School of Agriculture, Yangtze University, Jingzhou 434025, China.
Institute of Pesticides, Yangtze University, Jingzhou 434025, China.
Molecules. 2019 Nov 20;24(23):4207. doi: 10.3390/molecules24234207.
To find good antifungal substances by the bioactivity-guided isolation method, we tracked down the effective antifungal substances in the bark and leaves of , and isolated three antifungal compounds , , and The structures were identified as xanthyletin, luvangetin, and avicennin by H-NMR, C-NMR, and HRMS spectra. Particularly, compound had several isomers, and the H-NMR spectra of in different solvents showed a significant difference. To determine the stereo structure of 2, a single crystal was prepared and identified by X-ray diffraction as Luvangetin. Moreover, the difference of H-NMR data of between in solvent dimethyl sulfoxide-d (DMSO-d) and deuterated chloroform (CDCl), and other reported isomers were discussed for the first time. The bioassay results indicated that the three compounds , , and displayed low to high antifungal activities against tested phytopathogenic fungi. In particular, all compounds , , and showed excellent antifungal activities against Pyricularia oryzae and , with the values of half maximal effective concentration (EC) ranging from 31 to 61 mg/L, and compound was also identified as a more potent inhibitor against Fusaium graminearum (EC = 43.26 ± 1.76 mg/L) compared with fungicide PCA (phenazine-1-carboxylic acid) (EC = 52.34 ± 1.53 mg/L). The results revealed that compounds and were the main antifungal substances of Z. avicennae, and can be used as lead compounds of a fungicide, which has good development value and prospect.
为了通过生物活性导向分离方法找到良好的抗真菌物质，我们追踪到了 树皮和叶子中的有效抗真菌物质，并分离出三种抗真菌化合物，，和。通过 H-NMR、C-NMR 和 HRMS 谱确定了它们的结构分别为黄皮酰胺、芦丁和阿魏宁。特别是，化合物 有几个异构体，在不同溶剂中的 H-NMR 光谱显示出显著差异。为了确定 2 的立体结构，制备了单晶并通过 X 射线衍射鉴定为芦丁。此外，首次讨论了化合物 2 在溶剂二甲亚砜-d（DMSO-d）和氘代氯仿（CDCl）之间以及其他报道的异构体的 H-NMR 数据差异。生物测定结果表明，三种化合物，，和 对测试的植物病原菌真菌表现出低至高的抗真菌活性。特别是，所有化合物，，和 对稻瘟病菌和禾谷镰刀菌均表现出优异的抗真菌活性，其半最大有效浓度（EC）值范围为 31 至 61 mg/L，化合物 也被鉴定为比杀菌剂 PCA（吩嗪-1-羧酸）（EC = 52.34 ± 1.53 mg/L）更有效的 Fusaium graminearum 抑制剂（EC = 43.26 ± 1.76 mg/L）。结果表明，化合物 和 是 Z. avicennae 的主要抗真菌物质，可以作为杀菌剂的先导化合物，具有良好的开发价值和前景。
