Shuangshuang Zhao1,2, Biao Wang1,2, Kailin Tian1,2, Wenxia Ji1,2, Tianyi Zhang1,2, Chuan Ping1,2, Wei Yan1,3, Yonghao Ye1,2. 1. College of Plant Protection, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Nanjing Agricultural University, Nanjing, People's Republic of China. 2. Key Laboratory of Integrated Management of Crop Diseases and Pests, Ministry of Education, Nanjing, People's Republic of China. 3. Department of Chemistry, The Scripps Research Institute, Jupiter, FL, USA.
Abstract
BACKGROUND: Phytopathogenic bacteria, such as Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (Rs), seriously threaten crop production and are the cause of enormous yield losses. Endophytic fungi are abundant sources of bioactive metabolites that may be potential candidates in the development of new agrochemicals. This work emphasizes the discovery of bioactive polyketides from endophytic Alternaria alternata ZHJG5 and reports their structural elucidation and antibacterial activities in detail. RESULTS: Five novel polyketide derivatives, isotalaroflavone (2), (+/-)-5'-dehydroxytalaroflavone (3a/3b), (+)-talaroflavone (4b), and bialternacin G (7), along with five known compounds (1, 4a, 5, 6, and 8), were obtained from the Cercis chinensis-derived fungus A. alternata ZHJG5. The compounds' structures were characterized using spectroscopic methods and X-ray diffraction. Chiral high-performance liquid chromatography was used to separate the racemates 3 and 4, whose absolute configurations were unambiguously confirmed by comparing their experimental and calculated electron circular dichroism data. All isolated compounds were tested for antibacterial activity against the phytopathogenic bacteria Xoo, Xanthomonas oryzae pv. oryzicola (Xoc) and Rs. Compounds 1, 2 and 8 showed pronounced antibacterial activity against all tested bacteria, with minimal inhibitory concentrations ranging from 0.5 to 64 μg/ml. In addition, compound 1 showed a potent protective effect against rice bacterial leaf blight caused by Xoo with a protective efficacy of 75.1% at a concentration of 200 μg/ml. CONCLUSION: These findings highlight the practical potential of antibacterial compounds as candidates for the discovery of novel bactericides.
BACKGROUND: Phytopathogenic bacteria, such as Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (Rs), seriously threaten crop production and are the cause of enormous yield losses. Endophytic fungi are abundant sources of bioactive metabolites that may be potential candidates in the development of new agrochemicals. This work emphasizes the discovery of bioactive polyketides from endophytic Alternaria alternata ZHJG5 and reports their structural elucidation and antibacterial activities in detail. RESULTS: Five novel polyketide derivatives, isotalaroflavone (2), (+/-)-5'-dehydroxytalaroflavone (3a/3b), (+)-talaroflavone (4b), and bialternacin G (7), along with five known compounds (1, 4a, 5, 6, and 8), were obtained from the Cercis chinensis-derived fungus A. alternata ZHJG5. The compounds' structures were characterized using spectroscopic methods and X-ray diffraction. Chiral high-performance liquid chromatography was used to separate the racemates 3 and 4, whose absolute configurations were unambiguously confirmed by comparing their experimental and calculated electron circular dichroism data. All isolated compounds were tested for antibacterial activity against the phytopathogenic bacteria Xoo, Xanthomonas oryzae pv. oryzicola (Xoc) and Rs. Compounds 1, 2 and 8 showed pronounced antibacterial activity against all tested bacteria, with minimal inhibitory concentrations ranging from 0.5 to 64 μg/ml. In addition, compound 1 showed a potent protective effect against rice bacterial leaf blight caused by Xoo with a protective efficacy of 75.1% at a concentration of 200 μg/ml. CONCLUSION: These findings highlight the practical potential of antibacterial compounds as candidates for the discovery of novel bactericides.