Concise Total Synthesis and Antifungal Activities of Fusaric Acid, a Natural Product

Abstract

The total synthesis of a natural product alkaloid fusaric acid (FA), which exhibits herbicide, fungicide, insecticide and even diverse notable pharmacological activities, was accomplished in four steps using commercially available materials. The synthesis, based on a unified and flexible strategy using 6-bromonicotinaldehyde as a common intermediate, is concise, convergent, practical and can be carried out on a two-gram scale. This approach could be readily applicable to the synthesis of its analogues. In addition, FA had a wide range of inhibitory activities against 14 plant pathogenic fungi in this study, which demonstrated that as a leading compound, and it has great potential to be further developed as an agricultural fungicide.

Design, Synthesis, Structure–Activity Relationship, and Three-Dimensional Quantitative Structure–Activity Relationship of Fusarium Acid Derivatives and Analogues as Potential Fungicides

“…FA, which is known for its powerful phytotoxicity, can accelerate the development of symptoms, such as internerval necrosis and foliar desiccation . Studies have demonstrated that FA has many pharmacological activities; e.g., (i) it is used as an antihypertensive , and anticancer drug; (ii) it is used in the treatment of Parkinson’s disease; and (iii) it is an important insect phenoloxidase inhibitor and has a positive insecticidal effect. , In our previous study, FA was reported to demonstrate considerable antifungal effects after treating 14 pathogens with FA, such as Colletotrichum higginsianum (EC 50 = 31.7 μg/mL), Thanatephorus cucumeris (EC 50 = 22.4 μg/mL), and Colletotrichum gloeosporioides (EC 50 = 90.8 μg/mL) . Therefore, we postulate that FA and its derivatives have considerable potential for their development into new fungicides.…”

“…29,30 In our previous study, FA was reported to demonstrate considerable antifungal effects after treating 14 pathogens with FA, such as Colletotrichum higginsianum (EC 50 = 31.7 μg/mL), Thanatephorus cucumeris (EC 50 = 22.4 μg/mL), and Colletotrichum gloeosporioides (EC 50 = 90.8 μg/mL). 31 Therefore, we postulate that FA and its derivatives have considerable potential for their development into new fungicides.…”

Maisnarben – eine (un)bekannte traditionelle Arzneidroge

“…Ein Effekt, der auch für die Droge beschrieben ist [12]. Darüber hinaus besitzt Fusarinsäure antivirale, antifungale sowie antiproliferative Effekte [21].…”

The Fusaric Acid Derivative qy17 Inhibits Staphylococcus haemolyticus by Disrupting Biofilm Formation and the Stress Response via Altered Gene Expression

“…Fusaric acid (FA), 5-butylpicolinic acid, is a mycotoxin that has been isolated from certain species of Fusarium and is a kind of Fusarium natural fungal metabolite ( Bacon et al, 1995 ; Thanh et al, 2020 ). Studies have shown that FA has good antibacterial effects ( Huang et al, 2020 ). However, the antibacterial effect and molecular mechanism of FA against S. haemolyticus are still unclear.…”