title: Novel synthesized 2, 4-DAPG analogues: antifungal activity, mechanism and toxicology.
abstract: 2, 4-Diacetylphloroglucinol (2,4-DAPG), a natural phenolic compound, has been investigated in light of its biological activities against plant pathogens. To improve its potential application, fourteen 2,4-DAPG analogous were synthesized through the Friedel-Crafts reaction using acyl chlorides and phloroglucinol. Of the 2,4-DAPG derivatives, MP4 exhibited much higher antifungal activity against Penicillium digitatum and P. italicum, the major pathogenic fungi in citrus fruit, than 2, 4-DAPG in vitro, and significantly inhibited the development of decay in harvested mandarin (Citrus reticulata Blanco cv. Shatang.) fruit in vivo. It was found that MP4 resulted in the wrinkle of the hyphae in both fungi with serious folds and breakage. In addition, the expression of several cytochrome P450 (CYP) genes were also modified in both fungi by MP4, which might be associated with the disorder of cell membrane formation. Furthermore, the toxicology of MP4 by evaluating the cell proliferation effect on human normal lung epithelial (16HBE) and kidney 293 (HEK293) cells, was significantly lower than that of albesilate, a widely used fungicide in harvested citrus fruit. In summary, the synthesized MP4 has shown a great potential as a novel fungicide that might be useful for control of postharvest decay in citrus fruit.
authors: Key Laboratory of Plant Resource Conservation and Sustainable Utilization/Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, Guangdong Province, China.
authors: Liang
authors: L
authors: Gong
authors: Key Laboratory of Plant Resource Conservation and Sustainable Utilization/Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, Guangdong Province, China.
authors: Haibo
authors: H
authors: Tan
authors: Department of Food, Nutrition and Packaging Sciences, Clemson University,Clemson, South Carolina, USA.
authors: Feng
authors: F
authors: Chen
authors: Key Laboratory of Plant Resource Conservation and Sustainable Utilization/Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, Guangdong Province, China.
authors: Taotao
authors: T
authors: Li
authors: School of Minerals Processing and Bioengineering, Central South University, Changsha 410083, China.
authors: Jianyu
authors: J
authors: Zhu
authors: Key Laboratory of Plant Resource Conservation and Sustainable Utilization/Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, Guangdong Province, China.
authors: Qijie
authors: Q
authors: Jian
authors: Key Laboratory of Plant Resource Conservation and Sustainable Utilization/Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, Guangdong Province, China.
authors: Debao
authors: D
authors: Yuan
authors: Key Laboratory of Plant Resource Conservation and Sustainable Utilization/Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, Guangdong Province, China.
authors: Liangxiong
authors: L
authors: Xu
authors: Department of Food Engineering, College of Life Science, Dalian NationalitiesUniversity, Dalian 116600, China.
authors: Wenzhong
authors: W
authors: Hu
authors: Key Laboratory of Plant Resource Conservation and Sustainable Utilization/Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, Guangdong Province, China.
authors: Yueming
authors: Y
authors: Jiang
authors: Key Laboratory of Plant Resource Conservation and Sustainable Utilization/Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, Guangdong Province, China.
authors: Xuewu
authors: X
authors: Duan
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D002957:Citrus / Q000382:microbiology*; D003577:Cytochrome P-450 Enzyme System / Q000235:genetics / Q000378:metabolism; D004305:Dose-Response Relationship, Drug; D005656:Fungal Proteins / Q000235:genetics / Q000378:metabolism; D015966:Gene Expression Regulation, Fungal / Q000187:drug effects; D057809:HEK293 Cells; D054884:Host-Pathogen Interactions / Q000187:drug effects; D006801:Humans; D025301:Hyphae / Q000187:drug effects / Q000502:physiology / Q000648:ultrastructure; D008855:Microscopy, Electron, Scanning; D015394:Molecular Structure; D010407:Penicillium / Q000187:drug effects* / Q000235:genetics / Q000502:physiology*; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: C000627638:1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(butan-1-one); D000935:Antifungal Agents; D005656:Fungal Proteins; D003577:Cytochrome P-450 Enzyme System; D010696:Phloroglucinol