Innovation Center of Pesticide Research, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, People's Republic of China; Hebei Shengxue Dacheng Pharmaceutical Co., Ltd., Luancheng District 051432, Hebei Province, People's Republic of China.
Innovation Center of Pesticide Research, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, People's Republic of China.
Bioorg Chem. 2024 Jul;148:107479. doi: 10.1016/j.bioorg.2024.107479. Epub 2024 May 19.
Palmarymycins B (1), its regioisomer (2) and B (3) were synthesized via 10-, 9-, and 11-steps in 6.5 %, 2.3 % and 0.54 % overall yields from chroman-4-one (4), 4-hydroxyindanone (12), and 2,5-dimethoxybenzaldehyde (20) as the starting materials, using benzyl protection, enol trimethylsilyl ether by TMSOTf, Rubottom oxidation and deprotection with hydrogenation under Pd/C catalyst as the key steps, respectively. Their structures were characterized by H, C NMR, COSY, HSQC, HMBC and HR-ESI-MS spectral data. The structure of palmarumycin B was revised from 1 to 2 based on the total synthesis, 2D NMR analysis and DFT calculation. The antifungal assay results indicated that palmarumycin B (1) showed moderate inhibitory activity against Phytophthora capsica. Compounds 15 and 16 exhibited excellent in vitro antifungal activities against P. capsica with EC values of 2.17 and 8.50 μg/mL, respectively.
棕榈霉素 B（1）、其区域异构体（2）和 B（3）分别通过从色满-4-酮（4）、4-羟基-1-茚酮（12）和 2,5-二甲氧基苯甲醛（20）作为起始原料，经 10、9 和 11 步反应，以总收率 6.5%、2.3%和 0.54%合成，使用苄基保护、TMSOTf 的烯醇三甲基硅醚、Rubottom 氧化和 Pd/C 催化剂下氢化脱保护分别作为关键步骤。它们的结构通过 H、C NMR、COSY、HSQC、HMBC 和 HR-ESI-MS 光谱数据进行了表征。基于全合成、2D NMR 分析和 DFT 计算，对棕榈霉素 B 的结构进行了修订，从 1 修订为 2。抗真菌试验结果表明，棕榈霉素 B（1）对辣椒疫霉表现出中等抑制活性。化合物 15 和 16 对辣椒疫霉表现出优异的体外抗真菌活性，EC 值分别为 2.17 和 8.50μg/mL。
