Department of Physiology, Federal University of Sergipe, 49100-000, São Cristóvão, SE, Brazil.
Department of Chemistry, Federal University of Sergipe, 49100-000, São Cristóvão, SE, Brazil.
Chem Biodivers. 2024 Nov;21(11):e202400945. doi: 10.1002/cbdv.202400945. Epub 2024 Oct 3.
Chalcone (E)-1,3-diphenyl-prop-2-en-1-one and a series of 14 methoxylated derivatives have been synthesized via Claisen-Schmidt aldol condensation and characterized by FTIR, CG/MS/DIC, 1D (H and C), 2D (COSY, HSQC, and HMBC) NMR, and EMAR techniques. All molecules were tested at 1 mM concentration for antifungal (Sclerotium sp., Macrophomina phaesolina and Colletotrichum gloeosporioides), antibacterial (Acidovorax citrulli two strains), and antiprotozoal (Phytomonas serpens) activities. Unmodified chalcone (CH0) and derivatives CH1, CH2, CH8 stood out in terms of antifungal activity. CH0 presented IC values of 47.3 μM (9.8 μg/mL) for the fungus C. gloeosporioides. In addition, fluorescence microscopy indicated that CH0 promoted loss of hyphal cell membrane integrity. The CH1 and CH2 derivatives promoted the inhibition of Sclerotium sp. with IC of 127.5 μM (32.9 μg/mL) and 110.4 μM (29.6 μg/mL), respectively. All molecules showed high activity against the phytoparasite P. serpens with IC values of 0.98, 2.40, 10.25, and 3.11 μM for the derivatives CH2, CH3, CH5 and CH14 respectively. The results demonstrated that derivatives methoxylated in both rings (CH2) as well as derivatives with a furan ring associated with the methoxy group in ring A, as well as unmodified chalcone can be promising agricultural fungicides for controlling the fungi studied.
查尔酮（E）-1,3-二苯基-2-丙烯-1-酮和一系列 14 个甲氧基衍生物已通过 Claisen-Schmidt 缩合反应合成，并通过 FTIR、CG/MS/DIC、1D（H 和 C）、2D（COSY、HSQC 和 HMBC）NMR 和 EMAR 技术进行了表征。所有分子均在 1mM 浓度下进行了抗真菌（Sclerotium sp.、Macrophomina phaesolina 和 Colletotrichum gloeosporioides）、抗菌（Acidovorax citrulli 两种菌株）和抗原生动物（Phytomonas serpens）活性测试。未修饰的查尔酮（CH0）及其衍生物 CH1、CH2、CH8 在抗真菌活性方面表现突出。CH0 对真菌 C. gloeosporioides 的 IC 值为 47.3μM（9.8μg/mL）。此外，荧光显微镜表明 CH0 促进了菌丝细胞膜完整性的丧失。CH1 和 CH2 衍生物分别促进了对 Sclerotium sp. 的抑制，IC 分别为 127.5μM（32.9μg/mL）和 110.4μM（29.6μg/mL）。所有分子对植食性寄生虫 P. serpens 均表现出高活性，其衍生物 CH2、CH3、CH5 和 CH14 的 IC 值分别为 0.98、2.40、10.25 和 3.11μM。结果表明，两个环中均被甲氧基取代的衍生物（CH2）以及与 A 环中甲氧基相连的呋喃环的衍生物，以及未修饰的查尔酮都可能是有前途的农业杀菌剂，可用于控制研究中所涉及的真菌。
