Discovery of novel obovatol-based phenazine analogs as potential antifungal agents: synthesis and biological evaluation in vitro
Author:
Yang Chun1, Song Lili1, Miao Zhong1, Jiang Lingyun1, Li Ting1, Zhi Xiaoyan1, Hao Xiaojuan1, Cao Hui1
Affiliation:
1. College of Plant Protection, Shanxi Agricultural University , Taigu , 030801 , Shanxi Province , P. R. China
Abstract
Abstract
To explore candidate fungicides from plant secondary metabolites, 16 novel obovatol-type phenazine derivatives were semi-synthesized from obovatol isolated from the leaves of Magnolia obovata Thunb. The antifungal activity of synthesized compounds was investigated in vitro against four phytopathogenic fungi using the spore germination method. The bioassay results showed that eight derivatives (8b, 8g, 8h–k, 8i′, and 8k′) exhibited better antifungal activity against Fusarium solani than two positive controls, especially compounds 8b (IC50 = 64.61 μg mL−1) and 8i′ (IC50 = 79.97 μg mL−1) showed pronounced inhibition of spore germination activity against F. solani. They could be used as lead compounds for further structural optimization. Additionally, the preliminary structure-activity relationships (SARs) illustrated that the introduction of a benzene ring monosubstituted with electron-withdrawing groups into the obovatol scaffold could lead to potentially antifungal compounds.
Publisher
Walter de Gruyter GmbH
Subject
General Chemistry
Reference28 articles.
1. Ito, K., Iida, T., Ichino, K., Tsunezuka, M., Hattori, M., Namba, T. Chem. Pharm. Bull. 1982, 30, 3347–3353; https://doi.org/10.1248/cpb.30.3347. 2. Rao, K. V., Davis, T. L. Planta Med. 1982, 45, 57–59; https://doi.org/10.1055/s-2007-971246. 3. Koetter, U., Barrett, M., Lacher, S., Abdelrahman, A., Dolnick, D. J. Ethnopharmacol. 2009, 124, 421–425; https://doi.org/10.1016/j.jep.2009.05.040. 4. Seo, K. H., Lee, D. Y., Lee, D. S., Park, J. H., Jeong, R. H., Jung, Y. J., Shrestha, S., Chung, I. S., Kim, G. S., Kim, Y. C., Baek, N. I. Planta Med. 2013, 79, 1335–1340; https://doi.org/10.1055/s-0033-1350673. 5. Matsuda, H., Kageura, T., Oda, M., Morikawa, T., Sakamoto, Y., Yoshikawa, M. Chem. Pharm. Bull. 2001, 49, 716–720; https://doi.org/10.1248/cpb.49.716.
Cited by
1 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献
|
|