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.
Highlights
Citrus is one of the most economically important fruits with rich amounts of nutrients, but it is highly susceptible to plant pathogens mainly including P.digitatum and P. italicum
Tuning the amphiphilic properties through modifying the molecular dimensions and lipophilicity that used to break through the biophysical barrier, which should have a critical impact on the biological activities of the modified molecules. 2,4-DAPG is an amphipathic molecule with special diacetyl groups, which enable structural modification resulting in profound molecular diversity that could be readily achieved with chemical synthetic approaches[13]
The development of fungicidal resistance in P. digitatum and P. italicum has threatened the effectiveness of application of current fungicides
Summary
Citrus is one of the most economically important fruits with rich amounts of nutrients, but it is highly susceptible to plant pathogens mainly including P.digitatum and P. italicum. Speaking, these two pathogens account for approximately 15–50% of annual economic loss of the total amount of citrus production worldwide[1]. These two pathogens account for approximately 15–50% of annual economic loss of the total amount of citrus production worldwide[1] Chemical fungicides, such as iminoctadinetris (albesilate), thiabendazole (TBZ) and imazalil (IMZ), have been widely used to minimize the postharvest decay of citrus caused by P. digitatum and P. italicum. It is feasible approach to design a series of 2, 4-DAPG analogues by replacing its acetyl groups with substitutes in different lengths and dimensions to modulate the amphiphilic properties
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