Design, Synthesis, and Antifungal Evaluation of Neocryptolepine Derivatives against Phytopathogenic Fungi
Autor: | Gao Jianmei, Yu Sun, Xiao-Fei Shang, Jia-Kai Zhu, Rui Zhou, Ying-Qian Liu, Raymond Kobla Lawoe, Cheng-Jie Yang, Zhong-Min Zhao, Xiao-Dan Yin |
---|---|
Rok vydání: | 2020 |
Předmět: |
0106 biological sciences
Fusarium Antifungal Agents Cryptolepis sanguinolenta 01 natural sciences Rhizoctonia Rhizoctonia solani Structure-Activity Relationship chemistry.chemical_compound Spore germination Plant Diseases Botrytis cinerea Molecular Structure biology Chemistry 010401 analytical chemistry Sclerotinia sclerotiorum food and beverages General Chemistry biology.organism_classification Fungicides Industrial 0104 chemical sciences Fungicide Biochemistry Azoxystrobin Botrytis General Agricultural and Biological Sciences 010606 plant biology & botany |
Zdroj: | Journal of Agricultural and Food Chemistry. 68:2306-2315 |
ISSN: | 1520-5118 0021-8561 |
Popis: | Neocryptolepine is an alkaloid isolated from traditional African herbal medicine Cryptolepis sanguinolenta, and its broad spectrum of biological activities has been illuminated in past decades. In this study, neocryptolepine and its derivatives (1-49) were designed and synthesized from economical and readily available starting materials. Their structures were confirmed by proton nuclear magnetic resonance, carbon nuclear magnetic resonance, and mass spectrometry. The synthesized compounds were screened for their antifungal profile against six agriculturally important fungi Rhizoctonia solani, Botrytis cinerea (B. cinerea), Fusarium graminearum, Mycosphaerella melonis, Sclerotinia sclerotiorum, and Magnaporthe oryzae. The results of in vitro assay revealed that compounds 5, 21, 24, 35, 40, 45, and 47 presented remarkable antifungal activity against the fungi tested with EC50 values lower than 1 μg/mL. Significantly, compound 24 displayed the most effective inhibitory potency against B. cinerea (EC50 = 0.07 μg/mL), and the data from in vivo experiments revealed that compound 24 demonstrated comparable protective activity with the positive control boscalid. Preliminary mechanism studies indicated that compound 24 showed impressive spore germination inhibitory effectiveness and lower cytotoxicity than azoxystrobin, imparted on normal function of the cell membrane and cell wall, and arrested the normal function of the nucleus. Besides the excellent inhibitory activity against agriculturally important phytopathogenic fungi tested, the designed assemblage possesses several benefits with a high profile of variation in synthesized molecules, the ease of synthesis, and good cost-effectiveness of commercially available synthetic reagents, all of these have highlighted the potential worth of compound 24 as a new and highly efficient agricultural fungicide. |
Databáze: | OpenAIRE |
Externí odkaz: |