Phytopathogenic fungi have been considered as being an enormous threat in the agricultural system. In our search of new antifungal natural products, nine new halogenated cyclopentenones, bicolorins A-I (, and ), along with three known cyclopentenones (, , and ) were isolated from the endophytic fungus of by the one strain-many compounds strategy. Their structures and absolute configurations were elucidated based on extensive spectroscopic analysis, X-ray crystallographic analysis, and time-dependent density functional theory-equivalent circulating density calculations. Compounds showed antifungal activities against five phytopathogenic fungi (, , , and ). Especially, bicolorins B and D ( and ) exhibited strong antifungal activities against with the MIC values of 6.2 and 8.5 μg/mL, respectively, compared with the positive control cycloheximide (MIC of 8.6 μg/mL). Additionally, bicolorin D was proven to be potently antifungal against in vitro and in vivo. This work provides an effective strategy for searching antifungal candidate agents.

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http://dx.doi.org/10.1021/acs.jafc.9b06594DOI Listing

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