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The phytochemical investigation of Fraxinus hupehensis led to the isolation and characterization of ten compounds which were identified as fraxin ( 1 ), fraxetin ( 2 ), esculetin ( 3 ), cichoriin ( 4 ), euphorbetin ( 5 ), kaempferol-3- O - β -rutinoside ( 6 ), oleuropein ( 7 ), linoleic acid ( 8 ), methyl linoleate ( 9 ), and β -sitosterol ( 10 ). Structures of the isolated constituents were characterized by 1 H NMR, 13 C NMR and HRMS. All the compounds, except compounds 3 and 4, were isolated for the first time from this plant. Further, this was the first report for the occurrence of compound 5 in the Fraxinus species. Antifungal activity evaluation showed that compound 2 exhibited significant inhibitory effects against Bipolaris maydis, Sclerotium rolfsii, and Alternaria solani with EC 50 values of 0.31 ± 0.01 mmol/L, 10.50 ± 0.02 mmol/L, and 0.40 ± 0.02 mmol/L respectively, compared to the positive control, Carbendazim, with its EC 50 values of 0.74 ± 0.01 mmol/L, 1.78 ± 0.01 mmol/L and 1.41 ± 0.00 mmol/L. Herbicidal activity tests showed that compounds 8 - 10 had strong inhibitory effects against the roots of Echinochloa crus-galli with EC 50 values of 1.16 ± 0.23 mmol/L, 1.28 ± 0.58 mmol/L and 1.33 ± 0.35 mmol/L respectively, more potently active than that of the positive control, Cyanazine, with its EC 50 values of 1.56 ± 0.44 mmol/L. However, none of the compounds proved to be active against the tested bacteria ( Erwinia carotovora, Pseudomonas syringae, and Ralstonia solanacearum ).

Chemical Constituents from Fraxinus hupehensis and Their Antifungal and Herbicidal Activities