Citrus
canker, caused by Xanthomonas citri subsp. citri (Xcc), is a severe
citrus disease. Currently, copper-containing pesticides are widely
used to manage this disease, posing high risks to the environment
and human health. This study reports the discovery of naturally occurring
anti-Xcc compounds from a deep-sea fungus, Aspergillus terreus SCSIO 41202, and the possible
mode of action. The ethyl acetate extract of A. terreus was subjected to bioassay-guided isolation, resulting in the discovery
of eight anti-Xcc compounds (1–8) with minimum inhibitory concentrations (MICs) ranging from
0.078 to 0.625 mg/mL. The chemical structures of these eight metabolites
were determined by integrative analysis of various spectroscopic data.
Among these compounds, Asperporonin A (1) and Asperporonin
B (2) were identified as novel compounds with a very
unusual structural skeleton. The electronic circular dichroism was
used to determine the absolute configurations of 1 and 2 through quantum chemical calculation. A bioconversion pathway
involving pinacol rearrangement was proposed to produce the unusual
compounds (1–2). Compound 6 exhibited an excellent anti-Xcc effect with a MIC
value of 0.078 mg/mL, which was significantly more potent than the
positive control CuSO4 (MIC = 0.3125 mg/mL). Compound 6 inhibited cell growth by disrupting biofilm formation, destroying
the cell membrane, and inducing the accumulation of reactive oxygen
species. In vivo tests indicated that compound 6 is highly
effective in controlling citrus canker disease. These results indicate
that compounds 1–8, especially 6, have the potential as lead compounds for the development
of new, environmentally friendly, and efficient anti-Xcc pesticides.