in vitro,"
Food and Machinery: Vol. 37:
Iss.
9, Article 27.
DOI: 10.13652/j.issn.1003-5788.2021.09.027
Available at:
https://www.ifoodmm.cn/journal/vol37/iss9/27
References
[1] 张荣凯, 曲建强. 姜黄素结构修饰的研究进展[J]. 化学工业与工程, 2011, 28（5）: 61-67.
[2] 郑彬彬, 张维宇, 罗杨春, 等. 毕赤酵母生物转化制备四氢姜黄素的转化条件优化[J]. 生物加工过程, 2017, 15（2）: 30-34.
[3] 李杰. 四氢姜黄素衍生物的设计、合成及生物活性研究[D]. 沈阳: 沈阳药科大学, 2008: 35-37.
[4] 何延淼, 张小燕, 赵露露, 等. 带不同侧链的含L-DOPA环二肽的合成及其DPPH自由基清除活性的测试[J]. 海南大学学报（自然科学版）, 2019, 37（4）: 322-328.
[5] 肖星凝, 徐雯慧, 左丹, 等. 6种黄酮协同抗氧化作用及构效关系研究[J]. 食品与机械, 2017, 33（2）: 17-21.
[6] 谭冬明, 罗星晔, 陈全斌. 广西甜茶水提取物中不同分离部位的抗氧化性研究[J]. 中国食品添加剂, 2016（6）: 125-129.
[7] TANG Yao, LI Xi-hong, ZHANG Bing, et al. Characterisation of phenolics, betanins and antioxidant activities in seeds of three Chenopodium quinoa Willd. genotypes[J]. Food Chemistry, 2015, 166: 380-388.
[8] CHUNG Yun-chin, CHANG Cheng-tien, CHAO Wen-wan, et al. Antioxidative activity and safety of the 50% ethanolic extract from red bean fermented by Bacillus subtilis IMR-NK1[J]. Journal of Agricultural & Food Chemistry, 2002, 50（8）: 2 454-2 458.
[9] 周刚. 姜黄素衍生物的合成及对朱砂叶螨的生物活性评价[D]. 重庆: 西南大学, 2009: 26.
[10] SHIMODA K, KUBOTA N, HIRANO H, et al. Formation of tetrahydrocurcumin by reduction of curcumin with cultured plant cells of Marchantia polymorpha[J]. Natural Product Communications, 2012, 7（4）: 529-530.
[11] 刘俐, 华桦, 张可星, 等. 四氢姜黄素体外抗氧化作用[J].中国药理与毒理学杂志, 2019, 33（9）: 713.