Synthesis and Fungicidal Activity of β-Carboline Alkaloids and Their Derivatives.
A series of β-Carboline derivatives were designed, synthesized, and evaluated for their fungicidal activities in this study. Several derivatives electively exhibited fungicidal activities against some fungi. Especially, compound F5 exhibited higher fungicidal activity against Rhizoctonia solani (53.35%) than commercial antiviral agent validamycin (36.4%); compound F16 exhibited high fungicidal activity against Oospora citriaurantii ex Persoon (43.28%). Some of the alkaloids and their derivatives (compounds F4 and F25) exhibited broad-spectrum fungicidal activity. Specifically, compound F4 exhibited excellent high broad-spectrum fungicidal activity in vitro, and the curative and protection activities against P. litchi in vivo reached 92.59% and 59.26%, respectively. The new derivative, F4, with optimized physicochemical properties, obviously exhibited higher activities both in vitro and in vivo; therefore, F4 may be used as a new lead structure for the development of fungicidal drugs.
Key Laboratory of Natural Pesticide and Chemical Biology, Ministry of Education College of Agriculture, South China Agricultural University, Guangzhou 510642, China. zhibun_li@163.com.
Zhibin
Z
Li
Key Laboratory of Natural Pesticide and Chemical Biology, Ministry of Education College of Agriculture, South China Agricultural University, Guangzhou 510642, China. csh-happy@163.com.
Shaohua
S
Chen
Key Laboratory of Natural Pesticide and Chemical Biology, Ministry of Education College of Agriculture, South China Agricultural University, Guangzhou 510642, China. chuk_shiuman@163.com.
Shaowen
S
Zhu
Key Laboratory of Natural Pesticide and Chemical Biology, Ministry of Education College of Agriculture, South China Agricultural University, Guangzhou 510642, China. luojianjun@scau.edu.cn.
Jianjun
J
Luo
College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China. zhangyaom@163.com.
Yaomou
Y
Zhang
Key Laboratory of Natural Pesticide and Chemical Biology, Ministry of Education College of Agriculture, South China Agricultural University, Guangzhou 510642, China. wengweng@scau.edu.cn.
Qunfang
Q
Weng
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests
D000470:Alkaloids; D002243:Carbolines; D005659:Fungicides, Industrial
fungicidal activity; structure–activity relationship; β-carboline