Huang Cong, Zhong Yuan, Zeng Rong, Wang Jie, Fang Qingwen, Xiao Shuzhen, Zhang Ji, Wang Zongde, Chen Shangxing, Peng Dayong
College of Forestry, East China Woody Fragrance and Flavor Engineering Research Center of National Forestry and Grassland Administration, Jiangxi Agricultural University, Nanchang 330045, China.
College of Chemistry and Materials, Key Laboratory of Chemical Utilization of Plant Resources of Nanchang, East China Woody Fragrance and Flavor Engineering Research Center of National Forestry and Grassland Administration, Jiangxi Agricultural University, Nanchang 330045, China.
Molecules. 2023 Sep 20;28(18):6713. doi: 10.3390/molecules28186713.
In order to develop a new type of antioxidants with high efficiency, a series of β-ionone thiazolylhydrazone derivatives were designed and synthesized from β-ionone, and their structures were characterized by H-NMR, C-NMR, FT-IR, and HR-MS. The antioxidant test in vitro indicated that most of the target compounds had high biological activity. Among them, compound exhibited very strong DPPH (1,1-diphenyl-2-picrylhydrazyl radical)-scavenging activity with a half-maximal effective concentration (IC) of 86.525 μM. Furthermore, in the ABTS (2,2-azinobis (3-ethylbenzothiazoline-6-sulfonate) diammonium salt)-scavenging experiment, compound exhibited excellent activity with an IC of 65.408 μM. Their biological activities were significantly better than those of the positive control Trolox. These two compounds, which have good free-radical-scavenging activity in vitro, were used as representative compounds in the anti-browning experiment of fresh-cut potatoes. The results showed that and had the same anti-browning ability as kojic acid, and they were effective browning inhibitors. In addition, it is well known that microbial infection is one of the reasons for food oxidation. Therefore, we investigated the antifungal activity of 25 target compounds against eight plant fungi at a concentration of 125 mg/L. The results indicated that these compounds all have some antifungal activity and may become new potential fungicides. Notably, compound 1u showed the best inhibitory effect against , with an inhibition rate as high as 77.71%; it is expected to become the dominant structure for the development of new antifungal agents.
为了开发一种新型高效抗氧化剂，以β-紫罗兰酮为原料设计并合成了一系列β-紫罗兰酮噻唑基腙衍生物，其结构通过氢核磁共振（H-NMR）、碳核磁共振（C-NMR）、傅里叶变换红外光谱（FT-IR）和高分辨质谱（HR-MS）进行表征。体外抗氧化试验表明，大多数目标化合物具有较高的生物活性。其中，化合物表现出非常强的1,1-二苯基-2-苦基肼自由基（DPPH）清除活性，半数有效浓度（IC）为86.525μM。此外，在2,2'-联氮-双-3-乙基苯并噻唑啉-6-磺酸二铵盐（ABTS）清除实验中，化合物表现出优异的活性，IC为65.408μM。它们的生物活性明显优于阳性对照曲克芦丁。这两种在体外具有良好自由基清除活性的化合物，被用作鲜切土豆抗褐变实验的代表性化合物。结果表明，和与曲酸具有相同的抗褐变能力，它们是有效的褐变抑制剂。此外，众所周知，微生物感染是食物氧化的原因之一。因此，我们研究了25种目标化合物在125mg/L浓度下对8种植物真菌的抗真菌活性。结果表明，这些化合物都具有一定的抗真菌活性，可能成为新的潜在杀菌剂。值得注意的是，化合物1u对表现出最佳的抑制效果，抑制率高达77.71%；有望成为开发新型抗真菌剂的主导结构。
