Central Laboratories, King Faisal University, Al-Ahsa 31982, Saudi Arabia.
Biochemistry Department, Faculty of Agriculture, Ain Shams University, Cairo 11241, Egypt.
Molecules. 2022 Oct 24;27(21):7177. doi: 10.3390/molecules27217177.
This study aimed to synthesize, characterize, and explore the eco-friendly and antifungal potential of precocenes and their derivatives. The organic synthesis of the mono-O-alkyl-2,2-dimethyl 2-1-chromene series, including the natural product precocene I, and the di--alkyl 2,2-dimethyl-2-1-chromene series, including the natural 2-1-chromenes precocenes II and III, was achieved. The synthetic compounds were subjected to spectroscopic analysis, HNMR,CNMR, and mass characterization. The antifungal activity of synthesized precocenes I, II, and III, as well as their synthetic intermediates, was evaluated by the poison food technique. Precocene II (EC 106.8 µg × mL and 4.94 µg mL), and its regioisomers (EC 97.18 µg × mL and 35.30 µg × mL) and (EC 170.58 × µg mL), exhibited strong fungitoxic activity against and . Some of the novel chromenes, and , which had never been evaluated before, yielded stronger fungitoxic effects. Finally, docking simulations for compounds with promising fungitoxic activity were subjected to structure-activity relationship analyses against the polygalactouronases and voltage-dependent anion channels. Conclusively, precocenes and their regioisomers demonstrated promising fungitoxic activity; such compounds can be subjected to minor structural modifications to yield promising and novel fungicides.
本研究旨在合成、表征并探索 precocenes 及其衍生物的环保和抗真菌潜力。成功合成了单-O-烷基-2,2-二甲基 2-1-色烯系列，包括天然产物 precocene I，以及二-O-烷基-2,2-二甲基-2-1-色烯系列，包括天然产物 precocenes II 和 III。对合成化合物进行了光谱分析、HNMR、CNMR 和质谱表征。采用毒饵法评价了合成的 precocenes I、II 和 III 及其合成中间体的抗真菌活性。Precocene II（EC 106.8 µg × mL 和 4.94 µg mL）及其区域异构体（EC 97.18 µg × mL 和 35.30 µg × mL）和（EC 170.58 × µg mL）对 和 表现出很强的真菌毒性。一些从未经过评估的新型色烯，如 和 ，表现出更强的真菌毒性。最后，对具有潜在抗真菌活性的化合物进行对接模拟，并针对多聚半乳糖醛酸酶和电压依赖性阴离子通道进行了构效关系分析。总之，preocenes 及其区域异构体表现出有希望的抗真菌活性；可以对这些化合物进行微小的结构修饰，以获得有前途的新型杀菌剂。
