Improved Synthesis of Asymmetric Curcuminoids and Their Assessment as Antioxidants
學年 110
學期 2
出版（發表）日期 2022-04-14
作品名稱 Improved Synthesis of Asymmetric Curcuminoids and Their Assessment as Antioxidants
作品名稱（其他語言）
著者 Yang-Je Cheng; Cai-Wei Li; Cing-Ling Kuo; Tzenge-Lien Shih; Jih-Jung Chen
單位
出版者
著錄名稱、卷期、頁數 Molecules 27, 2547
摘要 In this paper, the syntheses of twelve asymmetric curcumin analogs using Pabon’s method are reported. Generally, the previously reported yields of asymmetric curcuminoids, such as 9a (53%), 9c (38%), and 9k (38%), have been moderate or low. Herein, we propose that the low yields were due to the presence of water and n-BuNH2 in the reaction media. To prove this formulated hypothesis, we have demonstrated that the yields can be improved by adding molecular sieves (MS) (4 Å) to the reaction mixture, thus reducing the interference of water. Therefore, improved yields (41–76%) were obtained, except for 9b (36.7%), 9g (34%), and 9l (39.5%). Furthermore, compounds 9b, 9d, 9e, 9f, 9g, 9h, 9i, 9j, and 9l are reported herein for the first time. The structures of these synthetic compounds were determined by spectroscopic and mass spectrometry analyses. The free radical scavenging ability of these synthetic asymmetric curcuminoids was evaluated and compared to that of the positive control butylated hydroxytoluene (BHT). Among the synthesized asymmetric curcuminoids, compounds 9a (IC50 = 37.57 ± 0.89 µM) and 9e (IC50 = 37.17 ± 1.76 µM) possessed effective 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging abilities, and compounds 9h (IC50 = 11.36 ± 0.65 µM) and 9i (IC50 = 10.91 ± 0.77 µM) displayed potent 2,2’-azinobis-(3- ethylbenzthiazoline-6-sulphonate) (ABTS) radical scavenging abilities comparable to that of curcumin (IC50 = 10.14 ± 1.04 µM). Furthermore, all the synthetic asymmetric curcuminoids were more active than BHT.
關鍵字 asymmetric curcuminoids;curcuminoids; Pabon’s method;2,4-pentanedione
語言 en
ISSN 1420-3049
期刊性質 國外
收錄於 SCI
產學合作
通訊作者
審稿制度 是
國別 SWE
公開徵稿
出版型式 ,電子版
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機構典藏連結 ( http://tkuir.lib.tku.edu.tw:8080/dspace/handle/987654321/122659 )